Finding Our Way

Show Notes

Design leader Emily Campbell joins Peter and Jesse to share the pragmatic details of her experience as a VP of Design for an organization embracing AI as a medium, material, and means of development.

Emily Campbell: https://emilycampbell.co/
Jesse James Garrett: https://jessejamesgarrett.com/
Peter Merholz: https://petermerholz.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, we’re joined by design leader Emily Campbell. She’ll share with us her journey and perspective on building AI-empowered design teams. We’ll look at the implications of AI for hiring, metrics, team roles, cross-functional collaboration, leadership, and the value proposition of design itself.

There’s a whole lot in here, so here’s our conversation with Emily Campbell.

Peter: Emily, thank you so much for joining us.

Emily: Thanks for having me. I’m excited

Peter: We’re excited too. Before we get started, for our listeners who might not know you, how do you introduce yourself?

Emily: Yeah. So I’m Emily Campbell. I’m currently the VP of design at HackerRank, which is a technical skills and hiring platform.

Jesse: AI has been a strong thread in your thinking and your writing as a design leader for some time now. And I’m curious about how AI became a part of how you approach design and design leadership.

Emily: Absolutely. Yeah. I find it fascinating, and I’ll tell you why. I’ve been working with machine learning products for quite some time, but when ChatGPT dropped in, what, 2022? The company where I was leading design and research, Vendr, was very early to bring it in, and so we had to start to figure out what is this new material that our users and our customers are gonna be able to play with themselves? What does it look like to create those interactions on our end, and how do we define what it means to have a good user experience inside of this product and platform we were building?

Developing a language of AI interaction

Emily: And so I started to need to develop my own vocabulary for AI interaction, whether you are interacting with the model directly in these conversational experiences or working with places where AI would bring in, like, ambient insights or help to summarize and make sense of the work that you were doing inside of our products.

So that was the reason why I started to get into it. And then in January of ’24, I dropped a side project called The Shape of AI, which I continue to manage, and it’s a catalog of vocabulary I was developing to make sense of and then use to help my teams make sense of this material.

What is it? What’s actually happening behind the scenes? I think it’s very easy for us to get very fixated on what exists today, but this whole AI UX, agentic UX, everything that we’re working with right now is evolving so fast that the truth or the source of truth is evolving along with it. And so, yeah, it’s been this project of just trying to understand this moving target and then be intentional about working with it.

Jesse: One thing that struck me about The Shape of AI project was the way in which it was really designed to facilitate conversations. And it’s interesting to think about designers as facilitators of conversation and that as being part of what we do in design as a function. And I’m, curious about, I guess, your thoughts on how AI impacts how we think about design as a function.

The shifting responsibility of Design

Emily: I think that what you’re describing manifests actually on a few different levels. So I’ll, tell you what I’m seeing across them.

So the first is it just brings us all together, us being designers, product managers, engineers, business analysts, whoever, into kind of a common working group, because what used to stand in the way of us collaborating was the ability to write code and to assess data, make decisions based on it.

So the first thing I’d see is that AI has flattened this PED, or whatever you might call it, organization and really made it so that we can all contribute ideas and contribute directly even to the code base regardless of our position or our role or our background.

So that’s one of just like, our job as designers is not to show people the picture of what should be, it’s actually increasingly to play around with what is or turn this prototyping concept into a, more sort of realistic source of truth so that we can have a conversation together as opposed to having to have this kind of linear shifting of whatever the source of truth is over the course of the growth and fidelity of this thing we’re creating and then ultimately shipping. So that’s one. I think it allows us to be a lot more intertwined in how we work.

The second is that we are no longer building the thing people interact with. Increasingly we’re building the thing that determines the thing that people interact with, right? And that’s where this whole agent design world comes in because it used to be that we would determine, okay, well, someone comes in and they see this screen and these buttons and this information, and maybe there’s some differences depending on what their role is inside of the organization or the content inside of their algorithm, but we had a lot of control over the, bounding box.

And so that’s where we’d use like usability testing to say, “Did we build this right? Can people use this the way we expected to do this thing we think they’re trying to do?” Now we’re moving into this world where the humans on the other side are the ones determining their experience, and we’re just shaping the ecosystem.

And so there, I think it’s just the role of the design, and the thing that we’re creating is more abstracted away from like a screen that we are drawing a picture of. And so again, it really forces us to change the conversation about what are we trying to build? How do we know if it’s good? What are the risks? What are the different scenarios somebody might be in?

And it just forces a change of vocabulary and a change of focus as a group. So I’d say that’s a kind of high level summary of some of the changes I’m experiencing.

Is Adaptive UI actually a thing?

Peter: Something that’s been addressed a fair bit in the last year or two when it comes to design and AI is the opportunity for even more personalized experiences, I guess, where every user can have some user experience that is distinct to them thanks to the AI having done some work.

I kind of want to call bullshit on that just because it’s been tried before, right? The idea of personalization and purpose-fit interfaces for individuals is not new because of AI. Don’t get me ranting about how we tend to forget the prior 30 years of HCI when we do these things.

But, in any attempt to creating interfaces that evolve tend to get rejected because it turns out people like stability and fixity in their tools. That’s a mental model they bring from life and they want to have in software. And I’m still waiting for the examples of those interfaces.

You know, It’s been a couple years now that we’ve been playing with these tools, and I still don’t know of an interface out there that is AI-driven, where it re- forms itself for me, and my experience would be different than yours and different than Jesse’s based on my prior use of it.

At least nothing that isn’t just like what you already get when you shop on Amazon, right? And, what I see on Amazon is different than what you guys see on Amazon because of my prior history. So I’m like what am I missing? Or am I missing something?

Emily: No, I think you’re totally right. And I mean, the reality is we’ve had some degree of generative experiences because we’ve been living in this algorithmic world since, you know, 2006 when Facebook launched. Since these algorithmic platforms started to take over our life.

And I think we need to recognize that the people driving the discourse right now tend to be the people who build software professionally, where building something for yourself is just what we do. And so we can very easily adapt our mindset to, oh I’m going on a trip and I need an app that can let me plan with my friends. Well, let me just build that for myself, and then we can all jump into it.

So, that is certainly an extreme example that we will see, but the likelihood of that being something that catches on for the reasons that you’re describing, Peter, I mean, like, it’s one thing to create something for yourself.

As soon as you have another person using it, the complications of management and permissions and information and data goes up exponentially.

So, when we talk about generative AI or generative UI, like one of the examples where I do see it showing up is more at like the artifact level.

So I was researching a local issue here in Moab where I live, and I was surprised when ChatGPT actually threw a supply and demand curve artifact into the conversation that I didn’t ask for. But it was actually incredibly helpful because it was interactive, and it was giving me some information about a local budgetary question. But I actually could play around with the parameters that it was talking about. I think that’s a great example of where generative UI can actually be very beneficial.

Or say you’re talking to chat support, and you run into a situation where you’ve asked for something a couple of times and the agent hasn’t been able to fulfill your needs. Well, rather than direct you to a new page or ask you to go talk to somebody else, it might just give you the UI inside of the chat interface to say, “Hey, do you wanna just enter this yourself?” Or you know, any other type of interactivity that lets you get back on track.

So I do think that there is a world where it exists, but it exists more in the situation or the context of the engagement as opposed to like we’re all gonna have our own version of the digital web existing on our own devices.

And then the last thing I’d say is around these algorithmic experiences. Right now they are so opaque. So I spent some time over the weekend building myself a plugin that I could put on LinkedIn that would hide certain types of posts and replace them with artwork or vocabulary or poetry.

And it’s actually quite depressing. I’ll send you a picture , but let’s just say my for you page on LinkedIn is entirely cleared out by blocked posts.

But it made me realize the only reason I’m not engaging with that platform anymore is because the content is no longer relevant to me. If the incentive structure of LinkedIn were to get my attention back and have me engage with it, giving me some degree of control over what I see would actually be really beneficial.

And we’re actually seeing that happen on X right now where they’ve been playing with their algorithm. I would hope that we will move eventually to a world where that type of control is also available, where it’s not so much AI-driven, it’s a little bit more kind of playing with the machine learning knobs.

But that’s where personalization, it’s like the incentive doesn’t change for the company, but the way I reach it is more delivered through my priorities or interests, which might be different from yours.

Designing when you don’t know exactly how it will look

Peter: So some of this reminds me of when Jesse and I were little web design babies, and we… like, I worked for a graphic design firm in 1990–, make sure I get the timing right, 1996, so as it was embracing the web.

I was a web developer there. And one of the biggest frustrations I had is helping graphic designers understand that they could not detailed architect every pixel on the screen for their users, right? That they needed to lean into this web medium, understand HTML, understand that typography’s gonna change, and depending on browsers and all that kind of stuff.

And there was some success in doing that. Some designers realized that, like, you could only go so far in nailing down what the user experience was.

And then we reverted, I think, when it came to starting with mobile and then the web kind of picking up on that again where we were, thanks to CSS and all kinds of things, able to pretty highly specify what’s going on the other end of the screen.

And designers love that, right? Designers love to dictate what the experience is that their users are going to have. Or let me say many designers love that.

This is where I think you start hearing about craft again. Oh, craft. Delicious, delightful craft.

But what you’re talking about raises the question how do I judge the goodness of a design, right? If I’m a designer creating some experience for someone, but that experience can emerge based on all these contextual inputs, most of which I don’t have control over as the designer, what does it mean to do design and to do design well in that context?

Emily: Yeah. Again I, think that’s where we’re starting to see some separation depending on who and what you’re designing for. And again, like a lot of the conversation is being dictated by a specific type of designer, which is more oriented towards brand design or emotional design, things that are meant to catch the senses but maybe not help you do something else.

And so a lot of conversation around craft right now that I’m observing, at least in terms of like the general discourse, what you’re seeing on the platforms, is oriented towards how do you capture someone’s attention? How do you stand out? How do you appear authentic? How do you help people connect with something that they wanna interact with?

I mean, brand is increasingly becoming like community-oriented and I would say brand designers are more trying to capture that vibe shift towards the brand you’re representing as opposed to what like a product designer would be doing or, someone who’s working more in that medium.

So how we define good starts with what we’re trying to do in the first place and being deliberate about that.

But I’ll speak to my world which is a little more to this like product design side. One of the things I’ve had my team start to do is actually write specs for the more probabilistic parts of the experience.

And a spec really just meaning defining what good means upfront so that we have something to baseline off of when we get deeper into the process of actually seeing how the design itself is emerging and then also how people are using it.

So for example, HackerRank right now where I am has an AI interviewer product that is replacing what has come to be known as like a really nasty part of the hiring process for engineers where you get sent some take-home tests that you have to take and then send it back and now companies are very concerned about cheating and integrity so it’s led to some decay in the user experience.

So we’ve been playing around with, well, what if instead you could do the work and then talk through it as opposed to having somebody think maybe you were, cheating on the work itself.

So what does it look like to be interviewed by an AI agent? I mean, that’s a really distinct and kind of icky experience if it’s not done with care.

So we’ve had to think about, like, if a human was interviewing you, what would that experience look like in a way that would be good? Especially since interviews at scale, whether it’s a human or a machine, it’s just generally a little bit inhuman. It’s meant to be a repeatable process.

So we forced ourselves to say what does good mean? What are the different scenarios where things can go wrong? How would we expect a proctor or an interviewer to handle that situation?

And then as we start to design the experience with this AI agent, we have this real benchmark that we can look at the actual conversations for example that the AI is having with the users and say, “Oh, interesting. Here a user asked a question and we would expect the AI to respond one way, it responded a different way.”

That’s now an observed error and so we can improve the prompt or we can improve the harness or the interface context and so on to try and get a better outcome.

So I think a lot of what does good mean and what does it mean to design starts with being intentional, which has always been the case. Starts with defining what is a positive experience through the lens of the person experiencing it, and then the material itself, of how that experience is actually rendered, is the thing that’s evolving.

But I think we just can get very easily stuck in that when we’re still in the world of fundamentals.

So that’s some of the things that we’ve been playing with and I think we’re gonna keep seeing evolution there, ’cause there’s also all sorts of learning that’s starting to come out about like effective evals. It’s easy to use them in a way that actually gets the AI or the agent to behave in a certain way that’s almost like over-fitting to the situations you’ve observed, so we have to think about situations we haven’t observed.

So there’s a lot of really interesting discovery and research that goes into making sure that you’re casting a wide net as well.

AI as material and medium

Jesse: It’s interesting the way in which this brings, as you touched on, the probabilistic into the design conversation. And in the course of robbing designers of their auteurship, we open up potentially these new areas to play in creatively.

When I think about probabilistic design, I think about games. I think about video games or board games or these other kinds of complex interlocking systems that are built around, in some cases, probabilistic processes, the roll of the dice as the core.

And I find myself curious about how many designers can really make that leap to that probabilistic way of thinking? Because as Peter pointed out, the history of design tradition carries within it a degree of deterministic thinking. And those of us who’ve worked in digital design for the last 25 years, have had to cope with the variability of the digital environment in ways that design traditions historically have not had to.

And now this feels like an even further step away from… I’m reminded of a talk I gave many years ago that I think is on the web under the title Design for Engagement, although it went under a number of titles over the years, where I talk about design practice having historically been grounded in mastery of a medium.

And so graphic design has its dogma and its ways of thinking about problems that are rooted in the medium of paper fundamentally. And so a graphic designer can tell you what paper has taught them about things, basically. And an industrial designer can tell you what plastic and rubber and metal have been able to teach them about what it means to make something.

And I’m curious about how those people can find a way to embrace a new way of thinking when their identities have been so tied to feeling like you have mastered something.

How do you bring people along into this new world and help them see the creative opportunities there when their ideas about themselves and their practices and their value are really rooted in this mastery of a medium?

Emily: I came out into design about 2008, ‘ 9, ’10, when we were starting to see mobile design start to take up and we’re… Myself, we as designers were still working with code. Like, I wrote the CSS of the first platform that I designed for. So I think that for my generation of people in this industry, this idea of kind of like tinkering and playing around with the material or the medium itself comes very naturally.

Then you have a generation of designers who came out of art schools and simultaneously out of boot camps, where both were not fully capturing the other side of the world that each was seeing. So I think it’s a multifaceted challenge, I guess, that hits us all a little bit differently.

I’ll tell you this. The people that I’m seeing thrive right now are maybe not the folks who are traditionally working on the interfaces, but people who are service designers, conversational designers, more traditional UX designers, and design thinkers. Those are folks who are, at least in the world that I’m seeing, the teams that I’m building, really excelling.

In terms of connecting this more probabilistic world to the traditional or more classic design work, I don’t know that I have an answer for that, honestly. While still respecting the fact that everybody connects to their work and to why they do this particular work in a different way, I often find myself wondering if we rotate a little bit too far towards what design looks like at any time as a definition of what it means to be a designer versus kind of what are we trying to achieve, which in our world is helping people navigate information effectively, have command over their experiences, their data, their networks, and maintain their own sense of agency as they increasingly live their lives in this digital space, which might require us to be comfortable changing the surface that we are working within while still coming back to our roots.

Because the fundamentals are not that different than they used to be, at least as it relates to understanding bias, understanding how people cognitively process information, the upper limits of our ability to process information at scale as humans, and how we use these different technologies in an assistive way.

That’s what I look to when I look for meaning and purpose and coach other people on as well. But I do think that, we are at a moment where people do need to just touch into themselves and say, “What drives me? What feeds me? Why am I here?” And I do wanna just recognize, like I think it’s a very difficult moment for lot of folks who are having to go through that personal transformation at the same time that the work and the things that they are working on are transforming as well.

Evolving as a Design Leader these past few years

Peter: You’ve been VP of Design at HackerRank for about two and a half years, which is an interesting timeframe when we look at kind of the moment when these tools really started affecting kind of how design work happens.

And I’m wondering, in these two and a half years that you’ve been there, how you’ve changed as a leader. Like, was there certain set of practices or assumptions that you entered with that now, two and a half years later, you realize like, “Oh, I need to show up in different ways for my team, for others in the business”?

Like, how have you evolved in these two and a half years?

Emily: Oh my gosh, it’s night and day. It really is. I’d say every six months or so, I’ve had to completely reinvent my job over the last two and a half or three years.

So when I started, the team that I inherited was very disempowered. They were still operating in a world where a designer would wait for a product manager to give them a spec that they were supposed to be working on, and then they would work on it and be told by all number of stakeholders whether they were on the right track or not.

And trying to get information about how people intended to use this product, what they were trying to do, more traditional discovery was sometimes hard to come by. It was a pretty desparate situation, honestly.

And so the first six months was really just focused on how do we build a team of empowered people who have the resources, information, and time that they need to do good work? And then what does it look like to raise that bar for the folks who are practitioners so they know what they are capable of achieving and that they will be rewarded by opportunity and by empowerment and so on on the other side. So the first six months was really trying to pull this team into just a higher mature way of working.

And then something started to happen where the team started to spread out in a bell curve. And as this new technology began to come into our work life and also our personal life, some people naturally found themselves tinkering with it, attracted by it. Some people, for maybe intimidation reasons or because their work wasn’t as closely associated with bringing this in, were a lot slower to move.

And so we went through about a year where the team was really kind of all over the place. And I found myself and the leaders that I work with kind of pulling people up, but also meeting the frontline folks where they were and trying to stay relevant and current to what they were seeing, ’cause they were pushing everyone, including me, forward.

And then in the last six to nine months, particularly after last Christmas was around the time that we saw this Claude Code breakout and everybody could suddenly do all these great things with coding, the team has really come back together to the point where everyone is now actively using these in different ways, but actively pushing on this material and really reinventing themselves.

And if anything, I’d say it’s the most empowered the team has been, even if we’re doing less classical design work, where executives, product managers, engineers are coming to the design team and saying, “How should we be thinking about this? What are the different ways we might approach this? Hey, I made a prototype. Is this good? How do I know if it’s good? What does good design mean?”

And now we have designers who aren’t just at the table, but they’re actually driving a lot of the strategic thinking and a lot of the ideas around the user experience where they were completely left out of that two years prior.

And I’d like to say that I had a large part of that, but it’s also just the individuals, because now they don’t have to wait for me to create the permission structure. They don’t have to wait for some PM to say, “Okay, here’s some data. Here’s what we can work on.” They now can go and raise a PR. They can go and make a change to the point that we have this bot that lives in our Slack where if you have an idea of something you want to improve, you can just describe it and it’ll raise a PR.

The designers have been working with the engineers to actually improve how that bot interacts with them, so it now will actually create your own private node of this new idea. It’ll give you pictures of the before and after. Like, you can touch this material directly from within Slack, and that’s where I’ve seen the biggest change.

So from a leadership perspective, my world has definitely moved more into facilitating where information lives, trying to unblock people. I feel like I’m doing a lot more operational work as a leader, and then trying to find for myself and the team at the same time what does it mean to grow as a designer as we’re trying to reimagine what that even means.

So it’s, it’s been quite a journey over the last couple of years, and I’m sure I’m not the only person who’s feeling that exact same trip.

Creating alignment when everything is shifting

Jesse: Yeah. So much of it comes back to how you manage changing expectations both within the team as well as with your cross-functional partners, as well as with the executives. And the burden of all of that expectation management falls on the design leader.

And I’m curious about your read on, like, what are the biggest tactical challenges that you saw in creating that alignment when the expectations themselves might be a moving target, right?

Emily: I think it starts with understanding what our expectations are for ourselves and for our team because any expectation we’re being fed is completely under-informed because nobody really knows what’s going on right now.

So the perfect example is the executive who says, “Hey, can you do this tomorrow? You have AI,” with some magical thinking that AI is going to be able to fully replace our jobs overnight and why are we even here, but it’s a good thing ’cause we can give you this pretty picture or whatever you’re looking for.

In some way I think pulling people into the process has been the most effective guard of the process. When you have people creating their own prototypes, playing with the design, exploring the design system and our rules and so on, it becomes pretty aware to them quite quickly that this is more complicated than they realize.

So for example, we had an engineer who vibe coded an entire new way of thinking about one of our products and then realized pretty quickly that the information architecture was completely broken. He didn’t know it was information architecture. To him, it was just, “This is confusing. I don’t understand why this doesn’t just work.”

And so in that situation, the designer worked very closely with this engineer to actually, like, go through, what do we want someone to do here? What are the different situations you had in mind? And it allowed us to have a conversation about the reality that your ability to have that picture in your head it doesn’t account for all of those different edge cases, situations, circumstances, lack of context and so on that we would maybe be thinking about proactively as designers.

So just getting people realizing that design is not, quote unquote, solved, has allowed us to have a better hand at creating shared expectations about what we can do.

I think that’s probably the biggest place where we’ve seen friction is just, people thinking this is a magic box. I don’t even… I’m struggling to find my words here, for the reason that when I think about expectations, I don’t even know what to expect in six months. I don’t know what to expect in six weeks. So even just thinking about my expectations for myself as a leader or my team and how I’m coaching them to, to evolve and where I’m seeing growth, there’s a large degree of humility and trying to just be very comfortable with not always having the answers.

That’s also been a really difficult part of this moment that again I’m sure I’m not the only design leader or designer who’s feeling that tension and that uncertainty.

Peter: So earlier you talked about how when you rejoined HackerRank, I see two and a half years ago, the team that you inherited was somewhat disempowered, and now it sounds like the team that you’re leading is not only empowered, they themselves are leading internally.

You’ve explained some of the mechanisms, but I’m curious to what you would ascribe this to, either, did your team evolve to fit better within the context in which HackerRank operates and builds, or did the people outside the team, engineers, product, maybe marketing and executives, others as well, did they develop new awarenesses and understandings such that they could allow design to meet them?

I’m trying to figure out, like, where did the change happen that allowed for design to be perceived, to better integrate with the more strategic and, to have greater agency within the business?

Emily: Yeah. It was a combination of all of the above.

Certainly the skill sets that we’re hiring for and developing have changed. We have a much higher bar for technical fluency. Just curiosity. Curiosity is a skill that I explicitly look for when I’m hiring people and that I’ve been trying to help develop in the folks on the team to be comfortable asking questions not just about themselves or what they’re building, to understand the worlds that other people are building within, especially as we’re working more within these like code bases and shared spaces, and also just a curiosity about these models, this more probabilistic aspect of these things we’re building.

So I think that’s part of it. Like we’re definitely intentionally changing the shape of the team. That also has been met by the individuals themselves just leaning in and creating their own futures. And so I’ve seen my job just creating that space for them to grow and then letting them fill it.

And, you know, obviously when you’re managing a team, there’s different strengths and places where it’s not as easy for the individual. But that’s been another focus of just creating the space and then developing the skills that’ll help them grow into it. But we are seeing folks lean in from the outside, and I don’t know how much of that to take credit in terms of just, like, joining as a more empowered leader myself and allowing others to see more of what we’re doing and challenging them to understand.

Like I had a conversation with an engineer last December who told me he had not had a chance to work with a design team like this, and he was starting to have a better understanding of why we pushed back and when we did, and he was feeling a lot more excited about working with us. So I think it’s like a reinforcement loop.

We’re growing the agency, the skill set and the expectations of the individuals, but in return we’re seeing the organization meet us and wanna pull more out of that, wanna be more part of that. So that’s been not without its challenges, but I think it’s been two-sided.

And again, I think it also comes just down to this fact that we’re all working differently.

To be successful building products, you have to get out of your own discipline moreso than ever because success is no longer drawing a picture. It’s getting something to a form that can actually be interacted with ’cause it’s the only way that you can evaluate the probabilistic aspects to it and the data that’s going through it.

We have to be, at least as product designers it’s increasingly important that we’re actually working in this more interactive material. We’re still doing more traditional work. We’re still working in the canvas. We’re still doing exploration, but that drift between the two is a lot more comfortable and more frequent.

Leading when practice is disparate

Jesse: One of the patterns that I’ve heard people talk about is that when you have designers who are all on their own journeys with the AI tooling they develop their own quirks, their own dialects, their own rhythms and approaches to the prompt craft. And I find myself wondering about how you as a leader, especially from an operational perspective, but just, just in terms of having a common language, having a common way of doing things, how do you create the space for a bunch of different variant approaches to design and still feel like you can make apples to apples comparisons in terms of performance management or even just be able to set a cultural standard for quality or anything else?

Emily: I have had to let go quite a bit of things that I maybe had as like a security blanket previously, of being able to see the work evolve and always be aware of where things were going well or going not well. That’s been a big learning because increasingly, and this is a problem that I hope somebody will solve soon, but we’ll have five or six different versions of thought expressed through some artifact live at any given time, and none of them are the truth at any given time either.

And so as a design leader, in terms of holding that quality bar, I’m spending a lot more time in the more operational area, making sure that… Like for example one of the designers on my team has been completely redeveloping our design system component structure into a skills-based structure.

So we actually now have an like agentic first definition of our components that can be linted by an agent that capture the semantic intent of how this thing fits into the system and how it’s supposed to act, visual aspects and so on. That is one of the few ways that I can control for the inputs into the work. So that’s one.

We still spend a lot of time, I spend a lot of time one-on-one. Managers underneath me spend a lot of time working with me and then working with their teams on still getting back to these like fundamentals. So, hey, let’s put the screen to the side. What does this experience mean for the user? Where might they get tripped up? What are the things that are higher risk that we need to consider?

And again, that’s where like speccing it out and describing good beforehand. It’s like this barbell effect, where we’re spending a lot more time on the inputs and on defining the experience, defining the service layer and so on. And then I’m having to just let go of the work itself.

And then on the backside, and this is where more of this like evaluation work comes in, we have to make sure that not just the properties of the things we’re building, like the pixels, but also the agents and the unknowns that are inside of this experience are operating as expected as well.

And so I’ve pushed very hard to get designers involved in that, building rubrics, building evaluation loops, watching, like, actually watching and reviewing the trace data coming out of the system and then saying, “Hey, does this match our intent? And do we need to change this at the product level, at the prompt level?”

So it’s a lot of like system dynamics. That I love. I mean, my brain enjoys it but it’s an entire remapping.

And then in terms of like career development, again, there’s a combination of fundamentals that still matter. So the ability to translate in a language that is either clear to other humans or increasingly to these models, what do I intend to build? Is it intentional? What’s informing it? How much effort does it take to get to a good version of that? That kind of captures this question of, do I have that strength in the fundamental property that we would look for?

But then there’s this new category, which is like, how well can you work with this medium and orchestrate it and steer it and bring others into the process? That’s a lot harder to capture.

And so increasingly, individual performance is a mapping of these fundamental skills, but also the ability to work with this system and get better outcomes out it collectively.

We’re early in this. Six months ago, we were doing more traditional leveling and I’m remapping it right now, but I think it’s gonna keep evolving.

Tolerating failure

Jesse: Mm-hmm. Earlier you touched on giving people the resources, giving people the time and the space and the permission to experiment. It seems to me that going along with that permission, there has to be a certain cultural tolerance for failure that has to be encouraged because you want to try to get people to jump into the unknown and see what’s on the other side, and sometimes what’s on the other side is not very good.

How are you managing tolerance for failure?

Emily: I’ll say this, the people who are struggling, or to the extent we’ve seen folks struggle, been more a reflection of a hesitancy to leaning versus a reflection of what they did when they actually were playing around in this new world, if that makes any sense. So there definitely was some early resistance.

Like, there’s a lot of reasons to be resistant to what’s happening. Like, there’s, ethical and ecological reasons to be concerned. There’s a lot of concern at different levels of, like, what does this mean for me and my growth path? So I think it’s worth, acknowledging that.

So when I say resistance, it’s more like, not wanting to even try to see what’s on the other side, to have an informed opinion, even if that informed opinion ends up including things that you feel aren’t working well or could change. So that’s probably where I’ve seen, the most tension.

Outside of that, there definitely is a degree to which I’ve been focusing on creating this, like, risk tolerance pool, but it’s not only happening in design, and I think that’s the critical thing that it’s everybody who’s seeing their jobs evolve right now.

We’re seeing our markets evolve. We’re seeing the processes, the things that we could fall back on and unconsciously rely on. “Oh, well, and I do this, and then somebody else would do this next thing.”

So I think it really needs to be something that’s solved at the organizational level. It’s not something that at the individual department or individual business unit we can manage by ourselves.

So I spend a lot of time with my peers at the leadership level talking about what does it mean to have PMs and designers raising PRs? What do we need from engineers in order for people to feel comfortable leaning in? What do people need from us? So I think it’s a larger reconstitution of what is a team that develops products or develops experiences or services together that’s happening.

I, I have… I keep ending my sentences with these, like, dot dot dots because what I feel confident about right now, I’m certain I will not be as confident about some part of that in six weeks.

New ways of getting to understanding

Peter: But let’s take it directionally though. And a conversation that we’ve had with actually our prior two guests is around teams and teaming and roles and who does what, right?

In the before times, in 2022 let’s say, you had your designer, you had your product manager, you had your engineer. Maybe you had your researcher and content designer, and you maybe had your business analyst and quality assurance, right? People’s roles defined their work.

And in the new times, that’s getting all… that snow globe is getting shook up quite vigorously. And I’m wondering what you’re seeing then in terms of people coming together to do this work and what are the mechanisms that predispose that group of people coming together to do the work, to do it well, and maybe better than others who are not engaging in those mechanisms?

What are maybe some early things that you’re witnessing that suggest a trend towards some new ways of behaving, particularly around collaboration and in teams?

Emily: Yeah. Yeah. So the way I’ve described it when I’ve talked to folks about this is in the before times, which I love, that’s great, 2022, such an era ago. But back then the teams that won were the ones that were less wrong faster or less wrong more often. And by that, I mean the entire SDLC/PED team process was intended around the idea of we have to guess what this person downstream of us wants to do and what they need in order to do that well, and then build that thing accurately and as quickly as possible so we can get it in their hands and find out how wrong we were.

And you’re either wrong because you missed the mark in the first place, or you’re wrong because you were right, but it actually opened up even more problems to solve or the actual problem to solve, and you have to repeat it. And so a lot of our processes were around, well, how do we get information faster, which is where you get like move fast and break things and so on.

And so like the rise of product discovery as this core concept is what was feeding that engine. Well, the more information we have up front the more likely we’re gonna get to that faster, better answer. So, we’re still in that world, but a few things are changing.

Like, first of all, we can run more of this in parallel. Like we can be talking to customers, building five different prototypes at the same time. It doesn’t cost, certainly the engineering time and even less design time now to get to different ideas that are actually somewhat realistic.

And we can bring those back fairly quickly to our customers or people that represent our users, or even just internally for those conversations. So one thing I’d say is that we’re spending less time talking and more time doing, but not assuming the thing that we’re doing is the thing we’re ultimately going to ship.

So, that then has the effect of making it less important to have someone who’s like really good at building interactive prototypes, and more important to find somebody who can think and maintain their understanding of their system while they’re working in different, whether it’s in Figma or in code or documentation and so on.

And then where I think we’re seeing things slow down is more at that decision-making moment because we can build faster, so we have to actually make that call of what are we going to ship. And that’s where I think we have the most tension because who’s gonna ultimately make that decision becomes harder to determine

In our case, our founder has been a lot more involved as the CEO, helping us unblock decision-making because we’re actually not operating in a world where a product manager wrote a PRD and that’s the source of truth and we ship it when every single test case underneath that PRD is accepted.

Instead, we’re having to kind of vibe build our way into what do we think our customers want, ’cause realize, the people we’re building for, they’re transforming too.

Like at HackerRank, for example until a few months ago, the primary people we were building for were technical recruiters because those were the people at the front line to help find engineers to bring into the hiring process that would then later on be talking to a director of engineering.

But now that the directors of engineering are saying, “The people we need to hire are totally different than the people we needed six months ago,” they are the ones increasingly in the loop, which is then causing us to build more technical products ’cause we’re now building for the actual end-end user, not this person in the middle.

So that’s an example of how complicated this gets. Everything is changing all at once, but I would say the thing that is definitely evolving, I think in a very positive way, is we are not spending time waiting for somebody else to tell us the answer. We are collectively having to determine that for ourselves and make sure at any given time, as we get new information, everyone’s generally aligned on what it is we wanna ship, which has been, I think, what teams aspired to be back in the before time.

Those really fast, fast-moving, highly empowered teams were the ones who could ship quickly and get to decision-making faster. We’re just not hindered by the same constraints that we once had, so more teams have that available to them.

That felt like a word sandwich and I don’t, like as, as I say this it is this change.

It’s like change management isn’t something that can be done for you. Like we’re all in the process of going through change management collectively, which means as a leader, we need to be thinking about at any given time what is truth, what do we know isn’t truth, and what are the questions we’re managing, and how do we feel comfortable either managing that risk or at least coming up with a bet that allows other people to move forward.

So a lot more of that like shift left mentality is hitting us as well.

What does discovery look like now?

Jesse: You touched earlier on the notion of continuous discovery and Teresa Torres’ work around that subject. And in the AI transformation consulting work that I’ve been doing this has been a topic that comes up so often because what I’ve been discussing with leaders is the need to develop internal continuous discovery capabilities because you’ve got teams that are running off on explorations in every direction, and you’re getting different results in different places.

And there’s an element in this of taking that, as you described it, taking that lens that we have historically turned on users and turning it on ourselves to some extent and developing new internal capabilities to do that.

And I wonder how that process has been for you of building out discovery as not just a philosophy or a good idea, but an actual practice that’s going to inform the evolution of the team.

And what other kinds of practices you’ve had to build out or institute to facilitate this transformation?

Emily: So I mentioned building specs for agents, but it’s not just for agents, it’s for these like probabilistic experiences. So that’s been, I think, one of the most powerful anchors that we’ve put in place, which is, we don’t have a PRD representing a truth that we’re shipping downstream. We have almost a kind of declaration of what we think people will experience from the system or should experience, and that is the thing that’s evolving as we get new information.

So, it’s almost like a continuous truth. Maybe that’s the continuous discovery part, but it’s being contributed to by everybody, and it’s objective. It’s not someone’s role to produce. And it also determines then, as I mentioned, like how we evaluate the parts that we’re not directly touching, which is the AI aspects of it.

So that’s been a really helpful tool, and not just a tool for ourselves, but also a tool for evaluating the platform. We have more data available to us. We don’t need to wait for somebody to give us permission to talk to somebody else.

Like, for example, Fullstory has recently released an MCP. We can be working on something inside of our worlds, whatever harness you’re using to connect with some agent, and you can actually say, like, “Hey, if I were to build this, how many people who have touched this part of the product in the last month would be likely to see it? What are they doing right now?”

So we can almost ask the questions proactively, preemptively, which we always could do, but it was harder to get the data. And so even though it was available to us, it wasn’t always something that made sense or something that was feasible in the moment. So that’s another thing of just starting to realize the things that were blockers previously might not be a blocker anymore has also been really helpful.

And so one of the things we do when we’re working on a new question or so on is, like, what data do we already have? Versus that idea of like shipping something downstream to get the information.

Well, now, a lot of times we have the ability to ask those questions, and that means figuring out what questions to ask becomes the really important thing because the data is more available to us.

So that’s more of just yeah, building those parameters and then actually trying to find answers in the data that exists in ways we might not have mapped those patterns previously. That’s been another tool that we have found.

And then finally, yeah, the ability to just create many different things in parallel.

We have a number of large customers, we’re talking about a new part of our interview tooling that we’re talking to them about. We have different versions of our prototype that we’re showing. Now here, the delicacy becomes, well, if you show person A something, and you show person B something different, do you end up building both A and B, or who makes that decision about what this final thing should look like?

And that’s another place where having clear intent of who we’re building for and why, some founder-driven or determined decision-making able, whether that’s me or somebody above me, and then also maybe there’s some generative aspect, back to the start of our conversation.

Like, maybe there are places where we start to say somebody might be able to have experience A or experience B, and maybe that’s okay. And that’s something, we’re starting to grapple with as well.

I think what discovery has to start with though, as it always has, is that intent. Like, we have to ask the questions that we plan to answer. We have to have some idea at any given time of what do we think truth is.

To the extent we are spending time talking, it’s more in that realm. It’s having those conversations and looking at the system together and saying, “What do we know? What don’t we know?” And using that to make decisions as opposed to debating, “I like this, I don’t like this, you’re wrong, this is hard to build,” and so on, which is what was blocking a lot of teams previously.

Peter: You stated earlier how your role has shifted, if I understood right, away from as much maybe active design direction and more, you talked about operations and kind of enablement of the team to help them do their best work.

And I’m wondering if you were to work with some form of partner or mentor, what are the questions, like, what are your highest order questions right now? What are the challenges that you’re trying to solve that you would welcome some insight into going forward as you’ve shifted into this new vein?

Emily: That’s a long list. I have more questions than answers even at this point. Oh, gosh. So my team is still rather small. I mean, we’re somewhere around 12, 12 folks that I directly oversee, and then obviously providing leadership to a larger organization alongside my peers. But I imagine that the world I’m in and describing is very different than somebody who’s leading a team of 300 designers.

So I am not sure I feel confident that the really scrappy way we’re working scales effectively without adding additional layers of management, and that’s a question I have is, like, what does management turn into as we start to have these more empowered teams, as work is going faster, and as we’re increasingly working in these kind of like fuzzy boundaries?

What does the form of a design manager need to evolve into in a way that is valued and valuable? I find a lot of conviction that it is valuable, but I’m not quite sure I know at scale what that looks like. That’s a question I’m curious about and talking to people I admire and trust.

And then similarly, and you alluded to this earlier, within a smaller group it’s a lot easier to create new career paths, new leveling that can be digestible and that people trust.

But when you are working with a larger group of, for example, new talent and also senior talent, how is that evolving and how should I be thinking about coaching, direction decision-making, and so on… Rewarding? I mean, that’s another one… of trying to solve.

And of course, the labor market is a lot more fluid than it has been in the past for really top players. And so, what are those… Yeah, maybe there’s another one of, like, what signals are other people seeing as early signs of growth, of acceleration at the individual level or at the team level that might be more visible at scale or might be more visible in different scenarios.

That’s a third. Of just, I can generally sense that from the people I work with, from the closeness that I have to them or to their managers. But I’m not sure we have determined what younger talent needs to look like. And even then, you have, I don’t even mean younger in age.

Newer talent might be people coming out of their own explorations, like, autodidactical folks. It might be this kind of new form of education and boot camps that’s starting to emerge. And then of course, traditional education.

Like, I’m seeing a lot of signs that early talent is actually surprisingly competent right now because our tools can do a lot of the stuff that we learned as, like, the more rigorous parts.

“Oh, I don’t know how this tool works.” Doesn’t matter. I can now have Claude just do it. So how do we find signals of strength in those fundamentals, and how do we close that gap? These are just some of the questions that float around my head and give me anxiety on a week-over-week basis. The big one is, leveling, individual growth.

It shouldn’t feel like every man for himself or woman for herself. I hope that we continue to feel like we can build teams intentionally and support people and remain human-centered throughout this process and not just, hey, who can talk to the robots better are the winners. I don’t think that serves us, our companies, our users, our teams, and so on in the long run.

But it really is the Wild West right now.

Jesse: Emily Campbell, thank you so much for being with us

Emily: Thank you for having me. This was so great.

Peter: This was fantastic. Thank you.

Jesse: If people wanna catch up with you on the internet and find out what’s going on in your brain, how can they do that?

Emily: Yeah, absolutely. So I’m on X @elou, E-L-O-U, and increasingly trying to be active there. Now that I have my plugin that hides all the junk, I’m on LinkedIn as well, and sometimes active there. And emilycampbell.co is my personal site, and you can always find me there as well.

Jesse: Thanks, Emily.

Emily: All right. Thanks so much. Cheers

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Show Notes

Peter and Jesse are joined by organization designer Clay Parker Jones, author of Hidden Patterns: A Playbook for More Human Workplaces, who has led organization design work at Airbnb, Undercurrent, R/GA, and August. The conversation covers why roles persist, the importance of indexing on trust over role clarity, the difference between psychological and structural safety, organizational rule of law, and why demonstrating better teams beats trying to convince skeptics.
Clay Parker Jones: https://cpj.fyi, Hidden Patterns book

Jesse James Garrett: https://jessejamesgarrett.com/

Peter Merholz: https://petermerholz.com/

Transcript

Jesse: I’m Jesse James Garrett.

Peter: And I’m Peter Merholz.

Jesse: And we’re

Peter: finding our way. Navigating the opportunities- And challenges- Of design and design leadership.

Jesse: On today’s show we’re joined by organization designer Clay Parker Jones And author of the book Hidden Patterns: A Playbook for More Human Workplaces. We’ll get into the untapped value that is unlocked through organization design, why teams might be better off indexing on trust rather than clarity, and strategies for overcoming organizational resistance to change.

Peter: Clay, thank you for joining us.

Clay: Happy to be here.

Peter: You’re probably a little less standard of a guest- … on Finding Our Way, in that you’re not a UX design type. So for our audience who might not be familiar with you, how do you introduce yourself?

Clay: Well, firstly, when I was young, I did want to become a UX designer.

And I very much looked up to the both of you and the work that Adaptive Path did. So not being a good enough designer, I think, led me to be an organization designer.

Peter: Which is something I, I now share myself.

Clay: Hey, life brings us many changes. Okay. So how do I introduce myself? I’m an organization designer.

I am now an author. I’m now also a dad. I live here in Brooklyn, New York, with my wife and son and cat, Ian. I’m a former bicycle mechanic.

Defining Organization Designer

Peter: Organization designer is one of those roles that I think people have heard but don’t really know what they do. Yes. What would you say an organization designer does?

Clay: Like, the formal answer or the way that if I was trying to explain it to someone who’s going to be paying me would be something around the structuring of units to help people achieve a goal, or the reforming of an organization in its various constituent parts in order to deliver some improved outcome for stakeholders.

That’s, like, a real nerdy example or a real nerdy way to talk about it. I think the way that I think about it personally is waking up with a mission of the people that you’re working with being able to get more and better work done today than they did yesterday, and continuing to do that over and over again.

The idea of design is useful because it introduces, like, a category boundary. But I, I think so much of this work is actually just in… It’s in the margins. It’s in the meeting that goes well or goes poorly. It’s in the role that is well-described or poorly described. It’s in the team that knows that the other teams around them are gonna keep doing the things that they said that they were going to do and not always, or maybe increasingly so, not infringe on their territory or step on their toes.

It’s in people feeling really excited about their work. And whatever mechanisms we might use in order to get there, it might be a PowerPoint deck containing a org chart. It might be a piece of software. It might be a prompt that somebody gets or a prompt that somebody gives to a intelligence. It’s all kinds of things.

But it gets pretty narrowed into this idea of, oh, we’re making a deck for a senior leader that follows, like, this diagnose, design, deliver kind of pattern. And I think that’s increasingly unuseful or even unhelpful in the way that we define the field.

Jesse: What are some of the other tools that you’d like to see come into play in how organization design is done?

Clay: I think it’s more about the distribution of the knobs or the levers or, like, the palettes that we might paint with to more and more people. And I don’t mean that through terms or ideas like self-management necessarily. That may be something that happens, but mostly just that more teams are able to have more of an impact on the way that they are themselves designed, the way that they have agreed with each other that they’re going to work, and that more people are doing it more frequently at a higher and higher level over time.

So it’s less about, like, the tooling exactly, and more about, like, more people adopting whatever tooling it might be.

Peter: Mm-hmm. Correct me if I’m wrong, but org design, at least the way you practice it, is more defined by its outcomes of an improved org. Whereas while that had been the goal of UX design when Jesse and I were doing this 20-some years ago, UX design, over the last decade-plus, has been defined by its artifacts and its process and what it creates, less by its impact.

And I’m wondering, well, one, an opportunity, I think, right now for UX design is to be less defined by its tools and process and artifacts, and more by its impact. And I guess with org design, I’m wondering, have you seen it defined by its stuff, or has it been able to stay a bit truer to an orientation on impact?

Clay: I think that there’s, like, roughly two portions of the field.

There’s this kind of like structuralist portion that gets paid for doing organization design, and that is seen by stakeholders as org designers. And those people are typically at one of the big consultancies, less so like an August, less so like The Ready, and more so like McKinsey or Kates Kesler, now part of Accenture.

And they’re defined by outcomes, but they’re also very much defined by the actual artifact. There is a perceptible feel to one of their documents, that where even if it has the company logo at the bottom, you know who wrote this thing. And the outcomes are far, so far in the distance. They’re gonna come to us five, 10 years from now when we finally bring together all these operating units that have been operating on their own, with their own intention and with their own structure, and now we’re bringing them together and we’re gonna achieve some efficiencies. That’s gonna happen way far in the distance, and the outcome is not really even part of the conversation. It’s the output. It’s the thing that we all agree is, like, gonna be the effective transfer of power.

And then there’s, like, this, I refer to as, like, a mutualist side of the practice, which is more about helping people define their work together and giving them the tools and the technologies and the language to actually be able to do that.

And that is almost entirely outcome driven, and it gets paid a lot more reasonably than do, like, the structuralist org designers, right?

And I think there’s a little bit of the mission kind of getting in the way there to a certain extent, if all we’re trying to do is get paid.

But, at very least, there’s like these two sides. One is called org design, one is usually called, like, culture work or ways of working work, but it is org design. It’s changing the way that the organization is structured, intentionally, for good, usually, or that’s the intent or the hope.

And then the other side is we’re trying to, we’re trying to hack it, and sometimes we get called in, sometimes we get brought in after the big consultancies get called in, and that is entirely always going to be sold.

We always did at August, sell it in terms of the things that are, that our clients are going to be able to observe in the organization, not something that they’re gonna be able to hold onto, which maybe is a bad consulting strategy.

Peter: Mm-hmm. Mm-hmm.

Jesse: Some would say.

Clay: Sure.

The End of Role Clarity

Peter: The impetus to have you join us on our podcast was something that you published in February called The End of Role Clarity, which I ended up responding to in a newsletter article of my own.

But before we get into a dialogue, I think it would be good, for those who haven’t had a chance to read it, if you could just share the thesis. It’s a long enough article, so I’m sure you’re gonna have to elide some details, but what is your high order thesis when you were writing The End of Role Clarity?

Clay: Yeah. In large organizations, so much of the conversation ends up being about, “Oh, well, we don’t have role clarity.” And it’s something people say when they are trying not exactly to avoid taking action, but it often allows people to do that. We’re not going to take advantage of this opportunity because we don’t have role clarity, because I’m not sure if that person over there is supposed to be doing that thing that they’re doing that I think I should be doing, and it’s getting in the way of us being able to make a good decision.

And I wanted to offer with that piece this alternative view, which I think is more and more plausible or possible with, or maybe even required or will be forced upon us by the introduction of new technologies that allow more people to do things that they didn’t know how to do before. Whether or not they know if the output is good or not is sort of beside the point, but it is going to allow more people to be designers, be musicians. It’s going to allow people to do more things.

So that means that individual roles as we have defined them today, like an engineer or a product manager or a designer, become less useful or interesting distinctions between roles because teams are able to just say, “All right, yeah, I can kind of be a software engineer if I’m a designer with an interest in artificial intelligence and figuring out, like wading through the process of like getting Terminal working for me and being able to work in the command line. Oh, I can actually be useful, and I can make a prototype with the design sense that I have.”

Or if I’m a product manager, I can actually do some of the design work using some tokens that I’m pulling from a library that’s been well architected by actual designers. And that means that the more useful thing to be focused on is less, like, are they perfectly defined, and do they have no overlap between the two individual roles, or do they know how to work very well as a team because they have a clear team purpose, they have a clear sense of our focus areas, they have a clear understanding of how we’re going to be measured. They know where we’re going to work, they know and they’ve made an agreement together about how they intend to work.

That’s much more useful than this idea of role clarity, which feels antiquated and stuck in this idea of the org chart being defined by the employment agreement, which I think, again, is going to be less and less interesting over time for the people who, I don’t want to say the people with the most talent exactly, but the people who are like really leaning into trying new tools and building with AI.

Like they’re gonna want to be doing more, and that’ll change the way that we think about the team, and in ways that are in the near term probably not always so good and feel a little bit like, “Ooh, am I losing some of my identity in this?”

So that was the piece. I think I’ve stepped away from the computer for a while to raise my now 12-week-old son. So hopefully that is mostly what I tried to say. And I know, Peter, you disagreed with me to a certain extent, and you emailed me right after I posted it. “We need to talk about this.” Which I knew then that I had done something good for the world in introducing something that people may find disagreeable, if not a little bit useful.

Peter: The, the heart of your thesis is something that I think I tried to reflect on when I wrote Org Design for Design Orgs and in my own design leadership practice. And Jesse and I have talked about recently, even when we were back at Adaptive Path, where we tried to have just one role: You’re an experience designer.

And in that role, there could be a range of skills, and different people with the same title might have different skills, and that’s okay. Because we wanted to kind of support what you’re talking about. It’s less about you being tightly defined in this way and someone else being tightly defined in that way, and more this group of people is joining together to solve some problem.

As I’ve gone in-house, and then even after leaving, going in-house and becoming my own flavor of org designer, I found myself defining roles.

But, like, when I create career architectures, I always start with skills and not roles, where when you see, like, how most people create career architectures, they start with roles and not skills. But I start with skills.

I’m like, that’s the most important atom of effort, and then we can build a career architecture around that.

And so I largely agree with you. I also thought it was funny that something I’m seeing is that AI, and I put AI in quotes, is enabling many of us to dust off things that we were saying 10 to 20 years ago, and be like, “Maybe now. Is there… if we… Will you listen now? Because it was true before, but it’s actually even truer now.”

And I suspect that’s something of what you’ve got going on with what you’re writing.

Why Roles Persist

Peter: But the part that I wanted… that maybe I disagree is strong, but where I’m like, the hard part of it is, I think, there’s these three qualities of roles that are really hard to get over.

Roles are human shaped, and I think as an anthropologist, I think we process the world, right, through heuristics, and one of the heuristics is things that are human shaped make sense to us. So a role makes sense to us in a way that a pile of skills doesn’t, and so we start there. It’s a human shaped thing.

Thing two is, roles are, to use Seeing Like A State language, they’re legible by the bureaucracy, right? The bureaucracy loves roles. It knows how to post a job with the role title. It knows how to put you in an org chart. It knows what to pay you, right? There’s just something about roles that get taken up easily by these systems, that again, a pile of skills or, like, five people on a team doing a thing, whatever that is, what do we call them?How do we pay them? What do we… how do we reward them? How do they grow in that career or whatever?

And then thing three is something you touched on, which is identity. This is something Jesse and I have been talking about, well, for 25 years, and pretty much since the start of the podcast, is designers…

Like our industry, our colleagues, many of them went to design school. They’ve had design in their title. They see themselves as designers first and whatever else second, employees second, an employee at a particular company second or whatever. There’s something around design that has this connection or affiliation with identity that’s so strong.

So my question to you, and this is a big one, but I’m curious your thoughts, like, how do we overcome these three kind of, obstacles isn’t quite right, but just, like, realities of role-ishness in order to achieve the nirvana of a post-role team-oriented future?

Clay: Yeah. That’s, it’s a very good question, and I’m happy that you… It’s okay to disagree with a thing too. I appreciate that it sparked this, ’cause it is worth debating and it’s worth digging into. I think in the three things that you identified, two of them are really good and worth maintaining as we redesign a thing.

Or if we move from where we are today to where maybe we hope to get, or where I hope to get with more of a team-oriented networked future for work, I think that’ll be better for more people more of the time.

So human-shaped heuristic for understanding the work that’s happening in a team, that’s great. I wouldn’t change that.

The identity thing I think can be, can be good for some people and limiting for others. Being constrained by the way that an organization sees you coming in, or by the way that the field has defined what you wanna do. In the case of organization design, we get defined by what big consulting says organization design is going to look like. And we have to, like, figure out our way around that.

So it’s good and bad, but it is part of who we are. Like, I wouldn’t wanna build a future that, like, sullies the things that make us human, right? We don’t want that.

Legibility to bureaucracy is the thing that I think is most worth figuring out in this. What do we make legible? How do you make an organization understandable to humans, understandable to machines, understandable to other organizations? You can put machines and other organizations maybe in, like, a bucket together because they’re only able to, like, piece together what they know about the organization by, like, sending a request.

But making, like, the organization and the work visible to each other, being able to see a system so that we can change a system, I think that’s really valuable, and it’s a slippery slope to creating something that feels like a surveillance state within an organization.

Jesse: Right.

Clay: So we have all of this exhaust coming out of the work that we’re doing.

Like, we know that the three of us were on this call together today. we could instrument that. It would be actually relatively easy for us to understand that we were on this call together, that we had these emails that preceded it, that I had read some of the work that you all had done, and maybe if we had all seeing memory of what we had been doing, it might be able to help us, like, make this better and make this more interesting.

But it would also mean that the organization would know all of that about us, and I think that’s a challenging bit of this. It’s like we have this ability, to your point, Peter, around, like, these ideas that we had a while ago that we knew were good ideas then but now have become relevant because the computer can actually do the things that would be necessary for us to actually bring that thing to life.

Okay, fantastic, and it has this kind of scary side effect. I’m not sure what to do about that, but I do feel like it’s something that we have to contend with in helping organizations find their way toward better structures that put teams at the center instead of saying, “Manager is a person,” versus, “Management is a valuable thing that we do, and many people need to be good at it.”

Even at the very top of the organization, they are managers. Almost to the bottom of the organization, there are managers. And everybody needs to be good at that. Leaders need to be everywhere. Subject matter experts need to be everywhere. So it’s, I think, just a better matching of reality to what we’re able to write down.

Handling Scale

Jesse: Peter touched on our experiences wrestling with some of this stuff at Adaptive Path. And one of the things about that experience was, honestly, it pretty much worked. We had some challenges. We had some challenges with people who, going back to the identity thing, their identity wasn’t just designer, it was like, “Well, I’m not an experience designer, I’m an interaction designer,” and, “I’m not an interaction designer, I’m a service designer,” and on and on and on, where we had these sort of increasingly fragmented identities.

But in terms of how the work got done, it mostly worked. The people who were routing the work to the team knew the skills of the team and were able to manage that effectively and were able to assemble teams that could get a job done. That was at a scale when we were 30 people, 40 people maybe, and everybody knew everybody else. Everybody had worked with everybody else. There was a lot of the, kind of the intangible personal knowledge that was a part of our processes and how we made those decisions and how we made those choices.

And some of the things that I hear you talking about in terms of what do we do about the potential for these surveillance systems to shape this work, it seems to me that some of that is an artifact of scale, that you have to be able to architect these systems at a scale at which you’re evaluating the performance and evaluating the contribution of people who may be many layers removed from the people who are actually making kind of the big decisions.

And I wonder about how scaling can work when everybody is a pile of skills and every sort of interdepartmental or interpersonal contract is bespoke, so to speak.

Clay: Yeah. Great question. The prevailing answer in the scholarship and in the examples out there in the world is don’t. Just keep the elements small and knit them together with their own contracting and have something that feels more fractal in the way that it operates and the things that humans touch about it.

Like I’m with my seven people that I’m on a team with. I know them. I know them really well. I know that Peter’s really good at this, and Jesse’s really good at that.

And then there’s these other teams that I’m kind of like in a neighborhood with, and I know that they do that, and we do this, and this other team does that. And sometimes we do things together, and sometimes we do things apart, and they get value from us, and we are continually like negotiating that.

And then maybe outside of that group of 150, then there’s like, okay, that might be an organization. There’s maybe a bunch of teams within that or a few neighborhoods within that. And that way you don’t have to scale anything really, scale the human experience, but you’re able to build an organization that works well together because it can be knit together with something relatively simple, like a contract between a consulting client and Adaptive Path, or same thing with Undercurrent or August.

It’s through the contract, it’s through making something smaller, and it’s probably through building something that feels like a, like using consent in a different way than I normally would in org design. Like a consent-driven approach to like what’s disclosed by the individuals, what is gathered by the organization, and what remains like true to the person. What can they pull out of the organization? What can they determine they grant to the organization in terms of the information that they’re allowed to know about the way that we work, the kinds of things that we do?

And that networked approach that would shrink the interface, I think that might be the way out. I’m not sure. Yeah. I don’t think you can just try to import this stuff onto the top of a 50,000-person traditional command-and-control bureaucracy and have it work because people will want, “I need this thing defined. I’m here for a tour of duty.” The handshake is not between me and the company that I necessarily look up to and believe in the way that it would’ve been for Adaptive Path that makes things a little bit easier when people are coming in and more open to adopting a role that has like less clear definition.

Same thing with August, same thing with Undercurrent, et cetera. I’m not sure that it’s gonna work if we like have the same priors and try to import a system on top of it.

Jesse: Yeah. It’s interesting to think about the way in which if you kind of take down the level of clarity in the roles themselves, it has the potential to make the entire organization more nimble because people aren’t locked into a particular set of expectations.

I’ve been working with teams on their AI transformation initiatives for a little while now, and one of the things I’ve been saying to leaders is that this is a process of embracing the unknown, and in a team environment, it’s very difficult to do that if you don’t have a high level of competency across the team and a high level of trust across the team.

And the pressure on leaders now is to figure out how to create these high-competency, high-trust environments in which teams can rely on each other in the face of no contract at all, potentially, right?

Clay: Yeah. Completely agree. Completely agree. And I, I’ve ranted about this in a few different other posts and places, but it’s relevant to bring in here, too.

Trust and The Importance of Good “Teaming”

Clay: The trust thing, like leaders creating an organization that is high trust or that has a high degree of trust, means that there is trustworthiness between the organization and the individual. We have to say, “We trust you to try some things that are likely to be harmful to the organization, but we are interested in that because we are learning about how this new technology works. We have no idea. Anybody that does is wrong or lying or incentivized.”

And we don’t know where, like, where the motor in the example with the steam engines and electric motors, we don’t know where the motors are gonna go yet. We know that they’re gonna go in different places than we put the steam engines, but we don’t know where they’re gonna go.

And we have to dig into that by trusting our people and believing that they are more competent than we have believed they are in the past. I find all the time when I work with teams, that you give me 10 relatively junior people that the organization doesn’t think are all that great, and let’s put them in a team and do the things that we know to do to make them a team, to help them become a team, and they will achieve amazing things.

They’ll be seen as rock stars within the organization, if even if six months ago they were kind of like the cast-asides. Because people are capable. People are really good.

Peter: Just thinking of The Bad News Bears here.

Clay: Yes. I mean, it’s a sticky story. It happens over and over again because it’s real.

And I’ve seen it over and over again that just give me anybody. Doesn’t need to be the most talented people or the high potential people that the organization has determined are the ones who will rise up. Let’s see what happens. If we make them a team, they’re gonna do amazing things. It always happens.

It never doesn’t. It’s crazy. It’s not crazy. It’s super obvious.

Peter: So I have your book in front of me, Hidden Patterns, available wherever books are sold. And…

Clay: Thank you …

Peter: …you have as one of your foundational elements, something that I neglected in Org Design, but has since become core to my teaming practice, which is psychological safety.

And as you’re saying what you’re saying, right, there was the research that came out of Google a decade ago, maybe more now, Project Aristotle, where Google, a company built on high performers, right? Everyone is a rock star. Everyone has a PhD. Everyone is the best at what they do. And so there was assumption that the most effective teams would be those that had the best people on them as assessed by the system, and it turned out that was not the case. In fact, those were some of the worst teams.

Psychological safety

Peter: But the best teams were those that had high degrees of psychological safety. So I’d love for you to actually talk a little bit about your experience with psychological safety, creating psychological safety, and I think it touches on matters of trust.

Our audience is a bunch of leaders who are probably trying to make a psychologically safe space in their organizations. We hope so. And one of the challenges I hear all the time when I teach my masterclass, we talk about psychological safety, and they’re like, “Yeah, so I can try to do that for my team, but we’re operating in a much broader context that just has none, totally lacks psychological safety. So what do I do then?”

So I’m curious kinda how you encourage, foment, enable psychological safety for those that you’re supporting.

Clay: Yeah. It’s really hard, and it’s poorly understood, and the tools that leaders are often given, I think, are relatively dissatisfying. I went to a workshop for HR leaders six months ago, and we were there with some of the psychological safety and design thinking luminaries.

They were teaching…

Peter: Did you ever think that you were just an HR leader? Did, did, in your wildest dreams 20 years ago, you’re like- … “My aspiration is to be an HR leader.”

Clay: No, and that is something that I deal with every day.

Peter: Sorry for the interruption. I couldn’t let that phrase go, though.

Clay: No. Speaking to the identity point it’s not something that I had envisioned for myself, but it’s been very interesting.

And one of the things that we were taught as a practice, which I love, it’s an amazing practice. I’d never done it before exactly. It’s a team kickoff thing where you get groups of three together, and the instruction for the group of three is for one minute, one person must say to the other people things that they love.

“I love Post-Its. I love this little fan that cools off my son when he’s in his carrier. I love going on podcasts.” Like that. And it’s really hard for people, very frequently, to get to the end of a minute and continue to have things that they love. But there’s also a lot of, like, commonalities that the facilitator will inevitably pull out.

Did people mention their spouse? Did people mention their child? Did people mention their career? Da, da, da. Did you have any similarities? And this is one of the things that we’re supposed to do to increase psychological safety, and it feels so rudimentary. It’s good. It’s good. I don’t think it’s bad. It just is one of those things where you’re like, “Okay. If we’re gonna create psychological safety, one of the things that I need to do as a leader is ask better questions.”

Okay. Is that the whole book? Is that everything? Well, kind of, and absolutely not, right? There’s lots of other things that we need to be able to do. We have to have, yes, good team kickoffs. We need to ask good questions. We need to model, as leaders, vulnerability.

Structural Safety

Clay: We also need to address the structural parts. So if we’re able to, if we’re able to, as organization designers, get the keys to the top, the final boss, and actually do the deep structural work here. We need to address the lack of structural safety within an organization because you’ll have leaders within an organization that want to build psychological safety on their team, but they are not able to because that team could be deleted at the drop of a hat.

Peter: So that’s what you mean by structural safety as a distinction from psychological safety.

Clay: And we need both. We need both. And one of the things that we did and didn’t fully express in the way that I wanted to at August was set up a business where people have a very clear understanding of what will get in their way or what will cause them to be exited from the organization.

It’s by breaking these contractual boundaries that we have set up, and we all agree to them when we get started. They’re clearly written. We amend them only when we have the rights or the incredible data to change that constitution effectively. And that kind of thing, to me, is one of the reasons why August is still around 10 plus years on, right?

It’s an organization that has some durability to it because I think it’s spurred on even after founders like myself leave, because people feel structurally safe. So knowing what’s gonna get you kicked off the bus and actually knowing that that’s not like, “Oh, you did your expenses wrong,” but it’s like, “Oh, you weren’t trustworthy,” or, “You didn’t trust your teammates enough.”

Not that you spent too much money on this thing, or you made a bad decision, or the campaign didn’t work, or a client left, but that we couldn’t really believe in you as a member of this team, and people often found their way to leave on their own, right? So that structural safety that’s encoded into the organization, that is something that we need to establish.

Most organizations have nothing of the kind, right? You have all these things that you sign when you join that are, like, rudimentary guidelines about what’s gonna get you kicked out of any organization. Don’t do anything unethical. Those are important, but we forget about those. We don’t have anything that’s about the things that we actually care about.

So getting those things on paper, saying that we believe in them, actually believing them, and using them as the boundaries for membership, and then doing all the things that we need to do within a team, right? Have good clarity for what the thing is that we’re trying to do, what the rules of the road are within our team, how we meet, the way that we operate, asking good questions as a leader, kicking off meetings the way that we should.

There’s all these gigantic things and these really small things, too. So it’s hard, but it is the challenge, and great organizations and leaders who lead organizations that they believe in, I think, kind of do some of this naturally. It’s like, oh, we should have a skills framework for the way that we help people up level, but it’s not there to prevent you from up leveling.

We want you to use it. We want you to go, like, level up, become better. Those are the things that we know are powerful, and we just kind of neglect them. Sorry, that was a bummer.

Balancing Solidity and Rigidity

Jesse: Yeah. Well, I’m maybe about to make it even more of one. When you talk about structural safety, it’s interesting because when I think about organizational resistance to change, it often is because of kind of the dark side of structural safety, which is that you have functions or business units or departments or other elements of the business that are sacrosanct, that can’t be altered in any way, that have been sort of calcified.

And I guess I wonder about how you manage that tension between wanting to create the correct amount of safety without encouraging this kind of rigidity structurally that prevents an organization from evolving and adapting in the ways it sounds like you were able to build in at August.

Clay: Well, it doesn’t work all that often, sadly.

You know?

Jesse: Hmm.

Clay: This is one of those things where I think those of us who turn our eye toward organization design tend to be really disappointed and feel like, “Oh my God, I didn’t actually want to do this.” This is not the way that I want to spend my time thinking about what to do with that calcified organization over there, and the people who are resisting change, and maybe rightfully so.

They might have some wisdom that tells us that we should keep it the way that it is, and the leaders around them that perpetuate that. Like, that’s… It’s ugly. Organization design is often dealing with the basest human desires and some of the things that we don’t like to express about the way that work works or doesn’t work for people.

And when it works, though, it’s by creating a movement toward positivity. I had this rule for… I still have this rule. I maintain this. Don’t convince people. Don’t try. Just offer the thing, offer the better way of doing something, offer the better design, offer the better practice, and if they don’t wanna do it, they probably have a good reason, and trying to trick them into doing it is not worth your time.

Instead, what’s better, a better plan, is to go find teams that really want to get something done. Lavish your time and attention and tooling on them, and then show the organization what they’re able to do. “Wow, this team over here was able to re-architect our backend. It would normally take a year. It took us 11 weeks.” “Fantastic. How’d they do that?” “Oh, well, they used AI in a different way.” “Oh, it was an actual team.” “Oh, they had a designer on the team.” “Oh, the PM was not just a PM. They actually had some, like, engineering chops.” “Wow, fantastic. Amazing.” And they added some more clarity to their team, and they’re able to agree how they’re going to operate together.

And then building up those stories, it becomes more and more of a communications thing, and I think that’s where we’re at with this movement toward better ways of organizing and better ways of working, is that we have to have more and more of those, and do less of the thing that I see in corners of this work, which is purity tests around the way that we’re working or the way that we’re thinking about it or the framework that we’re using.

Mm-hmm. And instead, just keep pushing for teams that are working better and showing that they’re working better so that we can get more leaders on the side for this. ‘Cause the thing that I see most frequently is that when you introduce some of these ideas to mid-level, like it’s usually not the top of the organization, it’s usually not the bottom of the organization.

The middle of the organization, someone in that room will look at you a particular way when you’re talking about, “Okay, we’re gonna create some clarity on this team. Management isn’t just gonna be a role. It’s going to be a practice that’s going to be distributed across the team, and you, all you people who have great skills, you’re gonna get to do those skills again more than you were in the past.”

One person at least will be like, “Uh, this is… I don’t like this. You’re changing the handshake that I made with the organization. I like what I do. I like doing it the way that I do it. I do not want to give up the management authority that I have earned over many… many years, and I don’t want to do SME work anymore. I don’t know how to do that. I don’t like doing it. These people do, and I’m a good manager of them, or I think I’m a good manager of them.”

And they’re right in that. They’re right in that. So letting them, like, have a graceful off-ramp from that or just not trying to trick everybody into doing the thing that you want to do because it sounds nice or it gets more done, that’s one of the hardest challenges in this work.

Creating a Pattern Language

Jesse: Earlier, Peter touched on your book, Hidden Patterns, and this is a little bit of an unusual kind of a book. I wonder if you can tell us a bit about what inspired it and, yeah, some of the ideas behind it.

Clay: Sure. So it started in 2013 as an obsession with trying to break down problems of business strategy or corporate strategy or digital strategy or whatever it might be, into recomposable parts. So trying to understand the problem more accurately and then trying to resolve portions of the problem by finding solutions that were better fit to the form around it or the shape that we were trying to create.

That obviously touched on the work of, or was inspired by the work of Christopher Alexander, and I know that’s probably a big thing in your world as well.

And it was just rapturous for us to see problems in this new way. And we kept playing with that. It kind of became the root of the work that we did at August. When we got started with August and we started with one of our first clients, we wrote down all of the things that were working with our previous client work at Undercurrent, and we tried to make them as small as we possibly could so they could be recomposed into something that we could go deliver.

So we then rocked up to our big client and we were like, “Here’s our 50 things. We would like to go try these 50 things with some of your teams.” And they said, “Absolutely, fantastic.” It was our first client. We were so excited. And we got to, like, nine or so things that really worked. And I think August is still implementing roughly the same ideas.

So it’s this thing that has gone for me through multiple companies, has been a thing for me to try to take ways of working and break them down into not best practices, but patterns that preserve the context and tell you why you should be using those things and when they break and why you should modify them and, like, how they could fit together.

I had this idea that I’d been sitting on for a long time, and I feverishly wrote it and … ’cause I had all this material for it that was kind of like…

Jesse: Mm. Mm-hmm …

Clay: …poorly composed and things I’d half written or completely written and written seven different times. And I was able to, like, bring that into one thing and finally make the thing that I wanted to make that I would have wanted many years ago when I was getting started.

So it’s got, I don’t know, like, a intro that you can read in 30 minutes, and then 75 individual patterns that you can make your own, that you can remix, and that also are really interesting to play with with LLMs. You can use the stuff in the book, and I was intentional about putting it online for all people who have bought it and just tell me that they bought it, I give them access to the full text online.

Copy and paste it into your system of choice and use it to diagnose your problems. It’s cool to have something that feels like software instead of just a book of a framework that tells you the ways that you’re doing it wrong. So yeah, it was just kind of like a labor of love. It was, like, more of an art project than a business book, and when I was writing it, I had nothing to sell exactly.

So at the end of the book, it’s like, “Go work with my friends,” which I was very happy to do. So yeah, it’s a weird book. I love it, and it breaks things down from the biggest possible things like true purpose, structural and psychological safety, this weird thing that we encounter more and more every day, unfortunately, the idea of the importance of rule of law within the organization, and th- things all the way down to the physical space.

Thinking about the way that Valve puts all their desks on casters to let people move around to re-team with each other, and they couple that with the ability to actually dissolve the things that you’re working on and find the things that are most appropriate. So whiteboards everywhere and rule of law all in the same place, and everything in between.

Peter: Whiteboards everywhere. Very Christopher Alexander.

Clay: Yeah. Whiteboards every- ri- actually, it’s not whiteboards everywhere. It’s whiteboards at intersections. That’s the pattern, and I believe in that, and you notice the whiteboards that get used are in spots where people gather, and you end up seeing interesting ideas on them, and that’s the cool shit.

The Rule of Law

Peter: I’m curious of… You mentioned the 75 patterns, and you’ve identified a few. You highlighted rule of law, and that’s one, as I was looking at it, I’m– I’ve got my own project that I’m noodling on that I’ve realized is kind of adjacent to what you’re doing. I’m … I’m looking at a challenge that many who are listening to this will face is, and a question that often comes up is around, how do I make the company I’m part of more human-centered, right?

Jesse: Hmm.

Peter: Mm-hmm. And one of my missions in the work I do is enabling humanism within organizations. And so similarly-ish, I’ve been noting, like, what are maybe less patterns, kind of like criteria, components, elements, kind of these core operating aspects that either lean in towards humanism or lean away from it.

And been jotting those down, and then I’m between contracts, so I’ve been hanging out with Claude, throwing these ideas back and forth. But as I was getting ready for our conversation, I opened the book, I was flipping through it, and you have rule of law in there, which isn’t something that I had generated.

Like, the purpose stuff I’ve thought about, the psychological safety… some of the other things you’ve mentioned. But I’m curious, talk a little bit about rule of law, why it’s foundational. And you mentioned it feels hotter button right now to talk about it. Yeah. What is that?

Clay: Take a hypothetical organization Where there are different rules for different people.

Peter: Right.

Clay: And whether that’s a function that is better liked than another and is able to spend more lavishly on a conference that they want to go to, or a dinner that they wanna go out to, or that salesperson over there sells more than everybody else, so they get to do things that other people don’t get to do.

And this pattern, this idea of rule of law in the organizational sense, is just that we are going to live by the rules that we have written down, and we are going to adjust them when we have cause to adjust them. But we’re going to hold ourselves, regardless of the seat that we happen to be in, we’re gonna hold ourselves accountable to them through some mechanism.

Doesn’t need to be like a draconian mechanism, like, “Oh, if you break this rule, you’re gonna be out all the time.” It can just be, “Look, we’re gonna hold you accountable, and however we’re gonna do that, we’re gonna do that.” Might be a conflict management process, might be something else. And implied in there is that we are going to have a set of rules of the road that we actually think about, that are not handed to us by bureaucracy or by tradition.

So to me, it’s just holding ourselves accountable, everybody, to the same rules. Or if that salesperson over there does get unique privileges, write those privileges down somewhere and agree to them- Codify … so that other people can understand them. Once the rules are visible, people can challenge them.

That’s much more useful than making everyone guess which rules count. But Jesse, to your point a- around, like, fixing that ossified thing, fixing it starts with naming it and being able to address it, so there’s a few things that kind of like bleed out from the idea of rule of law, but that’s the…

Peter: all right, Wittgenstein.

Clay: …the idea. Sure.

“Design slows us down”

Peter: No, I, I, you know, I wrote my whole book on org design because I realized you needed to define these things. And we tend not to recognize the importance of agreed-upon terminology, and then we end up talking past each other and then wonder why no one knows what’s going on.

I’m curious, though, as you were talking about writing it down, I wonder if you get the same kind of pushback that design has often got, uh, UX design has often got, which is you’re slowing things down. If we do, if we wanna do things your way, it’s gonna make us slower by following these rules and programs and processes of documentation or whatever, and we don’t have time for that.

And if so, if that is a common pushback, how you’ve addressed that?

Clay: Very common pushback. Yes. Why don’t we just get started? Why don’t we just do the work?

Peter: Yeah. Why do we need a charter? We know what we’re doing, right?

Clay: Yeah, yeah. I will usually have basically a contest. You take one of your teams, and you keep doing your thing.

Give me another team, and let me show you what they can do. And the numbers are… They tend to be outlandish. We talk about, oh, AI is going to be, like, this enabler of super performance for teams. We already have it. It’s just a good team. A good team is super intelligent. We’ve all experienced, in the best teams that we’ve worked on, this feeling of a hive mind.

That’s what we’re going for here, so let, let’s just do that. Let’s just do that more, more frequently. And what I find is, over and over, the teams that actually spend a bit of time getting their shit together up front, they end up delivering. Whether that getting their shit together is writing it down or whether it’s going to a mountaintop and becoming one with one another through time and place, I don’t care.

It could be either one of those or somewhere in between. But just do that and see what comes out of it. And they get… Again, the numbers are crazy. It’s, “Oh, we had a 4,000% improvement.” It’s like, “What? Clay, that, that can’t be true.” Well, it- … it’s very true. Here’s a project that we’ve done before. We did it Clay’s way.

It was so much faster, and everybody was thrilled, and everybody stayed, and they hired their friends. It’s just, it’s… Everything about it is better, and it is free. Teaming is free.

Peter: I’m curious then, actually ’cause I agree, and, and I think org designers can be a bit like Cassandras. We’re just shouting truth that no one is hearing.

But I’m wondering what you make of the resistance to it, right? In a world that claims to be data-driven or evidence-driven, why so many decisions are being made that actively thwart the stated desired outcome? And, like, how, just through your observations, what do you make of this contradiction between, you have evidence that a different way works better, and yet most organizations are behaving in ways that are antithetical to their own success?

Clay: I mean, I have dumb answers to that mostly, and they’re like, look at the world around us. You have to believe in state capacity and institutions and people and the fundamental goodness of people, and you have to believe that people want to get more done. You know, you have to believe that the road is publicly funded, and having a grocery store that’s publicly funded is also fine.

The world is not in our favor when it comes to this stuff. I think it is also just, it’s hard. It’s hard to do this. Building a team within an organization that wants to operate in a particular way, and the rest of the organization operates differently. Dealing with that dissonance, that’s hard on its own.

And then helping people get over, this is a thing we experienced at August, is nobody expects you to be true to what you believe when you believe the things that I think we do. When you’re like, “Every role in this team is going to hold equal stature regardless of their seniority,” people are like, “Yeah, okay. I’ve heard that before. We know this, how this is actually going to go, and I’m not gonna trust your word on this.”

And people, like, getting over their well-earned baggage around the way that organizations work, the way that people are asked to lead, that’s hard, too. It’s just hard. It’s harder. But it’s better, and I’m okay with that.

Jesse: But maybe just a touch of optimism can get people through.

Clay: Thank you. I… Funny thing was the first person who read my manuscript, he’s like, “It’s kind of, if you read it all the way through, it’s kind of a bummer, because every single chapter starts with, ‘This is why the usual way you do this is broken and terrible. Here’s a better way of doing it.” And I’m like, “Uh, it’s a little late to change that.” And it’s true, though. I do believe that, it’s a window into my, into my soul, I guess.

Peter: Though it’s also, I mean, another way to take the book is that it is utopian.

Clay: Oh, yeah.

I

Jesse: think so. Yeah.

Clay: Yeah.

Jesse: Yeah. Yeah. I think so. And I do think that implicit in it is the idea that if we believe it’s possible, then it can be.

Clay: Yes. Great podcast title, by the way.

Jesse: Clay, thank you so much for being with us.

Clay: Thank you, guys. I really appreciate it. And seriously, as a super fan- … it’s so cool to be here.

Jesse: Thank you so much.

Clay: I cared about intranets so much when I was young, in ways that, like… yeah. Anyway. Yeah. So anyway, thank you for doing the work that you’ve done.

Peter: Oh, thank you.

Clay: Yeah.

Peter: It’s been great to have you- Yeah … on the show. Thank you for not just Hidden Patterns, but the commentary generally on… Well, we usually ask, so let’s ask. Clay, how can people find you on the internet?

Clay: Most places, if you just search for Clay Parker Jones, you’ll find me. Current website, because I’m bad at managing domains, is cpj.fyi.

And with the help of my friend Claude, I was able to get all of the back history on the back issues off of Wayback Machine onto the current version of the site, which means you can go back to 2006 and read some really dog writing from me. Terrible. So, but it’s there.

Peter: Awesome.

Jesse: Thank you so much.

Peter: Yeah. Well, thank you for, for what you’ve contributed as well.

Clay: Thanks.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions, featuring his latest thinking and the actual tools he uses with clients. If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one-hour consultation.

If you found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Show Notes

Intentional Design Leadership Circle

Are you a director-plus design leader looking to connect with others and grow your capabilities? Join Jesse and Peter for the fall cohort of the Intentional Design Leadership Circle, taking place on Wednesdays from October 7th through November 10th. Only 20 seats available for this live online program. Learn more and register.

About this Episode

Dr. Stefanie Hutka, design researcher, Berkeley educator, and author of What Your Machines Should Do, joins us to look to the history of industrial automation for lessons on AI transformation. From Toyota’s jidoka and the andon cord to Taylorism’s lingering grip, we explore why AI amplifies whatever conditions it finds, and why strategy and values must come before the tools.

Dr. Stefanie Hutka: https://sendfull.com/, LinkedIn profile, pre-order What Your Machines Should Do

Jesse James Garrett: https://jessejamesgarrett.com/

Peter Merholz: https://petermerholz.com/

Transcript

Hey everybody, before we jump into the show, I wanted to share with you something that Peter and I have been working on. It’s kind of special. We have poured all of the thinking and all of the wisdom that’s come out of the last several years of this show into a six-week leadership skills development and support program that we call the Intentional Design Leadership Circle.

It’s happening October 7th through November 10th, and there are only 20 seats for this live online program facilitated by Peter and myself. Find out more information and get your seat at findingourway.design. Now, on with the show.

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, we’re joined by Dr. Stefanie Hutka, design professor, researcher, and author of the book What Your Machines Should Do: The Science and Strategy of Human-Centered Automation. She’ll share lessons from the history of industrial automation to observe models to follow and models to avoid as organizations move towards AI transformation.

From the humble loom to the factory floor to the values that underpin our processes, let’s go exploring with Stephanie Hutka.

Peter: Stefanie, thank you so much for joining us.

Stefanie: Glad to be here, Peter and Jesse.

Peter: To kick off, I think it would be good just to get a sense of how you introduce yourself. I know you teach, and you write, and you speak, and you work, and so, who are you? Who is Stefanie Hutka in the world?

Stefanie: Yeah. So I’ve been introducing myself by way of hats, that I’ve been wearing a couple of different hats. Hat number one, and arguably the largest hat, the top hat, if you will, is as a researcher. So I have even more sub-hats under that field.

I go back, to early days, my PhD’s in cognitive neuroscience. I was very much an academic researcher. I worked as a research scientist, found my way into design research, and that is primarily the type of work I do today at my consultancy called Sendfull, that I’ve been running for about three or so years now. So hat number one, researcher, specifically design researcher today.

Then hat number two is as educator. So I’ve been teaching at UC Berkeley, primarily at the School of Information, but also at Jacobs, the design school. I teach Introduction to User Experience Design. I just started my fifth year of teaching that to professional master’s students. I also have designed some new courses, including UX for AI and Designing Future Systems, which dove into some systems thinking mindsets and toolkits, as well as some strategic foresight.

And then the third hat is as author. So I’ve written various things over the years, scientific articles, industry articles. But most recently, I have a new book that is coming out, my first book: What Your Machine Should Do: The Science and Strategy of Human-Centered Automation with Rosenfeld Media.

That will be launching in November and currently on pre-order.

What’s worth automating?

Peter: Wow. Jesse and I have been exploring the subject of AI and design, primarily design leadership, for the last almost two years now. And when we found out about what you were writing about we’re intrigued.

And so, unpack a little bit what the book is about for an audience of design and user experience leaders who maybe are still kind of grappling with concepts of automation.

Stefanie: For sure. So the book is a field guide for product and design decision makers to navigate this question of how do we automate and closing what I’ve called the automation strategy gap, where you have these dreams of fully automated futures and running after let’s automate everything, versus the reality of what’s actually valuable to our users.

How does this fit within their ecosystem? What is our organizational readiness? What is the actual capability of the tools at this time compared to that fully automated future? And so the book shares different frameworks and tools, some of which are derived from my own practice, some of which are derived from a synthesis of literature that I like to say is: it’s intended to be durable; it’s evergreen stuff.

This is not a book about how to use Claude Design or whatever tool’s gonna shift by the time this podcast finishes recording. I’m really looking at what can we learn across human factors, human computer interaction, management theory, cognitive science, and acknowledge that we are in a very new territory.

There’s many ways in which generative AI is unprecedented. Those three ways that I usually refer to that is: the unprecedented pace of development; the breadth of use cases that it can cover and what that means for human cognition and how much we can offload; and then the stochasticity of the output.

So it is definitely, you know… it has unprecedented elements. That said, we have been automating stuff, we have been building autonomous systems, for quite some time, so what can we learn from those principles so it doesn’t feel like we’re completely, you know, flailing as if there’s no prior, priors plural.

So the book is about those things.

How much of a burger is this?

Jesse: One of the interesting debates about this current wave of AI technology recently is the question of, well, how radical a change is this? And there is definitely this school of thought that holds that AI is, quote-unquote, “normal technology.” It’s just another wave of technological change.

It’s not very different from the things that have gone before. And then there’s this opposing camp, which is very much on the side that this is so fundamentally different that there’s not a lot that we can learn from the past, and I wonder where you fall on that continuum.

Stefanie: Yes. A little bit of column A or column B, or for my fellow design researchers listening, it depends. I think, you know, how are we, maybe how are we, defining AI, assuming we’re talking about generative AI, ’cause there are many types of AI. But yes, like the AI moment that we are in, I’ll start with maybe column B of what might be similar. So there’s something from one of your past episodes. I took notes on this ’cause I, I was excited about this conversation.

Jesse: She’s a researcher.

Stefanie: Exactly.

I was doing research, secondary research. This is what I do. The Paul Ford episode from a couple months back, you talk about compilers as an example of, now you have the sort of translation layer of intent going into the ones and zeros, and, we’ve had moments like this where we can articulate our intent in different ways that speed up our processes.

So from a technological standpoint, there have been big advances. We’ve had disruptive innovation. We’ve had mobile. We have had cloud. And those were definitely major events. We’ve had various tech bubbles before. We have navigated those. So we have, I think, from a disruptive innovation standpoint, we have some priors in terms of designing automated systems, like moving from human-in-the-loop to human-on-the-loop.

I mean, there are planes flying over us right now with autopilot systems that we’re presumably pretty comfortable. We’re not too worried about, how will the pilot lock back in with situational awareness when they need to? And we have figured some of these things out, so maybe we can learn from some of that.

So that’s what I’m talking about with some of those priors. Now, where I think AI is different right now is what I’ve called 10X cognitive offloading, and what I mean by that is, cognitive offloading is this just phenomena of delegating our thinking tasks to some sort of external device and often technology.

The classic example is Google Maps. I give this example. I bike to campus, to South Hall. I’ve been doing that route for five years. I’ve got that locked in. But the moment someone invites me, say, to Cheeseboard, which if you live in the East Bay, both of you know this, it’s not far.

It’s like a mile from South Hall, but I don’t do that trip very often, and I am entirely reliant on Google Maps. So I’ve offloaded my navigation capabilities to this digital map. And typically, when we’ve offloaded to technology, it’s been relatively finite in terms of our tasks, and I think the way, at least by default, a lot of these generative AI systems have been designed, like the phenomena of the prompt bar, it really invites kind of wholesale offloading, and we’re delegating the entire observe, orient, decision, act loop increasingly with agents such that if we are offloading, quote-unquote, “the wrong thing,” we can very quickly start to de-skill.

If we haven’t learned the thing in the first place, there’s gonna be a gap in our learning. And I think that getting to those three things I mentioned at the top of the podcast around one of those being the breadth of use cases to which you can apply this technology, I think that is where it is different, and combined with the pace and the inability for sort of slower moving systems, governance layer, for example.

We can’t build guardrails as fast as the tech is moving. I think that’s where things get unique.

Grappling with the pace of change

Jesse: It’s interesting to think about that pace challenge for organizations as they are trying to adapt themselves and adopt these technologies and actually get some meaningful value out of them, in that the technology is changing so fast that organizations hardly have the chance to orient toward one approach before the state-of-the-art changes.

So if we put this in the context of a larger history of industrial automation, right? Where we’ve had increasingly more and more machines doing things that humans used to do, if we can define automation that broadly.

We are now in a place where there is this kind of… this shearing force where the technology’s moving so much faster than the organization that the organization fundamentally breaks because of it. And I wonder about, in your research, from your perspective, what we can learn from the pressures that have been applied to organizations in the past, from past waves of innovation that might teach us something about what’s gonna make an organization resilient now in the face of what’s happening.

Stefanie: Sure. So what immediately comes to mind is a contrast that I draw, in a chapter where I get into systems mapping, systems thinking, is contrasting Toyota production system with General Motors’ approach. So Toyota production system, one of the key sort of tenets of this is automation with a human touch, jidoka, comes from the Toyota founder, as a young boy, saw his mother working at a loom and saw that she constantly had to be monitoring this loom and invented this mechanism such that when the thread ran out or got stuck, the loom knew when to stop.

And this was ultimately like, fast-forward, Toyota moves from textiles into auto manufacturing. Japan devastated after World War II. American automakers very, very resource rich and you get to Toyota saying, “Okay, how do we move forward given our limited resources?”

And you have this approach to automation that’s very complementary to people. You have this idea of kind of the andon cord, you pull it if there’s an issue on the line and everyone comes rushing.

And I think that’s interesting because it speaks to kind of the values that the company sort of organized around. Certainly there’s contextual factors, there’s different geographical, region, and cultural values, so on and so forth.

And there’s a psychological safety when you’re pulling that cord that you feel like, “Okay, I can pull that cord.” So, that’s an example of maybe automation done arguably well versus a much more sort of Taylorist approach that I think we see with, General Motors as a contrast, but we also see in a lot of our thinking now.

So in contrast, you have this mindset from like the early 1900s, if we can atomize work and, we can easily swap someone out to do it, and I think there’s an underlying mental model that there’s limits to our human capabilities and, if only we can sort of automate the human error out of things, we will be more productive.

If you’re driving on the I-80, if you saw any of those Artisan billboards in the last couple of years, like “Stop hiring humans” with hiring intentionally misspelt to imply that we are error-prone fleshbags, I think you see a lot of that.

Yeah, I just threw in fleshbags to wake up our listeners.

You see some of that same sort of Taylorist mindset that’s very efficiency oriented, so you get this sort of trade-off between efficiency and effectiveness that comes down to the values in which the automation approach is grounded.

So I think the shearing forces are coming from maybe this sort of Taylorist orientation, and this is challenging because this is like the paradigm arguably, like the underlying mental models that may be examined or unexamined that are influencing the values on which the organization moves.

Learning from looms

Jesse: You use this term in there, jidoka, which is a concept that I’m familiar with, but I think a lot of our listeners might not be, that is closely related to how this philosophy of automation was developed at Toyota, and I wonder if you can expand on that.

Stefanie: The Loom example is the one I go to, like, the idea of, you still have humans in the loop, but you don’t need to have them constantly.

There’s an element of there are things that are safe for machines, but there is a point at which the machine capabilities stop and, you need to bring the human back in.

It’s not necessarily any sort of value judgment, just like this is what the machine can do, and there’s going to be a point where the machine ends its capabilities and the human needs to take over.

Jesse: Yeah, I guess what I take from that is the idea that you build into the system the awareness of its own limitations and the awareness of when the system needs to stop and turn control back over to a human operator or a human intervention of some kind.

Stefanie: Yes. I was asked this similar question. I gave a talk yesterday morning. It was a Agentic UX summit, and one of the Q&A was like, “How do you know when the machine should stop?” It’s like, well, I’ve got a historical anecdote for you. Like back to your earlier question about what’s different this time, maybe the capability for adaptation of the system as you’re giving it feedback, like loops are all the rage right now, and we’re building agents, and this idea of there’s still a human sort of building that loop.

But if you’re optimizing the loop each time, the machine is doing incrementally more and you still need a human somewhere in there. But that dividing line isn’t static by any means. So I think that adds a new layer of challenge.

Peter: As you were talking about the Toyota manufacturing process I was thinking and I was doing a little research during that. There was also the work of W. Edwards Deming, right? It wasn’t just one person figuring it out, right? It was, like, this interesting confluence of thoughts and philosophies that led to things like lean manufacturing and the Toyota production process.

And the thing about W. Edwards Deming is funny is he’s an American who taught the Japanese how to manufacture cars because the Americans wouldn’t listen to him. He got no traction in the United States. Goes to Japan, teaches them, and then Japan eats our lunch, in the ’70s and ’80s.

Cultural contexts that encourage or enable a certain embrace of these tools and in maybe healthier ways versus less healthy ways, right? ‘Cause you also mentioned Taylorism, which is a bad thing, um, largely.

Like, I mean, you can make arguments for aspects of Taylorism, and efficiency’s not a bad thing in and of itself, but scientific management, when you go to those extremes, it becomes problematic.

What are you witnessing in terms of organizations’ ability to embrace automation in a healthy, good way versus perhaps in a toxic, damaging way?

The experimentation mindset

Stefanie: Sure. So I see an experimentation mindset, like what I’ve coined because, gotta coin stuff when you write books.

Jesse: I don’t know anything about that.

Stefanie: Yeah, it’s like you’re building with intention, experimenting with intention is something that seems to be a hallmark of organizations that are embracing this change.

And I think there’s something that doesn’t get enough airtime, which is a psychological safety aspect of leadership saying “Hey, y’all can explore in intentional ways. We’re going to make space for this.” One of the most interesting examples that I saw in researching this is Canva’s approach.

They’ve had a AI discovery week two years in a row. So the fact that they did it again this year suggests that perhaps it was valuable last year, and it’s basically like the whole company shuts down for a week and just focuses.

The first year they did it in 2025, an educational aspect, and then like a two-day hackathon, and you have everyone from like the chefs to the engineers to the marketing folks to the legal folks involved in building this, understanding of capabilities together and building intuition around those capabilities.

And then this year it was a little bit more agentic focused and people building out parts of their workflow. And again, the fact that we’re gonna get everyone together, we are going to just get hands-on, and you can develop the sort of taste for: the machines suck at doing this, but they’re really good at doing that. Okay, how might we work together with this?

And so we can debate about how does that translate to product development and customer quality. But there is an element of the fact that that was sanctioned and that everyone is just like trying stuff out together and learning together. I feel like there’s something that echoes the andon cord phenomena where we can pull the andon cord, we all rush to see what’s happening.

I think according to the literature of this, the first thing that people do to andon cord puller in the Toyota scenario is thank the cord puller for highlighting the issue. And so, I think that’s perhaps a parallel around, yeah, psychological safety, experimentation culture. Yeah.

Peter: You mentioned psychological safety. So I’ve been doing a fair bit of thinking around how do you maintain quality in the face of AI? One of the common concerns that I’m hearing from literally every design leader is, “We’re producing more stuff, but it’s not any better,” right?

And it’s either them, their own teams are producing more stuff, or ,more often these tools are enabling product managers and engineers and marketers and others to essentially produce slop that now the design team has to hold at bay.

And one of the things that I’ve been noodling on is what I’m calling the creating the conditions for quality work.

So quality, you have a set of standards, but standards don’t live on their own. You need to have a set of conditions to uphold and enact those standards. And toppest most of the poppest most of those standards is psychological safety.

Psychological safety predates AI, you know, at least in design work.

It’s been shown just to be a core value of any effective work team. There was Project Aristotle from Google, pointed that out, that the thing that mattered more than anything else in how do you get a group of people to do good work together is psychological safety.

Not talent, not skills. Those were way down the list compared to do these people have that freedom to experiment, to try stuff, to fail, to push back on one another, as long as it’s in the interest of making the work better.

So that’s one of the thoughts.

AI amplifies and accelerates

Peter: On my whiteboard behind me, I have the phrase, “AI amplifies.”

Stefanie: Oh, yes.

Peter: I’m curious what your research has pointed out. My hypothesis, or my postulate actually, would be AI doesn’t meaningfully change anything. AI takes an existing condition and amplifies it. So if those existing conditions are healthy and positive and good, now those people are just generating awesomeness.

And if those conditions are toxic and negative and problematic it only gets more so quicker.

Are you seeing that in your work?

Stefanie: 100%. For better or for worse, yes, I am still on, Substack. And I had one viral note, and then wrote a piece following up on it, which was basically, AI is an accelerant. What are you feeding it?

And I think it’s– we can say accelerant or amplifier but this is 100% it.

The joke I make is, you know, AI, you bolt it on, it’ll either accelerate your dysfunction or also strategy. And I think when people are like, “Oh, we can build and find out,” yes, build and find out or ship and find out can work if you have a clear strategy, you have hypotheses, you have metrics that you’re going to measure, like was this hypothesis supported or not?

And presumably, you will only ship a few times and you will learn something, and you will adjust. But what I am seeing more often is, it is ship and find out, and it’s the same dysfunction as before, but now you’re burning out your customers with basically an endless A/B test.

So at some point, they’re gonna wise up to the fact that you’re just, like, you’re building a product strategy by did this work?, ’cause we can vibe code it and ship it now.

So I think all that said, l ike, all the goodness of AI: oh, you can work fast with small teams, and you have a strong strategy it is going to amplify that. You can build faster and get that out faster and iterate faster.

If you have dysfunction, it will also accelerate that.

And I think same thing with inequity, too. Thinking about people who have access to these tools or education systems or if you have curriculum where students are being taught how to use AI effectively versus there’s already existing dysfunction, like student to teacher ratios, and students are just like using AI to write their essays ’cause they’re, like, time scarcity or don’t get enough attention, it will accelerate that inequity as well.

So yes, it’s a bolt-on accelerant amplifier. Choose your word here.

Jesse: Mm-hmm, It’s interesting the way in which it does amplify both the positives and the negatives within an organization, right?

And then in some ways for leaders, what that does is that makes it ever more glaring, the rocks that have been just underneath the water that maybe they didn’t even see, and it asks leaders to maybe let go of some dogma, maybe let go of some ways of doing things that have served them really well up to this point.

And I find myself wondering about adaptation and what it takes for leaders to adapt their own thinking to create space for some of the things that you’re talking about, the experimentation and the safety, the ability for the team to take chances, and how the leader might need to change what they do in order to make that possible.

From AI-first strategy to Strategy-first AI

Stefanie: Yes. I’m connecting this to this concept that I talk about in the book, which is going from AI-first strategy to strategy-first AI.

And we can argue that strategy, as defined by Martin and Lafley, the series of choices that you make in effort to pursue some sort of winning aspiration.

Like, where do you wanna play and how are you gonna win, and how are you using AI to support that?

So I think there’s a connection point between, okay, you gotta have a strategy and know where you wanna go, but also stuff is changing so quickly that is Horizon three even still a thing, or has it just been smushed down?

So I think there’s like this inherent tension of how fast things are moving and how that leads to what is our strategy, or how can we see around the corner, and there’s all these other, like, macro factors impacting where we wanna go.

Jesse: It feels like there’s something there in terms of how leaders balance their time and attention. So if you’re in a leadership role in a product development organization, it used to be that your job was basically to keep the process buttoned up, and to make sure that everything went according to some predictable cascade that was something that was repeatable and you could be held accountable for as a leader.

And now it feels like it’s much more… Peter and I have used the surfing metaphor in the past, where it’s much more about your ability to flexibly respond to the changes that are going on rather than your ability to set an expectation, and then drive a team through a process in a way that fulfills that expectation.

So when I think about, yeah, when I think about the skill set, I guess that’s where I wonder, like, how do leaders need to think differently about the work that they do?

AI as white water rafting

Stefanie: Yes. I love that the surfing metaphor, my editor was getting sick of all of my white water rafting metaphors. I happened to have written chapter six, which is about strategy and AI, in Chile in Futaleufu, which is known for some of the best white water in the world.

So yes, this flexible adaptation and I think maybe this metaphor of steering that, like, Terry Winograd coined that many decades ago. But how do you steer in the rapids?

And I think that mindset, there is definitely an embrace of ambiguity.

This goes back to the psychological safety piece, trusting that you have certain values. I think being very, like, value-centric ’cause again, to go back to my overused river analogy, when you are in the current, when you’re in white water, it’s like you can have the best laid plans, but it’s really, what are the sort of embodied values in that case of your procedural memory.

But here when we’re in those river— like, what do we stand for as a company? Do we, do we value quality? ‘Cause that’s the thing that’s going to be how you’re gonna navigate around the rock.

So I know I had this great back and forth with one of my tech reviewers ’cause I was talking about vision versus values. ‘Cause vision is dependent on seeing the future and if we’re not sure if we can confidently see too far out into the future, that falls apart a little bit. But if you have values, that can guide behavior when you are surfing/steering/white water rafting.

Peter: You used the word stochasticity. That is an easy word to say.

And I wonder if the stochasticity is related to this because, you’re not quite clear. You’re not certain. It is not determinist what is coming out of this system, so you have to be willing to kind of bob and weave with it and nudge and course correct it.

It’s very cybernetic. There’s always a dialogue as opposed to you do a thing and then it’s done. Is that a fair connection?

Stefanie: That is a fair connection. I love that because I was thinking of it primarily at the… what is a tool and the quality of our tools being stochastic has all of these bidirectional influences on our ways of working on systems, like macro systems, so on and so forth.

So I think that’s a very fair connection and I love that, and that’s something that I will be mulling beyond this call.

Peter: When you were talking about the Jidoka and the Toyota manufacturing process, and part of its reason for being is it came out of a resource-constrained reality.

And I think, likely the reason the United States did not embrace these approaches is because we had the resources. We’re not constrained. We don’t understand an approach that assumes resource constraint, whereas the Japanese that was where they were starting.

And I’m wondering, what is the analogy today with generative AI tooling in these environments and resource constraint?

I’m asking in part because I’m working with a bunch of massive legacy enterprises, hundreds of thousands of employees. They are not in any way resource constrained. I mean, the designers always feel like there’s not enough of them to do the work given the amount of work to be done or whatever.

But in any legitimate context, there are plenty of resources. That’s not the problem.

And I wonder if that’s actually why a lot of those companies are struggling to embrace AI, not just because of bureaucracy and legacy ways of working, but a philosophy or a need that just doesn’t exist for them. Whereas startups or earlier phase companies or entities that are struggling, there’s some, I don’t know, to overuse perhaps now a supposed Japanese philosophy of beginner’s mind, right?

Like there’s some willingness to really embrace this approach for what it is meant to be, as opposed to slapping it on or bolting on because you’ve been told, but it’s not really suitable given your context.

Jesse: Right

Making sure AI is fit-for-purpose

Peter: But those Japanese manufacturing processes or practices were born of resource constraint. What do we learn from that when trying to apply automation tools in an environment that maybe isn’t resource constrained? Does it just mean you can do more or is that a misfit? Is there something actually ill-suited to a resource-full environment and these kinds of approaches?

Stefanie: Ooh. Yes. So I’m thinking about what is the incentive structure to bring in that technology if you have unlimited resources. I think it’s a lot of the maybe incentive structures, our old processes and maybe reluctance to adopt new processes that is creating resistance, and maybe it’s just, like, how information flows.

It’s like the double-edged sword. If you have a big organization, there’s more information flows, it’s harder to institute processes.

So I think there may be an element of what we have seen historically, like when you brought in electricity instead of a steam engine into a factory, you know, decades and decades ago. It took 40 years for the ways of working to adapt to that because you didn’t redesign the factory.

And so is that related to constraints? I think it’s maybe getting very excited over what are the technical capabilities, but not realizing that the people side of it needs to change. We are sociotechnical systems, and you gotta give the socio part of the sociotechnical some love as well, and there needs to be this joint optimization.

And so I think that’s, if anything, what I’ve seen more in the research for this book, which is the over-pivot on we can automate all of the things, but not realizing that that also materially changes how we work and how we collaborate.

If roles are blurring, okay, we need a new process. We need maybe different team formations. We need maybe to bring in maybe different types of expertise. And so that’s more so how I’ve seen this show up.

Jesse: When I think about these large-scale enterprises, honestly, what it comes back to for me is they know too much, they’ve seen too much, they’ve been through too much. They have accumulated so much latent wisdom inside these organizations about what it takes to deliver whatever it is that they’re there to create.

And it could be 3M, it could be General Motors, it could be General Electric, it could be Verizon. Like, It could be any of these very large-scale organizations where, yeah, you know what? We’ve got decades of experience that tells us what it takes to deliver at scale. And this stuff flies in the face of that.

And for you as a manager to stand up among your peers and say, “We’re gonna ignore the 120 years of background and experience that we have in what it takes to run a railroad or an electrical grid or whatever the large scale thing is that you’re doing,” there’s a risk.

There’s a political risk that comes with that, and it means standing up for a value prop that may or may not even really be there.

And so I find myself wondering about sort of the chilling effect inside organizations that potentially limits leaders from stepping into the capabilities of these things because it means flying in the face of decades of wisdom

Stefanie: Yes. I’ve seen some of this in my interviews, like primary research for the book around folks who have successfully navigated this just around small AI pilots just saying, “Okay, we’re going to start small. We’re not going to necessarily redesign the entire factory, but let’s use this sort of like little cupcake. We’re gonna do the cupcake of the cake in this area. And this is the runway I need. This is what we’re measuring. And if that goes well, that can be a sort of safe way to introduce that if you have someone who’s going out.”

I’m sure you’ve seen, some of this as well.

But I think, yeah, absolutely that, is true. And then of course, no one is speaking up because they’re worried that that won’t go over well, and all of a sudden you have the company continuing to operate for steam when it needs to be adapting to electricity.

Peter: I think the risk frame is interesting because of the stochastic nature of AI.

Businesses love certainty and dependability. And so you might think that they would fear AI because what it produces is often uncertain and out of their control. But for some reason, businesses have just decided to massively embrace AI before really understanding the implications of doing so.

I think with the promise of automation and frankly firing a lot of people and cost savings.

And so it’s identifying this internal contradiction going on within these businesses. Like, there’s risk aversion to a point, but I’m willing to take that risk if the amount of money to be saved is just orders of magnitude.

You also mentioned values earlier, that there was some underlying value that maybe we hadn’t yet tapped into that is now being expressed when they’re behaving like, “Oh yeah, actually risk has been fine. Look at how we’re embracing AI.”

That means it’s not that risk is fine, but firing a lot of people is even finer or something.

Leadership v. Builders

Stefanie: Yes. Oh my gosh, yes. I have so much. I have, I have… Our listeners cannot see my little squiggles, but there are two squiggles on top of each other, and they represent leadership and builders talking past one another, And this gets to one of the keystone frameworks from this book, this autonomy decision matrix, that ultimately the axes are could you do it and should you do it?

And it’s designed to be the sort of common language where you have, okay, we wanna automate X, we wanna automate customer service. What does that even mean?

And so that you can ideally, if you have both parties or representatives from both parties in the room, you can hash out what are you actually talking about, ’cause I think we have dreams of fully automated futures, we need to report to shareholders at the top layer, and oh my gosh, AI can do all of these things.

And then to the stochasticity point, something that was coming up in the book is that even builders, like folks who are very technically skilled, they don’t even sometimes know the full capabilities of this tool. They’re like, “We’re still figuring it out.” So when leadership is like, “Let’s automate customer service,” and builder’s like, “Oh, wait a sec, no, that’s definitely…”

There are a lot more humans in the loop than you think, and probably will be for a much longer time, and they are talking past one another, but then there’s top-down mandates happening, and you get all sorts of weird stuff being like, “Here’s our spreadsheet of AI features,” and “Let’s start jamming those in according to a roadmap,” and just, you start getting this sort of breakdown from that initial talking past.

So one of the tools from the book, it is an attempt to be a common map so that you’re looking at how confident are we that we could do it from a capabilities and readiness perspective, and then from the should do it, what evidence do we have around, customer needs, et cetera, et cetera.

And we can actually plot this thing on a two by two, this thing being what we’re talking about automating, and starting to get precise.

Okay, when you say customer service, what tasks in customer service? What percentage of things are we trying to automate? Is it 80% of routine requests? Okay, what, how do we define a routine request? Can we go back into the data and define it? And all of a sudden you’re like, “Okay, maybe we can do 40% of that now, but we need to build a triage system today to go back to humans.”

I think is related to maybe some of the uncertainty at the builders level, and that is creating tension when you’re going back up to the leadership.

Peter: Well, right, ’cause the leaders expect this to behave like any other determinant technology, and the builders realize that’s not how this works, right?

Stefanie: Yes, exactly.

Jesse: When I think about these legacy companies and what the history of those companies has taught them about what it means to be successful, it feels like there’s a place where the technology starts to hold a different kind of meaning here because of its unpredictability, because of its stochasticity, because of the way in which we’re all now sort of, when I was leading AI work for Capital One back in the day, I used to say that this work is, it’s not about being a dog trainer, it’s about being a lion tamer, in the sense that the dog is eventually trained, the lion is never ever tame.

And so the work continues on an ongoing basis to manage and shape the unpredictability of it. And the decision-making cultures in organizations when nobody can know for sure what is actually gonna go down. And the implications for how decisions get made, what inputs come into those decisions, and what voices, to your point about the builders, what voices are involved in those decisions, whether there is actually a change that needs to happen in decision-making culture in order to actually leverage this technology to its fullest potential.

Stefanie: I love that. On my little blue piece of paper, I have a very rough and scrappy little stakeholder map with bubbles, and I have builders, I have leaders, and I wrote investors. We could put shareholders there if you want to. And the only reason I put them on the map and brought them into the mix here, I’m actually not betting against larger organizations, that, like, small organizations that are AI first are going to win out.

But I think that investor perception plays into this dreams of automated future thing, ’cause if you’re like, “Oh, there are these big companies,” they might be trying their darnedest to integrate AI in meaningful ways. But there’s this idea that because you can automate all of the things so quickly, you can cut out that middle layer of management, and you can just fire a bunch of people, and so therefore, smaller companies inherently will be able to do the same thing as larger companies.

Like the hill that I die on is there is a layer of tacit knowledge and situated action that like generative AI with large language models, there is an absolute ceiling. Sure, capabilities are getting better every single day. We can automate more than we are doing now, but there is a ceiling, and that information flow, you will still need those large organizations.

But the investor perception that we can automate all the things adds to the sort of preconditions that leads to the dreams of automated futures. And so anyhow, that is worthwhile to mention in like the pressures those larger organizations might be feeling and reacting to, which may not actually be true of even what is happening in the building.

Jesse: Well, it’s interesting to think about, what is the kind of the upper limit of all of this?

Stefanie: Oh, yes.

Jesse: Like just in the digital space where you don’t have factory floors to maintain, there are no chip fabs or assembly plants or shipping or logistics or any of that kind of stuff.

It’s just data. It’s just ones and zeros being produced. It leads to a question like, well, how few people could you run Facebook with? Like, how small a team could potentially enable a global offering? And in that case, what are the humans on that team doing and what are the robots doing, right?

Stefanie: Yes. So yes, how small, I won’t give you like a absolute number, but I’m thinking about the subject matter expertise of someone in, I don’t know, someone in legal, someone in software engineering, like that deep well of knowledge.

I think there are certain things that are not machine readable. No matter how much you, hook up your Slack or your email your, whatever’s in your knowledge base, the meeting that happened after the meeting that actually informed the decisions, probably not in that knowledge base.

The sort of embodiment aspect of just our being is not in that knowledge base. This is why I’m a lot more interested in, say, world models or even like biological models, There’s a lab in Singapore, very sci-fi, building this. But like there is a, there is a limit of how much of that knowledge you can make machine readable.

So at some point, if you’re building something that is more complex, maybe you’ll need fewer people, but you will still need some expertise steering these machines. So will you have a fully super dark factory? Like a, like level three automation where you have a super dark factory that’s basically like a child or like you’re someone who’s just autonomously navigating and forming their own goals.

There is no example of that yet, but I’d argue that we cannot get to that unless you’re literally just recreating people. And so will organizations be smaller? Yes, but they will not be as small as we might think.

Jesse: I love imagining the future headline, “Rogue automotive plant starts manufacturing kitchen appliances,” right?

Stefanie: Yes. No. It, it does raise the, yes, it has, it has formed its own goals, and it is now…

Jesse: Mm-hmm. It’s decided this is the business move.

Stefanie: Yes, exactly. That is… Is that AI first strategy? Very literally.

Peter: You guess?

Jesse: Yeah.

AI, the Double Diamond, and New Roles

Peter: Very, Very much so. Not wholly unrelated, but behind me on my whiteboard is the double diamond.

And it’s up there because when I talk to design leaders, I find that it’s a way to talk about AI and design and user experience in the modern workplace.

And given that you are teaching the next generation of folks who are going to be practicing this, I’m curious how what I’m about to say lands.

And with the double diamond there are two vertical lines in the middle of each diamond. And the idea is when you’re on the left of the front diamond, the people doing that kind of work in strategy, in ideation and concept development, fucking love AI.

I did this listening tour of design executives and what I’m saying comes from conversations with one in particular, but others have agreed as well.

Strategists love th-these tools. They love being able to produce visions of near futures, six to twelve months out. Put real information, real data in those. Put those in front of real people, get real responses, iterate on them in a safe prototypy way and start even building the thing, right? The tools are affording those abilities. So you have this strategy team that’s embracing AI because of the just more rapid sense-making and you don’t need to coordinate as many other people. You can do a lot more on your own in terms of figuring out some strategic work.

And then on the back half of the second diamond, the kind of delivery and ship parts of the process, that group is loving this because they’re now in Git, they’re now making pull requests, they’re now shipping code.

And that chasm that used to exist between even a design technologist and an engineer has just, in many organizations, shrunk or super blurred. There’s not a chasm anymore. You’re just walking from thing to thing.

But what’s happened is the folks in the middle of the double diamond are the ones who are struggling because partly they’re feeling it on both ends, right?

If the strategists are able to do good enough UX work, and I’ll call the middle of the double diamond, the end of the first diamond and beginning of the second , the UX-iest part of this. The strategists are able to not just produce prototypes, but they can then turn that into something that looks and works pretty well.

And the design technologists to front-end developers or the UI designers are able to kind of back up their work in using design systems and whatnot, kind of assemble a perfectly good experience.

And so the people who tend to operate in the middle of the diamond are getting squeezed.

At least this is what I’m hearing from some folks. I’m wondering how that framing lands for you, how you are thinking about the roles in user experience and design work as you’re having to be very intentional about it in the teaching mode that you sometimes operate in.

Stefanie: Yes, I have. I think being in that middle, like, when we talk about UX roles and I think we’re saying that UX as a discipline remains important. However, the roles certainly are changing in how they’re defined, and I feel like being in the middle of the double diamond is an artifact of what has happened to UX, like post-Agile, post-commodification with design boot camps, et cetera, and so on and so forth.

And how I am teaching design, I think, in many ways goes back to, like, the earliest conceptions of UX like, you know, sort of Adaptive Path, early user experience architect, and, going even farther back into the history of human factors of HCI and then service design feeding into that. A much more expansive definition where it is like, no, understand how both diamonds work, maybe have a deep well of knowledge on one part of this are you drawn to? But I don’t want you to go out into the world and just be operating at that middle layer, which is what many students who come into the classroom think they’re about to do.

Like I have Jesse’s Elements of UX diagram. I think it’s in our second lecture, and the assumption for many of the students are that UX is the top layer. It is the visual maybe design layer. It’s very execution.

Going Deeper in the Elements

Peter: I’m sure Jesse wants to comment, but I’m not gonna let him.

Because you mentioned his elements. So on my drawing of the double diamond, it might not be obvious, but I drew the five elements,

Stefanie: Okay.

Peter: And I talk about how those top two elements are what AI does really well, right?

So, so the visual and like the top el- elements of UI design, AI can do those.

And so when I think about the middle of the double diamond and the work that was UX, what I see is still an opportunity for those who might not find themselves at either end, or just an opportunity generally, is to go deeper into the elements of user experience.

Because for so long, digital product design has been so focused on UI that what all the tools are trained on is that, and they don’t know how to deliver quality structure, right? They don’t understand IA, they don’t understand real flows and conditionals and all that kind of stuff that leads to a robust software experience, right?

Everything got very superficial over the last 10 years in terms of these digital tools. If it’s more than you tap a screen, do a thing, and then tap back out, like these systems tend to be too hard to use.

And so part of me then is wondering, and I’m wondering if this comes up in your class, right, is there a renewed focus on the deeper elements of user experience given that AI is able to automate those top parts?

Stefanie: Yes. Oh my gosh. And I have a anecdote, so not to super flex. I get great teaching evaluations, but there was one critical piece of feedback maybe two years ago from a student, which was like, “This was too much of a UX research class.” And I think they’re attributing it to me being a design researcher.

I’ve made great pains in subsequent years to highlight that the bottom of the diagram is user needs, and that is how we determine the goals.

If you are making your text larger, it is ’cause you’re moving the user spotlight of attention ’cause it is related to their goals. Or if you’re using color to draw attention, like, it’s all connected.

And I think that is– I know as a researcher, obviously I’m very excited about focusing on that, but I do wanna emphasize that to students throughout that process you’re constantly doing research.

You’re tying it back to who is in this experience and trying to build a very, I think, holistic understanding of what is context. I think that is something that is lost, like the ethnographic nature of design research. I think that is quite new to folks in many cases if they’re not coming from a social science background.

So I certainly do emphasize that throughout the process and remind folks not only that there is a foundation to that diagram, but that they all ladder upon one another. You can pull that thread.

Jesse: So over the course of this conversation and indeed your book as well there’s been this recurring theme of connecting back to what’s gone before to learn from the history of automation and the history of organizational change related to it in order to make better choices going forward

I wonder about the parts of it that we can’t predict, the parts of it that are genuinely new. And for you, from your perspective, I wonder, what are the big unknowns that you’re interested in seeing the answers to over these next few years?

Stefanie: Sure. One of the big unknowns is to what extent will we be conducting, quote-unquote, user research on machines? This came up in several of my interviews around what is the output from machines? What are the gaps in the output? Can we do a log analysis of what’s coming out of our machines so we can understand either bias patterns or kind of understanding almost like the machine psychology. I think that’s kind of interesting.

I brought in a friend from IDEO who wrote a paper on synthetic users to do a Q&A with my class, and then got into a whole back and forth on LinkedIn with another practitioner, in a good way about the role of synthetic data in innovation in the earlier… in discovery.

And right now, I think that common wisdom is that these are regression to the mean machines, don’t use synthetic users, you know, LLM personas, like, random machine’s idea of a 23-year-old’s attitudes about iced coffee. Like that’s not gonna be predictive of actual behavior, so don’t make decisions based off of that.

But there are, if you look at, like, large data sets around okay, if we have a lot of historical user behavior and we’re essentially treating a synthetic model as a database that we are querying, maybe there’s actually some utility.

So like this gets to, to what extent can we bring in synthetic data earlier on in the process, I think is really interesting. And like right now, I can share if you want in the show notes, there’s a paper talking about like predicting how well prototypes will resonate. It was actually in a like scent study of all things, like different fragrances.

Peter: Oh, not even information scent…

Stefanie: Exactly, not even information scent, actual scent.

And it was like quite accurate, but, you know, it was very bounded. And there was a lot of historical data. So I think that’s interesting.

Something that was brought up from a guest speaker from Microsoft in my UX for AI course, he is designing computer use agents and I think my students’ minds were blown apart a little bit by the idea of having a persona or two personas, one of whom is a person and one of whom is an agent.

And that’s really kind of mind-bending, I think in many, many ways. And do we accept that? And is that, is that responsible? Should we be doing that? Is it just a reality? So that’s something that I’m really curious about.

And then I think maybe a fourth thing is designing for physical AI. I kn

Show Notes

Peter and Jesse are joined by Chengying “Z” Zheng, who shares her experience migrating a design team to be AI-first — off Figma and into code. She discusses how design leadership and operations divide the work, what happens to roles and titles when everyone becomes a builder, and how to make good design easier than bad design.

Z on LinkedIn: https://www.linkedin.com/in/changyingz/
Z’s Substack: https://changying.substack.com/
Jesse James Garrett: https://jessejamesgarrett.com/
Peter Merholz: https://petermerholz.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

On today’s show, Jesse and I are joined by Chengying Zheng, better known as Z, the design operations, or should I say experience operations leader with extensive experience in tech. She shares with us how she guided a design team through an AI transformation, setting aside Figma and building right in code, her thoughts on the evolution of roles and teams, how to maintain quality, and the new work of operations.

Hi, Zee. Thank you for joining us

Z: Thanks for having me

Getting the team off Figma

Peter: The conversation we’re having with you, for me at least, started, I wanna say, six to eight months ago, when you and I were in the offices of Figma at a gathering. There was a lot of folks there, but you and I had peeled ourself away from the crowd, and you looked at me, you looked around, you looked at me, and you said, ” It’s a little weird for me to be here because I just spent the last three months or so getting my team off of Figma and into AI tools.”

And we talked a fair bit about that. You’ve been writing about it in your newsletter, but I’d love for you to share the, the highlights of that experience. Yeah, the highlights of that experience. Explain a little bit about where you were and what that journey was like and how you did evolve a team out of Figma and into more kind of AI-native practices.

Z: Yeah, absolutely. It was a really interesting moment. I remember that conversation

A lot of folks at the time were talking about AI transformation. Everyone was thinking about it. This was still last year, still a little bit early in this curve about AI transformation, so a lot of people were thinking about it, and people were doing it, and some, of course, AI-native companies were way ahead compared to the rest. They were already out there.

And our team was interesting because we had this mandate, like any other tech company, right? So you will start to do AI transformation, to incorporate AI into your workflow.

So for designers, the first thing that we looked at was how designers prototype. We weren’t even thinking about how designers ship, we were talking about prototyping.

And of course Figma has been the de facto tool for product designers for many years by now, but in this new workflow, we were thinking about getting designers to prototype with the new capabilities, with all the vibe-coding capabilities.

And a lot of our designers started to see that Figma, instead of a prototyping tool, which is what we used it for before, had now become a wireframing tool. Basically, you come up with ideas and then draw them out in Figma, but then you- the prototyping is actually happening in the coding part, in the vibe coding, whatever the tool was back then, whether it’s Claude or OpenAI, whatever.

So I wrote about it. I audited our Figma. Of course, as the operations person, we look at our Figma usage and everything. I audited it one time, just on a random day, I looked at it. Out of our hundreds of licenses, there were 50-some people using it that day, and only five of them were from our product design team.

Most of the others were marketers, PMs, everything. So that was a very interesting moment for us to look at tooling and at the designers’ tool stack. But that was months ago, actually, compared to right now. Everything moves so fast, and that feels like so long ago.

Telling engineering what changed

Jesse: I wonder about the cross-functional aspect of making this happen, because there is always this sort of ripple effect whenever one team changes the way it does things, on how that team then interfaces with the teams around it. How did you manage the cross-functional conversations as you were transitioning the team out of Figma as their primary way of doing things and into vibe coding?

Z: Yeah, that’s definitely a lot of challenge and work. So I actually proposed it back in October last year, to our design managers, to design leadership. I said, “Let’s get our UX designers out of Figma.” Of course, everyone was like, “No freaking way. You are crazy. Designers are in Figma, that’s our tool,” and everything.

But the reason I proposed it is that it wasn’t just a random proposal, like let’s get rid of tools or anything. At the time, we had a new design system that was entirely in code, and we were fortunate in a way, because instead of trying to continue building multiple design systems and trying to move them along, to modernize all those design systems, from the top down there was a mandate. This is the design system we’re going to use. That design system is in code.

And that’s really what prompted this proposal. That didn’t happen, so by the time I talked with Peter, that was already three months after. I think we talked at the end of last year, and it was October when I was proposing it.

But by then, just de facto, no push or anything, designers were already out of it. But there was a lot of conversation. If I could have done this all over again, I would do it differently. I would be reaching out to the engineering team immediately and talking about this transformation. At the time, this just organically happened, and then by the time I talked to Peter, this is… That’s when we started to realize, oh gosh, we need to talk to engineering a lot more. Some engineering teams still required our designers to give them a Figma file. Some other teams were more open, and you could do other ways of prototyping. And there was a lot of discussion about what designers were doing in code, and we also had to go out and talk about it.

There are levels to “designers shipping code”

There are different levels of designers in code. So there’s the- One, the basic thing about getting designers into code is engineering empathy, right? So engineers now, instead of just coding, they do a lot of reviewing code as well. So what it takes to- for an engineer to build something, that’s something designers should understand as well.

And then another level is where we got our team to prototype, but then by the time February this year came around, our designers were actually shipping production-level code. It sounds so grand, production-level code or whatever, right? But by then we had worked with the engineering team, put a lot of guardrails in place, about what designers should not be touching in terms of code. If it’s an API, if it’s infrastructure, if it’s, say, if it touches a flow, these are things designers should not be doing.

And what we’re actually talking about when we say shipping production-level code is paper-cut-level shipping of code, right? So change a piece of copy, change a wrong component, small changes.

And so these are things people sometimes talk about, “Oh, designers shipping code.” They put it under a blanket umbrella that says, “Designers shipping code.” But there are actually really different levels of designers even touching code. People are not getting there because, “Oh, designers shipping code. Are we turning designers into engineers?” No, absolutely not, right?

So same thing, we opened up Figma for other cross-functional teams to use. PMs using it, engineers using it. Are we turning engineers into designers? Probably not. Are we turning PMs into designers? No. But we’re turning everyone into a product builder, a contributor, in a way they’re passionate about, wherever they see a fit with the tool.

Now we’re basically just giving everyone all the tools, not just keeping Git for engineering, Figma for design, or whatever the PM tooling is, but we’re actually giving the entire tool stack to everyone who is touching product and building, and they use the same tools we have. And so that’s where it is. But it takes a lot of talking, coordination, and it really does hit some nerves because everyone is jumpy, and designers say, “Oh gosh, engineers designing, PMs designing,” and the engineers say, “Oh gosh, designers coding, PMs coding.”

So I wouldn’t say it was all smooth, but at least that’s something we put a lot of effort into, and we saw results from doing that.

Standardization doesn’t scale anymore

Jesse: One aspect of your story that I think really resonates with what I’m hearing more and more, and what I’m seeing in AI transformation efforts broadly, is the notion that you have to meet people where they are inside the organization. And imposing a kind of one-size-fits-all policy for this technology is not actually going to get you there, that you need to be able to find ways to leverage potentially a broad range of different skills across your team in a way that you haven’t before, and to be able to accommodate a diverse range of different kinds of workflows, and setting different kinds of expectations accordingly, cross-functionally, with how product and engineering interface with and interact with design.

I wonder for you as an ops leader where your mind goes when you think about managing operations across a diverse, distributed set of work processes that no longer fall in line with a single paradigm anymore?

Z: Absolutely. So I come from a very strong operator’s perspective, right? So in the past, as operators, you were the process wranglers, basically. That’s what it is. You want to… The word we used for the longest time was standardization. Standardize the process, and that will actually scale, right?

So but right now we’re pitting speed versus quality. There are a lot of discussions in there, whatever. Like you just said, standardizing everything won’t work anymore because different teams move at different speeds, and different teams have probably started to adopt slightly different workflows. And some teams might… Some companies, some teams, might even allow them to use slightly different tools or whatever.

So I wrote about it, and to talk about it now from an operator’s perspective, I push a lot for shared principles, and then giving people the agency to work out the details, how to execute it, and to have a little more flexibility instead of standardizing across the board.

But shared principles are something every team needs to spend a lot of time aligning on, and also educating everyone and talking about, because if you think about shared principles, for designers, there are certain things, right?

Accessibility is a, for us, something we care a lot about, and engineers care about that as well. And engineers probably care a lot about their code quality as well. So their APIs, nobody touches, and as long as we’re clear about what everyone can contribute and that everyone should reach out to the experts to contribute, that helps the team move in different formations, but still moving in the same direction.

Should ops be leading the AI transformation?

Peter: I’m, so, I’m gonna continue on this thread because when we spoke about this at that Figma meetup, the light bulb that went off for me is that this type of AI transformation might be better led by operations folks than design leaders.

Whereas my kind of working assumption in the conversations I’d been having with clients and whatnot, design leadership was responsible for that. And, if they had an operations person, maybe would be leaning on them to help.

But something that’s also happened over the last couple years is a lot of ops teams have evaporated. And so the, the irony being we’re in now in this moment that is so operationally heavy, and many teams don’t have operations folks to help them through it.

And I’m wondering what is your relationship with design leadership through this type of experience? What are you responsible for? What are they still responsible for? How do you distribute authority? Who’s making what decisions? That kind of thing.

Z: Yeah. So if you think about design operations in general, with your leader, it’s always a balance. It is always challenging to divide that responsibility and accountability. It’s just because different teams work slightly differently.

So in my specific situation, it worked out really well because at the time, I reported to the head of design, and her mandate from the top down was AI transformation. And then my part of the work was actually getting that done.

And then the design leader coming in down to the team, this AI transformation, you think about it as a gr- grassroots effort. Everyone wants to use something, build something.

But to do it right, you absolutely need top-down support, to give people the time to do it and to give people the direction, where to go and what we want them to do. Do we want them to stop at prototyping? Do we want them to ship code? We do need to know what the end stage is that we need to get the team to.

And as an operator, then we can actually help the team achieve that and figure out the logistics, scaffolding the team step by step, how do we get there, get the designers into code.

I came from a very technical company. It’s extremely hard to get into our production code base, rightfully, and it should be. It shouldn’t be turnkey, where everyone can ship code. So there’s a lot of coordination. It’s my role and my team’s role to go out, reach out to our engineering partners, “Come on in, help us do it right, because you do want us to do it right. You don’t want to review crappy code. You want to teach us to do the right thing.”

And then so in return it helps them as well. And also a lot of explanation as well, “Hey, we’re not trying to be engineers. We’re actually trying to take care of the design debt that engineers never have the bandwidth to take care of, and they are very small paper-cut things.”

Leadership owns the what, ops owns the how

So my goal is really to focus on the how. How do we get the team there? But design leadership is the what. Coming in with the what, and giving the team the mandate. That’s really important.

With these things, if you just say, “whoever wants to get on the bandwagon, let’s do it,” it is really hard to move that fleet in the same direction. Those would just be sailboats, right? Everyone’s like, “I want to go. I want to go really fast. I want to do something.” And then someone else wants to do something else. “I want to use this tool.” “I want to use that tool.”

So the design leader needs to come in and say, “This is where we’re going to get people,” the what, and then the operators come in with, how do we get there?

And that worked out really well. And then also because we’re… We say it’s design operations, but on the other hand, nowadays my perspective on operations is that maybe we’re not design operations, we’re just operations, in a way. Experience operations, whatever. Reaching out to more teams outside the design team.

And after our transformation for the design team, I ended up going out, because of our training, we had everything in place, documentation, recordings, process, all the things in place.

Now other teams, these non-technical teams, came to ask us and say, “Can you train our team? Can you train our team?” So our team members, our operators, actually went out and thought more about how to leverage our knowledge to up-level the cross-functional, cross-board, company-wide AI transformation, everything.

So I’m thinking and trying to figure out, do we still use this term design operations, and does it still have a meaning? There might be, but there might be more. Maybe design operations needs to be more of just a higher-level operation. Experience operations.

Nobody should be design-led

Peter: I like the phrasing of experience operations. I’m, I’ve always had issue with the phrase design-led. A lot of companies, 10, 15 years ago were gonna be like, “Let’s be design led.” And that always, even as a design executive, that made me uncomfortable because it was elevating one function over the others.

I don’t want to be engineering led, I don’t want to be product led, I don’t want to be design led. Those are disciplines. N-no discipline should lead. I have always actually liked “experience-led” ’cause that’s an outcome. How are we all working together to achieve an outcome? And so this idea of experience operations resonates well with me.

But I’m curious, we might be getting a bit in the weeds here, but let’s go on that journey. How did your experience in design operations change? Because…

So when I think of design operations, I see two pillars to it. There’s the team operations pillar, right? The internally oriented pillar, career frameworks, and recruiting, hiring practices, and culture stuff that’s really specific to design.

But there’s also always been this program management pillar. When we wrote Org Design for Design Orgs and we wrote about design operations, it was pr- mostly around program management, which was how do designers work with other functions to deliver better experiences, to get back to that word.

And I’m wondering, did, has there been an, a meaningful change in design program management? I understood that role to already have a cross-functional mandate and set of relationships. Maybe I was either wrong and primarily, at least in, in your experience, DPMs were still primarily internally focused, just helping designers do their work.

Or maybe I was right, but there’s still something interestingly different about what it means to be a design program manager in a pre-AI world and now in a, I wouldn’t call it post-AI, but as we’re moving through this transformation.

Z: And AI transformation. Yeah, so I wouldn’t say it’s wrong, but also it was right for the time. What– And also it’s a different perspective.

You’re looking at practically how to structure our organization, right? But if I think about it, I like how this is also… I didn’t invent it, you know, that we sometimes frame design operations as a focus on how we work together, how we get work done, how we articulate impact.

And so if we look from that perspective, then it doesn’t really have to be divided into a people program and a DPM program. It doesn’t have to develop that way.

Say, on our team at the time, I had a small team. I had people focused more on people, and I had people focused a little bit more on maybe just research operations or something like that.

But then they don’t have to be in that vertical anymore. They can come out to help the operator, the operations team, think about how we work together. That’s how we’re changing our tools, changing our ways, changing our process, changing our workflow, all that.

And how we get work done, that’s where we can actually do more of the training, teach people, scaffold people to get these things, to use the new workflow, to use all the new tools.

How we articulate impact, that’s when we transform our team using the new way of working with AI tools. What did we do? And how does that move the needle, how does that impact the customer’s experience? Is it because we’re fixing a bunch of the paper cuts, the retention is better, the call tickets, the, the customer support tickets go down, whatever.

We haven’t gotten that far, but that’s where the measurement will be, how do we articulate impact. So then we don’t have to separate the organization so specifically, that as a TPM, you can only help the program. But as a TPM, you can, oh, or as a DPM, TM, whatever, you can come out and help the transformation as well.

So that’s how I see it.

Let it get chaotic, then rein it in

Jesse: One of the things that I think makes ops such an interesting leverage point for AI transformation is the holistic view that you have, in a way that even design leadership, they can only kind of– they can only see in certain corners at certain depths and so forth.

And this, as a process, it’s become increasingly clear that this is a process of learning as you go, that that every organization has to take this journey of taking stock of themselves and more deeply understanding what’s going on with their processes than maybe they ever have had to do before.

And I think about the feedback loop that is required to keep an AI strategy on track, right? You need to be able to do all the things that you’re saying about get the tools in people’s hands, get the knowledge in people’s hands, continue to educate, bang the drum for the right principles, et cetera.

And then you have to figure out what worked, to your point about articulating impact. But there’s a thing in the middle there which has to do with just taking stock of all of your experiments and understanding where those experiments are going and how that’s actually adding up to something.

So there is almost a a kind of a grassroots strategy element required here, where I’m imagining that you’re the one who is really setting the criteria by which things get bubbled up to the leadership and things become, new ideas become strategic recommendations.

Z: And ideally, yes. And in the past, a lot of that was reactive, right? Because it’s so new. Our– At the time, the org I worked for was pretty much on the far end. We weren’t an AI-native company building AI, but we were pretty close, one step behind, right?

And one thing is that you have to… I almost think you have to let it be a little chaotic first and then see where things land, and then try to rein them in to figure out how we can actually organize the buckets and everything.

So at first, the biggest challenge, again, back in October last year or whatever, was the fear. A lot of the discussion back then, if you think about it, was that it’s replacing our jobs. Are we actually going to, because of that, right? So that was the biggest d- discussion in October.

And the majority of people… I know, Peter, you just did a survey, everything. A lot of people now are moving to… If you look at a bell curve, they’re moving to the middle now. Actually, you see the whole industry is moving just from October to now. But if we were to do a benchmark back in October, the majority of people were in that, “Oh, stay back and let’s see what happens,” and I’m a little afraid, stage.

So when that happens, the biggest challenge for us is to get over that hurdle. So the way that we started was actually letting people just build whatever the heck they want, really, and just build, and then we’ll deal with it. And so we had… The first thing, we didn’t even talk about prototyping or anything, just build.

You can vibe code. And designers loved it because, “Oh, I have a problem. I could never get an engineer to build it. I’ll build something for myself.” And then so we did it, and everyone built that… I did a, a series of vibe-coding trainings. And then in four months, we had 30-some apps spin up within our team. Given that we were a 40-person team at the time, right?

And it was a little bit Wild West, and then people started to find out, oh, we’re building similar things. We’re building contradictory things, maybe, to what other people are building.

And but that’s good, actually, because then we see that, and then we start to think about what’s actually worth building upstream and everything.

And so I think it has two sides, grassroots, and also you need to let it grow a little bit and then see where it lands, and then start to put in some kind of principles to get people back together to keep moving. And I don’t know, I, I just started with a new team, whatever. But that’s the learning I’ve taken, and then go to- getting to a new team and they say, “Okay,” so I start to see we’re definitely far over that curve now, so people are not in that reluctant stage anymore.

Everyone’s getting a little bit more towards the accepting side of everything. But I still see the same thing. Everyone’s building. Everyone’s building their own, and there are really amazing tools now, some really good tools. However, these tools still don’t talk to each other, and there’s no really good function to govern any of these tools that get built, that every individual builds.

And yeah, so that’s a new challenge for me right now.

Roles, labels, and what’s worth keeping

Peter: I wanna rewind a bit and get back to the conversation we had. Something that you wrote about on, in your newsletter that I drew from based on your experience doing the kind of AI transformation work, was on people’s relationship to their roles and who does what in a team.

And I’m bringing this up because I was just in a conversation… Oh, with one of my clients. I, one of my thought partnership clients, and they’re actually going through… It’s funny. They’re go- They’re not even going through the AI transformation yet. They’re going through a simple product operating model transformation. They are that far behind that they’re only now adopting things like product discovery, and how do we work three in a box, and what does it mean to have a product designer as opposed to a separate UX designer and UI designer?

So that’s where they’re at. But obviously, they’re going through this transformation during a time of AI, so there’s going to be a lot of turbulence. And the question they asked me, and I’m… want to ask you, is around roles and role definition and who’s doing design and how many people are doing design.

And let’s say not just design. Design, research, content, that full suite of kind of classic UX practices. And what you witnessed in terms of how practice is done, who’s doing… what’s worth maintaining, if anything, and what’s worth throwing out and trying something new. What was… What have you seen in, in this shift?

Z: That’s a loaded question, isn’t it? To me, and this could be a very radical perspective, and I’m always a little bit on that edge. So to me, the only thing really worth preserving is the agency for people to do what they love to do, and the role specifically, and it could be design, could be engineering, could be PM, the traditional EPD model, and those are just labels.

And so people have their passions. I’m more passionate about designing and about… I also code. I love coding and all that, right? I want to see if there is a way that, instead of thinking, everyone has expertise, but they don’t have to be labeled as a designer, an engineer, or a PM, and their expertise is customer-focused experience.

Their focus can be something like that. And I want to see a world where people have more agency to assemble organically. And so it doesn’t have to be strictly a proportional EPD ratio. You’ve got one designer, one PM, two engineers to build something. What if I have a designer who is an excellent coder, so I could have a design coder, a design engineer, work with the PM on it?

Or it could be something like, I have an engineer, I have, some engineers have an excellent design eye, but their passion is coding, so they can actually lead that maybe with the PM. And then we also have a lot of designers who have excellent business sense. They have been founders, they have run their own agencies, they understand the business so well.

But maybe it’s a designer and engineer formation, so I want to see that organically formed, whatever you call it, squad, po- pod, whatever, to actually focus on the product to build. And but everyone still has expertise. So if I go in with the engineering team, I don’t even try to pretend I’m, that I can code, engineer, anything, but I understand where they’re coming from.

That’s why I see the AI era as excellent, because it gives people certain abilities that they didn’t have before. They always wanted to do it. Maybe there was no time, maybe it wasn’t their top passion or anything. And now designers can come in, do a prototype, code something, and then do it, and then maybe if we train everyone right, maybe that code is good enough to even… for engineers to just take it, polish it up, and then ship it and everything.

We talk a lot about AI-native companies, and they’re shipping so fast. Designers’ code, a lot of the time, gets into the engineering product anyway. I’m less precious about labeling.

And I am a designer. If you ask me, I’ll say, “Okay, I’m rooted as a designer,” or I put that down as my passion. I am always biased towards the design team. That’s my root and everything.

But where I came from, I also saw a lot of the engineering perspective and everything. I worked for a company way back. We did a lot of pairing. I would sit down with my engineer every Friday, just watch them code and everything. So I want to see that more organic way.

And I know that there are a lot of people who said, “No way. How can you take out the discipline, the designer discipline?” And that’s been their whole identity for the past couple of decades and everything. But for me, myself, it’s not… I’m not that precious about that particular label, but I’m more precious about what I’m passionate about, what I can do, and I’m an operator now.

I can label myself an operator, but I’m also a builder. I also could be a strategist or whatever. I’m working on the strategy level or whatever, but it’s about capability.

Battleships, not sailboats

Jesse: Peter and I once ran a company where we didn’t believe in titles and role definition and things like that, and we basically treated our entire group of consultants as a kind of one category in our systems. One thing that came out of that experience was that it made things like performance reviews really challenging because it made it a lot harder to make apples to apples comparisons against some sort of rubric, against some sort of standard of performance or quality.

So everybody’s performance review ended up being tailored to their bespoke set of strengths and accomplishments, and I wonder about the scalability of that. Ob- obviously there’s more than one way to approach this kind of a situation, but I think the, the challenge still remains of having just way too many distinct ways of doing things in order to be able to, again, evaluate what’s even working effectively anymore.

And I wonder how you scale that.

Z: I wish I had it o-on hand. So I was heavily influenced by Corporate Rebels, their way of thinking about a very progressive organization. And then part of the thing is talking about this flat organization style, whatever, right? So you think about designers or engineers or PMs, if you put them all in one bucket, how do we really evaluate performance and everything?

Because what we’ve been trying to label as the craft or whatever, that is one thing we’re being evaluated on, right? So that’s a thing. But it could potentially be more two-dimensional, right? So everyone, you have your strengths, that craft, what… It’s your strengths, whatever, and then you can be evaluated against that.

But there are just other dimensions, how you work with other people, how you push product, how you impact the business, and all the other dimensions. Everyone’s the same. I’m contributing from a design perspective. You might be contributing from an engineering, more engineering, perspective, whatever.

And so we have that little sliver. And then, but the other dimension is everything else, how we actually move the product forward, it could be.

And I don’t think you have one size fits all, but that’s why I’m interested in the organ- in the more progressive organization style to think about.

The team can decide. My pod can decide this is how we’re going to… This is our goal, and this is how we’re going to evaluate at the end, do we, how do we achieve that goal? And the team can decide a little bit. But of course, from a larger organization, you’ve got to think about, again, you’ve got to set the team goal, and then the team can actually organically evaluate themselves in order to reach it.

And it’s hard. I think I wrote that this is the best time for ICs to build stuff. Excellent. This is the hardest time for leaders to lead because it’s really hard to figure out the how now, because there are so many different ways. But I think the most important thing, I don’t remember who talked about this, is that as a leader, you’re the commander of a fleet of battleships. You’re not a commander of little sailboats. So if you let the team build as sailboats, then it’s super challenging. However, if you can run the team as a commander leading a fleet of battleships going in the same direction, they’ll have a better chance of getting everyone moving in the same direction.

But each battleship, they… Their own commander has a lot of decision-making agency.

Peter: So many thoughts.

Z: Yeah.

Ego death, 18 months later

Peter: This, this role conversation and how roles are defined, touches on identity. You mentioned that earlier, right? I am a designer. I went to a design school. I have had the title… I’ve had the word designer in my job title for 15 years. That defines me.

And so I’m curious, so that’s one thing, though. Like, how have you handled the soft, squishy, human kind of aspect of this and helped people through that?

Jesse and I, a year and a half, almost two years ago now it feels like, but at least a year and a half ago, when we first started talking about the phase shift, one of the things, one of the themes was ego death, right?

We’re gonna have to let go of our identities as whatever, designers, because it’s getting in the way of our ability to have impact.

But 18 months later or whatever, people are still attached to those identities.

I’m curious. I’ll limit myself to two questions. I’ve got five, but I’m gonna limit myself to two questions.

I’m curious how you’ve helped people navigate that identity shift, but then, and it’s related how do you recruit and hire, right? What is the title on the job posting when a designer could also be a developer or p- maybe a PM, or it’s one flavor of designer versus another or whatever, right?

One of the benefits of clearly defined roles is you can signal, ” Hey, we need to hire someone with this set of skills,” and this title equals that set of skills. Now, though, when titles and skills are becoming decoupled to some degree, or at least not as tightly bound there’s a very practical challenge of how do I recruit and hire.

So on one side, how are you… how have you brought people along throughout that identity challenge? And on the other side, how are you making sure that the people you’re bringing in are the right folks for the work to be done?

Hiring in the Wild West

Z: Yeah. So let’s talk about the recruiting side first, because that’s the Wild West right now. You can go out and do a search. There are a lot of designer-labeled jobs, sure, but you also see a lot of companies that start with things like member of technical staff, whatever those labels are, right?

And then you have people s- tell… putting out titles I have no clue about now. So it’s challenging for people to look for a job, it’s challenging for companies to hire, and it is really challenging right now, but that is also the Wild West right now.

We are eventually going to figure it out. Honestly, I think for operators, I’m a little bit used to this scene, because for the longest time, design operations had no title, and there were all kinds of descriptions and then trying to figure out what it is. We’re finally just about to have some kind of titles, DPM, design operations, research, finally.

But now that I’m talking about, let’s move this out of order. Let’s talk about other capabilities, right? So I’m a little bit used to this. It is challenging, I have to admit, and a lot of the time even the job description is very challenging. People are going to just throw… It’s a kitchen sink. You gotta be this, you gotta be a designer, you gotta be able to code, you gotta understand design systems, you gotta lead, do strategy, and all these kinds of things. It is a kitchen sink sometimes because they don’t want to forget something, because they don’t know what they really want.

So that being said. But hopefully when people come in to interview, it’s also challenging when people come in to interview if the company doesn’t know what they want and then they go back and forth, it’s super, super draining for the people who are interviewing as well. So these are definitely… I’m not gonna get in depth about the hiring side of the problem.

There are a lot of discussions out there, but the thing is, I talk to the designers. You can still call yourself a designer, you can still call yourself a builder, however you want to call yourself. What is super important on the talent side is that you’ve got to be extremely clear about what you want to be, and then go talk to the company and find out if that’s what they’re really hiring for.

And when I look for jobs, I always look at three things. Whether the company’s values align, the company’s values, that’s like don’t be evil, right? So basic things, that’s something I care a lot about. Another thing is c- about the people on the team and the work that you’re doing. And then another thing is also trying to think about the technology side I want.

I want to be a little bit on the cutting-edge side of the technology. So that frames how I go look for a job. I can look for jobs in design strategy, design operations, business opera- whatever the title, I don’t know, but I’m super clear about what I want. So hopefully designers can form that, I want to work for A, B, C, and then go look for that job, on both sides, to help the company also form a little bit of what they’re hiring for.

And I get it. I really, I personally don’t care about titles, but I’ve been around for a long time, and for entry-level job seekers and everything, titles matter, whatever, right? So take whatever you’re happy with and then go with it. You can redefine it or not, or start to build on top of it, whatever.

And then, but I think, again, I’m always on the side that I care less about the labeling and more about the substance of what it actually is. So…

Peter: You and I care about that, but we’re weirdos.

Z: I agree. I agree. I am. So it… But that helped me and the—helped me a lot in looking for what kind of job I want. I always go into every… So far in the past three jobs I’ve had, I always go in looking for what that job is. Eventually we figure out whatever the title, you can call yourself whatever, right? So it’s figuring out that title.

But I care a lot more about the job I’m going into. And that helped me find jobs as well, because I’m super clear. I’m not… if you ask me, “Oh, what do you want?” And everything is like, “Oh, whatever you have, I will do it,” you will never get anywhere. So I’m super clear. This is what I want to do. Are we aligned?

It’s a, it’s like a marriage. You gotta be a match, right? So I want to match with my job. So this is what I want. Is that… We can go back and forth a little bit, but overall, do we match? If it’s a match, then we go forward, right? But that’s the hiring side. And then talking about how do we talk to the designers right now, right?

So most likely nobody’s gonna change the titles, changing them for the companies that have been around, say all of a sudden we’re gonna change the entire design org to staff of the tech- technical staff or member of technical staff or some… Not likely. But so the deal is, again, caring more about their capability, and you’re a designer, your expertise is customer experience if you’re a UX designer, right?

Your cu- your expertise might be customer experience, everything. But then also what else that designer has actually been really interested in. Some of our designers are more interested in the business perspective, so they actually transitioned themselves into a designer PM, whatever you call them, but they’re actually leading the product and everything.

And so some other designers might be more interested in the technical things. They’re moving to the… So design engineer is even a traditional title, right? It’s been around for a long time. However, they’re moving more towards the design engineer side. So I know I…

You two talked a lot about the design engineer or the strategist. These two ends are taken care of. It’s all the people in the middle. It’s a little bit harder to focus on. But the thing is that these are the people we can actually start to help understand where they want to be. And there might be even new possibilities. Instead of a design PM, a design engineer, could that be a design salesperson?

I don’t know. Go-to-market designer or s- I don’t know. And but it’s, again, going back to that organically formed idea. If this product needs something, can I be the right fit to push that? And I’m still a designer, but what I do might change slightly now.

Design ops as service design

Jesse: I notice that what that asks of the leader on sitting on the hiring side is for them to be, as you put it, much more aware of their own needs, but also to really take on the role of intentional curator of a team, and not just hiring resources because they fit in a box, but rather to be evaluating them.

Like you talked about looking at it as a two-dimensional problem. That it’s not just about craft and skill, but it’s also about organizational compatibility, collaboration, working together and how effectively they can do that. And the conclusion that I’m drawing from this is if I’m a manager, a leader engaged in an active hiring process, I need to be paying a lot more attention to that second dimension of how people work together and form trusting relationships than I’ve ever had to before really.

Z: That’s why design leaders benefit from operations support, because we are always looking at these things, right? So as operators, we’re always looking at the capabilities, how things work together, how do we scale things, how do we move everything together, and as a partner.

Jesse: That touches on something interesting that you said in your newsletter a while back that, that struck me, in which you compared design operations to the practice of service design. And I wonder if you can expand on that idea a little bit. What do you mean by that?

Z: So my thinking has also expanded a lot compared to when I wrote about it. So a lot of the time I say I’m biased, I believe operations is extremely valuable, important, and all that. And also, in reality, I know it’s also a, a luxury a lot of the time for a lot of teams, everything. But I am rooted as a designer, and coming from a service design perspective, maybe not UI.

I was trained as more of a graphic designer, but then evolved into all different things. I had my own business for a long time. And so I really evolved myself into looking at these things. What is the problem at hand, right? So when we started as a design operations discipline, we were trying to solve a problem, a challenge the design team had back then, right?

So that’s how this whole discipline started to form, to become a label and everything. Essentially, we were service designers to the design team at the time, right? So that’s more of our perspective. So w- we are looking at a service design approach to what is the challenge or what’s the problem on ha- on hand for the design leaders.

How can we come in to help the team solve these challenges and everything? That’s exactly service design, and it’s just service design for the design team. But now I even see it more as service design for the product or the org and everything. I’m trying to push really hard to start to lose that design operations label and to be more of an experience operations.

And I think that’s really important. And for us to think about what is the problem at hand now. It’s not… Now, especially with all the AI transformation, it’s no longer just the design team’s problem anymore. Everything the design team does will touch everything else now. And then with AI, it just comes faster.

And then you don’t have that luxury to think, I can go through a double diamond for a year and then figure something out. For many tech companies. So you’ve got to think about, when you move as a team, how that ripples out to all the different teams, everything. And I think the operator, the experience operator, is the best person to see that bigger picture and to service that service.

Peter: It’s a, it’s an analogy or a an alignment that I’ve also seen and experienced as someone who, when I was a more n- normal designer, I was more of a service, I was more of a service designer, right? At Adaptive Path, we were doing, we called it UX, but we realized pretty early on that our UX design approach was a service design approach.

We were looking at the broader organ- organizational systems of the, our clients and in order to better understand their ability to deliver these experiences, right? And so that required a service design mindset. And then when I became an executive and I needed to start thinking about shaping my team. Two things.

One, I would adopt a service design mindset in terms of thinking about, like, how do I, how can I use a journey model to organize design? ‘Cause I think that is m- more responsive to the needs of our users. But then to your point, when you start getting into a systems mindset, you’re looking at your team as an organism and how do you operate effectively?

Everyone says they care about quality

And this kind of starts to dovetail to something you’ve been writing about more recently, which is the relationship between operations, and I’m gonna continue to use your term experience operations, to the relationship between experience operations and quality. One of the biggest concerns that you hear from designers is that because of speed, because of ease of access, more stuff is being made and it’s broadly mediocre.

This is borne out in research, Figma’s research, Lenny’s research. They’re like, “Yes, people are going faster, but no one is happy with actually the quality of what is being produced.” Everyone feels supercharged, but then when they reflect on what they’ve made, everyone’s “Eh, this is crappy.” Or it’s not bad necessarily, but it’s it’s not getting any better.

I’m curious, you’ve been writing about this a bunch, so I, I’m not gonna ask you to repeat everything that you’ve written. But as you think about this responsibility, maybe that experience operations has in helping establish quality bars, quality rubrics, w- how do you approach that?

What do you make of it? Yeah.

Z: So speed and quality, a lot of the time we see them at two ends of that spectrum. But I don’t like to see it that way, actually. And part of things that… Ask a designer, “Do you care about the quality of the product?” Not just the design, just the product.

The answer is 100%, absolutely, right? So you go ask any CEO, “Do you care about the quality of your product?” You’re getting 100% the answer, “Absolutely. I care about the customer, I care about their experience, and of course, I care about the profit and the business as well, but I also care about the business and the quality of the product.”

So that’s actually aligned. As an engineer, do you care about the product? They care from the code perspective, about the product and everything. Everyone cares. So if I, as a designer, go out and say, “Hey, engineer, you just shipped something. This looks so crappy. It’s bad quality and design.” Is it true? Yes. But have we ever articulated to the engineer what is good? We probably never actually spent that time to go out and tell the engineer, “This is why we care, and this is what is not quite right, why it matters.” We never spent that time.

Peter: I know it while, when I feel it, Z. I, I it’s… I just feel it.

Z: Okay, so how do you feel it, why do you feel it that way, and is it because the color is wrong? Is it because the experience is jarring? Is it… I can ask you that, right? So it’s teaching people that you feel it, and how you feel it, and why you feel it, and that’s important, I think.

And same thing, an engineer can teach us about code, why my code is crappy code, they can tell me, right? So I will learn in that process and everything.

I also wrote a lot pushing on this, sp- speed is really not the enemy, but it’s really for us, if we can, not hold this design craft just to ourselves as a moat, but really think about it. The best thing is, 20 years ago, fewer businesses were talking about design thinking, and now you think about business, they understand, at least they understand the idea of design thinking, understand that focusing on the customer results in good business or whatever.

At least that is actually progress. We might say, oh, we’re rolling back or everything, but it’s a spiral. We’re actually moving towards a better position. So I talk about how I want to see design maybe as a discipline eventually dissolve or everything, but design thinking become more of a human nature. Everyone, whether you’re a PM, whether you’re a designer, whether you’re an engineer, business, or sales, you’ll care about this design thinking approach at least.

So that also, I think a designer… Now it’s the best time for designers because we understand, we can deal with ambiguity, and we understand the design thinking approach, we understand the customer, and if we can learn more, I think for designers to understand the business and everything, this is the best time for designers.

Peter: Let me just do a quick follow-up. My question might, is quick. Z’s answer might be long. So we need to articulate standards of quality. We have to go beyond feeling to what leads to that feeling. What is the role of experience operations in that conversation?

Z: Build in layers of quality control. One, what can be automated, what has to have a human involved? So from an operator’s perspective, and right now in my- in my new role I’m working closely with the folks who are talking about QA and everything, I ask a lot about what can actually be built into the system so that it makes, creates a condition where doing good design is actually easier than doing bad design.

And for non-designers, that’s one, from an operator’s per- perspective. Another thing is that if this layer didn’t catch all that, then that needs to come to the human, and then we designers can come in to do the human check, can do the human education to talk about it and everything. So that’s the operations perspective, to build this system to make doing good design easier than doing bad design.

Beyond the language model

Jesse: So as that perspective continues to evolve with new technology, I’m curious about what for you is the biggest unanswered question that you’re curious about the future of your own practices in design or experience operations?

Z: I, again, do not hold this particular label or anything that dear to my heart, in a way. I’m passionate about it, but on the other hand, if you look at my career trajectory, it’s always different, slightly different. It’s not a straight line. And I think all that experience coming in helped make me how I operate these days.

And so what I’m curious about is really, I honestly think this is the best time. AI gave us a lot of capability and everything, but right now we’re actually stuck in this language model. And I’m looking forward to seeing a spatial model and everything, other kinds of AI.

And I want to see all these new technologies, how that eventually will actually impact humans and human progress, and it doesn’t have to be about being an operator anymore, it’s just more the grand scheme of life, right? So how that can really absolutely enhance our experience to be more human and to do the– to make those decisions only humans can make, and come up with those ideas that actually progress the human race and everything.

I’m looking forward to that, and I’m curious where that goes, because I truly don’t believe we are going to be s- stuck with just language models forever.

Jesse: Z, thank you so much for being with us.

Z: Of course. Glad to be here.

Jesse: Where can people find you on the internet if they wanna learn more about you and your thinking?

Z: LinkedIn is the best place to find me, to get in touch at a high level, and I write a lot d- on my Substack and everything, so we can share the links. And those are the two places to find me easily.

Peter: Got it .

Jesse: All right, fantastic. Thank you so much.

Peter: Yes. Thank you.

Z: Thank you for having me.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Show Notes

In this episode, Peter and Jesse compare notes from Config, Figma’s AI study, Lenny’s newsletter survey, and countless conversations to read the current state of design leadership. The signals: existential AI panic has cooled into exhaustion, organizational chaos and leadership churn are the new normal, and design still stumbles on business acumen. Their case for thriving—lead, don’t just design, and reclaim design’s unfinished mandate.

For more from Jesse James Garrett, including his AI transformation practice: https://jessejamesgarrett.com/

For more from Peter Merholz, including his newsletter, his consulting, and thought partnership: https://petermerholz.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, Peter and I are listening to signals of the current state of design leadership. We’ll get into what we heard in our recent conversations with design leaders at events such as Config in San Francisco, and what recent research studies from Figma and Lenny’s newsletter reveal about the emotional toll of the current environment on leaders and teams.

Plus, we’ll explore what leaders can do to keep the promise of design’s value alive with the rise of AI.

Peter: I wanna start with this question.

Jesse: Okay

Peter: Have you seen the movie Backrooms?

Jesse: I have not seen the movie Backrooms, Peter.

Peter: I finally saw it four or five weeks after it was released, and it is easily the most interesting thing happening in cinema right now. Full stop, end of story. If you like movies, you need to see Backrooms. If you think it’s a horror movie, it’s not. If you don’t like horror movies, don’t worry about it.

Go see Backrooms.

Jesse: Okay. All right, thanks

Peter: I haven’t walked out of a movie kind of excited about the form in a very long

Jesse: Cinema yeah.

Peter: In cinema. No, for real. But what’s on your mind, Jesse?

Jesse: Well, you know You know, here on this podcast, Peter and I, we’re like the great psychologist Fraser Crane. We’re always listening. And we’ve been listening a lot over the last six, eight weeks, since the last time we recorded this podcast.

We’ve been listening to the signals out there. We’ve been having conversations with folks. We’ve been together at a couple of events. We’ve been taking in what’s going on, and there’s enough going on out there that I thought it would be worth us getting together and talking about our reactions to some of the signals that we’ve been seeing out there.

So, for example, you and I were at Config, the largest design event in the world now, it’s gotta be, in San Francisco just a couple of weeks ago in June. Had a chance to talk with a lot of different design leaders about their challenges and about what they were seeing, and of course, all of us were trying to read the tea leaves of Figma’s product strategy and what that meant for design teams and what they were maybe seeing about where all of this is going.

They published the results of their latest survey of design practitioners and design leaders about the state of AI in their practices and had some interesting insights and reflections based on that.

Config 2026: from existential dread to exhaustion

Jesse: But I’m curious about what stood out for you. Let’s just start with Config. I mean, there’s been a bunch going on, but let’s just start with Config. What stood out for you about the conversations that we had and the experiences and the ideas that were in play in that gigantic gathering of 10,000 designers in San Francisco?

Peter: What stood out from Config specifically for me was that AI was no longer seemingly an existential concern for design and design leaders the way it had been in the prior two Configs.

It was two Configs ago when Figma was like, “We’re about product people,” and didn’t really mention design much. And designers started freaking out that they were about to be replaced by AI. I mean, yeah, so that was

Jesse: Or simply product managers.

Peter: Or product managers…

Jesse: You decide which fate is worse.

Peter: Sure. And then in 2025, Figma said, “Psych, we love design. Design is great. Here’s a bunch of tools for designers,” and that’s when they launched Figma Make as well.

But the conversations I had last year were deeply existential, It was around that time last year that you and I started really hammering away on the kind of liminal concepts and the phase shift concepts and all that kind of stuff coming out of this dialogue that was occurring.

This year it feels like folks have settled in. This AI stuff is real. They’re still figuring out what to make of it, but it’s real. It’s not going away, but it’s also not causing the kind of existential crisis it had before. It’s a tool. It’s a means to do their work.

And yeah, so folks were far less hair on fire than they had been the prior two years.

But what’s replaced that or what, has emerged, I think, as the dominant sentiment is they’re just tired. Everybody is fucking tired. Everybody is exhausted.

I think a big reason they’re tired is that all this new stuff has simply been layered on top of whatever their existing job had been. And so folks are just expected to do more. Even though the promise of this new stuff is that you don’t have to do as much ’cause the machine does it, instead, the reality, at least right now, is, perhaps while people are figuring it out, it’s like you have to do your old job, which already maxed you out.

You were probably already at

Jesse: least…

Exactly. Everybody was already plenty busy.

Peter: Yeah. Yeah, you were already maxed out, and now we’ve just layered on this new thing you have to figure out, and we’re pretty much giving you very little guidance about that.

So that’s my primary takeaway from Config. I honestly could care less about Figma and its product suite and whatever that indicates. I don’t think that’s nearly as much of a bellwether or harbinger as maybe it used to be.

But yeah. The sentiment curve has shifted from fright to just tired.

Jesse: Mm-hmm. Mm-hmm. Yeah, I think it’s interesting to note, first of all, the emotional tenor, I think the optimism is there, but it is I think somewhat muted relative to previous years. The people who are optimistic are a little more cautiously optimistic. It’s like the two sides are kind of meeting in the middle a little bit, that the skeptics are learning to appreciate a bit of what the technology can do and where it’s going, and the optimists have maybe had their irrational exuberance tempered a touch by the intervening year.

But I think that one of the things, and we touched on this in the Liminal conversations as well, one of the things that is a recurring theme for these leaders is the emotional resilience required to continue to manage ongoing change, and the fact that none of this is gonna be settled soon.

And in fact, the new steady state is an extreme unsteadiness for a lot of leaders in a lot of organizations. And in some cases, I feel like people, what they’re honestly looking for is something to anchor to that’s proving hard to find.

Corporate chaos and the broken job market

Peter: And I think it will continue to be hard to find for a while. Earlier today there was a post on LinkedIn that I ended up reposting with a bit of commentary. I forget the name of the woman who wrote it, but she was talking about her job hunt journey.

She’d been… I don’t know if she’d just quit or been laid off in January. It is now June or July, she’s starting a new job. And she had statistics to go with her job hunt experience. Within those statistics was, she got through all rounds with 10 different companies, right? Which is a strong signal at least when I run recruiting and hiring. If you make it through that round, you’ve got a one in three or one in four chance usually, right? There’s not many candidates get that far.

So 10 companies, she made it through all rounds. But then after getting to that point, she pointed out with four of those companies, something went haywire. The hiring manager quit or got fired, there was a reorg, there was layoffs, there’s something organizational occurring in 4 out of the 10 companies.

So these are companies that thought they were stable enough to go through a recruiting and hiring process, get through, I’m sure, multiple candidates through many rounds, and oh, and then at that point it turned out they weren’t that stable.

Some organizational chaos occurred and the job just disappeared, right? The requisition disappeared.

And what that to me was a sign of, or is a sign of, it’s anecdata, but, I’m seeing other indicators, and it goes with the exhaustion thing, is that companies have lost their collective minds right now. The degree of instability within corporations, I mean, it’s been high for a while, and it seems higher now.

When you talk about listening and signals, like one of the signals I’m getting is just a greater degree of uncertainty. It’s not necessarily layoffs, although that’s part of it. You and I have had friends recently who just found themselves without a job in the last few weeks that…

Jesse: mm-hmm.

Peter: At large, massive, otherwise seemingly very stable companies.

Jesse: Stable-looking. Yeah.

Peter: Yeah. And it’s just like, the analogy that just came to mind is, we’re all on a ship.

That ship is just rocking, and we’re all just holding on to the ship for dear life as waves are coming overboard, and we’re just trying to make our way through this period until the seas calm down.

Jesse: Trying not to get too sick over the rails.

Peter: Well, yeah.

Jesse: Yeah. Well, I think that, and you touched on some of these teams that have been really decimated in the last year, design teams out there that have been for whatever reason, one reason or another, they ran out of runway before they could get aloft and what these teams are facing now is, in some of these cases, you have these teams that have been so severely cut back that they have to renegotiate their mandates because they can’t keep doing what they were being asked to do before under these new structures. And the leaders are in the position of having to do that renegotiation of the value prop of their team, right? Of what we’re here to do and what we’re here to be measured for and what you can look to us to provide.

The organizational and cultural shifts are as, at least as radical as the technological and process shifts.

Leadership turnover and its ripple effects

Peter: Well, y- yes, and I don’t think it’s necessarily just a matter of cutting back, though that’s definitely happening. So I conducted a listening tour, or I’ve been conducting a listening tour of design executives. It was something I was doing in May before I went out on a family vacation.

And I talked to about 20 design executives. I’m still poring over the data. But something that was intriguing to me is of those 20 design executives, three or four were between jobs. Like I hadn’t realized when I’d reach out to them they weren’t working.

But they hadn’t been laid off because of reduction. Each of them wasn’t working because there had been a leadership change in their organization, and the new leader didn’t want them in the org. Which, kind of, again, is speaking to a certain organizational chaos. The senior leadership are encouraging change within design organizations that involves just getting rid of current leaders.

Not the whole team, just like, “That person doesn’t belong here anymore.” And sometimes it’s a new leader wanting to put their people in place. I just had something outside of the listening tour, but a friend just got fired really, not even laid off, because a new CTO is like, ” We’re gonna do things different now.”

And I think as part of this chaos, something I believe is at the highest levels of a lot of these organizations, there is leadership turnover right, in the C-suite or just below.

Jesse: Mm-hmm.

Peter: That seems to be happening more often in the last year or two, and what we’re seeing is the impacts of that, the ripple effects of that within design.

It might take three, six, nine, 12 months to finally get to design, depending on the size of the company. One firm that you and I are familiar with, had 50,000 employees, so it took a good nine months between the new CEO…

Jesse: yep.

Peter: …And the leadership shift. But in most of the cases I’m aware of, it’s not about reduction, it’s just about turnover, and, on the part of these senior-most leaders, a total disregard for the turmoil they are causing.

Jesse: Hmm. Mm-hmm.

Peter: Just disregard, disinterest. You’d think you’d want some degree of stability so that the business can do its work well, and there’s absolutely no interest in that from what I’m witnessing.

Jesse: Yeah. Well, it’s interesting to think about just the sheer number of people who have some qualifications for leadership or management roles in a digital product development or design organization who have been turned out on the market in the last couple of years, which has really made it a buyer’s market, so to speak, when it comes to especially middle management.

So, I’m seeing the same pattern that you’re describing of these wholesale leadership turnovers. You get a new CTO brings in a new CPO brings in a new VP of design, and the ripple effect goes all the way down. And just by virtue of having been in the organization a while, you become perceived as a liability to the new order, so to speak.

And so for leaders, it then becomes this politics game of proving in that nine months, that you deserve to stick around.

Peter: You used the word order.

Jesse: I know, and you’ve been talking about chaos.

Maybe executives are just bad at their jobs?

Peter: Well, and I think concomitant with this upheaval is, at least for me, an increased recognition that the people running these companies, that m- many, I don’t know about most, executives are just bad at their jobs.

They’re not accountable, right?

They’ve had– they wouldn’t be in that role if they hadn’t had some success. I tend to, in private conversations with folks, just disregard this class of executives as dumb or stupid and that’s probably overstating it ’cause, again, they probably would not get into that role if they were categorically dumb. If they were just dumb. They clearly knew something, figured something out, got into a position of authority and influence.

I suspect their wisdom is very narrow, though, and now they’re in this broad– they have the much broader mandate, and they’re trying to apply this wisdom from their narrow point of view to the broader mandate, and that’s where the stupidity is.

And as I continue to reflect on that, design was probably never in whatever that narrow band was.

Jesse: No, it never was. Yeah.

Peter: And so the moment it expands to include anything that might include design, design will not be treated well because those executives, like we saw with Cloudflare where once the design system was put in an LLM, the CEO’s like, “We don’t need designers anymore.”

Because he’s an engineer, and he just sees the world as, like, a machine you fiddle with or salespeople to sell it, and has no understanding of kind of the actual value that design was delivering, ’cause the only sense of value he perceived was the creation of assets or screens for engineers.

Jesse: Yeah. Yeah. So again, it comes back to the value the design is delivering, the way that value is perceived, and whether it’s your AI transformation strategy or how you manage the politics of this kind of organizational change, it’s on the design leader to keep their eye on what that value prop is.

Peter: Well, and to figure out how to communicate it in a way that resonates with, hopefully, people who are listening. Something I wonder, you said earlier that this is this new kind of unsteady state.

Jesse: Yeah

Peter: I was about to call it a steady state, just meaning we’re gonna be in this state for a while, but that state is…

one steady state of unsteadiness, yeah

of unsteadiness, yeah.

This is something I’ve found myself thinking about potentially developing some training material around which is, what can design leaders do to

maintain resilience and even ideally not just maintain, but thrive in this discombobulated mode. I’m wondering where your thoughts go.

Jesse: Yeah, no, I think you’re right to call that out. I had a client a while ago who went through another performance review and said to me, “Look, I’m tired of being called out for my resilience. I’m tired of my brand being my ability to take a bunch of hard shit and stay standing. I’d like for this career to mean something more than that to me.”

And I think that’s right on. And in, again, going back to the liminal conversations, those explorations, I think were about trying to figure out, well, what is the skill set that allows you to remain upright and not be knocked about as much? But I do think also that thriving means taking control of the narrative. I think thriving means taking control of your destiny.

In a lot of organizations, the constraints are so severe that becomes practically impossible for leaders. And, it almost goes back to the leadership ceiling kind of stuff, like where can you actually move your constraints or influence your constraints to create new opportunities for yourself and for your team?

Lenny’s survey: chaos is the new normal

Jesse: A lot of this stuff also resonates with the survey that was released a couple of days ago through Lenny Rachitsky’s newsletter. And I’ve forgotten the name of the researcher who conducted the study, but

Peter: Noam Segal.

Jesse: All right. So Noam, thank you for your work. It’s very interesting stuff.

What came out of this, especially as it connects with some of the things that have already come up in this conversation, one of their findings is that the current norm is chaos, that across the board people are reporting just organizational disarray broadly.

And they don’t do a lot to try to identify root causes for that, but it definitely is one of the big patterns that came out in their study.

So they talked to I think close to 6,000 self-reporting, subscribers to Lenny’s newsletter who volunteered to take the survey. The other thing, aside from the chaos, actually this was a finding from Andrew Hogan’s work for Figma as well in their AI study, which was that there is no one central kind of experience that people are having right now.

Everybody’s experiences are all over the map. It’s like I was saying about AI transformation a couple of episodes back. Every path through this wilderness is different because every organization is starting from a different starting point with different resources and different cultural advantages and liabilities that determine how steep the climb is through all of this stuff for people.

Peter: Yeah. In a pre-AI world, things had settled into a few different archetypes of organizations, at least with respect to their relationship to design. Think about your maturity model or something, right? And it’s got three or four stages and where you fit in that.

I’m doing a bit of just follow-on research. I launched a pulse check survey specifically for designers to get a sense of how they’re feeling.

And after 100-some results what’s interesting is a similar story, which is there’s no narrative. There’s no theme. It’s scattered. My listening tour revealed that as well with the 20 executives that I spoke with. And I guess that’s part of being in this moment.

One has to imagine shit’s gonna settle down. But It’s interesting to me that as things become less existential, I would think we’re starting to approach this with a more pragmatic point of view, right? As opposed to a hair on fire point of view. You would expect the settling to start, but it’s not.

So I’ve got Lenny’s thing up here, and there’s a chart showing that from 2025 to 2026, burnout increased by 20%.

Jesse: Mm-hmm.

Peter: And optimism decreased by about 10%. And so even though we’re kinda getting our hands around this, we’re not feeling any better about it.

It’s not getting us into a calmer mode. It’s also weird, though, he had this question about how much better are you at your job? And about half of the respondents said very much or extremely better. Now, I would love to see that cross-tabbed with different functions.

I’d be curious what percentage of designers would say that. I mean, engineers, yes, I’m sure they consider themselves largely better at their job. But I still suspect a lot of designers would say that they are feeling very much to extremely better at doing their own work, if they can just put a little boundary around that.

But also recognize that, yes, I can do my thing better, but the space in which I’m operating,

Jesse: But the rest of you

Peter: is not.

“More work, same pay” and the employer’s market

Jesse: Can’t be trusted. Yeah. It’s interesting to think that people can more readily feel optimistic about the individual scale impact, but when that starts to add up to an organizational scale impact, then they get nervous about it.

One of the things in Noam’s survey was the notion of What are you afraid is gonna happen with AI? And people are not afraid of losing their jobs. They’re afraid of having more work piled on their plates. To your point, they were already busy before this stuff came along, and more than half of the people in the survey said that their worry, the top of their list, was: expected to do more work for the same pay.

So the sense is that the executives and management are just going to continue to increase this pressure on teams to be productive and to perform. Again, which is why for managers and for leaders I think you’ve gotta get really clear on the value that your team is delivering and making sure that you’re optimizing for that.

Peter: Well, and this is an expression of executives taking advantage of what they see as an employer’s market, right? When it was an employee’s market, you get a bunch of glorious perks. You get massage and free lunches and all this other stuff. Plenty of vacation time and all that.

But when it’s a employer’s market, at least in the United States where we are without any meaningful employee protections, yeah, they’re just gonna keep piling stuff on you, and if you can’t do it, they’ll fire you and see if they can find someone else who will do it.

Jesse: Yeah.

Peter: And they’ll find someone who will raise their hand to do it ’cause there’s a bunch of people out there who need work.

Jesse: Mm-hmm.

Peter: I don’t quite know what the solve is for that besides unionizing or uh, some other form of collective bargaining. But that’s not actually u- unions won’t aid many, most of the people who listen to this podcast ’cause they wouldn’t be in a union because they’re management.

Jesse: So what is, do you think, the impact for people who are in management or leadership roles here? So if, and this is another finding from Noam’s study, the burnout is becoming sort of the dominant place where people find themselves in this industry, as leaders, we have to take responsibility for that. We have to take ownership of that in some way, even if we ourselves are also feeling it.

Why design and research are the lowest rated career recommendations

Peter: Related to that, and if we wanna talk more specifically to our podcast audience, in answer of the question: How likely are you to recommend a career in your role to a friend starting out today? Far and away the lowest scores were design and research. Everything was actually below zero, so no one– on average, no one would be recommending a role in tech to a friend, which holy shit.

But design and research is far and away the lowest.

Which also actually pairs with another finding in here, about the value of management and managers and how manager effectiveness was correlated to burnout and job enjoyment. And so people who felt their managers were extremely effective rated four out of five on job enjoyment and well below the average on burnout.

But and then there’s a note, there’s not specifics, the worst rated managers cluster in data/analytics and design.

Yep. And so, there is a need for our peers, many of the people listening to this podcast. Though probably if you listen to this podcast, you’re a little ahead of the curve.

Jesse: We hope so.

The craft trap and the business-acumen gap

Peter: We hope so. But, we’re not doing our job. Why are design managers the worst rated, right? What is it that they’re doing or not doing, causing their teams to feel ineffective and burned out and hate their jobs, right?

I could speculate but regardless of the speculation, it’s easy for designers to point fingers at others in situations like this, but I actually go back to part of the reason I wanted to write Org Design for Design Orgs a decade ago was because I saw designers pointing their fingers at all these other people about why their team was not as effective as it could be.

Product isn’t doing this, and engineering isn’t doing that, and leaders don’t understand us. All of which might be true, but if I looked at almost any design org in 2015, they were poorly run.

The person in charge didn’t know what they were doing. They didn’t know how to set up a team, an organization, a structure.

Jesse: Yeah

Peter: Yeah, so I wrote the fucking book to, like, here’s a playbook to, like get out of your own way so that at least you could then credibly start complaining when others aren’t doing their job, or when their behavior is affecting your team’s ability to perform.

I suspect though that, a decade or so later, that most design orgs are still just poorly run entities because the people in charge don’t know how to do it.

Jesse: Yes and, maybe this is too charitable a stance, I don’t know. A lot of design leadership roles are not set up for success. They’re reporting to the wrong people. They are supported in the wrong ways. They are granted the wrong scope of authority to actually deliver on what they are on the hook for. So I think it is important to separate incompetent managers from poorly constructed management as a system in an organization.

Peter: I have research that would support some of what you’re saying. But, part of me would want to be able to control for those factors with other functions, right? Does, engineering perform better or whatever because it’s in the right place in the organization or given the right mandate? Marketing, sales?

Marketing and sales is actually funny in this report because there’s a section in the report around, different functions in their relationship to whether they are destabilized or diminished, tired, overwhelmed, anxious, worried about losing their job, or would recommend to others. And what I thought was super interesting about that was that sales and marketing folks, would do things like, they would score badly on things like being tired.

They’re more tired than most other functions. Salespeople are more overwhelmed than most other functions. But sales and marketing folks were also the least anxious and the least worried about losing their jobs. Oh, and the least destabilized in their role, they felt like they’re just continuing to do their work.

And so I thought it was super interesting and so it was design, research, engineering, operations, PM, data, sales, marketing, and whether or not you were a founder. Sales and marketing are the two functions that are not specific to tech…

Jesse: mm-hmm.

Peter: That have been in businesses for 180 years or whatever.

Jesse: There are a million, billion businesses out there that do nothing with tech that have still got those functions. Sure.

Peter: Not only that, but 130 years ago when General Motors or whatever, railroad or Procter & Gamble or whatever company is, starting, like they know they need sales and marketing. So there’s a longevity there as well that seems to be allowing these folks to be less anxious and worried regardless of if they feel like they’re tired or overwhelmed.

And so part of it is likely due to the newness, right? Of all the functions, this is something I beat on. Of all the functions, particularly that have gotten some degree of first-level recognition within an organization in design and research it’s spotty, but it’s there. Design is the newest.

Design and Research

Jesse: Yes.

Peter: are the newest.

And so I think part of it is we’re still figuring out where we belong. We’re still figuring out what our mandate is. We’re still figuring out our value proposition, both ourselves and communicating it to others.

Which then leads to another contention that I continue to have, which is that design leadership is the hardest of the leaderships because of this. I occasionally get pushback on that, but there’s mounting evidence to support my contention.

But the design leaders are also just perfectly willing to shoot themselves in the foot and wallow in their ineffectiveness by not shutting up about craft, right? Like, lauded, elevated, vaunted members of our practice, their primary message is the importance of craft when literally no one else in their organization cares about that stuff.

And it’s fine. Craft matters. We all know that it matters. But if you as a design manager are spending most of your effort on ensuring craft within your organization and not effectiveness, right? The word that they used in this research was effectiveness. ” Not effectiveness” as a manager. And effectiveness I would expect it to mean, if you’re asking if a manager’s effective are they able to have an impact and get things done and move things forward or whatever, right?

Jesse: Mm-hmm.

Peter: Craft is interesting only to the degree to which it drives impact. But designers are really bad at caring about impact and caring about being effective, right?

And that’s where I … It doesn’t matter where they are in their organization, who they’re reporting to, or whether or not they’re set up to succeed. There’s still this mentality that many design leaders and design managers have that their job is not one of effectiveness and impact. And then they get dinged in surveys like this.

Jesse: So if I think about where the leverage point is on this topic it seems to me that it has to do with the tone that is set by design leaders, the culture that they create, and honestly what they hire for.

In that if you as a design leader have put in place a bunch of senior practitioners who are all craft-forward ICs, and that’s all you ever hear those guys talk about, you’re creating an environment in which these are the ideas that we care about, these are the ideas that get reinforced, these are the conversations that we have about design on an ongoing basis.

And it seems to me that to break out of the craft trap, the manager has to consciously, deliberately, intentionally drive a different kind of dialogue within the design team itself about what they’re doing and why.

Peter: I think that’s right. Some of this goes back to my mediate the membrane concept, right? Where the work of design is just so different from the work of the rest of the firm that designers are part of, and the role of design leaders is to serve as this interface between the two. And part of that is communicating to the design team the importance of understanding the business context in which they’re operating, ’cause that is how you become effective.

And vice versa, communicating to the rest of the company the distinct practices and value that design can deliver. We talk about not just clarifying a value proposition, but expanding that value proposition.

Jesse: Yes.

Peter: There’s work that the design team could and should be doing that’s likely not happening, that the design leaders need to articulate in some way that it will resonate with those folks outside of that design org.

And, that takes work to figure out how to land those messages. I had an interesting conversation this morning related to this. So I’ve been teaching a masterclass through IF Design Academy, the class wrapped up, so we were having a wrap-up conversation, and then we were talking about the most popular other class in the academy, which is on hold, hold… business and design.

The class that people are most interested in taking is basically an MBA 101 class. And it is far and away the most popular class because all these design leaders are like, “I need to understand business.”

The first thing that Garan does in his class is say, ” We are never going to talk about the business value of design. We are not gonna talk about clarifying the value of design. No one in the business cares. I am going to teach you about business. I’m going to assume that you’re like a, an MBA student, and you’re here to learn how business works, and that is what I’m going to teach you. Afterwards, you can figure out how to take what I have taught you and make it relevant to your world, but we are not here for you to justify or validate or whatever the business value of design because no one cares.”

And as this was being explained to me, I was reflecting on it. I’m like, ” Yeah, like, everyone else in the business understands that calculus…

Jesse: right

Peter: …except for designers.”

Jesse: Yeah

Peter: They all are just running spreadsheets and making, doing math or whatever the thing is to communicate in the language of the business. And designers just can’t get over themselves enough to just do that, to shut up about design for a while and just take part in that conversation.

Jesse: It’s so interesting how this stuff just keeps coming back to fundamentals. The fundamentals of politics and managing those relationships with your executive stakeholders as well as your cross-functional partners. The fundamentals of business and design and spreadsheets and all of that stuff.

Peter: As this was being shared with me, I was reflecting how 25 years ago, almost to the day or something, right, Adaptive Path published a report on ROI and design, right? And we talked about ARR, and we talked about NPV, and we talked about all this shit. And I’m just like,

Jesse: What’s

Peter: why isn’t it sticking, and why do design leaders continue to say that this is the most important thing for them to learn, say that this is the lacuna in their practice?

I heard that on my listening tour as well when I asked folks how they could be a better leader. Almost half of them said basic business acumen.

Jesse: Yeah

Peter: One, it’s not that hard. The heart of business is the simplest, dumbest math.

And it’s not like it’s been a secret for the last 25 years, much less, just, you’re in a business, of course, you should understand how business works.

It’s mystifying how there’s something about this subject that is just…

The image I have in my mind is designers look at this subject, and it’s as if they’re looking through a clear glass window, but then the glass turns opaque, and they’re just like, “Doop.” Just poof. Nope.

Jesse: Yeah, I gotta wonder about, I mean, first of all, I think it’s important to look at Noam’s study with, a bit of a grain of salt in that again, these are people who self-responded, people who were subscribers to Lenny’s newsletter. Design and research together only make up a little over 10% of total respondents to the survey.

Product management nearly closing in on 50%, 46.9. So nearly half the people who responded to this survey are coming from an entirely different perspective. In fact, almost everybody who responded to this survey is coming from a different perspective than the perspective of design and research.

And I would say the other thing is that it skews really senior because of his newsletter and its audience. So he’s got uh, right around 11% are people in design and research functions, and right around 11% are also people who are founders or, senior level executives. So, the founder class is as represented as the designer class in this data and it skews accordingly.

I thought this finding was hilarious that founders are the happiest ones in technology, ’cause I’m like, ” No shit, man. When has that not been the case?”

Peter: Well, yeah and the implication I would argue is that things would skew even more negative if these populations were normalized. And when they do slice it by these populations, you see that negativity shine through. ‘Cause I still think even though it’s only 10%, if you combine design and research, 10% of nearly 6,000 is still 600, right?

So that’s a decent population. I’m– I feel good about the signal he’s getting about design and research more than I would say about data and analytics at 3%,

Jesse: Yeah. Well, all I’m saying is that when he’s not talking about design research specifically, that data we ought to be looking at through more of a product lens, because those are the people who are responding. Yeah.

Unfinished: reclaiming the broader mandate

Peter: So something else I wanted to bring up, which kind of touches back on our podcast miniseries, Liminal, and our friends Jorge Arango and Greg Petroff, who have a business called Unfinishe. Because So I’m helping prepare or program the Design Leadership Summit in November, taking place in Toronto.

And as Preet, who is the primary organizer for the event, and I have been talking about the programming, we were batting around thoughts on theme.

And the theme that we are landing on is this one of unfinished. For me, it all started with our conversation with Roger Martin, and trying to figure out what happened after 2009 when there seemed to be this opportunity for design to be more expansive, to have that broader value proposition.

And then over time, that just narrowed and narrowed until starting around 2015, 2016, and we adopted product designer as our primary mode, and that was seen as someone who produces screens. And the AI moment has really highlighted that limitation, but also an opportunity, to recast our value proposition.

And as I’ve been thinking about that, I’m like, I feel a little bit like Jack from Lost. “We gotta go back.”

Jesse: Spoilers

Peter: Sure, for a 20-year-old television show.

And, go back to that period of fecundity and hope and potential that we were scratching at in 2006, ‘7, ‘8, and ‘9. And embrace that broader mandate.

And I’m hearing and I’m seeing some signals to that. Something I didn’t mention coming out of Config not a big thread, but a persistent thread, and I hadn’t only heard it at Config, is the rise of service design. Is this something that you’re hearing?

Jesse: A bit, yeah. Yeah. I mean, there’s definitely, I think, an increased interest and awareness of the value of it, if not necessarily… You know, the investment is always gonna lag that. But I definitely had more than one conversation with design leaders about service design at Config, and in the last several months it’s been coming up more.

Peter: Yeah, I’ve been surprised by that, and I think there’s just something about the overwhelming complexity that,

Jesse: I think

Peter: everyone is facing.

Jesse: Everybody needs more context in order to make better decisions, and if that context is something that can be incorporated into some of these AI-driven workflows, then that’s an advantage.

You know, my hope is that there’s mountains of good, valid service design work out there that’s currently languishing in PDFs on various shared drives that can be potentially unleashed here.

Peter: Going back to this theme of unfinished. So not just that we need to go back to 2008 and pick up that thread, though that’s part of it.

But this recognition that to a certain degree, design is always unfinished. I’ll read here some language that I came up with.

Design’s work is never done. You wanna treat design not as a fixed function, but ongoing infrastructure. The work of design is, if we get to Herbert Simon-land is to improve conditions. To be a designer is to always improve, and if you’re always improving, you’re never done, right? You’re never finished.

If I don’t wanna be down on things, when I’m trying to pick myself up and look at the potential, there’s potential. There’s some signals, like we just talked about with service design.

There’s some signals like we’re seeing some teams are shifting left as the production function is being…

Jesse: yes

Peter: …consumed by AI.

And I think as there’s an opportunity to reintroduce that broader mandate for design, hopefully, we can take advantage of the things we’ve also learned in the subsequent 20 years about doing a better job communicating, connecting with the people around us.

One of the reasons we struggled back then, or the mandate didn’t stick is, that expansiveness had very little to do with our express effort to make it so, and instead was more a reflection of forces outside of our control. Apple’s success and some other kind of realizations that like, oh, people want good experiences and are willing to pay for it. But not really driven by design.

And now 20 years later, how do we make that better case for ourselves to connect with these things and not wait for,

Jesse: Yeah

Peter: moments outside of our control to give us permission, but instead how do we make our own permission, kind of like making our own luck to do this broader work?

Jesse: Yeah. And I think that’s an example of what I might call out as the general pattern or the general recommendation that I would make here, which is to use your leverage to be the antidote to these negative trends.

If the trend is burnout, create a culture that better supports people. if the trend is disempowerment and commoditization of your team and its value, then fight for and work toward a less commodifiable…

Thinking again about the comparison with sales and marketing. They have skill sets and knowledge and expertise that is not easily replicated by automated processes. That’s why they feel secure. Find that same security for yourself and your team. I think the opportunity for leaders is to take the microphone, is to set a new tone, is to assert what’s true because in this place of chaos right now, going back to liminal, the chaos contains within it the seed of possibility.

It contains within it the opportunity to create a different kind of order out of this chaotic moment.

Peter: And it will require design leaders to lean on the leadership part of that phrase and not the design part of that phrase.

Jesse: Yes, exactly so Peter, thank you so much for the conversation

Peter: This has been great. I’m actually excited by where we landed

Jesse: Cool. All right. Thanks

Peter: Until next time.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Show Notes

Dave Gray, author of Liminal Thinking and founder of School of the Possible, joins Peter and Jesse to examine what’s actually getting in leaders’ way right now: not the disruption itself, but the expertise that blinds them to it. The conversation moves from beginner’s mind to the compression of corporate work, landing on a provocative question — what does your value look like when you define it yourself?

Dave Gray’s School of the Possible: https://schoolofthepossible.com/
Dave Gray on The Practice Economy: https://schoolofthepossible.substack.com/p/the-practice-economy
More on Peter Merholz, his consulting, coaching, and training offerings: https://petermerholz.com/
More on Jesse James Garrett, his AI Transformation Consulting and Leadership Coaching practices: https://jessejamesgarrett.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: This is Liminal. On today’s show, Peter and I welcome Dave Gray, veteran design consultant and author of the book Liminal Thinking. We’ll get his perspective on the mindset and skill set that can help leaders navigate this liminal moment. We’ll also examine the blind spots that result from too much expertise, the future of corporate politics in agentic companies, and defining your own value outside the terms of the corporation.

Peter: Dave, welcome to the show. Thank you for joining us.

Dave: Thank you for having me. I’m thrilled to hang out with you both. It’s been a long time, and we’ve had many experiences together. I’m happy to see you again.

Peter: We have. I remember events going back almost 20 years now where we’ve talked together. But the reason we asked you to join our show is, we’ve been doing this series of sessions on this concept of liminal, liminality, the liminal moment we’re in. We remembered early on in that, that you wrote a book… called Liminal Thinking: Create the Change You Want by Changing the Way You Think.

And so we know that you’ve been thinking hard about liminality and the role that it plays. And so, yeah, we wanted to get your thoughts on this matter. But maybe even before we dive into that, what have you been up to? I know what I last recall is you were a consultant at Xplane, and then you’ve been on your own, and you host communities. What do you do?

The story behind Liminal Thinking

Dave: Yeah, so before we leave the topic of the book, I don’t know if I ever told either of you the story of the book.

I didn’t start out with some idea that I wanted to write about liminality. It started out as something totally different, and it evolved into that. So maybe we can get into that.

But yeah for 30 years I was a design consultant, an innovation consultant. I did a lot of drawings and mappings for large organizations, helping them think through change programs and complex technologies and making them accessible, to sell them usually.

And I exited that business, and I was faced with the question, what are you gonna do now? I sold my company and I just started thinking “Well, what is Dave as a service? What would that look like? What is it that people come to me for when I’m not selling anything? What is it that I like to do? What is it that people come asking me for?”

The School of the Possible

Dave: And yeah, so that’s what I’m doing right now. You could call it Dave as a Service. My name for it is The School of the Possible. It’s a company of one. Me doing the stuff that I enjoy doing in service to a community of creative people.

It’s kinda like a Zoom version of a bar.

Peter: Okay.

Dave: I’m like the, you know, the bartender…

Jesse: everybody knows your name.

Dave: Yeah, everybody knows each other’s name. Make sure that everybody has a comfortable seat and it’s like a bar meets an art studio.

Jesse: You know, one of the reasons that we wanted to talk with you is because liminality has been such a focus of our conversations lately, and you literally wrote a whole book about it. It’s not a new book. I was astonished to discover that this book is almost 10 years old now.

But it is a book that has had some resonance over this last decade. It is a book that I continue to see people reference and call back to. And for people who aren’t familiar with the book, I wonder if you can encapsulate a little bit about the origins and the ideas that came out of that, and what were the big themes that you were trying to drive with writing a book on liminal thinking?

Dave: Yeah. The story of the book, it’s not one that I tell very often, but I think it’s a really interesting one, because it started out with mutual friend of ours, Lou Rosenfeld, he’s, very good about remaining connected with his authors and prospective authors.

And I just had been his friend. And he sent out a little note to his email list asking if anybody knew anybody who wanted to write a book about Agile, Agile software development. And I was like, ” I think that’s really interesting.”

I had just finished a book called The Connected Company. A lot of it had to do with Agile kinds of approaches and techniques to organizing business. And I said, “I don’t really know much about it, but I would love to write a book in the kind of journalistic style. I’d love to go out and interview people and learn about it and write a book that way.”

And he said, “Great.” So I started out to write a book about Agile and

Peter: This is, like, 15 years ago or something now?

Dave: Something like that. And so I started interviewing these people. Agile software development, coaches, professionals, experts, and I’d ask them about agile, and they would say “We know what agile is, but we can’t do it.”

And I’m like, “Okay well tell me about that.” And I kept hearing from these people, who all seem to look like me. They’re, like, very homogenous from a diversity perspective. And I kept hearing the companies are structured in such a way that “We can’t do it. We can’t be agile.”

And I thought, “Okay, that’s not agility then,” to me, because agility, to me, is you’re able to do things in spite of the environment, or you’re able to navigate within an environment that you don’t control in such a way that you can maintain some kind of balance or equilibrium.

So I went back to Lou and said, ” I think we gotta think about this book differently.” And I expanded the group of people that I was talking to.

It got much more diverse, much more interesting. Talking to people, soldiers, people who are in environments that they can’t control, literally, someone’s opposing their efforts. Humanitarian aid workers, firefighters.

And I started learning about real, I guess, what I would call real agility. People who are able to operate these very complex, super volatile, rapidly changing environments. They’re able to achieve some kind of results without having control.

And I think that’s very connected to what you guys have been talking about, this idea of, feeling like there’s rapid change going on. You don’t control it. You’re not in control of the situation, and yet you have you have things that you wanna try and achieve.

And that’s where the book ended up going. And what was really interesting to me is a lot of it ended up being about mindset, and a lot of it ended up being about a lot of the stuff that gets in your way in operating in these kind of volatile complex environments is your own way of thinking about them.

A lot of the barriers are inside your own brain, so to speak.

The Agile Moment vs The AI Moment

Peter: Before we got on mic, we were talking a little bit about the tenor of the discussion right now in places like LinkedIn. Where there’s a lot of people having a lot of feelings. They might be anxious feelings, they might be positive feelings, excited feelings. We’re in a heightened moment. Feeling like they’re out of control.

And it’s interesting to me that those initial folks that you spoke with for the Agile book felt like they lacked control, because agile was seen as a net good, right? Companies were becoming agile, and, like we’re hearing about AI, there was, like, almost this mandate: We’re going to adopt Agile.

And then people like, I’m assuming the ones that you were interviewing, are brought in to help us become agile. So these folks should have tailwinds, right? They’re the ones who are being seen as the ones who are gonna lead us to the promised land.

But even those folks were feeling stymied, right? They got frustrated. They kind of threw their hands up. Which is a little different than what’s happening right now in a lot of organizations where we’re getting this top-down executive mandate about AI, but no one knows how to do it.

Like, at least there was a group of people who could claim some expertise or some understanding of how to drive agility with some evidence in it. Right now, with rare exceptions, it just feels like we’re all making it up as we go.

In the Agile moment there were these organizational or corporate constructions or strictures that prevented agility from arising.

I’m curious, as I’m sharing, a little compare and contrast, what you make of these different moments. When agile was imposed on us, and we had the right people to help get us there, and we couldn’t figure it out, what hope do we have in this moment?

Dave: Oh, wow. We’re all probably roughly somewhat near the same age, and we’ve probably all lived through a lot of different disruptions over the course of our lifetimes.

I remember before the internet, at least before it was a thing that people used all the time.

And I feel like I have a little bit of an advantage because I have been through so many of these that I’ve start to see a lot of common themes.

And when you think about AI, the one that feels the closest to me as a designer was more like in the ’80s, when PowerPoint and graphical user interface, and suddenly everybody was able to make presentations and, PageMaker and, suddenly, you know, a lot of people who were in the design field were really freaked out because now my boss can make the whole magazine, like whatever.

That was at least what we were afraid of at the time, and it’s like, there’re still designers, but there have been so many times when there’s been a prevailing idea that design is going away or that technology’s gonna take over that job.

I forget who the painter was who’s, when photography came around, said, “This is great ’cause now we know what painting is not.”

And I think it’s like, as we look at AI, one way to look at it is to see all the things that it’s gonna take away from us.

But another way to look at it is to say, think of that as an editing out of the stuff that maybe we didn’t need to be doing anyway.

Jesse: So you talk about identity. You also talk about skills, skills and tools, and the way in which we get attached to those things as a part of who we are. And we’ve talked on the show in the past about this same moment that you’re talking about here, where digitization starts to supplant really well-established practices that have been in place for a really long time.

The example that comes to mind for me is in the field of accounting. Let’s go outside of design altogether. Accounting practices stayed more or less the same for hundreds of years until computerization started to change what your role was, and suddenly your penmanship didn’t matter as much.

Whereas previously, like, this was part of how you got the job in an accounting office, was you could write clear numbers that other people could read, and these kinds of granular skills that then become much more fungible as the tooling evolves.

But I wanna come back to the notion of the liminal mindset and what came up for you in your explorations of how people address these moments of change and what it takes for them to not get left behind, to not get left in that place where they’ve got the paste pot and the X-Acto knife instead of the mouse and the keyboard to be able to do their jobs back in the ’80s and ’90s.

What You Know That Just Ain’t So

Dave: I have a quote that I love. It’s from Mark Twain. It’s an old one, but he said, “it’s not what you don’t know that gets you into trouble. It’s what you know for sure that just ain’t so.” And for me, that’s such a great quote and so relevant today.

Another way of saying the same thing is, Shunryu Suzuki who said, “In the beginner’s mind, there are many possibilities. In the expert’s mind, there are only a few.”

And I think this is the thing. Over many years, you build up expertise, and the expertise enables you to be very effective and efficient, like ability to use certain tools, your penmanship, to your example, other things. Those skills, you start to think of them as part of your identity, of who you are.

But all that focus, it’s kinda like horse blinders. It eliminates your peripheral vision, and it actually gets in the way of you seeing what’s actually going on if things are changing in a very fundamental way.

And I think that’s what’s happening now. Things are changing in a massively fundamental way. To a beginner, someone new to the workforce coming in, they’re not gonna have all the knowledge that gets in the way of them seeing what’s actually going on. They’re gonna be like, “Oh, I can just get on AI and I can do this, and look at that, I made an app. Whoa.”

And I think this is a common theme of a lot of these tools that come along. They create a new level of abstraction that wasn’t available before to the work. For example, when I started, before the Macintosh, before PageMaker and all this stuff, it was really important that you had to be able to use a ruling pen. Okay, a ruling pen is, you dip it in ink and it would make a very straight black line. With Adobe Illustrator or even MacDraw, that’s not a skill that I need to have with my hands anymore. And the people who are attached to the old craft are like “Yeah, but you don’t know how to draw a straight line. You’re letting the computer do that for you.”

The Abstraction Ladder

Dave: A good analogy for me is you go from walking, to getting on a skateboard, to riding a bike, to driving a car, to getting on an airplane. At each stage you’re losing some level of contact with the ground and the detail and the granularity. You’re not gonna see the landscape in as rich and detailed a way from a car as you are from a bicycle or from walking. But, you’re increasing your capability.

So, what happens with the tool is they abstract you away from the ground. So now I don’t have to know how to write Python to code an app anymore. So there’s things that are happening that I don’t understand. Like, let’s say riding a bike. If you ride a bike a lot you have the ability to fix it yourself probably. You really understand how the whole machine works. You can look at it and understand it.

When you’re in a car it’s a little more complicated, but actually, a car is probably easier than riding a bike, as you gain more power and control at a more abstracted level, you’re losing power and control at the more detailed level. You’re losing your attachment and your groundedness to the work, but you’re also increasing the scope and scale of what you can accomplish.

And I think AI is just doing this at such a dramatic level. I’m not sure what corporations are gonna look like after AI’s finished, you know, burning its way through all the, all the- the shit, honestly, that we’ve been doing that is not gonna really matter that much when the AI can do it.

It’s like the version of the ruling pen in a corporate world, a lot of it is, oh, just the politics. Think of all the political back rubbing or whatever you wanna call it that goes on in a large organization and the jobs that are honestly, not that hard.

As a consultant going into large organizations, I felt, wow, there’s so much about just people’s egos and just making them feel important and so much political stuff about, oh, I don’t wanna piss anybody off and all this. When all that work is being done by agents, they’re not gonna need to, kiss each other’s asses.

Jesse: So, are you suggesting the rise of ass-kissing robots?

Dave: I’m actually saying I don’t think they’re gonna need it as much. A lot of that effort and energy and cognitive overhead that’s going into just managing the human aspect of bureaucracy is, I just think it’s gonna be dramatically changed, at the very least.

And I think, I have a picture of what work’s gonna look like on the other side of it. I think a rough sketch kind of picture of it. But I think it is gonna be much less of the fake relationship stuff and much more of the real relationship stuff that you don’t see a lot of in the large organizations.

The Practice Economy

Peter: Before we talked, you shared something you had recently written that I think you’re maybe starting to allude to, that you call the practice economy, and you talk about these waves of work and, agriculture being an early wave, and then you had industry and factory work being this subsequent wave as agriculture declines. And then industry declines as you have essentially corporate work becoming the latest wave.

We’ll link to the article in the show notes. There’s some charts and graphs that are a part of this. And you show the corporate wave actually peaking around 2000. And it’s actually been in decline for a while in terms of, this is the percentage of people doing this type of work.

And you can probably tie it to broad adoption of computers and the internet in the workplace, that initial decline of just what percentage of people are doing corporate work.

‘Cause you can imagine in a pre-internet life, you needed all these manual laborers who were, like, secretaries and assistants and all this kind of moving of information around. But once you had computers and networks, the mail room evaporates, and those types of roles go away.

Dave: Yeah, we used to have typists. That used to be a job,

Jesse: Couriers?

Peter: You think about “Mad Men.” Everybody had a secretary.

So that stuff’s already been going away, and I think what you’re suggesting is that it will go away maybe even more rapidly with some of this new tooling.

And what you have replacing it is the practice economy, and I thought that was interesting.

I’m gonna ask you to define it in a moment. But in our last episode, Jesse and I were talking about, maybe I had some mindset constraints because so much of my thinking as we’ve been talking about liminality is trying to help people survive in their current state, right?Wherever they are at, how can they navigate this uncertain moment and recognize that uncertainty as opportunity and come out the other side with some victory?

But I had, I think, implicitly been imagining people staying at their jobs and trying to make it work. And it was in our last conversation where I’m like, why am I assuming that? Why wouldn’t… if there’s a group of people in a company who recognize an opportunity, a new way of working, instead of trying to win over a bunch of executives or something as to do it, why not the four, five, six of them just leave and do the thing? Especially with the tooling we have now. You can get much closer to the work and just be gone.

I had to free myself of this assumption of working at a co-, context, and that’s the sense I have from what you’ve been writing with Practice Economy. So consider this a little tee up. I’m curious how it aligns with what you’re thinking or where your thinking is going here.

Dave: Oh, yeah. If you think about you think about the tech giants today, right? Mark Zuckerberg, college dropout, started Facebook. Apple, started by, in a garage, pretty much every single one. You know, EBay, a guy programmed it on a weekend.

Peter: Google in a garage by two guys who maybe didn’t finish their PhD. Yeah.

Dave: Yeah, right. And I have friends, and I’m sure you do too, that it is like even with a large organization with tons of money, so Xerox basically created Apple. They built the research center out of which Apple came.

They invested, they put the money in, they had all the creativity. They weren’t able to turn that into a company, turn it into an organization because, again, of that, I don’t have a name for it, but the expert blind spot, whatever you wanna call it.

Peter: They already knew, and they knew that would never work.

Dave: Right. You have an infrastructure in your mind, just like any company has infrastructure, and you have a blind spot that’s associated with what you can’t see because of what you know that just ain’t so, to go back to Mark Twain again.

In a big company, with all the tons of money and resources and capacity that a big organization has, it’s still easier to quit and start it in your garage than it is to innovate within that structure.

It’s mind-boggling ’cause companies pour tons of money into this. And they also buy companies and then destroy them. Like, they buy them without understanding their value.

I saw it at Business 2.0. It was a magazine. It was a very successful magazine in Silicon Valley. You guys might remember it.

It was bought by Time Inc. And they fired the sales force, and the sales force was the engine that ran that whole media business. The salespeople were basically selling into Silicon Valley, into the technology companies, and Time was like, “Oh well, we already have our sales force.”

They had a sales force of people that would go into Ford Motor Company and just basically take orders. They didn’t understand the industry. And so I watched, I had been working for the company as a consultant, like an illustrator, saw the company get bought.

You know, it’s like you buy a car and you take the engine out, and it was like watching it get thinner, and the bureaucracy blaming everything but themselves for the problem that they created.

And I think this happens a lot in business. But again, it’s that expert blind spot that gets in the way of seeing… And I think we each have it ourselves, too. It gets in the way of seeing what’s possible.

Jesse: Yeah. We’ve talked in the past about the work of the philosopher Thomas Kuhn. “The Structure of Scientific Revolutions” is this book where he introduced the concept of the paradigm shift to the popular discourse.

And when I think about what you’re talking about, when I think about these blind spots, I think about the risk of being trapped in an old paradigm, in an outdated paradigm that no longer applies.

And, for our audience, design leaders, I feel like this is a place where they just dwell in this absolute terror field of the Rumsfeldian unknown unknowns, the blind spot that by definition you don’t know is there. You can’t tell that something is being hidden from you by your own perspective because that’s what your perspective does. It filters your reality.

And I wonder what leaders need to do as they are simultaneously dealing with the pressures from executives in their organization, as well as the expectations of the people within their teams to escape that trap of the genuinely invisible blind spot.

How do you see those unknown unknowns?

The Corporate Drug

Dave: I think one of the big unknown unknowns is just assuming that I’m gonna be in a corporation. I’m gonna be in a corporate job. Whether or not it’s the one that you’re in now, I think that those are the things that are most likely to be getting in your way.

Okay, so a design leader in a Fortune 500 company. That’s what I know how to do. Whatever I do, I’m gonna be a design leader in a Fortune 500 company, ’cause that’s how I understand the world. That’s what I know how to do.

What happens if there is not that role, there is no design leader in a Fortune 500 company in your future?

What happens if that role requires a whole different kind of person than you are? In some ways, a corporate job can be like a drug, like an addiction, and if you think about it, okay, addicts are usually not gonna give up voluntarily a drug until they hit some kind of a flat wall that they can’t continue to keep using it.

Jesse: Right. They’ve gotta hit bottom.

Dave: Yeah, so what is that for a lot of corporate leaders? It’s you get laid off at an age where you don’t have a lot of prospects.

And I think one thing, you know, it’s like death. You don’t wanna think about it, but it’s probably good to think about it. Do you have a do not resuscitate order? Have you got your will? You have life insurance? It’s not fun to think about your own death, and I think the same applies to your corporate death. Maybe it’s not fun to think about it but it’s wise to consider what your alternatives might be and to think about that realistically and say, Okay, let’s just say you’re not worried about your job today. That’s great. Maybe if you think about five years from now or 10 years from now, maybe there is something to worry about. What can you do? You could start saving money, number one, right? You could be more thoughtful about your expenses. You can be actually actively cultivating your social network outside of just your immediate colleagues and the people who can do something for you today.

You can start to actually think about your social safety net differently than just thinking about what is available to you inside your company.

Like one of the things I realized after selling my company was that I had a social network that I had invested a lot of time and energy in over many years. Many of those people became my customers when I decided to do Dave as a Service. There was a lot of people out there who had read my books or had been interested in something I had done and, when I was a corporate consultant, If you didn’t have at least $25,000, there was no point in us having a conversation ’cause there was nothing I could sell you, but there’s a lot of people who don’t have $25,000 to spend on a project who maybe I could provide some value to.

The corporate world is all about division of labor. And so we’ve become divided in some ways. The value proposition has gotten so splintered and divided that our value proposition is this tiny little role in this big machine. And, think about the user experience designer, the information architect trying to explain to the taxi driver what you do, right?

“Well, I design experience.” What does that mean? You know, and I think this is the case of a lot of corporate jobs. You can’t explain it to an average person in a restaurant or on the street. And the thing is, if you can’t explain it, that should be a big warning sign in the world that we’re in today.

Because what the jobs, I believe, of the future are gonna be, you have a role in a community, and you know your role.

It’s almost like going back to hunter-gatherer times. Everybody knew their role in their community. Everybody knew why they were useful, how they were useful or not. Everybody understood. If someone runs a Thai restaurant in your neighborhood, you don’t have to ask them to explain what they do. You know exactly what they do, and what they provide. It’s not something that is hard to understand or hard to explain, and I think a big part of what’s happening is all this kind of divided labor is stuff that can be more easily done by agents.

It’s the stuff that’s more tightly bundled, where the value proposition is not so easily automated, that is, about a role that you’re serving in a community, a usefulness.

In the article, I mentioned this friend of mine who runs a newspaper here. It’s a one-man newspaper. He’s been doing it for 40 years. AI’s not gonna take his job away. No way. He shows up at the community meetings. He knows people. They come to him with stories. He’s got advertisers. People write stories for him. He’s deeply interconnected with the community. Everybody understands the role that he plays in the community, and he understands the community.

So I feel like part of what’s gonna happen is, as we get more abstracted and we have more capabilities and powers, you’ll be able to do a lot of things without having to hire employees. And if you are in that corporate job, one thing I’d be thinking about is how do I think about this job not as something that I need to hang onto like a life raft, but something that can actually help be a vehicle for whatever I might wanna do next? And then take a more expansive perspective on what’s out there.

Dave as a Service

Dave: Like when I sat down to say, “What is Dave as a service?” There are a lot of things that did come up. People come to me when they lose their job. They come to me for advice on their career. People come to me asking for advice about writing books and publishing books and doing creative.

So there’s a lot of things that were happening that were not part of my corporate career, but they were in my life. They were in the background, and foregrounding those created a whole different kind of way of thinking about what I actually look like.

This is a question I think any corporate employee should be thinking about. If I were to be a service, you as a service, Peter as a service, Jesse as a service, and I had to do it all by myself without a team, what would that look like? What might that look like? What could I do that I could show up with, joyfully every day, even if it’s something simple as making sandwiches? What could I do that I could really enjoy that would connect me with a community?

Like my newspaper friend, it’s a local thing, but I don’t think a community has to be local in this day and age. And I think that’s what practice work, the shape of practice work is, and it’s older than history.

But whether you run a restaurant or whether you’re a tailor, you know your customers personally. And I think, how many people in a design leadership job in a Fortune 500 company can say they know their customers personally? It just would not be possible.

But I think we’re moving towards a future where you are gonna be required to articulate your value to the people who are actually paying your bills, the people who pay you. And they might not be your boss.

So I feel like the big skill that is gonna be required of all of us is learning how to create a customer. Both of you, I think, are very aware of that is a skill. That is a skill you can develop and that requires a way of thinking about how you show up in the world that’s very different from pleasing a boss to get a paycheck.

Jesse: It’s interesting to think about the implications of this for leaders of design teams inside organizations. So let’s say I don’t want to quit my job. Let’s say I love the leverage that comes with being able to make design decisions that touch literally millions of people every time we deploy.

If that is what’s exciting to me as a leader, then I am there to advocate for something else, which has to do with what design as a function contributes toward the value that we collectively create. And I’m there to stand for that contribution on my part and on the part of my team.

And, as you were talking, I find myself wondering about, how we define community, how we define the value that we create within community, and the shape of these evolving organizations, if it really does become, almost this gravitational pull away from hyper-specialization back toward a little bit more of a generalist kind of a value prop for people in these organizations.

But that generalist value prop is then built upon, as I hear you describe it, personal trust and a certain track record of value delivery. And that’s the means by which you get things done rather than rigidly defined areas of authority and hierarchical structures and things like that.

So then the challenge for the leader is not just to advocate for themselves, but also to advocate for the thing that they are there to spearhead and champion. Which, for us, for many years, it was human-centered design. All of us came into this work during a time when there was no voice of design anywhere in any kind of software development, and the software that we had was painful and difficult for people.

Dave: Yeah.

Jesse: And that gap presented a market opportunity, basically, that created this field.

And now I think there’s a new potential value proposition that design leaders have to advocate for, that doesn’t look like that anymore because it’s no longer about those things. And in fact, as you describe it, the organizational context itself is potentially shifting. Where your title on your business card doesn’t mean you get to make or influence certain decisions, right?

Dave: Yeah. So I was just reading about the guy who made the movie “El Mariachi,”

Jesse: Hmm. The great Robert Rodriguez.

Dave: Is that his name? Okay.

He went to Mexico and made a whole movie for $7,000, like a feature length film.

So this is the kind of thing that people in the film industry are like you can’t even make a trailer for less than $20,000.

And he had a film teacher who said, “No, you’re gonna need a, you need a…” He said, “I’m just gonna hold the camera myself,” you know? “And well, you need a director of photography. You need a…” And you learn the film industry by going and working on a film, and you see all different jobs, and you learn one or two jobs, and you grow in the industry that way.

Whereas he just said, “I’m gonna take a camera. I’m gonna tell a story. I’m gonna go take a camera to Mexico, and I’m gonna do this.” That was a successful movie, and he’s gone on to make other movies.

So that kind of mindset is, I think, what we’re gonna need more of in this AI age. Like, my brother worked at the FDA, and they’re a bottleneck because the people coming to propose different kinds of medical equipment and drugs and different things, they have such a long wait time because of the way they do it.

And I suggested like platform-type things like Kickstarter and other, kinda crowdsourcing, some of that. Because he worked for the government, he was so embedded in a way of thinking. The only way that he could think of to scale the pipeline was hire a lot more people, like triple in size.

Whereas now if you’re making movies the traditional way, you’re never gonna try and do something for $7,000. You wouldn’t even think to try that.

Whereas the potential of AI is that there are things that we just can’t even imagine are possible because of the way that we’ve done them before that are going to be possible. So the way you describe that design leader, “I’m someone who… I care about, I make the decisions, and we push a button and it impacts millions of people.”

Are you gonna need the corporation for that? Or could you do that? Jesse, you’ll be happy to know that the working title for that whole practice economy thing was “The Structure of Economic Revolutions,” which, ’cause it is kinda based on that whole Kuhn thing.

And we’ve had three of them in, the course of human history. One was agriculture, the second was manufacturing, and the one that’s happening now, that’s compressing now, is corporate work. When things get compressed, they don’t go away. We still have farming. We still have manufacturing. And we’re still gonna have corporations.

But the number of people required to run a farm, like one farmer, one person used to generate about five people’s food, like a family. Now one farmer generates about 100, 200 people’s worth of food. So it’s one person. They’re just like 50 times more effective.

And I think the same’s gonna be the case with a corporation. To be making the design decisions that you push the button and you affect the lives of thousands or millions of people, you may not need that corporate infrastructure to do that anymore.

You might be better off thinking like the El Mariachi guy. I’m sure there’s a lot he didn’t know that worked in his benefit, work to his favor. And so that’s where the beginner’s mind comes in, I think, is, what you don’t know that you don’t know, that can actually be your best friend, ’cause you don’t know that it’s not possible. You don’t know that it can’t be done. And so you have the temerity to go out and say maybe I can just do this.

Peter: I’m curious, as you were, years ago, researching liminal thinking, if the beginner’s mind thing came up then and what you saw. ‘ Cause, as you explained it earlier, the people you interviewed were under even greater constraint than anything we’re talking about here, right?

And so you were trying to figure out how do people who are under great constraint still do good work, work they’re proud of, make their way there? Was beginner’s mind part of it? And how do you tap into beginner’s mind when you’re already an expert, right?

Is there a way, like, my desire is, I want both. I want to be able to leverage my expertise, right? 30 years of hard-earned awareness. It’s not for nothin’. So, I, also am a service. I sometimes refer to myself as Peter as a service. And people come to Peter as a service for 30 years of expertise. That’s what they’re buying.

But in moments this, where assumptions probably are worth at least calling into question, I wouldn’t say dismiss them all, they’re all useless. In fact, I think some of that thinking is problematic. There’s plenty that we can take from prior experience into today that, if applied well, I think would make things easier.

But that aside, like, how to balance beginner’s mind, expert mind, and succeeding or, getting traction when you’re not in control of the situation, and it feels like you’re operating within someone else’s imposed structures?

Dave: It is a great question, and I believe I have a great answer. We’ll see what you think.

So when you hear new ideas, right? And you hear them all the time, right? Crazy ideas.

Generally speaking, the first evaluation criteria you have for a new idea is does it fit within what I already know? Does it make sense with what I already know? If it doesn’t make sense within what you already know, the tendency is to reject it and say, ” Okay that’s just an anomaly. That person was just lucky that happened.” And just basically find ways to reject it.

But the thing is, the new ideas that fit within what you already know, you’re not actually gonna learn anything dramatically new by accepting the stuff you already know. It’s the stuff that looks really strange, doesn’t make sense, I think you have to open up your aperture to be able to become aware of those.

So you’re gonna hear things that, you wanna reject it, because it actually challenges something you already know. That’s the stuff where you actually have the greatest potential to learn something new.

There was one that I just saw where it was like some guy started a whole AI company, I forget the name of the company, but he started it all by himself. He’s already making multiple, I think, millions of dollars on this company. He’s only one running it, and what it will do is you go there and it’ll make an AI company for you.

It’s like an AI company that makes AI companies.

That to me is mind-bogglingly weird. I think part of it is just learning to cultivate your curiosity about things that just either grate on you or just things that create that disconnect in your brain, that’s the stuff that’s actually most likely to generate some kind of new insight or learning, the stuff that you most automatically reject.

The story from “The Connected Company” book is the story of the American auto industry. They were like, “The Japanese are making these cars, and they’re so cheap.” And the first thing was the cars aren’t that great. And then they look at the cars. It takes them 10 years to figure out, oh, the cars are actually pretty good.

Then they go to Japan and they actually see the way that they’re making the cars, and people come back and they’re like, “Maybe that works in Japan, but it’ll never work here.”

And there’s all this stuff that they already knew about how to make cars that they couldn’t learn because they already knew.

And so even though they were getting all these signals for 20, 30, 40 years, it took them that long to actually recognize that there’s something happening there that, somehow people in Japan are able to make factories that make cars better and at half the price that we pay to do it, and it’s about the method and, like, lean manufacturing we call it now.

It’s like those expert blind spots. One way to start to mitigate for your expert blind spots is to start paying attention to stuff that you think that can’t be true. That’s the stuff that is most likely to generate some new insight for you, right? Because what if it is true?

Acting As If

Dave: There’s a thing that I talk about in my book called “acting as if,” which is, you don’t actually have to believe something, an idea is true or valid in order to test it. All you have to do is act as if it were true.

Let’s just say, take the example, Jesse, that you gave of the design leader who assumes that they have to be in the company to do the work that they wanna do.

You could also ask the question: What if I didn’t have the company behind me, and I wanted to do the same thing? What would that look like?

And you can act as if it were true, so act as if you didn’t even have the company or act as if you could do it for pennies on the dollar and see what happens.

The nice thing about acting as if is you can suspend your own disbelief about your own behavior. You can suspend your disbelief about anything long enough to try the experiment. You don’t even have to believe that it’s gonna work.

Jesse: Yeah.

Dave: You can act as if it were true. What if I only had $7,000 and had to make a movie and I wanted to do it, and I basically said, “It’s going to be a feature length film”?

Jesse: So I think part of what I hear you suggesting within all of this, and you’ve maybe touched on this a couple of times in this conversation, is the idea that really the whole software industry might look really different a few years from now than what we’ve become accustomed to up to this point.

Dave: I think it’s not just the software industry. The only thing in our world that doesn’t have a lot of competitive pressure on it is government, maybe healthcare, certain industries that are highly regulated, so they literally can’t innovate because there’s laws that keep them from innovating.

But everything else, AI is a really interesting to me technology.

I work with people on it, there’s people in my school who are working with AI, and I am too, and one thing that I’m noticing is that it’s the first tool that I’m aware of that actually can teach you how to use it.

And that’s incredibly interesting. And I’ve seen people go in a week or a month to where they’re talking about concepts that would not even have been intelligible to them a week ago.

The learning curve is rapid. People are making such rapid progress that I can’t even get them in a room to be able to even communicate with each other. They’re so widely distributed on this learning slope that once you get start on that journey, to find someone else who’s at your level is not that easy because people are progressing so rapidly.

I don’t think we can even try to make predictions, but I think what we can predict is it’s just not gonna look like what it looks like today. When the smartphone came along, I don’t think any of us really predicted the way that it was gonna change society.

Peter: Well,yeah, especially if you look at movies from pre-smartphone that, were trying to be future forward, they didn’t take it into account at all.

Dave: Yeah. We thought we were getting connected and we’re really getting more isolated. It’s almost like the opposite of what we thought.

Peter: But on that point actually, ’cause you were talking about Dave as a service. I’m Peter as a service. Jesse’s kind of Jesse as a service.

Jesse: I’m serviceable.

Peter: And while I appreciate the freedom that my independence affords me I have to admit that, I am seduced by the stability of that drug of corporatism that you were referring to before, right? To be independent, to be on your own, is a lot of hustle, a lot of uncertainty, a lot of trying to figure out what the market wants from you and when you do, the market changes and now you’re having to change, right? It’s not easy.

And we touched on this, Jesse and I did, in our last Liminal conversation, which is around kind of collective action, ’cause you’ve also talked about community. And I’m trying to understand how we operate as individuals, but not to be alone, right? ‘Cause I can feel quite lonely in my work, writing or whatever I’m doing.

And it’s nice I have clients, but I meet with them an hour here, an hour there. I don’t have a team that I’m doing stuff with, right? We’ve all been in environments where there was a team and we did stuff with the team and that was powerful, and we’ve all lost that.

I guess I’m just curious, Dave, how you’re dialing that size of productive unit. It doesn’t have to be a massive 300,000 person scaled organization, but is it really just gonna be a bunch of individuals, or, what are you foreseeing there?

Projects, Not Companies

Dave: This is just all speculation and intuition, but I find a lot of interest in the film and music industries. The music industry is a great one because you got a lot of solo artists who are also in bands or you got The Beatles, they started as a band and then they became independent artists.

You’ve got people like Willie Nelson, spent a lot of time with other bands, And I think there’s something about maybe thinking in terms of projects like that.

I’d like to believe that we’re moving towards a society where you could think of things in terms of projects and collaborations and have some kind of fluid movement between, being a solo artist and in a band.

What is a great band? They get together. They know each other. They have that chemistry. They can perform really. They know each other’s strengths and weaknesses. They balance each other really well. There’s something great about that.

And then there’s, we’ve all been in the team that’s dysfunctional, right? That’s like, “This is not a band that I wanna be in again.” So the project to me is a nice way to say, “Okay, if we really do a great album, and we really enjoyed the whole process, then we’ll stay together. We’ll do another one. We’ll do another one.” But for me if I start to think about looking towards the future, what does that look like, I think maybe projects, as opposed to companies.

And even if you look at the way that most companies operate they are projects even for serial entrepreneurs. There’s people who they’ll start a company. They grow it. They sell it. Maybe it was a company for the investors, but for them it was a project.

Jesse: So with all of this change and all of this transition and potential, what are you most looking forward to seeing unfold in the days to come?

Dave: We’re learning what the robots can do and what the computers can do, the computer can now kinda turn itself on, it can run itself, it can operate itself, we don’t have to be computer operators anymore.

And I think there’s something really liberating about that. I don’t think it’s gonna happen without pain and distress.

Not that we shouldn’t have been thinking about this for a long time, but we really ought to be thinking about universal healthcare. Because a lot of people are trapped in these organizations because our healthcare system is forcing that on them. And a lot of people, that’s a big barrier to them going off on their own, and that’s just a failure of our system. So there are some things that we can do to kinda ease the suffering, I think.

But what’s happening in the corporate world today is very similar to what happened in the factory and steel working and the mills and so forth. It’s undergoing a compression, I believe, and there’s gonna be displacement.

And I think as a society, we need to be thinking about how we make that transition easier for people. I think universal healthcare is kind of like a no-brainer. So many other countries have actually done it. But I look forward to what happens when people get on the other side of it.

The Storm, and What’s On the Other Side

Dave: We’re in this turbulence mode. It’s like we’re in the middle of a storm, and the storm’s gonna pass, and the waters are gonna get calm again, and we’re gonna see what’s on the other side of it.

Doesn’t mean there won’t be a lot of destruction, like Katrina kinda level destruction of our economy. I think that’s likely. And we’re in the middle of that storm right now, trying to cling to the rafters or, bailing water or just trying to do what we can do. We have this sense of this storm raging around us. We don’t know what is actually gonna be left or what’s gonna be destroyed or what buildings are gonna still be standing.

It makes sense to be in that mode, but I feel like there is gonna be another side, a calm after the storm, and I think it’s gonna be beautiful.

Peter: Wow.

Jesse: Dave Gray, thank you so much for being with us.

Dave: Thank you. Thanks for having me.

Peter: Yes. Thank you so much.

Jesse: Dave, if people wanna find you and your work on the internet, where can they do that?

Dave: schoolofthepossible.com.

Jesse: All right. Thanks again.

For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Show Notes

In this episode, Peter and Jesse compare notes from on how AI is reshaping design teams. The conversation moves through the operational chaos of proliferating tools, the urgent need to articulate a value proposition, why design operations got cut right before they were needed most, and the window of expertise power that won’t stay open.
For more about Peter Merholz, his consulting, thought partnership, and teaching offerings: https://petermerholz.com/
For more about Jesse James Garrett, and his AI transformation and leadership coaching offerings: https://jessejamesgarrett.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, Peter and I explore the emergent challenges of AI transformation for digital design teams. I’ll share insights from my seminar of the same name and compare notes with Peter on the larger trends we’re seeing. We’ll get into issues like renegotiating your cross-functional relationships and your value proposition, the cultural implications of running a team where everyone has their own custom tools, and just how long to hang on to people on your team who don’t want things to change.

Peter: Hello, Jesse.

Jesse: Hello, Peter.

Peter: What’s up?

Jesse: I thought it would be useful for us to get together and reflect a little bit on this last series of conversations that we’ve been having because for better or worse, there is one topic that is front and center in the minds of design leaders these days, and that is AI. How AI plays out in their products, how AI plays out on their teams, and how it impacts how design interfaces with the entire larger organization that it’s a part of.

The Burger is Real

Jesse: On this show, it has now been the better part of a year since this started dominating our conversations, going back to our conversation with Andrew Hogan back last August, talking about what he was finding out about AI adoption through his work leading research for Figma. Since then, we’ve talked with bunch of folks that are people who have been well-known to you and I for a long time.

People like Christian Crumlish, Christina Wodtke, Jorge Arango, Paul Ford, Dan Saffer. People who’ve been really immersed in this work for a while and who have seen this cycle turn a few times. And we have been talking with them about the ways in which this current cycle evokes and reminds them of the cycles of change that we’ve seen in the last 30 years or so.

And we’re also talking about how this time is different. And I’m curious where your thoughts have landed about those questions and what really genuinely is different this time? You know, Jorge brought up the idea that a lot of people are looking at this and questioning whether there’s a there there, you know.

And it has been reinforced through the conversations we’ve been having that, as Jorge put it, this is not a nothingburger. This is a burger.

Peter: Aha!

Jesse: And that has implications. And I’m wondering, reflecting on the last several months of these conversations for you what are the patterns that you think leaders need to be paying attention to as they are trying to guide their teams through this change?

Peter: You and I were part of a conversation last week that Jeffrey Veen instituted called the Design Futures Assembly, a half-day set of conversations and presentations on the intersection of AI and design, with some very heavy hitters in the room: OpenAI, Anthropic, Google, Microsoft, Figma, Adobe.

Also, I’m doing what I’m calling a listening tour of design executives trying to get a pulse check of what they’re thinking and feeling in this moment. And so I’m bringing that to bear. And it’s not a nothingburger. Definitely a burger.

And even if it was a nothingburger, the way people are acting, you can’t ignore it, right?

There’s something there. You have to, engage the…

Jesse: perception, if not the reality, right?

Peter: The perception and just the overwhelm or something, right? There’s just so much about it. You can’t ignore it. The thing is, what is it? I think it’s an interesting question.

And what I’m making of it, what we’re gonna definitely see, is how design operates will change. That is becoming truer, at least. That is changing.

I just had a conversation with a VP, we’ve heard variants of this story recently, where they have their own Git repo’s. They’re committing to prod, right? We’re collapsing the distance between the work of design and the work of development.

But there’s a potential risk when this happens, where when design gets associated with production, which has been the overwhelming mode for the last 15 years, the next step is to think you can automate design away because it’s more straightforward to automate production.

Three kinds of designers

Peter: The conversation I had with this particular design leader was interesting to me because she has, well, three types of designers in her team.

Design strategists who were loving this. They’re able to imagine futures, visiontype, but do it in ways that feel more real. Quickly build things that you can put in front of users, get that user input, iterate. It’s just this unlock for these more strategic designers who are quite generalist in terms of strategy, research, content, design, to, with just one, maybe two of them, just do a lot more than they could have ever done before. So that’s at one end of the spectrum.

On the other end of the spectrum were designers on her team that also wanted to play with code, but maybe in the past couldn’t quite get there. They probably built their own prototypes and stuff in code. But now, with these tools and technology, they’re in code, they’re partnering directly with engineers. They’re able to kind of bleed into that realm. So it’s a different kind of generalism, right?

You have design strategy as more of this, let’s call it first diamond generalism, and I don’t know if she had a term for it, but let’s say the kind of design technologist as the second diamond design generalism.

And what she pointed out is, there is a population in the middle that’s getting lost. Like she wanted to make it clear that it’s not all wine and roses, that there is a population getting lost.

But something else that she did, actually, that I think you would appreciate based on the talk you gave last week about AI transformation. As it was becoming clear that AI was going to be important, she took two people on her team and turned them into a AI enablement squad. They got removed from their product work and their job was to figure out how this team was going to embrace AI, figure out the tooling, figure out matters of process, figure out how do you get repos, be the bridge to engineering, talk to them, understand what all those things are.

And that ended up spurring the creation, essentially, of this platform design team that’s dedicated to UX excellence. So if it’s not AI, it’s design systems. If it’s not design systems, it’s defining quality, right? She’s realized there’s a role there for this team, even beyond AI, to help set standards for how the team operates.

And I say that as a story. You know, it’s clear that the edges of design practice are blurring, and there’s a lot of opportunity for design to evolve and blur into those edges. And that is the part that, I think, is the burger, is navigating these adjacencies.

At least– It’s a big part of the burger for me.

Jesse: Yeah, I would say there are two things that stood out in what you talked about. Last week I did this online seminar that I called AI Transformation for Digital Design Teams, where I talk about the patterns and the strategies that I’ve been employing in my work as I’ve been helping teams and supporting leaders in developing strategies for tackling all of this stuff.

And you touched on a couple of things that I think are really key from what I’ve seen. First of all is, like you gotta clear the decks for somebody, whether that is leadership within your team, whether those are, again, like maybe the principal IC level might actually be a sweet spot where you can really offer an opportunity to people in the organization to leverage their hands-on skills in ways that can benefit a larger organization.

But if you don’t have the ability to clear the decks for people and get them engaged with a team like you’re describing, then to bring in a fractional leader from the outside, somebody like me, who can take a view of all of it and get it all organized for you, can really help to accelerate things.

The second piece of it, though, which I think is really key, is that the opportunity is not just to do what you’re already doing better. The opportunity is to take a step back and look at what design is and means for an organization and how this tooling can support that.

Articulate a value proposition

Jesse: And I think that the challenge and the opportunity for leaders is to apply a bit of a quality filter to all of this technology that’s being thrown at them and to ask themselves, “How is this supporting the value proposition that my team already has in place and/or How does this support the extension of my team’s value proposition towards something new, towards something bigger, and towards something that is maybe having more impact than we’ve ever had before?

Peter: You said the words value proposition. You said the phrase, “How do I use this to act upon the value proposition I already have in place?” It turns out, I would argue, most design teams haven’t articulated their value proposition…

Jesse: oh, sure. right?

Peter: I suspect it’s those teams that are having some of the biggest struggles right now, ’cause they don’t know to what end they would be adopting this.

It’s just whatever they’re doing, keep doing more of that faster, as opposed to this one leader that I was talking to, you know, there had been some strategic mandate, there had been desires for vision, there had been a recognition of how this group can be maybe more horizontal, looking across an end-to-end experience, while, you know, product and engineering is more vertical, focused on specific applications.

I was surprised how energized this leader was when I was talking to them about AI, but I think it was because they had conditions, right? They had the conditions in place to enable flourishing with these new tools and approaches.

Whereas I suspect most design organizations lack those conditions to enable that flourishing.

Perhaps an… adaptive path?

Jesse: Yeah. So one of the things that I called out in the talk that I did was just the fact that every company is gonna have its own unique path toward how this new tooling gets implemented, because every company is bringing its own legacy into it. The ways that things have been done in the past, the expectations have been placed on design teams in the past, the data structures, the decision-making structures, the organizational structures that constrain what’s possible within any given context.

And I think that’s a big piece of the task for leaders, is to figure out what’s actually gonna work here, as opposed to what works at the big companies in Silicon Valley or what works at the little startups in Silicon Valley or, you know, what’s working for our competitors or what is the standard that’s been set within our particular product category or industry segment.

But to ask ourselves based on what we have in place, because I think your point is right on. If you don’t know what your processes are It’s gonna be really hard to upgrade those processes in any kind of consistent way to incorporate this tooling. If you don’t know what your value proposition is, if you don’t know what the expectations are that your cross-functional partners are bringing to the table, you might be investing a whole bunch of energy in AI initiatives that have nothing to do with what is actually being asked of your teams.

And so for the leaders, the responsibility then becomes, again, to be this filter, to be the evaluator of where these investments make the most sense and deliver the most value and deliver the most impact both within the teams and cross-functionally.

Peter: You said something along the lines of every team charting their own unique path. You might call it an adaptive path.

Jesse: You might call it that, yes.

Peter: But, one of the risks, I think, of the direction that you’re suggesting, is that every organization starts building digital product differently.

In some ways, it sounds great. Purpose-built, totally bespoke, this process for this context, this company, this time, dial it right in and boom, they can just flow.

And that sounds good in some theory, but it doesn’t allow for mobility, interoperability, translation. And so if I’m a designer who’s working in a team that’s operating in its own unique way, and then I get reorged, and we know this happens all the time, and I’m now reorged into a team that operates totally differently, they charted their own unique path, now I have to spend a lot of time figuring out how I work there.

Whereas a year ago, by and large, design worked the same in most contexts. Used the same tools in roughly the same order.

One of the things we’re hearing now is not just the proliferation of AI-empowered tools that are out in the world, Figma with Figma Make, or Lovables and Cursors and Replits and v0s and Claudes and all that kind of stuff.

But I’m talking to design leaders who are like, “Oh, yeah, and we’re building tons of custom internal tools to solve problems that we have.” Which sure, ’cause of Claude, it’s relatively cheap and easy to build internal tools. But then you leave your company and you go to work for someone else, and they have a totally different internal tool suite that has nothing to do with the kind of internal tool suite you learned…

Jesse: right.

Peter: are you spending three months before you’re useful in this new context?

That doesn’t make sense to me, right?

And so I foresee some shaking out of some patterns, some stable patterns of ways of working, and input and output of tooling.

Jesse: I can see that. At the very least, I think that you have to have two things. You have to have consistent internal expectations just to be able to compare the work of different designers across the team and be able to evaluate who’s actually delivering and who is bringing a sophistication of craft to their work.

And then secondarily, there are those external expectations, your cross-functional expectations, your expectations at the executive and leadership levels, your expectations with your business owners that also have to be managed in here.

And you’ve touched on one of the big open questions, which is, like, how standard can it get while still embracing the inherent flexibility of the new tooling itself, which is literally a world where software costs nothing, a world where you don’t need to figure out how to build the custom tool.

You don’t have to get a developer’s time to build the custom tool. All you have to do is describe the outcome that you want, and a robot will make it for you. I think that fundamentally changes the role that software itself plays in people’s workflow.

Peter: We are in a very active period of discovery about exactly this, right? The more I think about it, the more I talk to folks about it, it’s not just about design when we’re talking about digital product.

It’s design connecting with product, connecting with engineering, possibly other teams, right? The workflow is not just one function, it’s a cross-functional workflow. And if, the design team has some combination of seven to 10 externally created tools plus 10 to 20 internally created tools that they’ve got going on, you could multiply that by all the other teams, and it starts getting out of hand.

But it’s a bit like that university landscape that was part of the inspiration for the name Adaptive Path, where, like, we’re seeing the paths people are laying down, and the ones that work are the ones that people continue to lay down, work on, and then we’re gonna pave those, right?

Those are probably the, some of the next big product opportunities.

Jesse: Mm-hmm.

Peter: There will probably be some shakeout where it’s not as rigid or as constrained as it had been a couple years ago where workflow processes were broadly assumed.

But I don’t foresee a chaotic future of ways of working ’cause that… I think there’ll just be too much organizational resistance to allow that to happen.

Jesse: Yeah. It’s not scalable in a couple of ways. It’s not scalable from an orchestration perspective, and it’s not scalable from an operational perspective. You know, this was the big question that I brought to the floor at the Design Futures Assembly last week. I was asking, what are the operational implications when every designer is creating their own flavor of prompt chain that helps them to get to a particular result?

How do you operationally assume or assure any kind of consistency across, especially across a very large team, where you’re potentially looking at, you know, there are teams out there of more than 1,000 people now, right? Design teams.

We cut operations just as we needed them most

Peter: Yeah and for me, this is something I literally just wrote about earlier this week in a newsletter titled “The Overlooked Solution to AI Confusion.” That overlooked solution is design operations, right?

Jesse: Yeah.

Peter: I think a lot of teams wound down design operations,. I mean, I’ve literally had a conversation with a different company where I was talking to the lone remaining design operations person, whereas a few years ago there were four, now there’s one.

And I think that’s a pattern that happens in a lot of places, because starting in 2023, belt-tightening, do more with less, layoffs, whatever, it’s easy to let go of your operations people because they’re not builders. They’re not delivering direct value.

It turns out, though, that they are exactly… You know, your whole talk on AI transformation, which suggests in part a transformation team that sees the organization through, that transformation team is, you could call it an operational team. It’s not 100% operational, but 50% to 75% operational.

Jesse: It has a significant operational function, for sure. Yeah.

Peter: Yeah, when you talk about communication, coordination, planning, ways of working, those are all operational matters. Process improvement, tooling, those are all operational matters.

And it’s like we got rid of operations right before we needed them most.

Good work, everybody.

But, you never want operations to run things, and my ops friends might object to me saying that, but I believe it to be true.

And that becomes a problem, right? In agile transformations, you know, you bring in all the agile coaches, you bring on scrum masters, you bring on some flavor of program manager or whatever that assists with agile.

And now all of a sudden, no team can do anything until those operations folks have allowed it to happen, right?

That’s not what I’m talking about here, and I think that’s where a lot of antipathy towards operations comes, is what sometimes happens is operations shifts from being an enablement to a…

Jesse: compliance.

Peter: It becomes governance in and of itself, right? It’s not enabling governance across, it’s “We are the government.” Yeah, and that’s no go.

But any organization that’s going to effectively embrace these ways of working is either going to have to bring on operations folks or, to your point, retask individuals and give them an operations mandate for some period of time.

We were talking about prior models and there was this whole industry set up to support agile transformations, with, again, agile coaches and scrum masters and all this kind of stuff.

Which was good for a while, but then we kind of lost the plot, which was that those jobs were always meant to be temporary, until the teams could do it themselves. But, “temporary,” like, that’s just not a word that lands in most organizational contexts. And so you had these folks sticking around long past their due date.

And so, my thought here is, like, you need to set an expiration date.

Jesse: Yeah, I can’t remember which organizational thinker said that bureaucracies exist to sustain themselves, but that is basically the idea. That once you have roles in place they’re gonna seek ways to continue to make themselves relevant or prove that they should be relevant regardless of as you put it, their expiration date.

I think the challenge with that when it comes to AI is nobody can see the top of the mountain yet, you know? Nobody can actually see at what point we get to the other side. It is just climbing and climbing. And as the mandate for this foreseeable future is climbing, you’ve got to optimize for climbing the hill, moving into the unknown collectively as an organization, as a skill set for yourself as a leader and for your team as a collective.

Peter: So do we need AI sherpas?

Jesse: There is an element of that, for sure.

Peter: You were, you know, talking about one of the challenges with AI is we don’t know how high the mountain is. You could imagine there was a similar challenge… Like with agile transformation pretty soon we knew how high that mountain was. Turns out it was pretty fucking low.

But I could imagine, you know, if we had applied our way of thinking in the mid-’90s, we wouldn’t have known how high that original UX design mountain was, right? It took actually a number of years. In fact, we helped start a company in part to do the survey of the mountain, right? To figure out the shape of that.

And when we started Adaptive Path in 2001, user experience was already a thing for about five or six years, not broadly, but it existed. Now clearly AI has spread like wildfire in a way that UX did not back then. It can take a while to understand the shape of something.

Gardeners and head coaches

Peter: I’m finding metaphors interesting right now, more interesting than I have in a while because I think they can give us some frames of reference, the blind men and the elephant, what is the shape of this thing, right? We’re all kind of picking at our part, but we’re having trouble seeing the whole.

I’m preparing a talk for an internal session right now, thinking about leadership in this moment. And I’ve got two metaphors that I’m currently playing with and both of which are about the act of setting conditions, right?

So I said earlier that setting conditions is kind of my frame of mode, right? I think we, when we think of design leadership, we tend to think of it as an active role of setting direction. This is what good looks like. This is quality. This is the vision. Let’s move toward that.

I’ve always believed design leadership has been more about setting conditions than delivering direction. I think that’s become irrefutable right now.

And I think what we’re seeing with AI is there’s just too much going on for any individual to set direction of.

So then if the challenge is to set conditions, create conditions, I’ve got two metaphors I’m working with.

One is that of a gardener, right? As a gardener, you are understanding your soil, understanding your sunlight, understanding your climate, so that’s the context setting. You are planting seeds. You have a vision for what you want in your garden. Is it gonna be a pretty flower garden? Is it gonna be a vegetable garden? Is it gonna be a bit of both? Is it gonna be landscape? So you have some vision of what you want.

You plant the seeds. You water or pray for rain. As things grow you encourage, you clip here, and you prune there, and you put up a trellis to get it to grow in that way, right?

But you’re never telling that one flower, “Be like this.” The flower knows what it’s going to be, but you’re creating the conditions to enable that garden to emerge in some way that you imagine… though possibly not, right? You know, there’s, I’m sure some improvisation in gardening. So that’s one metaphor.

The other is being an NBA head coach. And I think about this because it’s an analogy I used in the org design book, ’cause we talked about Steve Kerr. So before Steve Kerr joined the Warriors, good team, playoff team, but they never got past the second round. Steve Kerr joins the Warriors, pretty much the exact same players, and his first year, they win the championship.

He set a different set of conditions than the prior coach. He created a different operating model in terms of literally how they played on the court, but also how they worked behind the scenes. He brought joy. This is one of his kind of prevailing values, is joyfulness in work. And, you know, by changing the conditions for the same set of people, got a different and better outcome.

And the reason I think about head coaches, though, is, like, they’re not players. They’re not on the court. They’re not doing the thing. They’re trying to set it up, but then at some point you kind of have to step back and let the team make its way there.

The other reason I like the head coach analogy, is that we often tend to think that our design leaders have to be the best designer in the room. The head coach, Steve Kerr, was never better than the eighth or ninth best player on any team he ever played on. He was never the best player. He had played with Michael Jordan. He was far from being the best player, right?

And I think there’s something to remember that leaders don’t have to be the best practitioners. They have to be the best at getting the most out of those practitioners, and we lose sight of that, particularly in design.

Jesse: I think one thing that you touched on within this that I think is really important, and I think honestly cascades from the highest level decision-making all the way down to individual designers trying to deliver against individual requirements, which is that the introduction of this technology introduces an essential role of probability management on everybody involved.

That it’s no longer about perfect replicability and getting your systems so dialed in that you are getting exactly the same product off the assembly line every time, because that doesn’t play to the strengths of the technology. Playing to the strengths of the technology means creating space for variation.

It means creating the opportunity to pursue directions that might not actually ultimately work out. Which means that in a lot of cases, folks who came out of general assembly 10 years ago who were like, “Okay, here’s your tech stack and here’s your process, and now you can go get a job, and you can have this same set of expectations no matter where you land.” That stuff just straight up doesn’t apply anymore.

And the varying levels of maturity that you’re gonna see across these organizations are, in a lot of ways, going to be driven by the maturity of their leaders and the maturity of their expert-level practitioners who are going to provide that perspective that the leaders can’t get on their own.

Because to your point, they shouldn’t be knee-deep in the tools because they’ve got to be going to bat for the teams and what the teams need.

Peter: It’s funny though because… when you said that leaders shouldn’t be knee-deep in the tools, something I’m hearing from these design executives, not uniformly but mostly, is all of them feel like they do need to get into the tools in a way that they haven’t for the last, even, 10 years.

I talked to one leader who’s “Yeah, I never used Figma. I, you know, would go in there and make comments, but I couldn’t auto layout my way out of a paper bag. The last tool I used was Sketch or even Photoshop in terms of making designs, right?”

VPs who’ve had that mentality now are like, ” Oh, I gotta open up Claude Code. I gotta play with Lovable. I gotta build now in a way that I haven’t.” Which I find interesting, and I’m actually still coming to terms with that as someone who hasn’t been in the tools for a very long time.

Jesse: I think it’s necessary to be conversant with the technology in order to make informed judgments about how to deploy it. So as I talked about in the AI transformation talk, as I talk about with my clients, I think it is important for leaders to come to the table with a point of view on how this technology is best applied, where it really makes an impact, where it really makes a difference, and what we want to preserve of the human influence within these processes.

But I don’t think you can get there if you haven’t been at least a bit hands-on with it.

I guess that the thing is that I wouldn’t want leaders to think that their role is now kind of orchestrating this multi-variant operational condition-setting machine, because you can’t direct the design to the same degree that you used to be able to.

But you still have to provide for some variation and some context specificity within these design processes to enable designers to go their own way here and there, you know?

And that becomes a part of the organizational culture, that becomes a part of how people think about design.

Return to the Wild West

Peter: Some of the people who are navigating this best are folks who’ve been around a while and who came up in early web, 1.0 in the mid to late ’90s. And I think it’s in part because that was also a bit of a Wild West. There was no, I heard the phrase for the first time last week, “go-to tech stack.”

There was no go-to tech stack. We didn’t really have a process. We were making it up as we went along. The technologies were variable. There was an explosion of tools. There was something similar in terms of that environment, but also from specifically a design standpoint, what’s interesting to me about this is there were those of us who were web native who recognized you could not lock down the presentation layer in a web browser.

But then I worked with many trained designers who all they wanted to do were put up giant GIFs because they wanted to maintain the typography and the color scheme and the brand and all that. And that’s not this medium. That’s a different medium, right?

And we got away from that, right? You know, by the early 2000s, those designers with their giant GIFs let go a bit. There were things like Flash that allowed maybe some tighter controls, but we were in a fluid area for a while.

And then I think essentially with probably these frameworks, your React- type frameworks, as well as just mobile design and development, for the last 15 or so years, we’ve gone back to, you know what, I, as the designer, can actually specify the pixel perfect experience that every customer is going to have in an identical fashion. I can lock that down.

And now to your point with AI, all that’s taken away if you wanna lean into this material, right?

One of the talks at the Design Futures Assembly was from Josh Clark and Veronica Kindred. They have a book called “Sentient Design,” and the mindset behind it is what does it mean when AI is the material?

And to your point, when AI is the material, it’s not something you lock down, right, going back to the gardening metaphor. It’s this thing that you’re like shaping some conditions and seeing what happens, and what happens might be better than what you could have predicted.

The last 10 to 15 years where as you said, you know, you could learn in a boot camp how to do this work. That was for a material and a mindset that we’re not in any more. in

Jesse: Doesn’t exist anymore. Yeah.

Peter: But the other thing that you said, you used the word orchestration, and that’s a word that I’ve been coming back to.

You gave a talk at an UX Week or something in 2008 or ’09, where you defined UX design as orchestration, right? Not detailed delivery, but how do I bring together all this stuff?

And I think design leadership is once again going to have to adopt an orchestrative mindset, not like a conductor necessarily, “You, that violin need to play that note in exactly that way,” but that there is this altitude that we’re operating at, a higher altitude of coordination of elements that are meant to work together, and the job of the designer is to influence that, shape it.

Not shape it like a sculptor, but nudge it. And also this is where the gardening metaphor comes back. There’s feedback loops, right? And you see something, and then you do a thing. You prune it here, you nudge it there, you do a thing. So it’s not always on shaping, it’s responding to the system as it evolves.

Jesse: You know, I have to say I am hearing the voice of one of our listeners, I don’t know who, but somebody out there who is thinking right now all of that is well and good, but I have no authority. The shape of my team’s work is basically constrained by the expectations of our cross-functional partners.

And all anybody is asking me about or looking for or talking about with regard to my team is delivery. And I think the question for somebody like that in that position is: How do you start to evolve both your team and the expectations around your team toward a different value proposition?

‘Cause it seems to me that’s what you’re suggesting, right? That a delivery-oriented team is going to have to find new ways to deliver value. Is that– Do I have that right?

Peter: Yes, either a delivery-oriented team is going to have to articulate a new value proposition or maybe, as we said earlier, articulate a value proposition. I think…

Jesse: to begin with, yeah.

Peter: many delivery-oriented teams have inherited their value proposition from their product leader or engineering leader or whomever they report to, as that’s the value they are delivering.

They’re gonna have to get out in front of and be intentional and mindful in the creation of a new value proposition.

You were asking earlier what’s new, what’s not. This is one of those what’s not, right? Like basics of leadership, and one of the basics of leadership is having a vision, having an agenda, having an idea of what is the change that you seek and articulating that, right?

And that doesn’t change just because it’s AI. You just need to apply that leadership practice to this moment.

What is the change you seek? If you’re a delivery-oriented org and you realize that you have two paths ahead of you.

Getting much smaller because much of that delivery can be handled by the robots. I was talking to someone who, their design systems team is turning into a UI infrastructure team, which is just gonna be in engineering. That’s just an engineering function now. It’s not even a design function. Maybe there’s some designers on the team, but they’re approaching it with an engineering mindset.

So that’s one path, and if you’re fine with that path, great. But if you’re not, then you need to articulate what change you seek, what potential you believe that you have in terms of positive impact within the organization you’re in that aligns with desired value as articulated by your leadership, and start doing the work of your team is delivering on that desired value.

Who’s not on the bus?

Jesse: You know, one thing that has come up in my AI transformation work that I have heard from other folks as well that I think is a really important theme to consider in here is that everything that you’re describing assumes that the team is ready and willing to come right along with you and support that vision, you know?

And for a lot of designers, and honestly, I think it in some ways this afflicts the more junior designers more than the senior designers, although there are maybe different flavors of it, they don’t want this change. They don’t want different tools. They don’t want different processes. They don’t want to rethink their value proposition. They have the job that they wanted, you know?

And now you’re telling them that they don’t get to have it anymore. And so another thing that I think we’re gonna see, especially within design organizations, although we might see this more broadly beyond design, is a bit of a cultural schism between the people who are ready to embrace new tooling and the people who are pretty comfortable where they are and feel like they’re delivering plenty of value doing exactly what they’ve been doing.

And for leaders both from an operational as well as from a cultural perspective, they have to set a tone that is inclusive enough to cover that whole spectrum.

Peter: It has to be inclusive enough to cover the whole spectrum, but do you believe it is acceptable for some designers to remain intransigent?

Jesse: I think every organization is gonna reach that point by its own path. In some organizations, there’s gonna be a lot of tolerance for continuing to do things in old ways, you know? And it’s like that print shop that has that one computer back in the corner that still has the CRT because it’s the one that the guy who runs the shop trusts and knows how to use and doesn’t need anything different. And maybe everybody else around him is using some other kind of tooling to do their jobs.

But, I think you’re gonna see… kind of a long tail to this, where you’ll have a few organizations that are at the very front of the pack that are very aggressively in with the new, out with the old, churning their processes to arrive at some new patterns and some new paradigms and some new form of consistency.

Because I agree with you, It feels like we’ve gained too much, in the last 25 years, operational wisdom to just throw it all out because we’ve got new tools now.

But then I think, further down the tail, you’re gonna have a lot of organizations that are gonna live in this kind of hybrid space for a while, where there’ll be a few people who are embracing certain kinds of processes, and maybe other people in other parts of the organization for whom, you know, we only see an incremental gain from you taking up new tooling, and you’re doing perfectly fine as you are, and so we don’t need a new anything here.

And there are a lot of organizations that’ll be making that call probably for years to come, you know?

Peter: I find myself wondering about that if only because the conversations I’m having. So with this listening tour, when I talk to these VPs or chief design officers, if they’ve got, let’s say, 100 or fewer designers, all of them are expecting their entire teams to become IA-enabled. AI-enabled.

And in fact, one of the conversations I had today was with a design leader who’s like, “Yeah when it became clear that there were some folks who weren’t on the bus, they were shown the door.” Yep.

Jesse: I’m not saying that won’t happen and isn’t already happening, but based on the conversations I’ve been having, I’m not aware of a lot of organizations that have seen enough gain from new tooling, new processes to actually justify those kinds of cuts.

Usually, those kinds of cuts are coming about because they had other reasons. They had already overreached in their hiring in some meaningful way, and people are looking to this as almost like a preemptive strike to cut the team before it gets to a place where you’ve got a lot of extra people hanging around that you’re trying to figure out what to do with.

Peter: Yeah and as I say that, I’m not saying it because it’s what I want or necessarily what I think is right.

I’m just, thinking about these conversations, and I’m realizing that most of the design leaders I’m talking to are like, “Yeah, not only should my teams be AI-enabled, resistance to AI enablement is an indication that that person is probably not right for my org.”

Not even because they won’t use AI, but because it’s suggesting some incuriosity or intransigence or just some other kind of personality characteristic.

Jesse: Attachment to an identity, attachment to a kind of a craft.

Peter: Whereas I do think what you were talking about will likely persist in some organizations, but I suspect that in much the same way that every design team adopted Figma, were more than happy to get the hell out, first out of Photoshop and then out of Sketch, and they adopted Figma because they saw the value in it.

It probably them a little while. I’m sure there were teams that were like, “Wait, I don’t want PMs all up in my business.” In fact, I actually, as I’m saying that, I remember hearing designers saying, “I don’t want PMs all up in my business” right?

And that was the risk of Figma. “They’re gonna comment on my files.” But now it’s just an assumption and it’s fine. It’s fine.

And in fact, design was the entity that drove that adoption. Even now in organizations, you know, we have a shared friend, Z, the design ops leader, who’s like, “Yeah, my design team uses Figma less than product and marketing.” We drove the adoption, but now other teams actually see more value out of it.

I suspect that AI enablement will eventually be adopted in a similar way by design orgs. I don’t know exactly of what, but it will be seen as an absolute good. I’m sure there’ll be benefits and drawbacks, but in the calculus more benefits to drawbacks, and that any resistance to AI will be organizational, right?

So at the Design Futures Assembly, we had an old friend there who works at a giant bank, and he’s like, “In no way on planet Earth or throughout the galaxy will they ever let designers commit to prod at this bank. That is just not a thing that’s gonna happen.” Cybersecurity, info security, compliance, regulatory issues, et cetera, et cetera. The amount of effort it would take to get designers up to snuff for code- committing like that’s not worthwhile, right? That’s where it’s more likely for the constraints and barriers to be, than inborn of design practice.

Jesse: Yeah. And I think that’s part of the long tail effect that I was talking about. You know, each organization’s legacy and constraints are going to dictate where you fall on that tail in terms of how far toward new tooling you have permission to move, how much latitude you have cross-functionally as well as with your business stakeholders and people like policy and compliance and regulatory and all those kinds of things.

Different organizations are gonna find themselves in different places, and that’s why I think that this adaptivity ultimately ends up being not just a core skill for leaders to thrive, but a core skill for their entire teams to thrive as well.

And I can see, to your point about if they’re not curious about how to evolve their practices, let them go, right? This suggests that the culture of design teams going forward has to be one that is more experimental, that is more driven by individual inspiration and vision, that is more exploratory in finding new tooling, finding new techniques, finding their way to do this work.

Peter: It’s funny as you say that ’cause again, this feels like a throwback to me. I’m like, “Oh, 2003 called and wants its design profile back.” And I don’t disagree. The responsibility of the leader is to then make the space to allow that to happen, right?

‘Cause right now, I think a big reason for burnout and for anxiety and for whatever problems you see bleeding through spaces like LinkedIn or various design meetups is, even before AI, designers were overtaxed, spread too thin, supporting too many PMs, given too much to do, and as a result of a lot of that, found their value narrowed to a production or delivery mode, ’cause that’s the one kind of touchpoint between their work and the rest of the organization that people recognized as worthwhile.

And now, all of that is still true, and we’ve just layered on, “By the way, figure out this AI stuff. Peace be with you.” And they’re overwhelmed with which of these 15 tools do I use and in what combination? And this is your argument for AI transformation teams and practices and processes.

But like even when we get kind of over that hump, you know, this is a drum I’ve been beating for probably 25 years, which is how do we make work sane? When I was young and I worked in what I would now probably think of as moderately insane organizations, I was young and so I didn’t know any better, and I was willing to be insane.

And then, I was 28 when we started Adaptive Path, and one of the core operating principles of Adaptive Path was a sane working environment, right? That’s not necessarily what people outside the company understood. They thought it was about great user experience and…

Jesse: I’m not sure that’s what all our, people would agree that we created.

It was definitely an ambition.

Peter: You posted about the 25th anniversary. There were comments from Adaptive Pathers of days of yore who were like, “That was the best work environment I was ever in.” And that was something we were very explicit about creating, which was you can do great work without running yourself ragged, right?

And that, for some reason, is some revelation. It shouldn’t be. There’s no reason for most of these organizations that they operate the way they do, except that they don’t know any better or they just think in order to work, people have to be working 50, 60-hour weeks now.

They have to be always on. They have to be willing to respond to emails you know, nights and weekends and all this kind of stuff. And it’s like that doesn’t…

Jesse: 9-9-6, baby.

There’s

Peter: no evidence that 996 delivers better work, and in fact there’s evidence that it doesn’t. Evidence that, like, 35 to 40 hours a week turns out to be an optimal amount of effort. And when you ask people to work more than that, the quality of the work beyond that suffers such that then they have to work more to undo the bad work they did when they were overtaxed, right?

And so when you talk about experimentation and exploration, that requires leadership to fight for a sane working context that enables folks to do that kind of exploratory and experimental work.

Jesse: Yes. Yeah, I completely agree with you. In the talk, I refer to this as air cover.

Basically, this is the leader setting the context, both within their teams and again, cross-functionally and with the leadership about the ways in which their processes might not look like what they used to look like, and letting everybody know that you’re embracing a culture of adaptivity, and that’s gonna have consequences for how the team shows up.

One of the main reasons that I am advocating for design leaders to spin up these transformation teams and transformation initiatives is that by giving it this dedicated focus, by clearing the decks for a few people to really focus on driving these things, you can give it that extra level of attention that is not just about technology policy and not just about process, but about culture, about how the humans in the organization engage with the work, and what keeps those people engaged with the value that is actually being delivered by the larger team.

And in a lot of ways, what this is, is it’s not just about a culture of experimentation. It’s not just about a culture of exploration. It’s also about a culture of reflection and prioritization and a kind of ruthless evaluation of what’s working and what isn’t, so that you can scale those methods in meaningful ways.

And I don’t see how you can do that given the mandate of the leaders that most organizations already have in play, right? There’s just not enough space if you don’t dedicate somebody to it.

Peter: I was thinking about something Marty Cagan said at an internal presentation he gave at a company that was one of my clients. And this is a company that was trying to embrace a kind of product transformation, agile transformation. Not scrum transformation, but, let’s embrace dual track agile, let’s embrace product discovery, let’s build product the right way. What has kind of been conceived as the right way.

And the thing that Marty pointed out is that the single biggest constraint to that transformation does not come from product, design, and engineering. They do have to change how they work and there’s gonna be some resistance ’cause there’s always resistance to change.

But by and large, those teams get it. They’re like, “Yeah, we want to work this way ’cause we know what it unlocks.”

The biggest constraint to their ability to succeed is everyone else. And it’s how does finance think about funding models for teams? How does HR think about career pathing and performance evaluation and compensation for teams? How does sales and marketing engage with those teams from a, say, a requirements perspective? It’s all the other functions.

And what Marty pointed out is he had never seen a truly successful agile transformation or product transformation that didn’t involve the CEO. It needed the toppest down mandate of the CEO because the CEO could tell the non-product functions, ” Hey, you’re gonna have to change.”

But if the agile transformation was only being done from the CPO down, they’re gonna continue to behave as they have, and what’s gonna happen is kinda like a kudzu. You’re gonna clear the field briefly, and then over time, the practices of those other functions are gonna push back on product development.

And it might look agile. They’ll adopt agile rituals, but they’re gonna be behaving as they always have because of the larger forces at play. And so that’s to the point we were just making about experimentation and exploration. That’s the risk for AI transformations, is how are the rest of the organization reshaping their ways of working to enable that productively?

Jesse: And the leader’s gotta be managing those expectations, right? The leader has got to be the bridge between functions that helps those on both sides understand what each is bringing to the table, and what each can reasonably expect of the other so the politics doesn’t go away, you know?

Peter: No, the politics are as, if not more, politicky.

Though, it was funny, I had a conversation again today with a leader whose team is embracing AI and has AI enablement and there had been a top-down mandate. It wasn’t like metrics-driven. Like it wasn’t every team needs to use 20% AI or somewhat… You know, you hear about some of these arbitrary numbers in terms of AI application.

But there was a top-down mandate from the C-suite that teams need to be AI-enabled. And this leader’s like, “Okay, let’s figure that out,” and tasked folks to make that happen. One of the things that ended up happening is, because the way this leader approached it within their organization, they got out ahead of product. Design and engineering both took a similar approach in their realms and then partnered with one another.

And design got out ahead of product such that he who controls the prompt controls the product. Yeah, where design is starting to lead product strategy because they had demonstrated expertise in this area that was considered important right now and were able to leverage that for a kind of political gain.

That wasn’t the motivation, but that ended up being the byproduct. And as part of that, at least in my conversation with this leader, this is someone who used to have a seat at the table, and then that seat was taken away because of layering that occurred a year or two ago. And now they’re slowly creeping back to the table because of the team’s ability to do good work.

Jesse: Yes.

Peter: It’s delicate because you and I encourage leaders to recognize the politics in the organization they’re in. But the reason for this person’s success is they doubled down on, “My team is gonna work really well.” So it wasn’t political. It’s “How do I set them up to, make the most of this moment?”

And it turned out others recognized that and saw the value in it, and they didn’t have to manage up. They could just do the work really well. And I wonder if there’s something about this moment right now that you might not have to be as political if you can demonstrate capability. It’s a thought.

Jesse: Yeah, I think there’s potentially a lot less political legwork involved. But I will say that the political calculus for the leader is exactly the same, which is to understand the needs and the perspective of your various cross-functional partners as well as your business stakeholders and influencers, and make sure that stuff is represented in the choices that you’re making.

But yes, what you’re describing is exactly as it was foretold in days of yore. When I gave that talk last year, it was the pattern that I was seeing, if you got there first, you were gonna get that seat at the table.

The window of expertise power

Peter: I think about power dynamics and usually what’s considered the most powerful type of power within an organization is relational power, and that’s still largely true. But there are ti

Show Notes

Journalist, technologist, and Aboard co-founder Paul Ford joins Peter and Jesse with the perspective of someone running a services firm in the middle of being remade by AI. The conversation covers the collapsing cost of software, blurring roles, what machines do well and badly, what design’s value proposition becomes, and Paul’s practical advice for staying upright through indefinite change.
Paul’s company: https://aboard.com/; Paul’s LinkedIn: https://www.linkedin.com/in/ftrain/
Peter’s website: https://petermerholz.com/
Jesse’s website: https://jessejamesgarrett.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, journalist, technologist, and agency founder Paul Ford joins us to share his perspective from all of those perspectives on the tidal wave of change from AI. We’ll talk about shifting expectations, shifting identities, holding onto the human in the face of rapid change, and a whole lot more.

From the pages of Wired and The New York Times to your ears, here’s our conversation with Paul Ford.

Peter: Paul, thanks for joining us.

Paul: Oh my goodness. Hello friends. It’s good to see you.

Peter: It’s good to see you. I’ve been following your work on the internet for probably 20, 25 years.

Paul: This is it’s just ridiculous at this point. Like it just… the three of us, anyway, it’s great to see everyone. I don’t even know if we’ve even met half the time. Peter, I think maybe you and I have been in a room a few times, but

Peter: yeah.

Paul: It’s lovely to see everyone just getting our career started, getting stuff moving.

Peter: Career. I think we’re getting our career restarted.

And maybe that’s a place to begin. It appears you’ve been going through it the past few years, and I’m curious how you introduce yourself, how you talk about what it is you’re up to now.

Getting Our Careers Restarted

Paul: It’s changed from time to time, but essentially I am the president of a services company. It works like a services company. People come to us and they say, I want you to build my thing, just like the industry I’ve been in forever, except the nature of building a thing has changed really fundamentally.

You can spin up software very quickly and, I’m the president of Aboard. We are a AI, sort of, delivery org. We help you get your head wrapped around a lot of these changes. And we help you ship software very quickly. Sometimes with our custom tooling, sometimes just using Claude Code or whatever.

And so I come from that background. You’ve all been in and out of services, like I have throughout your career, and actually it’s, kind of relaxing for a minute because a lot of times I’m talking as someone who is also a former journalist and I have to be on and know everything.

In this case, you understand where I’m coming from. I don’t know what the hell’s going on. Like I used to charge a certain amount of money. I used to, I used to be like, Hey, I’m gonna do this and I’m gonna get a product manager. I’m gonna get a designer. Maybe a junior designer too, and a couple of engineers. One for back end and one for front end. And then I’m gonna give you a thing and it’s gonna break, and then we’re gonna figure out how it needs to work. And then about six months later, you’re gonna gimme a lot of money, like hundreds of thousands of dollars, and you will have your thing and it will be good.

And that was 20 years of my life. And that is not the case anymore. And I think you guys are probably dealing with this just in the exact same way. I’m curious what, where you’re at.

Peter: Before we answer that, I have one specific question. No. ’cause you had an agency, you had Postlight, Jesse and I also had an agency in ye olden times

Paul: What was it? No, you gotta, you gotta name it’s for the people.

Jesse: Name it for the people,

Peter: Oh, they know Adaptive Path.

Paul: There we go.

From Product Company to Agency (Again)

Peter: And the sense I got, and correct me if I’m wrong, ’cause I’m witnessing this from afar, you left Postlight, you started Aboard, which I got the sense was started as a product company, you had an idea for a thing, you were gonna build a piece of software to put into the world.

And that was my operating assumption until literally three days ago when I went to your website and I was like, wait a minute. They’re an agency. Why? What happened? And I’m curious what that story is, ’cause based on what you were just saying, I think it’s probably illustrative of something going on right now.

Paul: Yeah, no, fair enough. So I was the CEO with my co-founder, Rich Ziade, who was the president of Postlight, which was a product focused software development firm in New York City, very New York based. We did a lot of work for big banks. We did a lot of work for the MTA.

And so everything that you would expect about boutique and it scaled, it grew pretty quickly. And it got to about a hundred plus employees many in the US, a few globally. Especially in Beirut, which is where Rich is from. He’s from Lebanon.

And all those things selling all day long, so on and so forth. We, during the pandemic, stepped back, new leadership took over and it felt like time to move on.

The company was purchased by NTT Data Americas and became part of a big product group. And I was contractually obligated not to sell services because my power as a salesperson is so incredible.

Jesse: Yeah.

Paul: Just, Just, if you’re not careful, I will sell you a six month product engagement while you’re not even looking.

Peter: Alec Baldwin has nothing on you.

Paul: No, exactly. I’m just ready. I’m ready at all times. I love to close. A, B, C.

Jesse: A, B, C.

Paul: Exactly. But Richard and I really like working together and we didn’t go with the acquisition.

It was one of those where they were just like, cool, we’ll take it from here. And so what we sat down to do was to build, and it’s now been through many iterations, a kinda white label….

We were like, let’s take the advice everybody always gives you. Let’s build a version of what we used to do at the agency that we could license. So every project you sit down and you build Kanban and you do user authentication and integration with Microsoft a lot of just the basic data and scaffolding stuff.

And so we built that. That was version one.

And then we were thinking, there’s just a series of decisions that you make when you’re building something, some of which are good and some of which are bad. So we made a version that was a little more open to the world where people could manage data, but the theme has always been from day one that we would take this to organizations, and organizations would use it to accelerate software development.

And so that felt good. And we had leads and we had clients customers really, because you’re selling a product and they were using it internally and all those things were happening.

And then ChatGPT showed up and started writing code. And I was like, whoa, this is gonna change everything.

And we all kind of agreed. And so then the last couple years have been about iterating in reaction to the fact that the cost of software is going down. And the need for acceleration, even as a concept, is becoming commoditized because you can just deliver stuff all day long.

And so a lot of the things that I thought I was way in the future on, I’m not anymore. Nobody is.

Because what the hell is a Kanban board? Or like sales or a CRM if you can build a credible one in two hours?

And so we’ve been riding that wave and what’s happened is that you react to your inbound. And our inbound has been orgs saying, help us get organized around this. That’s great that you have some custom things that you’ve built that help us build. We love that. That’s really nice. Good for you. But we’re just trying to get this going here. Can you help us solve this? Can you help us integrate these three things? And by the way, could we also make sense of AI while we’re doing it?

So we’ve backed into kind of consulting plus custom tooling as opposed to custom tool with consulting around it.

Jesse: I think that one of the challenges that’s going on for enterprises right now is that they don’t know what they do know, and they don’t know what they don’t know.

Paul: There is a great Reddit thread now, where I think it’s in just like the Claude Reddit where an engineer is just like, CEOs keep giving us code in engineering, and I’m losing my mind.

right?

Jesse: terrible. It’s like the worst case scenario. And so it is this interesting sort of tension that teams find themselves in where the walls are collapsing. And the gap between thought and reality is shorter than ever.

Paul: Which we should be excited by, given our careers.

Jesse: We should be. Yeah. exactly.

And then I wonder about these teams, your clients, our clients, the people who are inside these organizations who are trying to get things done inside these much slower moving cultural environments,

Patrick Swayze in Ghost

Paul: I gotta tell you, I don’t know if you have this experience, but you’re dabblers, we’re all dabblers because we were early in this technology and that was what kind of got us into it.

And I just wrote a post about this for our newsletter. I feel like Patrick Swayze in Ghost: I’m telling everybody what’s happening. Like, You’re in trouble. There’s danger. And everybody’s like, wow, it’s cold in here.

I keep having that experience and what I realized is that what has happened is so weird. It’s so weird. And we’re used to weird things, but most of the world is organized….

i don’t know if you guys had this experience, I’m gonna be another web old timer, but like, there’s a lovely program. I taught it for a while and it was with people like Jeffrey Zeldman at the School of Visual Arts, the MFA in Interaction Design.

And there was a point where I went in, and it’s like me and Jeffrey and Karen McGrane and I’m like, oh, we’re the older weirdos here. We’re, like, the early ones because there were these just very put together graduate students who were like, I’m gonna learn interaction design, I’m gonna build a really good career.

And then they would go to FAANG companies like right away. They were good product people. And there’s that moment when you realize oh, this is becoming professionalized. That’s really good. That’s actually healthy. People are seeing this as a stable thing, as opposed to a wild wave to ride and figure out.

And I feel that that gulf has never been more profound in my life. Like, it’s very hard to see something so transformative. And then you take it to people and they’re like, yeah, but what about those Mets?

Like they’re just kind of like, they just would like, please, can we not discuss this anymore?

Peter: in my experience, it’s one of two things. Either, this is the only thing people want to discuss or this is the thing everyone’s trying to avoid. It’s hard to have just a casual conversation that might touch on it and then discuss other things.

Jesse: It’s got a gravity well, right.

Paul: Yes.

Peter: It is the gravity well. It reminds me Paul, I don’t know if you know Matt Jones, from the UK, one of the people behind BERG. I remember his frustration in 2004 or five, where all anyone wanted to talk about was the web. And he is like, there’s more to the world than the web.

And he was right. And I’m sure there’s more to the world than AI, but right now, like this is the actually intellectually interesting thing as well.

There’s something here that’s forcing us to reconsider stuff that we felt was maybe assumed. You outlined it.

And that’s been a theme that Jesse and I have been pursuing how for 20 years, from about 2000 to 2020, 2022, there was just this nice, steady kind of pace of growth and development and reliability.

Jesse: It felt like we were building a stable new thing

Paul: That’s right.

Jesse: For about 20 years, right. And then suddenly it wasn’t stable at all anymore.

The Tinkerers and the Professionals

Peter: Right and something’s happened. Even pre-AI with the layoffs and stuff in 23. But it’s definitely kind of timed to the AI moment.

You were talking about professionalism and you were talking about how we started as tinkerers. And I wrote on the whiteboard behind me the word humanities because the three of us went to school at around the same time, and all studied, I studied anthropology. Jesse was a journalist, and you studied English, the famous degree of futility.

But with our generic humanities backgrounds and not being afraid of technology, we were able strike out on these emergent technology of the web and the internet.

And now there’s a group of folks who… It got professionalized at places like SVA or bootcamps and other things in the last 15 or so years. And the thing I’m seeing, and I’m wondering what you’re witnessing, Paul, is that folks of our vintage are in some ways less rattled by what’s happening now because we came up in a discombobulated moment and in fact many of them are excited because it’s like, Hey, this feels like the late nineties again.

Whereas folks who arrived when it professionalized are the ones who are maybe the most off kilter because their assumptions are now shattered.

Paul: I think that there’s a few ways to hit at that.

I’ll take two angles. So angle one is, there was a great quote. They asked Linus Torvalds, who created Linux, who’s a little bit older than us, but not much. And they’re like, what do you think about AI? He is like, oh, it’s wild. All the vibe coding, it’s really interesting and it’s gonna really, it’s a real accelerator. Like he’s just vaguely into it as a technologist. He’s not shocked, he’s not an open source purist about it. He is just oh, there’s gonna be vibe coding. It is what it is.

But he is, like, but let’s be clear, nothing was as transformative as compilers, which was a really funny thing to say.

But then when you think about it, until compilers, you had to literally put in the code that the CPU runs in like hexadecimal numbers and, like, you were flipping switches and then one day you could issue a list of English-like instructions.

And that’s like at a thousand times cognitive speed up. Like, so many people, we just take it for granted. We take it for granted that you can have something that looks like Python or JavaScript and that will run, or even HTML and it will do something on the computer and you can learn that and you can teach it and so on.

And that, that actually wasn’t there for a really long time in the history of computing for all sorts of reasons. And so I really liked that framing because I was like this is another transformative thing. It is accelerated, it is different.

But we’ve been through major transformations before. That said, what’s different is it was not a, multi-trillion dollar, 30-million-person industry as it is today. And so the change is being felt really radically.

And so, we are very interdisciplinary by nature. It’s what attracted us to the medium because it was the first time that you could smosh the humanities degree with the technology, with the visual, with the written.

Like, It all started to congeal and you could kind of mess with all of it. And nobody could tell you no, you know, nobody could be like, you’re not allowed to do that. ‘Cause there’s the web, you can do whatever the hell you wanted. And so I think that is always very attractive to us.

But most people really want a little stability in their lives, like they really do. And we’re the freaks here, right? Like, we’re like, ah, well more chaos. Let me just huff it up.

Boy, that’s some good disaster. Get me more.

Peter: I dunno, I think I’ve reached a certain age where I’m fine with stability.

Paul: This is the thing…

Peter: Maybe when I was younger, chaos I could thrive on.

Paul: But think about actually, Adaptive Path is a good example. It was a transitional moment where you guys went, okay, wait a minute. We actually have to make this boring. And I don’t mean that in a bad way ’cause I’ve done it many, many times.

Like, I need to go to a bank like the one that eventually acquires you and I need to help them make sense of this because their world is interacting with this, but their systems can’t tolerate so much change.

And that’s you as little babies, you’re little babies going okay, we gotta figure this out because rhis change is so difficult for relatively nice people who I have meetings with. So we gotta actually systematize and structure this. We’re gonna make lots of diagrams with boxes in them, and it’s gonna be okay.

And we’re just not there yet with this stuff because every fricking week Claude is oh, by the way, it can make shoes now.

Jesse: You’re right. Yeah.

Paul: What would Adaptive Path be for the vibe coding era? Jesse?

Jesse: I, well, yeah. Okay. What would it, all right. Hang on. It’s such an interesting question because I think that a lot of what we did was about deliberately diving into unexplored territory. We were continually inventing methods and developing techniques around things that we had no idea what to do because no one had ever done them.

And so we had to improvise and adapt from a methodological perspective around the work, and what was actually to be delivered.

So we just recently celebrated the 25th anniversary of the company. And one of the things that I pointed out to folks is we did not even call this work design when we started doing it because we felt like we were after something bigger than what people thought design was.

And in this moment, in this time, people think they know what design is.

You Sold Empathy for Large Systems

Paul: No, I mean, let me make an observation about what I think you actually sold. I think you sold empathy. You said you had a lot of skills, but I think you actually sold empathy for large systems. It was like we’re a big system and we don’t really know what to do next. And you were like, I have the skills that you need.

But more than that, ’cause that’s tactical, I actually have empathy for the fact that you’re doing the thing you’re doing and I would like to understand it. I’m curious about it, and I would like to bring my skills to it. And I think that was very comforting to people with the change, right?

And so when I think about the organization I’m building today. Everyone is a solution engineer. That’s like a mix of product manager, design, engineer, ’cause if you can ship anything, right? So let’s call everyone a solution engineer.

But our job is to be empathetic to people who are driving through this change who want to be able to access the system without destroying everything on day one. And I think that’s what you guys were too. I think it like that’s what everybody’s really hungry for as far as I can tell. They don’t wanna just build, they want to understand.

Can the New Computer Clean Up the Old Computer’s Mess?

Peter: I’ve got two questions about your business. The first is, is there a type of client or type of project that is pretty typical that is coming to you and what are those?

Paul: So there’s what’s in-house and then there’s what’s inbound, right? And I can describe both in broad terms.

So in-house is like helping a big insurance company doing things to help them manage policies in new ways and analyze data.

So it’s a portfolio of, like, projects, like classic projects with a little bit of AI and a little bit of acceleration and a little bit of strategy and kind of putting that together.

The larger orgs are like that. They’re like, let’s just try to get this in. Let’s see what we can get. We like the advantages of it, but we’re gonna take it step by step. Security is very important. Auditing is very important.

The other in-house is, it’s a giant medical informatics play from a big not-for-profit. They want to aggregate lots of data around children’s health, and they need to do it in a HIPAA compliant way that’s very secure and safe. And then they want to be able to almost talk to the dashboards, right? Like they wanna be able to ask natural language questions about how services are being delivered across a large number of clinics. And so, that’s another one.

Those are kind of like almost classic big project engagements that are enabled and interesting because they’re AI. You know, there’s a team on them and so on.

What I’m finding more and more is that if there’s a theme, it’s that, wow, computers made a mess of everything, and if we don’t have to live with it anymore, that would be really awesome. Can the new computer clean up the old computer’s mess? And the answer is yes.

Like the huge pile of documents that was OCR’d can now be really rendered way more useful. The invoice system can be better.

The number one question that everyone asks on Earth, as far as I can tell, including babies, is what would it take to get me off of Salesforce?

That is like the absolute, like, literally people who are dying, their last words are, I wish I could have gotten off of Salesforce.

That’s, please don’t let me go…

Peter: They don’t want to have spent more time with their family. It was just off Salesforce.

just get me off Salesforce.

Paul: Why couldn’t we ever get off Salesforce?

I hear a lot from people who either tried to build up from SaaS products into a kind of a working system and then just find endless friction every day. I hear a lot from people with legacy systems who would just like to move a little bit faster. And then I hear a lot from people who are just like, I gotta get this into the org, but I don’t know how. And so those are the shapes.

And then at the same time, a lot of the things I’m seeing and living, delivering the services are really confusing because the design phase is different and the engineering phase is different.

Building the Product During the Pitch

Paul: And sometimes, and I have had experiences, a lot of times I’m building the product during the pitch, right? Because it’s just so fast.

And so then do I show that to them? When do I show them the value that they can have access to? Not because I want to get them… but literally ’cause it’s so overwhelming.

I don’t know if you’ve had this, but you create these artifacts and people don’t write back for two weeks because

Jesse: it’s

Paul: so hard to metabolize like what they just saw.

Jesse: This gets back to a very old tension between Peter and myself in our consulting practice, where I was always reaching for the farthest frontier that the client could possibly see, and then complaining that they didn’t sign on to my ideas.

And Peter’s like, well just, you know, don’t give them the 10 mile view. Give them the one mile view and get ’em to sign on to that.

Peter: Yeah. Give them the thing they can actually do.

Paul: No. We’re gonna just, I just want to pick at this scab. This is exciting.

I think, look, I’m with both of you, right? I like to see where the future’s going. And actually if there’s anything, my dynamic with my co-founder, I’m probably more the Jesse and my co-founder is more the Peter in this, but it’s always that collaboration, right?

Because I’m the guy who’s wow, whoa. I literally, I hit Claude Code in November when it got really good and I walked in the next day and I just turned to Rich and I went, death is coming.

That, those were my words. And he is like, slow down. The insurance industry doesn’t move that fast. And actually the insurance industry, if death is coming, they’re like, cool. We priced that in. It’s all great.

Jesse: Yeah.

Paul: So no, I think, it’s very tricky. Organizations cannot metabolize change.

I will say, I think there is a thing coming for all of us that no one has fully factored in yet, which is the security profile of the entire industry has to change because it’s much easier to hack systems than it used to be.

So I think if you were to really think about the right way to walk this into an org and just be like, let’s do some automated auditing and figure out where some of this stuff could be like made a little more firm and stable using AI, like let’s clean up some mess. Let’s think about security. Let’s audit your open source. Let’s make a good auditing trail.

Like, there’s a lot of system stuff that’s gonna have to happen because you can hack all day now at a nation-state level for $200 a month.

And so those changes are coming and they have really high costs. And I think probably we do have to react to them as an industry way faster than we were even expecting.

Or not. Or not maybe, hey, things work out. Security is one of those things.

Jesse: be fine.

What Is Design’s Value Proposition Now?

Jesse: You touched earlier on the blurring of lines as you’re defining this role of solution engineer for yourself within your organization, and for a lot of the folks that we hear from who listen to this podcast, they are in-house design leaders.

They have got teams of 20, 50, a hundred, 500 people who are dedicated to design, whatever that means, as a value prop inside their organizations.

And now they’re looking at engineers doing what they used to call design and product managers doing what they used to call design. And their designers are looking for purchase within this landscape. They’re looking for a place where they can get some really meaningful traction. And so it comes back around to this question of what even is the value proposition of design as a function anymore in this blurrier environment? What do these leaders and these teams have to look forward to in terms of what they bring to the table and what they can potentially offer?

Paul: I think this one is thorny and it’s not thorny in a like, oh my God, time to start that bakery kind of way. I think it’s more complicated than that.

Let’s take this step by step. I’ve been doing a lot of thinking about this, I think there’s a few realities. One is an average human being in a technical context, an engineer or product manager can do far, many more design tasks without asking a designer than they used to be able to.

And I think one of the ways we get in really big trouble is we go, well, that’s not really design. But if it has a function for the audience and the audience doesn’t really feel that they’re being duped, then you’re at a loss now.

It might be disrespectful of the discipline, it might be not at a level of quality that you would ever put out for yourself, but the reality is you are at a loss because the audience has gone, oh, cool, that’s there. And it’s there in 10 minutes. So that’s, I like that. It feels good. It looks like an app to me.

And then there’s the secondary thing, which is that some of the models are good at certain kinds of design. I’ve absolutely had moments where I was like, that would’ve been a junior designer. I’ve never seen anything that come out where I’m like, that’s a senior designer level artifact. But, absolutely things that are, like, wireframe-plus or relatively light, type heavy, here’s how the onboarding would work, right? I, I’ve seen good product.

So I think you have to get close to that and you have to know it, and I think you have to know how to steer it and understand it so that you’re delivering it with the information that you have in your discipline as opposed to getting frustrated with other people for doing it.

You have to enable them. Now if you’re in a hostile environment, there’s a lot of bad blood in our industry, right? There’s a lot of like, oh, design always takes forever. And then like product is snooty, but also can’t do anything. And engineer….

And the reality is everybody thinks they can do everybody else’s job. And then it always blows up. And this has been going on way before AI, so product is so excited that they don’t need engineers, ’cause engineers are exhausting.

But I keep seeing product managers ship the same fricking thing that just looks like a spackled together database that they’re like, I’m vibe coding, aren’t I amazing?

And I’m like, yeah, but honestly that’s like, you could have done that in Airtable. Like, I get it, I get that. It’s cool, but it’s not really a product even though you’re the product manager. Like you forgot that part. Everybody keeps forgetting their actual thing, right?

But I gotta say our design team, we’re relaunching our marketing website because of course the company changes. And we were trying to use… Figma has this product that lets you actually publish straight to the web. Now I would not recommend that but we’re doing a lot of Claude Code based automatic translation, like out of Figma straight to the site.

It is good, it’s a little too much tailwind for my liking. Like it’s a little too garbled, but it’s good, it’s credible, it’s a first pass. We’re gonna need to turn it into a proper CMS template and that’s gonna require human intervention and engineering.

But those are designers. And at one point I said to one of our designers who’s like, look, I really wanna learn this stuff. I was like, okay, I’m only gonna talk to you for 10 minutes. I won’t give you any more advice. You have to go do this and then report back. Go create a component system to solve, I might have said video or like some sort of problem related to one of our clients. And I was like, make a component system and then I want you to ship it as a React storybook, complete, and figure out a way to host it.

And two hours later he came back. He’s like, wow, I, that’s okay. I can do that. It wasn’t the greatest React storybook, it was missing, there weren’t a lot of animations. There weren’t a lot of variations, but it was pretty good product, right? It was okay.

And so designers are not out in the cold, except in that way that designers always put themselves in the cold.

You’re like, I’m a small bean, and I cannot think technical thoughts, only art thoughts. And like we all have to get over that.

Peter: So I wanna unpack a little bit of what you were just saying.

You mentioned earlier how everybody in your organization’s a solution engineer, but when you were just telling that story, you were referring to designers. So you still have a mental model of people maybe in the roles that they had been in.

Paul: Oh yeah. Let’s not, yes, I’m the president of the company, but I’m also a solution engineer who uses the tools that we’ve created that are sitting in our GitHub repository and lots of Claude Code in order to prototype.

However, I really don’t push things to production in the org. I’m mostly here to explain where I think things are going work with my partner, et cetera.

Our engineers are absolutely able to think in architectural ways that our designers probably won’t, and our designers are able to think in terms of visual systems. What I’m finding, and I think we’ll see it, the novelty of it is so wild, right? Where it’s like, Hey, use giant component system X.

If you tell it, if you say, Claude, man, I just want you to use IBM Carbon, good system, go to town. It will make you something that looks very component-y and good and solid, and then it all starts to look the same. I don’t know, is design in the future just skinning component systems? I don’t know.

An enormous amount of our work still ends up going through classic design processes. But if a designer can solve a problem by typing words into a box, they should be able to do that. They shouldn’t necessarily have to wait. It should be auditable, somebody, a product manager.

So there’s different kinds of ownership, right? Like a designer should be able to do stuff if we’re really just changing a component and I can see a future state where that could ship to production without a lot of other people involved. We’d be willing to take that risk.

Someone whose background is design probably shouldn’t establish an authentication system, and push that to production.

But they could say, it’d be cool if login worked like this. And I actually prefer email based login. That’s better for this than trying to do OAuth. And somebody might be like, yeah, that makes sense. And then everybody types like three sentences into the box. Somebody goes, Hey, it looks pretty good.

Jesse: Yeah.

Peter: It’s a canard now around roles blurring. And, your adoption of solution engineers struck me as a recognition that whatever we might have been once, we’re all doing something similar.

Paul: Now that we have returned to our services roots, what is a solution engineer? It’s somebody you can talk to who has an understanding of technology and platform who can help you figure out. What the next step is, and often that is before a contract is signed. And so a big part of this is just when an organization comes in or a person comes in and they want some help, you’re like, all right, talk to a solution engineer.

A solution engineer might be coming out of design, product management, engineering, front and backend might be an organizational leader or just a pure manager, but they’re able to do something. They can make you an artifact that looks and feels like code, and so I think that it’s working backwards from that change as opposed to like this very prescriptive role.

It’s just like when someone walks in, I want to introduce ’em to someone who can solve their problem. Hence that title.

Peter: And this touches on something I’ve been thinking about. So I do a lot of thinking on organization design, and I’m wondering how you think about shaping teams as roles blur. What is your organizing principle to say this collection of people, anywhere from two to five or however many, are the right collection of people to solve this client problem that’s coming in? Like how does that calculus operate?

Paul: It’s still pretty classic, right? First of all, I don’t believe, in general, people should not go alone in any client engagement. It’s dangerous.

Jesse: It is dangerous to go alone.

Paul: it is, yes, exactly. Take this and I hand you, Claude Code.

Like I don’t like to sell alone. I don’t like alone in a services org because you should always have a couple people thinking thoughts. But when I think of currently org structure, what I’m finding is that product manager as solution engineer kind of depends on the profile.

If they’re more technical, they can really get through to the very advanced demo, they have access to, like a good platform, they know how to get things into production. They can do an awful lot.

Validators, Not Producers

Paul: It’s really almost, and I feel sad about this. I’m not really ready to commit to it, but I feel that the roles become more about validation than about production, right? So it’s like a product manager validates that this is a real product. It’s not just like pixels slapped on top of a database, but that it really actually understands the flow of the business or the organization and their needs.

A designer thinks about experience and they think about components and they think, honestly, a lot of times designers are thinking about scalability of a design experience. They are willing to use all the tools necessary to make sure that people can have consistent, reliable experiences when they come and sit down. That is a validation pass, if you are not the one who is moving the pixels around.

Now they might mock something up in Figma, but then a robot might build that rather than sending it to an engineer. But an engineer should review that robot’s output to make sure that it is valid, good, stable output. And I’m not imagining a world actually where all we do is say the robot did a good job. Because I think there’s lots of stuff that needs to come from people, and I think there’s a lot of stuff we need to do.

But that said. I’ll give you an example. I have an automatically generated newsletter every day, but I built a lot of tooling around it. It reads five or 600 sources. It keeps sources connected to summaries and so on. I never share the output of it. It’s just there for me and a couple people, and it’s my AI coordination newsletter, and I use it to know what to post on LinkedIn and so on.

I have to go read the articles, I have to do lots of stuff. It extracts numbers, so on and so forth. I am the validation before any of that content can reach an audience on LinkedIn or in a newsletter. It has to be there because otherwise it’s really meaningless. The Pure newsletter experience, I think is interesting, but unless somebody’s using it that way, it’s not that great of a product.

It’s a very good product to feed what I’m doing, but it’s not a good product unto itself.

Jesse: So it’s interesting to think about what all of this means for the leaders of design teams inside organizations as they are trying to reshape, resculpt their teams and honestly their value propositions, right?

Paul: What are you guys hearing? Like you know, more designers than I do.

Jesse: Yeah. So in the conversations I’m having with design leaders all the time, they’re terrified.

Paul: Yeah, that’s fair.

Jesse: The thing about it is that what the machine is best at is mediocrity. Which is the thing that designers have been fighting against this entire time, right? Like designers really see themselves as holding the levees against the incoming flood of mediocrity that executives are so desperate to unleash upon customers.

And then as you point out, then the question becomes what are you bringing to the process anymore? It’s not execution against base level design standards, best practices, value propositions. It’s gotta be an elevation. Right?

Paul: Yeah, it’s not like you’re like, Hey, here’s the branding guide. Like the fantasy now is I gave you the branding guide and the robot will do all the design for you based on the branding guide. It is, it’s very scary.

Let me describe a future state, but I, here’s what I’m gonna describe a future state, but I don’t really have a way to get us to the future state.

So right now you have these big

Peter: So you’re an underpants gnome.

Paul: Yeah, exactly right. No I, the problem is I think that the bullet point two or three, I can’t remember what the underpants …

Peter: Steal underpants. Two, question mark. Three: profit.

Paul: Yeah, bullet point two I think might be like a lot of chaos in reorganization.

We have a podcast at work. You can find it on our website, aboard.com. I just interviewed a really wonderful writer and thinker. His name is Andrew Leland, and he has a degenerative eye condition, so he is losing more vision every year. And so he’s become, even though he used to edit the Believer, he is become a really good…

Peter: Oh, I’ve read his work about that. Okay.

Paul: He’s wonderful. He’s wonderful and the reason I wanted to talk to him is he’s become a big sort of nerd, right? Because he is in text editing and using Claude Code and he started to talk about how blind users and low vision users are hacking their own tools and building their own systems.

You know, like Wikipedia is very accessible, but it’s not always really scannable to someone who doesn’t have vision. And so people are making ways to read and find Wikipedia for themselves, right?

So I want you to think about a future in which those needs, which could be the needs of a disabled person or the needs of a corporate leader, it’s like they have really specific things that it could actually help them do their jobs. But literally somebody who’s good with this stuff could sit with somebody who realizes, who’s starting to lose their vision, but has other particular needs or websites they really must visit for their job or things like that, and build a solution just for them.

And a designer would be incredibly useful there. They would be thinking about things that aren’t visual actually. And at the same time, I don’t wanna be too utopian here. You need to fix the real problems first.

But what really stuck with me is that, if you think about a future where everything is commoditizable and moves fast, and people can have very customized stuff, then individual needs can be addressed in ways that they couldn’t before and maybe they’ll scale out to other people.

But how do you get there from a 400 person team inside of like a giant electrical utility company? I don’t know if there’s an organic step-by-step path where everybody gets to keep doing what they’re doing.

The Cycles of Disaster

Jesse: It’s interesting to see where the personal meets the professional within this, because the web, as you pointed out, kind of made its way in enterprises because people inside realize the value of these tools and they advocated for them and they set up web servers under their desks and all of that stuff.

And in this age that you describe, which I imagine as an age of infinitely disposable software, that you can create something incredibly complex, incredibly bespoke, that would’ve cost you $500,000 for a team to build for you, that is just for you to plan your vacation and you’re gonna use it for just that purpose, and then you’re never gonna look at it again.

But the cost of it is almost nothing to actually create. So with that in mind, then, what you see inside enterprises is every team has its own tooling. Every lead designer has their own way of orchestrating and architecting the solutions that enable them to deliver what they deliver.

Paul: Yeah. So now we have to build unified systems for bringing all of those systems together. And then everybody’s gonna hate the unified system and go and vibe code their own solutions. Except it’ll be for Claude Opus 35. And it’ll do it just ’cause they whistle at it.

And that’ll generate a whole lot of data and be insecure, like the cycles of disaster that define our ridiculous industry are also getting accelerated.

I can tell you from history, right? Like I’m in New York, I’m very publishing adjacent. I worked on a lot of big content platforms and so what happens is everybody has one unified content platform for the entire magazine conglomerate, right?

And everybody hates it. And then they fire the CTO and the new CTO comes in and is it’s cool, you can use WordPress. And then five years goes by and they fire that CTO and the new one comes in and goes, how the hell can everybody be running their own WordPress? This is a disaster. We’re gonna bring everything, we’re gonna build our own custom CMS, we’re gonna bring everybody into it.

And it is a beautiful cycle. It’s like a, it’s like a, it’s almost mythic, right? And I think you’ll just get that, except it’ll be like literally on a four-month interval, which will be tough for the CTOs ’cause it’s hard to source that many.

But here we are.

Peter: Jesse mentioned design leaders being terrified. I think I’m seeing a broader swath in the conversations I’m having.

I have one design leader, I mentioned this person in one of my newsletters, who’s actually primarily frustrated because he is so far ahead of the rest of his own organization that he doesn’t know how to bring them along with using this tooling.

Paul: It is the ghost problem. He can’t, yeah, I get it.

Peter: Well, yeah. he’s seeing opportunities for this tooling to improve how the business operates, and he can’t get anyone else to care about it. They just are like, no, I’m just gonna keep doing what I’ve always been doing. So there’s frustration.

I’m seeing empowerment from some leaders. Jesse, you and I have been talking about Z from CloudFlare, and she’s an atypical design leader, but she’s a design operations leader at CloudFlare, and she’s been writing on her Substack, and I’ve had some conversations with her about it, about how she’s gotten the 30 some designers at CloudFlare outta Figma and just into an LLM that has the design system, and they’re just like making live prototypes that they hand over to engineering to be wired in and shipped.

And she’s like, this is awesome. We’re designing faster, better, closer. There’s fewer levels, fewer stages of interpretation where things can go wrong.

You hear this from some other design leaders where now they can have their own repos and clean up three years of design debt that was never gonna be prioritized by engineering. Engineering’s like, please have at it. Stop bugging us. We are more than happy to let you just solve those problems.

Paul: Yeah, right now, but like a year from now, they’ll be like hold on a minute. Wait a minute. I’ll take it. I’ll take it. It’s okay.

Peter: Well maybe.

And then, I just had an email from a head of design at a large bank, and he was somewhere in the middle, which is just like uncertainty. What do, he was asking me, what are you seeing? We don’t know what’s going on.

And so it wasn’t fear so much as just ah…? And then yes, there are the anxious and fearful folks.

And so I’m seeing a spectrum and I keep drawing normal curves because the normal curve is helping me categorize what I’m seeing, which is that, the farther you are along on your AI maturity, right? There’s folks who are here and they’re on the more confident end of the spectrum and they’re doing fine.

And then there’s people in the middle who are like, I don’t know what, and then there’s people on the kind of the other side. We just had Jorge Arango on, and he had this line: don’t think that this is a nothing burger. This is a burger, right?

He, we might not know what kind of burger it is, but it’s a burger.

But there’s folks back here are the, either the nothing burger, or, to overextend the metaphor, they’re looking at the menu and they’re just like, all the burgers are like about to fall upon them. They just can’t make sense of the variety of burgers that are out there.

And so there’s this spectrum and I don’t quite know what to make of it. Except that it feels like the folks who are feeling best are those who aren’t afraid. They’re approaching it with curiosity as opposed to anxiety.

Paul: I will tell you how I approach this.

So first of all, I think that, as a technology landing, this is the worst rollout in history, right? It never made sense. It shows up out of nowhere. The leaders of the companies are, they have many qualities, but they’re not great communicators about what’s coming. They don’t know the capabilities of their own platforms.

And it comes on a level of hype that is essentially trying to match Bitcoin hype, but with a weird database that talks to you.

Like, a lot of folk narratives have emerged, you know, it uses more water than anything. And then people come out and they’re like no, it doesn’t use that much water. But I’m like, let ’em have it. Let ’em just have the fear. Let ’em have the sense that it is ecologically bad. Let ’em have it. Don’t fight everybody tooth and nail on the fact that some of these things are very destructive and they’re very confusing and they’re not good for society and they’re messing stuff up.

So that’s a, just go in with empathy and know, and I felt this, I’ve been writing about it in public and my God, you take some heat when you say, I think this is real, because people are very committed to a narrative of the nothingburger.

Peter: Well, in particular, people with background similar to ours, but who are not as technical, who stayed in humanities practices and who have seen more directly, I think their livelihood threatened by these tools. And so they’ve just been like, they’ve noped all the way out.

Paul: That’s right. I gotta tell you though, I just had a class come in, it was a journalism class from the New School. It’s a very progressive school in New York City, and they came in, and I actually thought they were gonna be grad students.

They’re all undergrad and they were, they’re babies. They’re just lit–, they’re so young and they’re just full of ideas. And I didn’t have to say much. They just asked questions.

And at one point I was like, look, what do you guys do with this stuff? And almost universally, I would say, they’re all, yeah, average age is like 19, 20. And they were like, oh, I don’t use it. I’m in college for my brain. And it was just this very weird moment where you realize this has been there since high school for them. It’s very normal.

Some of them said they use it for work. One person was a vibe coder and so they were using it those ways, but their relationship to it, and I think what happens is, everything gets to such a fever pitch so quickly that we forget that humans are higher primates capable of reasoning and organizing their lives, even with new technologies.

And I’m looking at them and I’m like, ’cause you go online and it’s just like, it’s either people saying like, everyone who even thinks the letters AI should be shot and thrown in a river. And then other people who are like, the Lord came to me last night in the form of a prompt.

And you’re just sort of like, you’re caught between it and you just get this assumption, especially ’cause the news is so bad and like…

Peter: Yeah, this couldn’t have happened at a worse time, at least in the United States from a geopolitical standpoint.

Paul: And also from a climate change point of view, like the timing’s terrible and everyone who is in the news running the shop is an absolute reprobate right now.

And so you assume that that is the world. Most humans really just want to have a nice dinner with their friends on Friday and actually don’t want to talk to the robot all day.

And, but then the thing is also we are talking to the robot all day, I think we get very skewed. I think a lot of people don’t take this anywhere near as seriously as we do.

Now that said, you go back to that design team of 500 people. Is this existential? It could be, and we have to be honest about that.

I don’t know, but when I talk about a future state where everybody can get their thing, and that’s very utopian and positive, but if we talk about what would happen to go from step to step, it’s a lot of pain.

So I think there’s probably balance in here. I don’t think we get to this moment where we’re like, ah, that was fun, but it’s over now. Let’s get back. Let’s open up Aldus Freehand,

Jesse: Right.

Paul: and get back to work.

Jesse: I think that touches on an interesting thing in here. You and I both come out of a writing tradition, a journalistic tradition. And for me that writerly approach has always been a part of the way that I’ve approached desig

Show Notes

For more about The Future Of… Design conference: https://www.thefutureof-conference.com/.
Use code FINDINGOURWAY for 26% off the registration price.
Find out more about Jesse James Garrett and his upcoming live session on AI Transformation at https://jessejamesgarrett.com/
Find out more about Peter Merholz at https://petermerholz.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, it’s our first ever live broadcast on YouTube. Recorded April 3rd, 2026, design consultant and industry analyst John Gleason returns to the show to explore the ideas behind his forthcoming design leadership event: Are you ready to lead? We’ll talk about the role of boldness and vulnerability in design leadership, how leaders can position their teams for greater strategic impact, and how to advocate for a larger value proposition for design. Now here’s our unedited live conversation with John Gleason.

Peter: Hi everybody. Welcome to an experiment in, for us, at least in podcasting, not that others don’t do this already, and, that’s what we’re doing right now.

Jesse: We are finding our way in more

Peter: We are finding our way with live streaming and get, kick us off here. Just a quick, introductions. Most of you will know Jesse and myself as the hosts of your podcast, finding Our Way, and we have with us our returning guest, John Gleason.

John is a, I think of you as a, you can change this, if you choose, but I think of you as a design and business consultant. You have a background, primarily in business, but you were at Proctor and Gamble during their design revolution. And we got to know you because about a year ago this time, you hosted an event called, the Future of Design, where you posed the provocative question is design dead?

Jesse and I didn’t attend that event, but we heard the things that came out of it, were intrigued, and we had you on our podcast last June to talk about it further.

And we know that you are planning a new forthcoming event, for the future of design in, mid-May, but now you’ve got this subject, are you ready to lead?

And so we thought this would be a good opportunity to dig into what’s going on with design leadership, what you are seeing with your background in packaging and brand design and industrial design, what we’re seeing in the worlds of UX and digital product design, and see where this conversation takes us.

We are live. I will be checking the chats because, you know, at some point we would love to engage some audience involvement. John, anything else you want to say, before we dive into the conversational part of our discussion?

John: Part of the context that I wanna offer I’ve known about the two of you for a long time and then became a long time listener, first time caller when you invited me to join the podcast last June.

Peter, if recall, part of it started with, oh, I’m glad those things don’t happen in our world. This idea that design’s dead and declining, a decoration station, and then you and I talked and chatted and we both had some revelations and realizations that maybe there’s more commonality across the types of design activity, than differences, because the activity is different or the outcome or the artifact or the thing being created.

So I’m delighted to be here in part, to open up some dialogue for me to have a chance to continue to learn, but also expand the dialogue and the discussion around the ability for design to influence growth and culture and other things.

Jesse: So John, I’m curious about this year’s event and the direction that you see the conversation heading.

Here in the tech space, it continues to feel like a lot of bleakness, a lot of uncertainty, a lot of doubt about what the future holds. And I guess I’m curious about where you see the conversation headed that helps to resolve that.

John: I think one of the, I guess it’s an aspiration that we had last year when we, the three founding partners for the future of conference, decided to do the silly, crazy, stupid thing of, let’s produce something that gets people together, was born out of observations that I’ve made as I’ve had a chance to peek inside 150 or so big companies in the last 15, 20 years.

And that is… most design and business leaders, and this is true of marketing or supply chain or finance, they’re in their world, inside their company solving problems and managing challenges. But because they don’t often get a chance to get out and meet with their peers they think that those problems are unique to their own circumstance. And then because they think it’s unique, they think it’s confidential and sensitive, so they can’t talk about it. And then because they can’t talk about it, they have to go try to solve it themselves without help, without guidance, without a roadmap. So part of the original ambition was, let’s create a forum that gets people together first to build awareness that their problems are probably not as unique as they think they are.

And then use the power of the community to help solve for some of those things collectively, to accelerate the ability to change the trajectory or direction or arc of where and how design contributes to business impact, to career development, to cultural dynamics.

So that is a foundation. One of the things that came up during the conference last year many times, which led to the theme that we have this year of, are you ready to lead, is there’s all kinds of training in schools and university degrees and the like for the craft of the businesses that any of us are in.

Jesse: Right.

John: But there’s generally nothing that teaches those people how to navigate complex organizations, how to influence people with more power and more stripes and more influence than themselves.

How to set a vision for something and get alignment for that vision. And so part of that is let’s use the forum that we started to create with the future of and begin to use, step two or round two of this as the opportunity of people sharing what they’ve learned on their journeys. The hard knocks. The things that that maybe they did really accidentally or on purpose. Again, as a way of trying to accelerate the ability for people to use some of those tools and frameworks and roadmaps and checklists and principle what, whatever that people are willing to lead with as a way of trying to arm the industry more broadly as a way of trying to elevate design more strategically and more profoundly.

Peter: It’s interesting you say that. I’ve been having a similar thought where… So as Jesse suggested, in, in the field that we’re primarily in, this UX and digital product design, there’s a fair bit of consternation and uproar. AI is feeling like it’s being imposed on people as opposed to them organically adopting it.

And that’s causing people to feel like they don’t have autonomy or agency in their own work, which causes people to stress out. There’s layoffs, there’s a whole bunch going on that leads to anxiety or even fear for some folks.

And the realization I had was, I think everybody is dealing with this on their own.

And we need ways to enable folks to deal with it collectively. So my, my initial thought was, I’ve been writing a little bit about this, for design leaders to, I think, we, we need design leaders to be more vulnerable right now. I keep coming back to that.

People look to their leaders for answers and solutions.

But this is a moment where many leaders just don’t have that. They’re figuring it out like everybody else. But I think those leaders aren’t comfortable acknowledging their lack of awareness or their lack of understanding of exactly what to do. And so they’re pretending like they’ve got it together.

And, but then they ask me, my teams are anxious and frustrated, and what would you say to help unlock those teams? And I’m like ,you need to unlock, right? You need to show that you don’t have all the answers, that you’re figuring it out, so that you’re modeling for your teams that they can be open and vulnerable. I have the Brene Brown book here, ’cause I’ve been thinking about this.

So that they can be open and vulnerable and so that you are all operating with more full information about one another.

And then once you do that, once you share that, or once you discover you have shared kind of challenges, now you can work together to address them instead of everyone feeling like they have to do it on their own.

And I’m wondering, John, how, what you’re seeing in your world when it comes to some of these kind of more existential crises, like last year, even pre AI, you were asking, is design dead? Now in this, not, maybe not specifically pre AI, but AI has definitely accelerated since then, what are you seeing? What are you seeing that’s working maybe in terms of, kind of, leadership approaches that you’ve witnessed that are causing, maybe the temperature to come down a bit?

John: Let me take a step back and build on the point you just made Peter around vulnerability and consternation and fear and those things, those are feelings that don’t only exist in design.

Marketing, finance, supply chain, CEOs, CFOs, all the people that are supposed to be the proud leaders all have their own set of fears and uncertainty. And part of the challenge, there’s not a school or a training program to teach design leaders or anybody for that matter, how to navigate complex political organizations.

Part of the reality around one, one of the reasons I believe vulnerability doesn’t exist broadly in corporations and even agencies and consultancies, by the time people get to a certain level in their company, they feel like they can no longer admit they don’t know something.

So there’s a lot of faking going on. Oh yeah, we’re gonna go do this and we’re gonna go do that. And, or they’re hedging their bets and they’re waiting to make a decision until, the clouds part and the angels sing. So part of this is if you think about… vulnerability is one of those characteristics that infers psychological safety…

Jesse: right.

John: And design and designers are the pent-ultimate people and organization that, that are wired to experiment. If there’s not the safety to explore, they won’t explore and you’re not gonna get the best of people.

And so part of this is basic psychology, basic human resources. But most companies today, especially today with the economic circumstances we’re facing, are faced with the belief that they can’t fail. And this quarter, next quarter is the planning horizon, which doesn’t play well to a designer’s vision horizon, if you will.

Jesse: Right.

John: And so some of this is, it really does take individuals, unless the culture is so good systemically, and as time goes on, I find that there are fewer and fewer of those that have a systemic positive growth oriented culture, because everyone’s trying to cover their backside.

Jesse: Yeah. I think that’s a big piece of it. I think it’s important to acknowledge the emotional reality of the position that the leaders find themselves in now, because I’ve talked with a lot of people in the last year, since the last time you were on the show, John, who have had to figure out how to cut a third of their team and then be the one to deliver that message, even though it wasn’t their idea.

And then they still have to turn around and justify their value proposition to their executives as well as to their cross-functional partners. And the idea that in a circumstance like that, somebody is just gonna blossom into vulnerability as a leader, I think it’s a pretty big ask.

John: And vulnerability is, and perhaps I’ll be a little bit sharp. Vulnerability is viewed as a weakness in many corporate cultures.

That’s a big thing that reasons why people don’t go do that.

But I’ll talk about one, one point that you make. Again, Jesse you talk about these people who are being mandated that they need to go make these big cuts and then deliver those messages. Again, not unique to design.

And so part of that is, is I think because there is the perception and a great deal, the reality that there is a higher emotional quotient among a design community, that there is more empathy and understanding in those circumstances than, somebody that might sit in a in a more linear, numbers oriented, kind of business function, where it’s, okay, these are just numbers. We’ve gotta go do this.

And I think the one, one of the topics that came up in, in last year’s conference was the question was posed: it was first posed as a framing. Look you designers, you play in this empathy space every day. I don’t hear you talking about having empathy for your CEO who has to go deliver some things and the bosses of people who are perceived not to understand what design might contribute. And it, it really was interesting how many people in the room went, oh yeah, could benefit by trying to better understand fears and the pressures and the things that they’re under, even though most of those people don’t seem to openly show and outwardly show fear.

Jesse: Right.

John: And so part of it is, how do we build the tool set so that people have the confidence to be able to stand up and offer okay, we can make these cuts, but here are the likely implications and consequences of those actions.

Just so you’re clear, hierarchy, I’m happy to go be a good corporate soldier and go try to do these things, but if you’re trying to grow, if you’re trying to innovate, if you’re trying to disrupt, if you’re trying to create a culture of curiosity and openness and vulnerability, you probably sever most of those things when you cut a third of your organization.

And I know part of this is about survival.

Jesse: right.

John: About hitting your, the numbers that Wall Street expects. And again I’m being facetious in some of these comments, but part of it is most designers aren’t armed to be able to have that business implication conversation, or they’re not confident in being able to have those things.

And so I, I think it would surprise a business leader if a design leader were to step up and say, okay, here are the business implications if you go do that.

Peter: So generally, I agree with the need for design and user experience leaders to have empathy for the challenges that others are facing and that yes, we’re not alone in this situation.

But a couple thoughts that I’m tying together, one is something you said John earlier, which is like, how it feels like in… Our organizations are decreasingly safe. Like something shifted in, in the last, I don’t know how many years, three, five years where things have become less safe.

And then something that Jesse and I have discussed on a forthcoming podcast, it’s in production, but hasn’t been pushed, is ’cause you mentioned empathy for the CEO, and at least what we’re witnessing is that once you get above a certain level of executive-ness, it tends to select for sociopathy, right? People who do not care about other humans. People who do not see people as people, but as resources, right? I think part of the reason they succeed is they can make a decision, a spreadsheet decision, and they see people cost x and chairs cost y and facilities cost Z and they’re like, okay, let’s get rid of people. That’s a cost we can now reduce or whatever.

And so I want design leaders to demonstrate empathy for their leadership, but sometimes their leadership is toxic and broken and there seems to be a wave of that, like in tech, right? Jesse and I primarily work in tech or tech kind of adjacent spaces, and that those folks have ripped the mask off and demonstrated their toxicity.

I’m curious, again, I’m looking to you to give us a kind of parallel perspective. Are you seeing similar things? Are you seeing different things? Like how is that playing out in, in, in your world?

John: I think the things that you describe are, again, similar if not identical to consumer facing, consumer products, consumer services, finance, healthcare, that the people at the top often that have a letter C before their title or as part of their title.

There, there is this aspect of removing the humanity from the way they make decisions.

And I want to clarify when I say having empathy for the CEO, I’m not necessarily saying you need to go put your arm around them and say, oh man, I feel for you. And but part of this is there’s and for those of out there that might listen to this now or later might, might giggle for those who know me, there isn’t a conversation that exists that I don’t talk about rewards drive behavior and so the rewards of a CEO

Peter: So incentives. Yeah.

John: Or a CFO or whatever are not to make people feel good. It’s a responsibility to drive shareholder value. And for some, a responsibility, I’m gonna be very callousy or a responsibility to drive their own bonus system.

Jesse: Yeah.

Peter: Oh, very much

John: and so part of this is the things that reward them and things that drive them often aren’t values and culture and purpose, unless it can lead to, unless those are things that can lead to other things.

And I say that this isn’t about the way we talk about empathy with users or consumers. Have we walked in their shoes? Do we understand? But there is a need to try to figure out, okay, A CEO that takes over a declining business. Their priority is to turn around the financials the tactical metrics and KPIs of that business, revenue share, profit, shareholder value. There are lots of different ways that to do that.

And I’ll use an example. I had a round table event of corporate side design leaders, and I invited a CEO into the room, and I know this person well, and I said, your job, a, listen to what this group is talking about, what appears to be important to these design leaders, and I want you to chime in when you think you’re ready.

And it was a round table, so it was very organic. When you think something strikes a nerve that they’re helping achieve the CEO’s mandate, or maybe not. And this was back in 2018, 19, so capital was very cheap. Profits were running into the business, quite well, for most companies. Stock market was going well.

And the people in the room were talking about identity and equity and brand and long term and all those things. And this person chimed in and said, everything you’re talking about is important and is needed. But what you need to understand is I’m here to drive shareholder value. And in today’s economy, I could go out and borrow a billion dollars and buy back my own stock and add 10% to shareholder value, and I’ve added more value to my enterprise in 30 minutes than… What you are talking about adding value might take five to 10 years, just took the oxygen right outta the room.

Jesse: Oh, man. Yeah. I think this question of where the value comes from is a really important one because we’ve seen this whole wave of change, especially if you look back like 20 years. Innovation was gonna save us all, right? And every big enterprise was gonna have a big mature design organization at the top that was orchestrating insights and prototypes and concepts and design philosophies that were going to drive product development for decades to come.

But instead, after a certain amount of time, the C levels looked at it and saw a bunch of low value activities. Generative ideation… Why are we, that doesn’t sound like something we should be spending our time on.

Or yeah, you’re going out and getting customer insights, but it’s not really actually driving any kind of meaningful product impact.

And so design leaders now find themselves in the place of defending this, like this sinking island, this increasingly smaller value proposition. And I think for a lot of them they’re wondering like, what? What is the stance that I can take with the larger organization that genuinely speaks to design’s value, but also doesn’t sacrifice design’s values?

John: Yeah. In fact, there are a couple of comments that kind of address that, that notion of, how do I stand up, especially if I’m a lone wolf in my organization. And part of this is, I think, some of this is linked to the skill for a design leader to translate and communicate the work they do into the reward systems and the business outcomes that their business partners are expecting. Can you translate a new product into revenue growth or profit growth or new segment of consumer that we’ve not been able to reach.

One of my favorite requests when I go in and I work with a head of design or a head of innovation or marketing or anybody else, is have you put the big bogey on the table for your senior leaders to, to ponder?

And so for example I was consulting with the head of design of a company that is about 18 to 20 billion in revenue. And I said, what if you were to go into the CEO and the, in the executive lead team, maybe the board and say, I can get you a billion dollars of incremental revenue. Here are the things that need to happen in order for me to help go do that.

So A, if they don’t give you the things that you need to go do that, you can say, Hey, I didn’t get, item four, seven, and nine. But part of this is it gives you the ability to start a business conversation and do it on the context of growth. And, some of that plan, some of that billion dollars may be how do I fix some of the leaky buckets in some of the businesses that we have? How do we create some new things? How do we get into businesses that we’re not currently in?

And it forces the design leader to think about what are the levers that I could pull? What are the levers that I own? And what are the levers that I can assist with that, that I’m gonna need the head of innovation and the head of finance and the head of supply chain to go do some of this, and how do I get them on board?

And because I think the thing that I caution anybody that I… ’cause I get to put this out on the table and then I get to walk out the door, and this…

Peter: yay consulting.

Jesse: Yeah.

John: Person has to live with, oh, shoot, John convinced me to do this, but I don’t know how.

But part of it is the senior most leaders of the company, especially depending on the general health of the company at that time, they’re gonna remember the bogey. They’re not necessarily gonna remember all the conditions to get to the bogey.

And so part of that, is, like any good brand, it’s how do you reinforce when every time you show up?

And again, one of my favorite exercises with teams is every time the design person shows up, you should be asking about the consumer. What did the consumer tell us about this? How did we get to this initiative? What’s the line of sight to the insight that caused us to say that cinnamon was the thing we need to do, or move the button to the bottom of the page.

Apple’s most recent update that moved the search bar to the bottom of the screen instead of the top. It still drives me nuts because I’m not used to it. And, and it’s like what caused them to do that?

But part of this is if you can show up every time, the 27th time, the team’s gonna say, oh, shoot, John’s gonna ask about the consumer. So we better be prepared to answer the consumer.

And I think that gets to how do you reinforce vulnerability? How do you reinforce curiosity? How do you show up that way every day?

And part of it is until you wear them down and then they say, oh, okay, we should be poking around at this.

But I think so many design leaders, whether you are new into an organization and into your career or you’ve climbed the ladder and you’re now leading teams and organizations, we forget about the consistent repetitiveness of some of the things we need to do to remind people.

It’s no different than I grew up in Texas and so everywhere I went Drink Coke was on everything. And it’s on billboards and side of cars and trucks and gas stations and grocery stores.

And the subliminal notion of that is at some point I probably drank Coke because I didn’t think twice about it, ’cause it was in my head.

And what’s the drink Coke, the repeated drink Coke version of some capabilities and activities.

Jesse: Right. When Peter and I were running Adaptive Path together, we wrote a talk together that we called our stump speech, because the whole intention of it was to capture the messages we knew were going to need to be repeated over and over again, and then go out and do that, and each of us gave that talk dozens of times.

Peter: Dozens of times. No, and it tracks with, you mentioned Coke and there is that marketing, aphorism. Basically something on the order of, it takes five to 10 times for someone to hear a thing, for it to actually sink in.

And I think your point stands that many design leaders, we still tend, we have an inclination, we have a tendency to believe the work speaks for itself or the case speaks for itself.

And given what you’re saying what’s this bogey and how are you going to help others understand it? And that you do it once and it’s evident and then if you don’t get acceptance, then I guess they’re just not gonna do it.

And you and many design leaders at that point will give up, like, well, I tried.

And that’s not how this works. You have to beat them over the head with it. And start risking, I don’t even know if it’s risking your own kind of social capital, but like you have to put yourself out there.

Jesse: It is a risk. It absolutely is a risk. Yeah.

Peter: Yeah. And which is something that, as you were talking, John, I had another kind of constellation of thoughts, and one is, you mentioned this bogey and the billion dollars, and I was like, is the issue that we’re seeing with design leaders that they’re not being bold enough. They’re not being big enough, right?

Because design, every design leader I talk to understands the basics of how their work drives business value. And can, good usability means that people can move through the funnel more easily and we’ll see more people adopt or activate or whatever, or good usability encourages retention, right?

Like we, we know these things, but I think it tends to be, it’s incremental, right?

And I’m wondering if what you’re saying is, sure, yes, but you also need, it’s not like a branding play the way you’re talking about it. You need, you can’t simply incrementalize your way to the change you seek. You need to have your brand moment, your pitch deck.

Jesse, I think a little bit about what I imagined Scott Zimmer before Capital One acquired Adaptive Path, and he was the chief design officer and the team was 40 people, and he was like, no, it needs to be 400. And what was that pitch deck?

Or John, I know at your event, Phil Gilbert’s gonna be there, right? And somehow he shook a hundred million dollars out of Ginny Rometti for design. I don’t know what the pitch was. Maybe you do, but is that what we’re lacking? Is a big enough story?

John: It doesn’t have to be a big story, it just has to, I think there’s an aspect of it that has to connect with what are the reward systems of the people that you have to convince to make those investments or to behave differently.

And so your example about usability. If there is a relatively constant level of in of investment that needs to occur to improve usability, remove friction, all those things, but all of a sudden you’re gonna ask for three times that. Now you need to be able to convince somebody why you’re gonna get at least three times better business outcome.

Jesse: Right.

John: And I think that’s the challenge that design has, is when many of them do try to talk business impact, they use the verbal story around impact. Everybody knows if we improve usability, then it’s gonna lead eventually to better outcomes.

But it’s not necessarily obvious to the people who are responsible for driving those business outcomes. And John in the chat talked about, is it fair to say that top line revenue is one of, is a way to have financial impact? Absolutely. It’s one of the easy things to measure, but it’s one of the most impossible things to assign what was design’s contribution to that growth.

And I think that’s one of the challenges that design leaders face is there is an ethical reality to where designers play to say, almost everything we create requires other functions of other teams to go make happen. So I can’t go take credit for that, but as soon as they step away and don’t defend the fortress, then in, in my world, in the brand design world, the ad agency steps in and takes credit for everything

Peter: Our world, that would be the product manager.

Jesse: right.

John: And so I think a part of it is and John I’ll add one more thing that even though this wasn’t what you were asking, is if the business is coming to you whoever you are, marketing design, product engineering, to solve a business metric challenge, oh, we’ve got a revenue problem or we’ve got a market share problem or a profitability problem don’t accept that as the problem.

Those are symptoms of something else.

There’s a reason people aren’t buying your stuff, and that’s the, to me, that’s the real impact that design could have in this is, let’s go understand why they’re not willing to pay a premium, or why they’re, they stopped buying our thing, or why competition suddenly saw a bump in there. And that’s the thing that, that I, I think business people in general are too quick to say, oh, we’ve got a revenue problem. Go solve that. And most of the solutions are gonna look like, oh, we’re gonna take a price increase. And it has nothing to do with solving the underlying reasons why

Peter: Right.

John: something’s not happening or a profitability problem often becomes a cost cutting solution. We’re just gonna go lower the expense side of the equation and increase profitability.

And we had a saying inside of Procter and Gamble, despite the pressure every day to, to save money was you can’t cost save your way to greatness.

And I think Kraft Heinz found that when they implemented their notorious playbook, which was all about cost cutting, but eight years in a row, you can’t cost cut any longer ’cause you’ve cut everything out.

Jesse: It’s interesting to think about how this, you were talking about, Peter was asking about design leaders not being bold enough. And when we think about how we define boldness in this context it sounds yes, it’s about business impact, but it’s not necessarily about scale of business impact, but it’s more like there is a kind of business impact that design as a function can potentially bring that you’re not gonna get from any of your other functions organizationally.

And I wonder if the boldness here is really about asserting a value proposition for your team, for design as a function, that goes beyond what the people around you think your team actually does or can do.

Peter: And to follow on that yeah, ’cause this is something Jesse and I talked a bit about, right, is, and I think about it from an organizational standpoint, design is a function, marketing is a function, sales is a function. Supply, manufacturing, operations, these are all functions.

And as you were saying earlier John, it can be hard for design to identify the value that it is delivering as a function.

Whereas I think those other functions have a more straightforward story to value, right? Sales acquires a customer, cashes that check, marketing acquires a lead. And, that’s the promise. There, there’s, it’s just more direct.

And so I’m curious with your clients, how you help them frame, pitch, communicate, design as a function that’s driving value. What are you finding are the, either the nouns, the verbs the levers that seem to land when trying to present design as this function that is worth standing side by side with these other more mature functions that they already understand.

John: Your use of the word maturity is an important one here because fewer people question a marketing decision because it’s a function that has existed for a long time and supply chain and operations and finance. And design, as much as it has been contributing to the enterprise for a long time, the maturity in which it’s connected to the business is still relatively new, 20, 25, 30 years tops.

And even then, it’s not systemic. Most companies don’t question whether they need to have a chief marketing officer.

Jesse: right.

John: Most people don’t question whether they need to have a chief human resources officer or a chief supply chain officer. But design is still one of these things that, that in today’s world, based on some research I’ve done, design most often reports to a different function and the majority of those people don’t report to the head of that function. So it just reinforces that design is in service to somebody else.

Jesse: Right.

John: And they’re not able to touch the other thing.

So a design leader that reports to a chief marketing officer probably doesn’t have a chance to influence innovation ’cause that’s another chief somewhere that, that is responsible for things. Or influence employee engagement because that sits under somebody else.

And so the principles that could be enacted across those functions could help drive a different culture inside the enterprise.

But it, but by the, because of the way they’re organized, it takes somebody to have to go sell the chief innovation officer that, Hey, we need to put some design people connected to your organization somehow.

And so a part of this is the other example that kind of sparked a thought in my head, Peter, when you and Jesse were talking, is insights. And I’m probably gonna earn an awful lot of enemies and get some hate mail here.

The insights communities that I have seen and had a chance to peek into are more focused on the methodologies of research than what it is they learn from the research. They too are under pressure to cut budgets and do things faster. So internet surveys are way more popular than in-home ethnography or shop alongs because, oh, we don’t have time. We wanna get, we’re gonna put 12 questions out.

And I’m sorry. There’s no way you can phrase any of those 12 questions that are gonna get meaningful insight into innovation work. You could probably validate some things and confirm some things so that you don’t get fired when something does launch. But the learning opportunity, there’s no replacement to sitting next to a consumer while they’re watching, do it, performing an activity on their screen to understand why did you click there and why did you do that? And what are you looking for when you do that?

There was when Proctor and Gamble was in their very earliest journey to elevate design, the CEO, whose idea it was for design to be strategic, A.G. Lafley, he role modeled the behavior he wanted to see everywhere. So when he went to a new market to visit that market, there, there were two things he wanted to do before he got into a conference room to talk about the business.

He wanted to be in a consumer’s home and he wanted to be in a store shopping with a consumer. And then the third thing when he did get together is, what are we doing to serve those consumers?

And then came the business conversation, how’s revenue, how’s share, how’s growth? And so a little bit like my comment about showing up every day, saying the same thing, everyone knew when he was traveling to a market that they knew they were gonna do these things first. They better have their consumer story together and I just have not seen that level of role modeling from a CEO other than the way they happen to role model around finance and numbers and, oh, we need to hit our numbers.

And then one other thing I wanted to touch on is, and this came up in the conference last year, Ken Musgrave, who is a longtime design leader at Ford and HP and Dell, and is now serving at Whirlpool. He talked about the confusion of time horizons and he said, I think about it as a now, near, and far.

Design wants to work on far, but the majority of the capacity of the organization is working on the now or the near.

Jesse: Right.

John: And so part of that is, how might you align the proportion of your now, near, and far in a way that aligns with those priorities of the business.

And the more dire the financial circumstances that the company, the more that is now.

Jesse: Yeah.

John: than it is far.

Jesse: Yeah, that makes sense. The time horizons narrow, right.

John: And it’s rewards drive behavior. We’re gonna drive all of the short term stuff. And part of it is even in those circumstances, if design leaders and designers know that the time horizon is now, hey, that may not be super sexy work, but design could still use their superpowers of reframing something or problem finding before you try to jump in and problem solve around something that you’re unclear about.

And so there, there are still ways to leverage the design superpowers to go drive value and impact in the business. And it doesn’t have to take a big, bold, courageous move to say, I’m not gonna work on that, or, but part of it is, I think, there are a lot of design leaders I talk to say the short term promotion stuff, it’s just not important sexy work.

It’s what if you use that as the pathway to prove what you can do? Go build champions and let those champions then advocate for the periodic longer horizon.

Jesse: It’s often the wrap on design and designers is that they’re so in love with their own craft, that they can’t be bothered to pay attention to the value that they’re actually delivering.

And there are, frankly, a lot of designers and design leaders whose actions have played right into that perception.

I wonder about those leadership skills that we talked about earlier, what do you think are the things that design leaders are most likely to be missing in terms of their own skillset in order to achieve the things that you are describing?

Let’s paint the community with a broad brush here and just call out the stereotypes a little bit. What are design leaders most likely to need to focus on developing within them, within themselves in order to deliver on this promise?

John: The example I’ll use first, Jesse, in, in framing that is, is in the circumstances where I see a design leader feeling like they are under pressure and overstressed, which is most of us, most of them will recess into the project work and become project managers for the work activity, and to some degree completely step away from the organizational side of their responsibilities because it’s comfortable.

That I, I know how to do this, I know how to create stuff,

Jesse: Right.

John: and I know how to get project plans in place and assign resources and all those things.

And I really don’t wanna have to have a battle with the president of the Asia region because of some business pressure they’re under and they don’t feel like we’re solving it for them.

And those are very real and quite more often than you might imagine.

And if any of you are getting to that point, you may not be in your role much longer because the business expects people at a certain level, if you’re senior director, vice president, SVP, EVP, chief, you probably should be spending most of your time on the organizational, cultural aspects of the work, not on the projects, ’cause you have teams and people and agencies and consultants to go do those things.

I think the challenge is the first thing that I would suggest for design leaders is figure out a way to do a self-assessment. To look in a mirror to try to find ways to say, where do I think I’m missing something?

And if you need somebody from the outside or business partner that is willing to work with you and you can develop some thick skin to, to take some feedback, there, there is a self-reflection opportunity.

I think the other is, so many design leaders in so many companies are trying to solve their problems without having outside points of view.

And I just think whether it’s a paid consultant that’s gonna help or a friend that’s go willing to give feedback, that the ability to have a different point of view and a different lens that is not inside of the politics of the company, ’cause that, that to me is where some courage comes from for design, is people that are fractional and are consultants or contractors and things. I don’t care if I’m gonna get promoted or not ’cause I’m not in your culture. So I’m gonna tell you what you really need to hear.

Jesse: Yeah.

John: And too many people, and I see this with consultants and agencies as well, is they don’t wanna upset the client.

So they often will tell the client how smart they are and laugh at all their jokes and tell them how well they dress. Exaggerating of course, but part of this is many of them are not going to tell the client what they actually need to hear because they themselves have become so dependent on the income that comes from that client.

And so there’s this conundrum. Go outside to get candid input, but don’t go to the people that are likely to become dependent on you because they’re not gonna tell you what you really need to hear.

And so back to your question, Jesse. I think establish a vision for where you think you want to go with this. Test it with some people, trusted advisors, friends, colleagues. Create a board of directors for yourself as a leader.

Is it ambitious enough? Is it too ambitious? Are people gonna understand it?

And then find champions. I think that’s another thing that is under-leveraged in corporate organizations is find the people who you have helped make look very good, and remind them that you made them look good.

And some of them, you don’t have to remind them but part of this is they’re likely to go to bat for you. And then one of the other things that I often see, especially if you’re actively trying to elevate design, is, and this is a controversial one, is do not spend a lot of time trying to convince a significant critic.

Go deliver exceptional stuff with the critics, peers inside the company. Other businesses, other leaders, other regions, other functions, whatever that is. And let then let that business, that leader, come to you and say, Hey, how come I’m not getting this?

You mistreated it.

There’s a famous story inside of Proctor and Gamble where the first head of design, Claudia Kotchka, went into one of our business unit presidents and said, I’m taking all of your designers and design managers. And he said, you can’t do that. I can, you’re mistreating them and they’re all gonna quit, and I’d rather have them in the company than for you to stand on pride that you’ve got them.

And she took them and for six months they had to figure out how to go do that work themselves with agencies and marketers.

And they realized they weren’t getting the strategic output that design was trying to reinforce and deliver. And, six, eight months later, it wasn’t a full mea culpa, but it was, Hey, can we talk about getting our ball back so we could play

Jesse: Yeah.

Peter: Yeah. A theme here. And it’s something that I’ve witnessed and try to encourage with the leaders I work with, is I think a lot of leaders don’t understand the power that they do have.

I think particularly design leaders, perhaps because they weren’t in an MBA program, they don’t understand necessarily how these corporations operate, wield or have access to more power and influence than they think.

And instead they tend to get very, submissive isn’t quite right, but reactive or they don’t wanna rock the boat. And they feel like because they’re already, because they already feel like second class citizens, any attempt to stand up for themselves, they’ll will only cause them to get hurt more.

And I, we’re getting close to time and so I kind of like to end around the, the human and emotional challenge that I think these leaders are facing.

I kept coming back to a statement that Simon said much earlier, and I’m putting it in the stream. ’cause this is the thing you can do.

John: Look at that!

Peter: “I’m seeing good leaders stretch to the bones, to the point that they don’t take time to do the creativity work, to put humanistic business proposals together that makes sense.”

And there’s a lot there but I think the heart of it is the, what it says to the beginning, I’m seeing good leaders stretch to the bones.

And this is something Jesse and I are seeing. We’re talking about it with the Liminal podcast, where you’ve got the job that you were hired to do, but now there’s all this transformation occurring and now you’re telling me I need to advance and advocate for design, so it’s even greater, so now you’re telling me I need to understand business and make business cases and there’s so much that we’re being, that we’re asking of folks in order to realize this potential. And they’re just trying to get their work done.

And I’m wondering, John, like I’m sure that with your clients as well. Like how do you help them navigate this opportunity without getting overwhelmed and burned out?

John: I think, I, any please out there, anyone out there, take whatever I’ve said as one dude’s opinion about stuff. But I’d like to think it’s well informed opinion.

But part of this is like the old saying, you’ve gotta, chunk the elephant down into smaller pieces.

So part of it is think about what are all the things that are on your plate. Now that can become overwhelming if I’ve gotta coach people and I’ve gotta manage up and I’ve gotta mentor people and I’ve gotta do this and save money and deliver. But until you, you have a view about what you are responsible for and is that scope of responsibility aligned with what your bosses think you’re responsible for,

Jesse: Right.

John: Until then.

And then the third thing is, how does what you are doing ladder up to what the company is expects as a company? Too many people, I find that they can’t articulate how their job ladders to the company’s objectives and strategies and vision.

And as a leader, you are supposed to be the one that helps people make that connection. And if you yourself don’t understand it, then it’s gonna be hard for you to bring your team along to to say all of that.

One comment I want to add to a comment that was made. Roman, It’s 10 o’clock where you are. Thank you so much for listening in. He makes a comment that, that I’m actually gonna use to promote the conference, is the circumstances that we’re living in today are ripe for design to to make a, an impact and for design to step in and reframe some of the things that we’re all challenged with.

Roman, thank you.

Jesse: John, thank you so much for being with us. Tell us where people can find out more about the event.

John: Thank you. The event, you can go to thefutureof-conference.com, thefutureof-conference.com. The conference is gonna be May 11th to 13th in Chicago. Peter and Jesse are both going to be offering a session and participating in panels at the conference.

The other thing I’ll share is I’ve created a discount code for anybody in Peter and Jesse’s orbit that wants to come. The discount code is Finding Our Way, and you get 26% off. And yes, that’s in an intentional 26 for 2026, but it also rounds out to $650 savings if you want to join and come be a part of the conversation.

Peter: Fantastic.

John: Peter and Jesse.

Peter: Thank you for, yeah, thank you for joining us on our maiden live streaming voyage. Thank you to the folks who listened along and participated in the chat. Thank you to Jesse for putting up with all of this. And we’ll continue to try out new ways of engagement, but until then, it is a Friday before a holiday weekend for many.

So happy holidays. Good spring break. Happy Passover, whatever you’re celebrating. I hope it. I hope it’s great. Take care everyone.

Jesse: Thanks everybody. Thanks

John: Thanks everybody.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Show Notes

As of publishing this episode, the Intentional Design Leadership Circle starts in 5 days, on April 15.
https://www.eventcreate.com/e/intentionaldesignleadership
There are still a few spots left.

Also, Jesse announced “AI Transformation for Digital Design Teams,” a new online event taking place April 30.

For more information and registration, head here: https://www.eventcreate.com/e/aitransformation4design

For more about Jesse James Garrett, and his coaching and AI consulting practices visit https://jessejamesgarrett.com/
For more about Peter Merholz, his organizational effectiveness, leadership development, and coaching practices, visit https://petermerholz.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: This is Liminal. When everything is subject to change, how can leaders choose a destination and set the right course? On today’s show, Peter and I return for part three of our exploration of liminal leadership. We’ll get into extracting the signal from the noise of the liminal moment, the role of shared values and collective action in setting direction, and how to make good choices when you can’t predict the outcomes.

Hello, Peter.

Peter: Hello, Jesse.

Jesse: So today we are resuming our liminal conversation. There are little bits of these ideas that have been coming to the surface for us that have led us to this particular conversational series. And now after having spent a little bit of time on the show exploring it, you know, I had gotten to a place where I felt like there are some definitive statements that we can make about all of this.

And then I saw something on YouTube the other day that really kind of shifted my thinking about it, which is that for some reason, sort of out of the blue, YouTube started serving up to me surfing videos unasked for not part my usual rotation…

Peter: Are you sure YouTube hasn’t been listening? Are you sure YouTube hasn’t been listening our podcast?

Jesse: I can’t be sure of that. None of us can be sure of that, can we, Peter? And I found myself watching just, like this stream of live beach footage, which was just, not a big tournament and not your best pro surfers or anything like that, just the beach in a place where they have some really big surf and there are a bunch of people out there on any given day trying to catch those waves.

And what I noticed about watching it was how little of it looks like success in the ways that we would frame success. How much of it is struggle and failure and catching up and compromise. Because what you’ll see out there, if you watch just, like, raw footage of a beach…

Maybe there’ll be 10 people out there with surfboards. A big wave comes up and let’s say six of the 10, the wave just rolls right under them. Like they don’t have a chance, they’re not there and they’re just going to fall off the back of the wave.

Of the rest of them, three are gonna go, not over the wave, but under the wave. They’re gonna get swallowed by the wave. They never get a chance to get their feet on the board because the wave takes them down before they get that chance.

And then that 10th person out of 10 is the one who gets their feet up on the board and they’re up on the board for a minute. But there’s no such thing as a soft landing in surfing. And it becomes a question of, okay, now you are riding that energy, how do you create an exit that feels natural from what you’ve been doing?

And so, the way that I really started to think about it is, first of all, the wave’s not for everybody. This wave might not be your wave.

Like how many waves of technological innovation would you say that you and I have seen in the course of our careers?

You started out working for a CD-ROM company, my friend.

Waves of Technological Innovation

Peter: Careers? We could even go back a little bit further, I started as an Apple IIe kid.

Got a Mac for college. So I went from, command line interfaces into GUI interfaces.

The desktop revolution when I was in college, I had jobs where I used Freehand or whatever to make stuff. And, Microsoft Word, figuring out how to lay stuff out really precisely in Microsoft Word of all things, right? You had to figure out how to hack all the spacing and kerning and all that kind of stuff.

And anyway, sorry. That’s a bit of a, I’m getting, getting nostalgic.

Jesse: Peter. Hey Peter. Get back. Come back to the 21st century please.

Peter: Come back. But you had GUI, and then it was when I was a student at Cal, the web breaks.

Actually I had a job doing multimedia work in school, pre-web. I saw the web. I didn’t work on the web for a couple years, though.

I did work at a CD-ROM company. I then helped that CD-ROM company get on the web. I then worked for a design firm that was moving from traditional design to digital design and web design.

So you have the web, you have Web 1.0, you have Web 2.0, you have mobile, and people forget even before mobile, you remember WAP? Remember when people thought Nokia phones and the Palm Pilot was the future?

Jesse: Hey, I did a bunch of design in that space during that time, so dude, that was real work.

Peter: Yes. I’m I’m sure.

You had iPhone, obviously tablets, the move to the cloud. I already mentioned Web 2.0. And then it’s interesting because, as you talk about waves, there were these actual waves and then there were attempts at making waves. Right.

Jesse: Waves. Yeah.

Peter: Well, yeah, ’cause because pretty much very little meaningful evolved after mobile with the possible exception of things moving to the cloud.

People tried to make something called Web3.0 a thing. People tried to make blockchain a thing and crypto a thing. And the metaverse a thing.

Jesse: NFTs. All the stuff. Yeah.

Peter: Yeah. But yes, to your point we’re definitely now on a wave.

It’s a wave that feels possibly as meaningful as the shifts to web and mobile. Definitely as meaningful, as say, the shift to things like desktop publishing, and putting the ability to create directly in the hands of creators as opposed to needing a chain of labor to get from somebody’s idea to some produced thing.

Jesse: Yeah.

Let’s come back to the notion of liminality and the fact that there’s always another wave coming, right? That the waves themselves just keep on coming.

And in fact to be a surfer is not to find your one perfect wave and then step off the board. It is not just dust off your hands and declare a job well done.

It is more of matter of finding the waves and the waves within waves.

You touched on a couple of things. There are always these technologies that are coming to the surface, or techniques that are coming to the surface.

One of the big things that’s happening with AI is that the technology has reached a relatively stable state, but the techniques around the technology are continually in rapid evolution.

And the big open question, as people look around at these allegedly AI driven layoffs and things like that, is what have those guys figured out over there that we haven’t?

And in fact, the answer is probably not much, but it’s enough to give them a sense of what the future of their organization looks like.

And so surfing the liminality means acknowledging the trajectory of the data that’s right in front of you, right? To be able to read the wave and see where the wave is going so you don’t get drowned by it.

Waves of Practice Change

Peter: There’s a parallel here because you’re talking about the kind of these techno waves of technology and change and AI is the most obvious, latest example of it.

I stated how we haven’t really seen a meaningful technological wave since probably the combination of whatever was happening with Web 2, mobile, and maybe a shift to the cloud in the late two thousands, early 2010s.

But that’s not totally right in that in parallel… So those are waves of…

Jesse: Right.

Peter: Society-wide impact. But within our industry, within our field, someone was referring to the waves of design tools that we have embraced going back to whether it was, obviously Photoshop and Illustrator, some of us using diagramming tools like Visio and OmniGraffle.

Then you have prototyping or like early, like some of those, yeah, prototyping tools. Your Dreamweavers or whatever or, earlier web tools…

Jesse: Page Mill.

Peter: But then I… so I got off the design tool train sometime in the Photoshop, OmniGraffle era. I never embraced Sketch. I never embraced Figma. Though I know those have been waves, right, that people have had to ride. I use Keynote when I need to design something.

Jesse: Yeah.

Peter: That’s my little wave off to the side.

But I’m bringing that up to suggest, ’cause you said the word waves within waves, and I think something that maybe gets lost is things can feel very unitary or global or monolithic, right, it’s AI and it’s everything and it’s this one thing that we’re all dealing with.

But the reality is probably that this thing of AI is obscuring a lot of little waves within it that we’re having to figure out and navigate.

One of the things that’s coming up for me a lot in this liminal moment, what’s clear in the discourse is anxiety, and a just a generalized anxiety.

Attention and Anxiety

Peter: And part of me wonders if that generalized anxiety is because it’s not one monolithic thing, it’s a thousand little things, and your attention gets frayed. You don’t know what you should be investing your time in to understand and explore. You. start down one path and then you hear this other thing that comes up and you’re like should I do that, or should I finish the thing I started?

And like how to handle all the potential, not noise, but all the potential sources of your attention. And I think a not unreasonable response is just to peace out.

Jesse: Oh yeah. Oh, for sure. Just, yeah. Give into the overwhelm and go to bed. Yeah, I think that’s real.

I think that one thing that I notice in this is the question of what the transition asks of us. Because some of these transitions these past waves of technological change, some of these transitions for some of us asked very little of us, because it didn’t really require us to change our lifestyles. It didn’t really require us to change how we did our work. It didn’t ask a lot of us.

Some of these transitions have asked quite a lot of people to let go of and give themselves over to in terms of… Just think about the digitization of various industries over the course of the back half of the 20th century, and what that asked of every worker in every facility doing every job to engage with different technology that didn’t work the way that they expected, that they basically had foisted upon them by some central authority.

And so this is how automation gets a certain kind of stigma because it feels like something that is enforced upon people rather than something that is offered up as an opportunity or a genuine enhancement to their abilities.

I keep coming back to what this means for leaders, because as you pointed out last time we talked about this, they are the leverage point. They are the point of influence to not just to embrace the new, but also to acknowledge what is potentially left behind that somehow needs to be kept up, right? the fear of this highly automated world is that the soul is lost from the work, that the human voice is lost in the work.

And if no one else is there to defend it, like it’s got to be the leaders who make it happen. They’re the only ones with the influence.

Peter: To defend what?

Defending Humanity in this Liminal Moment

Jesse: Defend the soul, the spirit the human element. If it does turn into a wall of automation, it’s because we chose to automate things that shouldn’t have been automated.

And so it takes people with the thought and the feeling and the expertise, and as we talked about in the last episode, the background in understanding human beings and the sociological and the psychological grounding to understand what inhumane practices look like in order to instill that understanding in the systems we create.

And I think that applies both internally and externally in terms of not just like what constitutes automated abuse of customers, but what also constitutes automated abuse of your employees, right?

Peter: This is making me realize something that I hadn’t, I guess, acknowledged, come to terms with, which is that I’d been thinking of liminality as something that happens to us, right?

That as you go through life, as things shift and evolve, there’s going to be moments…

I think one of the theses of our conversations is that liminality is always there. You’re always going from something to something else, but there are definitely moments where it feels more heightened and this is one of them. And that’s just the way of the world.

Liminality is a common anthropological frame, rites of passage, certain points in your life where you’re about to step into some new…

Jesse: Seven ages of man, right? Yeah.

Peter: I was bringing some of that thinking to what it means to how we show up as people in our liminal moment and thinking about other themes that we’ve discussed, which is that this uncertainty that we are in can cause anxiety, but is also opportunity, right?

Because discombobulation means people are looking around for someone with some answers to settle things, right? And there’s voids that folks with ideas can fill.

But something you’re saying, and I don’t know the implication of it, but I think it’s definitely worth calling out, is that liminality isn’t simply something that happens to us. Much of the liminal moment that we are in has been imposed upon us by folks who are acting out of their own self interests, but are dismissive, neglectful of the impacts of that decision making on others.

And we’re all having to navigate that. And because when you talk about leader, you talk about power dynamics, and we live in a society where a relatively small number of people wield outsized influence that we all then have to react to. And figure out our reaction to…

Jesse: Yes.

Peter: and that seems to be something different about this moment, maybe than prior liminal moments.

There’s an arbitrariness to it.

Jesse: There are a couple of sides to it.

One thing I’ll say is that I called my business Intentional Associates. You called your business Humanism at Scale. We are both in the business of driving more intentionality in these organizations because I believe that we both believe that if we don’t stand for humanity within these systems, then no one else will, because it is Design, more than any other function, that is invested in bringing humanity to internal decision making.

And that’s what we have seen in our careers as the opportunity for design to create broader cultural change, both internally as well as at the larger social scale that you’re talking about. So there’s that piece of it, first of all Secondarily, there is a certain friction associated with the liminal moment that requires a grace, a fluidity, an adaptive path, if you will, that goes against the way that a lot of people think about their roles. And the way that a lot of organizations think about what success looks like.

And in some ways, when we’ve talked about creating that semi-permeable membrane, that bubble around design, it is in part to enable design to continue to keep that torch lit for humanistic practices.

But it is, I think, a question of that multiplier effect because the perception, the real perception at this point, is that major enterprises are going to start shedding thousands of jobs because they will figure out how to automate away a lot of the work that’s being done by human beings right now.

Regardless of whether we think that’s actually possible with the technology that exists, these technology companies absolutely want us to believe that’s possible because that’s how they keep their investments flowing.

I think that it is for us to answer that question as the upholders, the flame keepers for humanism within organizations, as to how much of this story we buy into and how, much of a counter narrative we offer and what that might look like.

Responding Collectively

Peter: Yeah, and as you talk about a counternarrative, that connects with something I’ve been thinking about.

Our past two conversations have been very much about what you as an individual can do, or the impact of liminality on you as a person, as you as a leader. How do you develop your own resilience, how do you ride this wave?

And maybe, as a leader, how do you bring others with you?

But it’s still been centered on this kind of individual, not just responsibility, but locus of action.

Jesse: Yes.

Peter: And personal choice, personal decisions.

I’m wondering what the role of collective action plays.

So at the end of the last episode we teased the idea of coming out of the liminal moment. And I think what we’ve realized since then is we may be not quite there yet, but, when you’re in a moment like this, I sometimes call it the Great Discombobulation, right?

You are not the only one being discombobulated. Literally everybody is, at least everyone you know…

Jesse: True.

Peter: …is. And we could all choose to address it on our own, or we could try to connect with others with similar ideals, values, to work together to shape an outcome that is aligned with those values.

You touched on our values of humanism and intentionality. And I think a little bit about the Margaret Mead quote, “Never doubt that a small group of thoughtful, committed citizens can change the world. Indeed, it is the only thing that ever has.” Right?

What does it look like to group, to connect, to look beyond yourself, to realize that others are in a similar situation?

Something I’m starting to see that might be a response, here in the city of Oakland are a bunch of communities springing up, primarily in storefronts, but in other locations as well, right, as a response to a collapse of some structures of community that, perhaps we’ve relied on in the past.

And trying to find ways that people can connect, particularly in a sensitive moment for community, at least in the United States. How do we connect and support one another better?

The Leader’s Role

Jesse: As we pointed out a little while ago, the leader is the leverage point in so many ways because they have the microphone, they have the leverage, they have, in some cases, the direct authority, the check writing authority, which counts for a lot. Money talks, bullshit walks, and if you have the opportunity to spend the money, then you are the person who gets to decide how things go in a lot of ways.

And so if we think about it in that classic up, down, and sideways like you teach in your masterclass, that if a certain amount of the relationship energy is going down, it is creating alignment, creating trust within your team around shared intention. Coming back to intentionality, right?

Intentionality is the way through the liminal because the intentional can hold you together cohesively as a team. When it comes to those sideways relationships, those cross-functional relationships, then it becomes about a desire for certain shared outcomes, right?

We might not have the same worldview as a Chief Design Officer and a Chief Technical Officer, right? We might have different ideas of what the priorities ought to be, but we do have a shared sense of the outcome that we want to create, or hopefully we do.

And that’s part of what a leader can create in the liminal moment that can guide the difficult conversations that unfold in there.

And then, when you’re talking about the relationships upstairs, then you’re talking about, are you reading the same signals that your boss is reading? Are you aligned to the same things that they are actually paying attention to? Because if you’re a Chief Design Officer reporting to a CEO, they are probably dealing with a whole bunch of stuff that is pretty far off the radar of design and you might need to be aware of in order to be able to effectively stay in alignment and not get thrown off the surfboard in that liminal moment.

Peter: As you were sharing that framework, and you mentioned developing relationships cross-functionally, you’re a design leader partnering with a technology leader around shared outcomes, I do believe that potentially a more fruitful path, if you can find it, is to connect with cross-functional partners who do have shared values.

I don’t wanna suggest that the design org is the only one with a certain set of values that others wouldn’t share.

Actually, I was having this conversation with a friend of mine who I used to work with over a decade ago who is a product person. I’m a design person. We had a really strong partnership because we both like to nerd out about organizational solutions to product development problems. And I was talking to him recently, not about liminality, just about, frankly, the broken state of tech.

And so he’s a VP of product and in his org there is a chief product officer. And the chief product officer was leaving and so there was an opportunity that he could ask for a promotion or apply for the role, right?

They wanted to replace that role and he was making an explicit decision not to, and when I asked him about it, what kind of revealed is, there’s kind of a waterline in a lot of these organizations between the senior executive staff and the folks below it. And below the waterline, even across functions, I think you tend to find more commonality, more desire just to like, let’s do some good stuff. Let’s put some good stuff out in the world. Let’s ship good product or whatever. Like an honest and authentic desire to deliver good stuff.

The Sociopathy of Executives

Peter: But above a water line, it starts getting weird and starts getting, frankly, sociopathic. Right? Where there seems to be a selection bias for senior executives around sociopathy. That I believe is because a way that you can be a successful executive is by looking at your organization as not a group of humans, but a group of resources, right?

That’s a sociopathic mindset. And to manipulate those resources, whether they’re people or money or capital assets or whatever, to manipulate those resources for some gain. And you consider people and computers and chairs and buildings to be basically the same. They’re just things on a balance sheet. And those who are willing to go there, are the ones who end up getting promoted into the senior leadership roles because they can succeed in a way that those unwilling to go there find themselves hitting a ceiling where they’re, like, that’s not how I want to operate.

Jesse: Yeah.

Peter: And so I think there are likely folks that you might not realize you have shared values with outside of your organization I think the prospect here is that in a liminal moment where stuff is uncertain and unsettled, if you can find fellow travelers, particularly outside of your function, you can band together, propose things, while folks are in this, ‘we don’t know what’s best’ mode.

If you can bring together a group of folks with a plan for meaningful, positive change, I believe, I might be wrong, but I believe something like that is likelier to be successful now than it would be in a relatively stable context where…

Jesse: Oh, sure.

Peter: …you would just be like, business as usual.

Jesse: Yeah, no, there’s just more on the table right now. If I were the head of product overseeing a product management organization of what I understand to be a typical product management skillset, I’d be terrified about what these new technologies meant for my team, because nobody on my team can actually write requirements to the level of specificity required to actually execute.

But you know what? My design partner’s team might. So I think it’s a very real opportunity to build bridges, especially at the leadership level. But I think that to your point, it might not be at that, like, the sociopathic C-level, which I have to completely agree with. It feels like that’s what gets selected for, right?

And what you end up with is that, yeah, everybody with a more humanistic bent hits a ceiling somewhere along the way that prevents them from gaining more authority.

But you mentioned shared values and I think that’s an important piece to bring into the conversation.

I talked about shared intentions with your own team. I talked about shared outcomes cross-functionally, and I talked about shared awareness with executive leadership to show that you were following the same signals that they were following.

But I think there is this deeper question of, are we on the same page in terms of where we see this going? Not just from a metrics perspective, but in terms of the shape of the organization that we’re leaving behind.

There is I think, not enough attention to legacy in leadership broadly. But especially in navigating the liminal, like if you are genuinely trying to set a team up for some future, regardless of how clearly you can see it, it’s still on you to leave it in a shape that they can actually execute on, right?

Broaden Your Horizons

Peter: Agree. I don’t have much to add to that.

And I find myself realizing that you and I might be falling into a bit of a trap with an assumption that the path forward is within the context in which you’re currently operating and trying to make sense of that space, and to navigate that space, and in this liminal moment maybe set direction within your current organization to help bring clarity to all that uncertainty.

But that could be a trap, right? A potential way forward, and we’ve seen this pattern in prior cycles, is that small group of people with shared values in your organization, leave that organization and do their own thing.

And there’s an opportunity theoretically right now, right? Given what we were told about these tools, to let a thousand flowers bloom, right? And maybe, the outcome, or an outcome of this liminal moment, well, an outcome of this liminal moment is…

It was with Jorge, we talked about the K patterns, right? Where the, the poor get poorer and the rich get richer.

A similar thing… ish? Is we see either: Fewer massive enterprises, right? Those that can just capture the space we’re in and the value therein and it becomes, Weyland-Yutani type shit.

And or a thriving marketplace of three to seven person businesses solving problems in a way that they couldn’t have sustainably done before for whatever the economies were, but now maybe have a greater ability to do so, to opt out of a giant corporate ladder climbing game and into a… I mean, I’m starting to sound solarpunk or something here, right? But, into a more emergent, I don’t wanna say the word artisanal, but I’m saying the word artisanal, distributed, hopefully gloriously chaotic as opposed to painfully chaotic, flourishing.

And I say it’s happened before, right after the dot bust. It took the dot bust and the wounds licking and the playing around with technologies. Adaptive Path emerges from the dot bust. Core early technologies, Flickr comes to mind, Facebook, a lot of the things that have now are dominating, kind of emerged from this period of firmament that occurred in that downturn.

I don’t want our thinking to be constricted, to playing forward the current situation or the current context, and instead recognize because we don’t know where this is going, we are freer to imagine other potential outcomes that might be more aligned with our values.

Discerning Which Wave

Jesse: Six outta 10 people don’t get on the wave, and maybe they wanted to get on the wave and they just couldn’t build up the energy necessarily to catch the wave. Maybe they just realized it wasn’t their wave and they let it go under them, and maybe the wave that’s happening in your company right now isn’t your wave right?

Maybe they are deploying these technologies in grossly irresponsible ways because they haven’t intentionally developed an AI transformation program and maybe they are advocating for things that don’t align with what you signed up for, what you even thought your job was going to be.

All of that is okay. It’s okay in a couple of ways. First of all, this is gonna be something that is gonna take a long time to make its way out. The ripple effect is going to continue from these organizations that are closer to the center, first of all, which are these organizations that are frankly under VC pressure to adopt certain technologies and meet certain metrics in their own growth.

And then you’ve got the companies that model themselves on those guys, which we already know about. Regardless of the right or wrong of how they’re actually doing things.

So then from there, you’ve got a whole long tail out from there of other organizations that are gonna be adopting these technologies at their own pace. I can imagine you can continue to basically, continue with business as usual, in the exact same way that you’ve done the job as a design leader for the last 10 years.

You could probably do that for five to 10 years more, easily, before it gets to a place where you start to run out of places that do things that way, because the tooling has evolved. Maybe not 10 years, maybe that’s too optimistic, but.

Peter: I think this is important; overlooked. We’re in a moment of such kind of anxious intensity where it feels like we have to change now, or in the next three months, and if we’re not, we’re gonna fall way behind.

To remember that these things take time, that every change that has felt like it was going to be immediate took time. As you were talking, I was reflecting on how most businesses still don’t build software well, even though we’ve known for 20 years how we should do it. We just ignore it.

That and, like, the agile revolution was some similar kind of upheaval internally for a lot of organizations.

How’s that borne out?

Jesse: Mm-hmm. Mm-hmm.

Peter: Many companies still really aren’t.

Not Burning Out

Peter: And the thing though, that we haven’t talked much about, is if this is gonna take time, people can’t maintain their current level of anxiety, energy, whatever that buzz that we’re all, that we’re all feeling.

It’s gonna burn them out.

And this is something that in my own, just personal kind of thinking through what it means to show up in this liminal moment, I’ve been wondering about, which is, how do you not burn out when everything is always feeling anxious?

Now you’re telling me that we’re gonna be doing this for five years or something. That doesn’t make me feel better. I’m gonna feel like I’m feeling today for five years. Is that what that means? There’s something about…

Jesse: That’s not what I meant.

Peter: I know it’s not what you meant, but there’s something about this, like, navigating liminality is frazzling, right?

Because of that uncertainty.

Jesse: It’s exhausting. Yeah.

Peter: I feel that as a solopreneur, operating in six or seven spaces and I’m constantly task switching and I never quite know what the next thing is that I’m going to be working on.

And so I have to be ready for a lot of potential opportunities depending on what turns up in what direction, and that’s exhausting.

And I’m curious, this might be something that you have some more formal, or at least mature thinking about, born of a coaching practice. ‘Cause I’m sure this is something leaders deal with all the time, which is managing their energy, managing a pace, cadence.

Right. A leader always has, even before a liminal moment, leaders always had more work to do than they had time to do it.

In a liminal moment that feels like it’s like everything else: accelerating.

How do people manage their own, energy, resources, so that they don’t burn out. When they’re in an environment that just feels like it continues to apply pressure.

Jesse: I think prioritizing your attention is a fundamental skill for leaders.

The ability to, as much as possible, shut out everything that isn’t the decision that you need to make right now, and be able to really let go of it until it’s time, and to trust yourself that you will create the time and create the space for that decision, and that you’re prioritizing the right things.

And if you don’t have the mental systems in place to prioritize the right things, yeah, you’re gonna be constantly scared that you’re spending too much time on the wrong things.

So I think that’s a huge piece of it.

To go beyond the surfing metaphor and look at something like sailing. Imagine that the leader of a team is the captain of a ship, right? And you’re standing on the deck of the ship and what are you paying attention to?

You’re paying attention to the information that’s coming up through your feet as the boat is rocking in the water, and you’re paying attention to what you’re seeing from the waves and the clouds and the other stuff that’s coming in, and you’re paying attention to, what you’re feeling from the wind that is gonna tell you how much attention you have to give to where we put the sails and where we put the rudder and where we, how we deploy the team to get the ship to where it’s going.

So if you’ve got calm waters, if you’ve got people that you can trust to keep an eye on the mainsail and all the rigging and the stuff, yeah, you can go downstairs and you can take a nap.

But if you don’t have those people, you can’t.

Peter: I like naps.

Jesse: I said Peter’s magic word.

Peter: Thinking about navigating this moment collectively.

A week or so ago, I wrote in my newsletter, what I’m calling the design management quality cascade, and it’s a response to witnessing VPs of design reviewing, like, delivery work in an organization of more than a hundred people, right?

It’s not like it’s a 10 person organization, that makes sense, but when there’s 150 people in the organization, the VP should not be reviewing delivery work.

But it was happening and it was happening for a number of reasons.

What the design management quality cascade lays out is how to locate the appropriate responsibility at the appropriate level, right? So you’re talking about the captain of the ship and there’s a certain set of things that they’ll be responsible for, and then they’ll have, I don’t know all the terms on a ship, but they’ll have their leaders reporting into them who’ll have their responsibilities, and people reporting to them…

And on a ship, this I do know, everyone knows exactly what their specific responsibility is. the ones I know In a design organization that almost never happens.

And so what ends up happening is that VP, that captain, ends up doing a bunch of work that they probably shouldn’t be doing. They’re not prioritizing well, to use your language, because they don’t know… they either don’t know or they don’t have the confidence in the people in their organization that they’re actually doing the thing that they should be doing.

And so they feel like they need to do it all.

Jesse: Yeah. Yeah. They don’t have people that they can turn their backs on. They don’t have people that they can trust to make decisions without them. And that’s what it comes back to is, like, how many decisions can you actually let go of so that you can give the maximum time and space and attention to the decisions that actually matter that only you can make.

Peter: Well, and that becomes exceedingly acute in a…

Jesse: Exactly so, yes.

Making Informed Decisions

Peter: Right? Because… because, a liminal moment, you’re going to be making new decisions, right?

Most of the time when you are making decisions, you’re making decisions where the outcome is somewhat predictable, right? And it’s usually choosing between trade-offs. We could go path A, we could go path B. Path A has this, path B has that. We know where both of those paths go. And your job as leader is to help figure that out.

In a liminal moment, you don’t know necessarily the results of those decisions.

Jesse: Door number three.

Peter: Though you are probably best situated to hypothesize, right?

Actually, probably the nature of the decision depends on the level of the organization, right? But at that senior level, because of the context you’re in, because of the information that you have access to, you understand a likelier outcome of decisions at a certain altitude.

Jesse: The more you expand your awareness as a leader, the better informed your decisions are. Full stop, right?

The more different sources of data that you are taking in, the broader range of the organization that you’re in connection with, you’re just gonna be more broadly informed.

And that’s what I mean about building shared awareness with your executive leadership because they have to be informed about everything. And if you are ignorant of two thirds of what’s going on in the company, because you’ve been paying attention to your own little corner, your value prop isn’t there as a participant in actually guiding the organization.

Peter: There’s gonna be multiple reasons of your ignorance, but if, a reason for your ignorance of what’s happening in the C-suite is because you are involved in decision-making in the, lower levels of your organization, that’s a bad use of time.

And so delegating responsibilities, placing trust in those people within your team, empowering them to make the decisions that they are closest to and should have full information on, frees you up as a more senior leader to tackle a kind of decision making, a different kind of decision making, where there is a risk involved, because there is an uncertainty and an unknowingness.

I’m thinking also about… it should be at that executive level..

Jesse: Yes.

Peter: Because you mentioned the power of the purse, right?

And this is something else, too many design executives don’t understand the power that they have, but that you get with being a vp, that you should have budget and budgetary authority. You get to make decisions, you get to carve out time to do things.

And I know that in many organizations, VPs have become disempowered. That’s a separate conversation. It’s an unfortunate one. But not just design VPs, like VPs across the board, like the C-suite holds very tightly to all kind of meaningful decision making.

Let me get back to my original thread, which was as a VP, as an executive, you should be able to initiate programs of discovery to sense your way through the liminal moment, right?

You don’t need to know where you’re going. None of us know where we’re going. But you have the means to…

Jesse: Read the wave.

Peter: Better hypothesize, to read the room, better hypothesize, and then place some bets. Yeah. To put probes out there, and then based on the information you get back from those probes, do the work of directing the organization towards healthier outcomes.

Shift from Reactive to Proactive

Jesse: That’s what I think is central to a leader’s value proposition, is the ability to generate from their own perspective, from their own point of view, those sorts of explorations.

If you don’t have the power and the permission to do that, I don’t know.

I don’t think any organization really just wants reactive leaders. I think on some level it has to be a part of what you do, that you scout for opportunities for your team to deliver new value and different kinds of value, and to continue to drive and explore that.

I don’t know, that’s me.

Peter: No, I think you’re right. I think you’re right. I think too many design leaders are reactive. They’ve gotten in a do what they’re told mode. That started with this mindset… I still hear from design teams that use briefs. ” We gotta receive a brief and then when we receive the brief, we now can respond to that, we know what to do.”

And I’m like, What? What…uh, briefs? No, no briefs. Full stop. Because briefs mean, you’re in service to, not in partnership with.

And when you’re in service to, you are not leading right? You are only reactive.

And if you want to make change, you need to shift that posture to one of problem identification and exploring solutions.

And as you were talking, a theme that’s been true about all this AI shit since we started talking about it is, because AI is an accelerant, kind of more than any other thing, what it does is it reveals cracks in…

Jesse: Mm mm-hmm.

Peter: …Organizational practices, that maybe had been filled in, or you could paper over or you could kind of ignore. But now with that accelerant, those cracks are starting to strain and break, if you haven’t been doing the right thing.

And I think what you’re talking about, what we’re getting to here, is that basically nothing we were saying about what a VP should be doing is new. This is what VPs should have always been doing. The difference now is when VPs don’t do the things that they should have been doing, the outcomes are magnified.

Because, let’s say, you’re that VP who’s looking at work, is too focused in the weeds. And thanks to AI, the amount of work that your teams are doing is accelerating. So now you’re just gonna be in the weeds more, right?

Which means you’re spending even less time with the executive leadership that you should be partnered with, right? That kind of thing.

Jesse: Yeah. In the same way that, as we talked about when we talked about the Elements of UX in the Age of AI talk it’s not just that it amplifies the existing value proposition, but it also magnifies the places where the process is not optimized. And those things are gonna continue to be coming to light for teams within their own processes.

You know, when I think about what all of this means for the liminal leader, so to speak, it does seem to entail a willingness to hold your own perspective while continuing to listen to others. Maintaining those connections with other viewpoints because, to your point about collective action, the organizations that are going to hold together through this are the ones that have the strongest shared values and shared practices and shared beliefs.

Otherwise, I think you’re right. People will spin off and do their own thing and maybe some of them will see this as an opportunity to move to a smaller place that is gonna be really lazy about adopting all these new techniques and technologies. And they can continue to build websites with Quark Express for as long as they want.

And there are other people who are just gonna get the hell out, right? And go open a pottery studio in Alameda or something like that.

Peter: And that’s been happening. Bakeries.

Well, Yeah. And a thought I wanted to make sure that got out, that I think captures a bit of what you were just saying, but something that I’d written down before we spoke: liminality is not about a destination.

You’re talking about: what does it mean to be a liminal leader? To be a liminal leader is you don’t know exactly where you’re going. So it has to be about the journey.

But, and this is tricky. It can’t just be random. You’re not just stumbling around. There is a direction that you’re moving in.

Liminal leadership needs to have confidence that even though you don’t know exactly where you’re going, you’re moving in generally the right direction, wherever that is.

Jesse: So this is where the three out of four people who get on the wave, get swallowed by the wave, because they misjudged where they were relative to the wave and weren’t paying attention to the right things. And they went under instead of over and didn’t get up on the board.

And what you’re talking about is really the ability to get up on the board, so to speak, to be able to calibrate yourself to the moment and activate in the moment when the moment arises.

Am I overextending the metaphor? Maybe.

Peter: No, and I think this is good place to end.

The thing I just realized, and I don’t know if that was always part of your intent, was that of those 10 people, it’s not the six who never got on the wave that are struggling. It’s the three…

Jesse: Thought they could catch it!

Peter: …Who thought they were ready and weren’t. Those six are actually better off having let that wave go by ’cause they weren’t ready for it, right?

Jesse: Yes, that’s exactly right.

Peter: So it’s having that, we talked about discernment with Dan, right? There’s a discernment here of your moment, right? And this is that prioritizing conversation as well. You need to be self-aware of what is your moment and what isn’t and with some of those surfers there was a misfit between what they perceived and their ability to take advantage of it, and they didn’t succeed.

Whereas those other six on subsequent waves might have been able to have a perfectly good ride.

Jesse: Yeah. Yeah.

Thank you so much for the conversation, Peter. It’s been fun.

Peter: Yeah, this was great. Thank you, Jesse.

Wow.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Show Notes

For more about Jorge, visit https://jarango.com/

For the Claude skills he discusses, visit: https://github.com/jorgearango/llmapper-skill

To learn more about Jesse and Peter’s Intentional Design Leadership Circle, starting April 15, visit https://www.eventcreate.com/e/intentionaldesignleadership

To join the first Finding Our Way Live! on April 3, visit our event page on LinkedIn: https://www.linkedin.com/events/7442678896506068992

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, consultant and author Jorge Arango is our first return guest, five years after his last appearance. We’ll talk about his current work in AI transformation, how AI has evolved his thinking on the craft of design and where information architecture still plays a role in this new landscape.

Peter: Jorge, welcome back. It’s been five years since we’ve last had you on the show.

Jorge: Fortunately it’s not been five years since we’ve talked. But I’m so excited to be back in the show.

Peter: Awesome. You are our first return guest. Five years ago, it was deep in lockdown, heart of the pandemic. We talked to you about some themes that are still relevant today, craft, practice. We were interested in your architectural background and how that was helping you think about design and design processes you were teaching at the time.

So you were very meta around your thinking and we wanted to tap into that, but it’s five years later. Which feels like a lifetime, particularly after the last couple of years. So what’s going on with you? Where are you at? What you up to? How do you talk about what you’re doing right now?

Jorge: You know, talking about five years, it makes me think that about five years ago people were tossing around the phrase “the before times” to talk about like the before the pandemic, you remember that? It’s like, “Back in the before times…”

Jesse: Right. “Before what?” anymore.

Jorge: Yeah, that’s the thing, right?

Like that phrase is, like, we keep using it. It feels like we’ve left the world behind, right? Things started changing significantly back in 2020. I mean, I feel like things had been changing even before then…

Jesse: Oh yeah.

Jorge: 2020 was a big inflection point with the pandemic. It moved so many people and processes that maybe had resisted going online. It moved everything. We were working remotely and all that stuff. We still are.

Getting Excited with the Work Again

Jorge: But then obviously, the breaking of AI into the mainstream as a thing that people are concerned with, interested in, trying to find how to use, is the latest catalyst, I think, in casting the past as the before times.

And as many people have, I’ve been trying to find my way in this new world, and I find that for me it’s about coming back to fundamentals, to first principles, to what is it that I’m uniquely suited to help add value with? And I’ve been on a path of rediscovering that, and I’ll say this right up front, I’m more excited about the work than I have been for a long time, as a result of all these changes.

Peter: What do you call the work? What do you mean by “the work” when you say that?

Jorge: Y’all know that Harry Max and I are doing a podcast. And Harry has this definition he’s used this in a couple of episodes. He has this definition for stupidity that I really like.

He says that, I’m reading now from one of the transcripts here, “Stupidity is a result of a series of decisions and actions that lead to results that are the opposite of the intended outcome under conditions of self-deception.”

Peter: Okay.

Jorge: So basically self-sabotage, right? Like, it’s like…

we,

Peter: I didn’t realize your podcast was about our current United States

Jorge: Well, this is like the discovery for me. You asked what’s the work? I’ve realized that my work boils down to helping people and organizations, particularly the people who have the most leverage, act intelligently.

Like, I bring up Harry’s definition of stupidity because that’s what you don’t want, right? You don’t want self-sabotage. You don’t want to declare that you are trying to do something and then end up with the opposite outcomes. And we have this catalyst in our midst, AI, which can either help or hinder our efforts to act intelligently.

And my work now is focused on… the way that I describe it in my website is, like, What’s the architecture of intelligence? Like how can we use this information that we have available to us to act more skillfully? And you won’t be surprised to hear that I think that, first of all, letting in the right information and then carefully structuring that information is a big part of how we act skillfully.

AI and IA

Jesse: So, you know, the three of us all met through the information architecture community back in the early two thousands where there was a real energy and focus building around the idea of, if we could just structure enough data in the right ways, we might be able to create systems that were better for humans.

And that, I think was the, continues to be the, innate promise of information architecture as a discipline. Now, and honestly, this was predicted by IA people. It’s so funny because I can’t remember who said it. I think it might’ve been Lou Rosenfeld. I think it might’ve been Peter Morville, I can’t remember which of them it was, but I feel like it was one of those two guys who, at some IA Summit said, we’re not going to crack the AI nut until we crack the IA nut.

And the idea being that if we master the structuring of information itself as a human discipline, then we will be capable of creating the intelligent systems that we actually need, that will actually serve us. And it feels like a lot of your work in the last year or so has really been moving toward that.

I don’t wanna project onto your career something that isn’t there, but I’m curious about, like, how do those ideas resonate with the work that you’re doing now?

Jorge: Yeah, they absolutely resonate. the way that I’ve articulated it, at least in my website, is that information architecture can be done more skillfully with AI. But conversely, AI can be better if the information that it’s fed is carefully architected, right? So, I’ve been trying to play kind of both sides of that.

Say, it’s like I work both sides of that loop, right? I’m trying to like understand how AI changes the work of structuring information with the understanding that the better a job you do at structuring the information you feed, particularly language models, the better the outcomes you’re going to get.

There’s work above that, which is like trying to figure out, like, what are the outcomes that we’re trying to get out of this? And you talked about, like, human goals that ostensibly you want to design systems that produce better outcomes for people and for society and that help drive us forward, and there’s a technical conversation about like, how do we structure systems to help us achieve our goals?

And then there is a broader conversation about what are our goals, you know, what are we trying to do here? And that has to be informed by a clean read on the context. Like where are we? What’s going on? What are our competitors doing? What is our organization aspiring to? Like, there’s all these things that stand above the technical discussion about how do we architect information, how do we architect AI or what have you?

A Lot Depends On Your Definition of Design

Jesse: I guess when I think about our audience and I think about design leaders and the pressure that they are under, in a lot of ways it is about simply having a story to tell about where this tech fits in as you see it as a leader, within your organization, within the boundaries and the constraints of what is expected of your team.

And in some design teams that expectation is super tactical. It is pixels and Figma and, moving the data into production. And on other design teams, it’s not that. There’s a lot more sort of strategic permission to engage with the bigger ideas behind the product.

And I’m curious about your perspective on how those things play out in the choices that design leaders have to make around where they focus their attention because their attention is spread so thin, right? It’s like, where can I pay attention to this tech where it’s actually gonna matter and it’s actually gonna create some traction for the team against an actual value prop.

Jorge: I think you framed the question correctly by stating upfront that there are different understandings of what design is, right? And I suspect that in a large number of organizations, design is seen as a production function that involves cranking out screens. And if that is the sense in which design is understood in a particular organization, the design leader will have a different engagement with these new technologies than in an organization where design is more, I’ll be judgmental here, more correctly seen as a more strategic discipline.

So let’s acknowledge that right up front. There’s an information architecture labeling problem there with the word design.

My sense is that it might not be worth a leader’s while to try to reframe the organization’s understanding of the discipline through rhetoric, through persuasion, right?

You’re working in an organization where design is seen as a production function, your best strategy forward might not be to try to convince your colleagues that’s not a good reading of what design is. You might be better served by trying to prove designs value within the constraints that apply to that particular organization, right?

If the organization sees it as a production function, then try to produce it as effectively and efficiently as possible.

Jesse: So this suggests tuning your approach to AI tooling toward the value prop that is already expected of you, right? On some level.

Jorge: There’s a step before that, which is, taking for granted that the design leader understands the context that they’re operating in. That might not be true, right? Like you might have expectations of what design is that are misaligned with how design is actually expected to function.

And again, you two have worked more closely with design leaders than I have, coaching them and stuff like that. So you might have more to say on that.

Peter: I have a lot to say about that.

Jesse: Yeah.

Peter: I wanna set aside the understanding context bit, which is important.

Jesse: For sure.

Peter: So Jorge you mentioned the challenge of rebranding design, it is commonly understood in some fashion internally. This is a challenge that nearly every design leader I work with faces, it’s at the heart of my masterclass and one of the core tenets of my class is you need to meet people where they are at in their maturity.

You as the design leader, are always gonna be way more mature than the rest of the organization about design. And if you try to accelerate or put forward your design approach into an organization that’s just not ready to receive it, you won’t get anywhere.

This gets a little bit back to something Jesse and I used to talk about years ago. When Jesse had this idea of the three maturities.

Jesse: Right.

Peter: I don’t think the idea though is simply to then give the people what they want and stop there, right?

That’s where you start, because folks around you have a set of expectations. If you don’t meet those expectations, they will then just dismiss you. So you need to meet their expectations, but you also then need to have some idea of where you want to take things, which as you meet their expectations, the theory goes, you demonstrate your credibility, the more credibility you’re demonstrating, the greater trust you’re earning, the greater trust that you earn, the more that you can then start bringing people with you.

But there’s a journey you need to go on. You can’t just again hop the queue or hop the maturity model and say, we should be operating at maturity level five. We’re at two. Let’s just go. You need to take the steps. You need to take the steps through it.

The Need for Clarity

Peter: I wanted to actually get back to something else you talk about, which is related, which is something that’s becoming clear as I read about AI and talk to my clients about these AI tools, is that perhaps the biggest gap, shortcoming, that teams are facing is a lack of clarity on the part of their organizational leadership, their senior most leadership. And without clarity as to goals, outcomes, mission, vision you get a lot of chaos with AI, ’cause you basically accelerate the current chaos.

Jesse: Amplify the noise rather than the signal. Right?

Peter: Yeah. And I think that’s starting to stress people out as, like, a lot more stuff is being done. But you also hear that people don’t feel like they’re doing better work. They’re just doing more work.

And I think the reason they’re not doing better work is there’s a lack of clarity as to what are those goals, what are those outcomes? What are we aiming for?

And so I’m curious, Jorge, it sounds like you’ve been doing a fair bit of work consulting with Greg and your practice with organizations. Are you, how are you helping them achieve clarity, or what is your relationship to the clarity story here?

Jorge: The three of us were working when the web happened, right? And that was a time of big change. Like now, that was a time when people were excited about a new technology and looking for ways to apply it. There was a lot of hype, there was a lot of misunderstanding. I remember, like, trying to explain the web to people and getting glazed looks, right? Like, what are you talking about?

And it was a time when there were a lot of solutions in search of a problem to solve, right? And people were putting the technology forward because it was like an exciting new thing. And in many ways, I feel like we’re in a repeat of that, but even perhaps more impactful than what the web was in that this feels like the ultimate general purpose technology that we can now apply to anything, right?

Like, it’ll just solve all your problems because it’s artificial intelligence and it’s so much smarter than people and all this stuff. And there’s a lot of misunderstanding about what the technology is that is very similar to the kind of a misunderstanding that we saw in the early web. Recently, I reread, do you remember John Perry Barlow’s Declaration of Independence of Cyberspace?

Jesse: Oh very much. Yeah, sure.

Jorge: Right? You go back to that and you read it and you’re like, man, you remember that kind of naivete that we had at the time?

It’s like it’s going to change the world, like nations of the world, stand aside. Here we come. There was this notion that this technology was going to somehow overcome human foibles, it’s like technology never really does that, does it?

Technology can amplify human

Jesse: Yes.

Jorge: You know, it’s understandable that we are now in the thrall of this new thing and therefore acting unskillfully in many ways. I suspect that needs to burn out and it will burn out. What I wanna do is, I want to help organizations and the people who are leading organizations use this new technology as skillfully as possible.

So like, how do we speedrun the path to a skillful use of the technology, meaning free from the delusions that come from our projecting into the technology capabilities that it doesn’t really have. Which in this case are quite tempting because it is, first of all, there’s been a lot of hype, and second of all, frankly, we work with the technology day to day, and I’m continually impressed by its capabilities, right?

Jesse: Yeah, no, the line is really fuzzy, right? Between what it can do and what it can’t do. In part because we are still exploring the boundaries of what it can do, but also because that’s changing. It’s been fascinating.

So my first vibe coding project was about like two years ago where there was no tooling and there was a lot of kind of figuring things out as I went.

And then to see this stuff fill in where there’s more and more support, there’s more and more understanding of the use cases, and this is where it actually gets exciting when we think about the application toward, going all the way back to what you were talking about, the value proposition of design and what design has to offer and what design has to bring.

Ever Greater Levels of Abstraction

Jesse: So the opportunity potentially is on both sides, right? On the one hand yeah, on this show we’ve talked about a few times, the fact that we are now sitting on a bedrock of 25 years of best practices of active user experience teams in organizations, building up understanding about baseline human experience kind of stuff when it comes to 2D pixel interactions, right?

And then you take that into a space where a robot can meet that baseline. And then I think you start to get into some really interesting territory because, on the one hand, there are a lot of problems the robot can solve that no human…

You could hire somebody to do that job and they would do that job well, I’m sure. And at the same time, they will be discovering nothing new. They will simply be reiterating something that has existed before. So it’s like UX, bricklayer kind of a role.

And then the other place of it, potentially, is that the robot helps you see something you didn’t see before about what’s possible and whether it can ever go beyond best practices. I did this talk last year, the Elements of UX in the Age of AI, and I talked about the fact that from my perspective what it will always be best at is mediocrity. And so what does that mean for the role of the designer in all of this?

Jorge: I wanna pinch and zoom on what you’re saying there, because what we’re being called to do, and now I think that we’re addressing perhaps practitioners, right, as opposed to like design leaders who tend to get ensnared by their identity as a practitioner of a discipline, right?

Maybe I’m speaking of myself, right? As opposed to I don’t wanna project on other people.

But one analogy that I’ve been using when talking about this stuff, and I’m sure it’s not original to me, is the trajectory that computer programmers have been on.

So the original, the initial digital computers, you programmed literally by flipping switches, right? Like you had to understand binary math. And you had to understand the user interface of the system, the way that humans programmed the computer involved thinking like the computer because the interface consisted of turning certain registers on and off.

And eventually higher levels of programming were invented where you had things like assembly language, which allowed the programmer to think in terms that we’re more human-like as opposed to like machine-like. And then if you want to go like a level of abstraction up, then you start getting even higher level languages, right? Things like when I learned computer programming in the early 1980s, it was BASIC, right? And it was called BASIC for a reason, right? And it was mostly English, highly structured English, but it was mostly English. Like I was not having to learn op codes.

Jesse: Right.

Jorge: And what we have now in that analogy is now you don’t even need to worry about things like you know, these higher level languages. Now you can just describe the thing that you want. And this is a progression of ever higher abstraction away from the way that the machine works at its core.

Jesse: Right,

Jorge: And the question is, how many challenges that we were used to flipping bits for, can we now abstract away from, because that’s what we’re being handed here. We’re being handed, like, some ways it’s like the ultimate abstraction machine.

Jesse: Yes. Yeah.

Jorge: One way to think about the implications of that for something like a design team is, you were used to sweating the details around things like the corner radius of buttons, right? And ensuring that those things were being applied consistently throughout a, imagine like a large suite of software applications.

And you know what, if you’re freed from that constraint, what if you no longer have to worry about that? Because you have systems that are abstracted enough where you can be sure that the details are going to be looked after.

And now you, the human setting direction, can focus on higher level directions, right? And you can develop new patterns.

So here’s an idea from software development, and I don’t know if this is true, but it’s my kinda read on the thing. I don’t know that you can come up with something like object oriented programming if your thinking is happening in bits. Like you have to think about what you’re doing at a higher level of abstraction.

Jesse: Mm-hmm. You can’t see the clouds if you’re only looking at the mist.

Peter: Right.

Jorge: And I think that what we’re being invited to do as designers is, I think that a lot of people, and they think design, they think corner radius is of buttons and it’s like, no, folks, we don’t have to worry about that anymore. Or, I mean, not everyone, like I, think that there’s still going to be a role for people who design these beautiful things, but we now have systems that can help apply them at scale in ways that is going to require a lot less human intervention.

And that’s going to free up designers to worry or to focus on higher level things.

Jesse: So the bifurcation still kind of exists within that. The idea of every design system having a robust AI behind it, right, that deeply understands the rules that’s gonna go like, Hey, you know what? Don’t make that corner radius five, make it four. That’ll be better, right?

Like those little guidances I think can really support design as a larger practice.

But then I think the question becomes where does the strategic impact come and where can the technology enhance that higher level of meaningful direction that we started the conversation with, where design can really inform where a product and a business ultimately go.

Everything is a K Curve

Peter: I want to follow up on that ’cause, ’cause, you used the word bifurcation and I’ve been doodling on this whiteboard behind me and one of the things I’ve been doodling that’s related to this is the concept of the K curve, which I don’t know if you all are familiar with, but I think it’s becoming a pattern that we’re seeing throughout anything that touches the internet, which is now all of society.

One of the most obvious expressions of the K curve is in wealth inequality, right? The richer, getting richer, the poor, getting poorer, and that’s getting exacerbated, even though, you guys mentioned John Perry Barlow, these technologies were meant to put forth a new society which was going to be utopian. And we’ll all link arms and everything will be great.

And there’s another K curve that I see… is within organizations, and this gets to what you were just talking about, Jesse. And a little bit actually what Jorge was talking about as well earlier, in terms of when we were talking about maturity and you need to meet people where they are and meet their expectations.

And that K curve is most companies building software do it poorly, right? They embrace practices like SAFe, scaled agile framework. They take Scrum and do it wrong. They think they’re being agile and they’re not. And the evidence being, there’s still a lot of crappy software out there.

Maybe it’s better than it was on average than 20 years ago, but not, the sea change we would’ve expected. Going from waterfall to Agile didn’t really drive a ton of material improvements in what was produced. It allowed us to make more. There’s software everywhere, but you could have a good conversation or good argument around, is it better?

My point with calling out how most organizations do it poorly is there are some who do it well. And I think that K Curve is going to apply to these organizations in the application of AI, where those who haven’t yet figured out how to design software aren’t gonna all of a sudden start doing it better thanks to AI…

Jesse: right,

Peter: They’re gonna do more of the bad stuff that they’ve been doing.

And those that have figured out how to do it better are gonna just like… rocket-ship past everybody else.

And I don’t know what those implications are because many of those companies that do it poorly have other things that protect them. So I do a lot of work with banks and insurance services firms, and they have these delightful regulatory moats that’ll enable them to produce mediocrity and thrive. Not even just survive, thrive. ’cause that’s not where the value is located.

But I find myself checking in with any utopian sensibility about how AI is gonna allow us to do better things, if we’re not taking into account the context in which that AI is being deployed and how it’s constraining evidently better things to do today.

Like, why would AI change that? How might AI change it?

Jorge, you have a podcast called Unfinishe. Jesse and I have been playing with Liminal. We don’t know where this is going but I feel like we’re at these edges here of something is coming that’s maybe revolutionary and what is our role, in moving towards whatever is coming?

Jorge: The podcast is called Traction Heroes. Unfinishe is a consulting business that I’ve spun up with Greg Petroff, which we can get into because the name is important. Like we chose that name with intent. And it’s “unfinishe” without the d so it’s literally unfinished.

There’s a quote from Christopher Alexander that often comes to mind, and I’ve pulled it up here so that I can read it verbatim because I think the words are chosen very carefully.

He’s talking about like the role of design, right? And he says, “We are searching for some kind of harmony between two intangibles, a form which we have not yet designed, and the context which we cannot properly describe.”

You Gotta Use The Tools

Jorge: And I really like that because I think that we designers think that the object of our focus is the object. It’s the form, it’s the thing, it’s the screen,

And in reality, what we should be taking in is the fit between that thing and the context it’s looking to address. And we cannot understand that fit if we don’t understand the context and in the context, I include things like the strategic direction.

Y’all had Roger Martin on this podcast, and Roger often talks about the fact that you can’t really separate strategy from execution. I’m not gonna put words in his mouth, but I think he argues that’s not really feasible, right? Like in some ways like strategy is manifest in the execution.

And in executing the outlines of the strategy, at a minimum its impact, the boundaries of where you can act, start becoming clear. It cannot become clear in the abstract. Like you actually have to do things in the world. You have to put the product out and see how people react. Are they buying it? Are they not buying it? Are people failing to discover this particular screen that is essential to the thing?

Those kinds of things you’re only going to be able to answer once the thing is out in the world. And the risk that we run here, this is to your point, Peter, is that we have this new technology that, if approached naively, will lead you to try to apply it to the old ways of being. The ways of being that were applicable before the technology came on the scene.

And you can try to use it to do it the same thing faster or with fewer people, but it might turn out that the thing that you were doing before was only really appropriate in a world where the new technology didn’t exist.

So it’s like you’re now, like, speeding away in the wrong direction, right? So, like, it behooves you to really grok what the technology brings to the table.

And you will only do that by actually doing stuff with it, which is why I’m so adamant in the idea that you have to work with this technology. Like you can’t think about it in the abstract. You have to make things with it. And you have to use it as a material to really understand what it brings to the table so that then you can reconstitute your strategic choices around what new capabilities this thing brings.

Jesse: I am so glad that you brought that up because it, touches on something that came up for me when I was reviewing our last conversation together on this show, and I’m gonna quote you back at yourself.

Jorge: Oh, no!

Jesse: I’m sorry to say. But it’s gonna be good. It’s gonna be good, I promise.

You were talking about working with students and you said, “the analogy that I use is that we are there as something like a strength trainer. You hire a strength trainer to show you good form when doing exercises, and the best trainers are the ones who will know how to do the exercises themselves, who’ve been doing it for a long time, who themselves manifest the practices that they are teaching you.”

So I think there is something to be said in here, coming back to our audience of design leaders you can’t be throwing this technology at everybody and not be immersed in it yourself and not to have your own opinions about what good practice looks like.

Jorge: Yeah. No, absolutely. It’s foundational. The story I often tell is, when I was a student myself in architecture school, we had a class called Materials of Construction. It had two sections. There was one section that was like the theory where you learned all the math around what’s the tensile strength of steel? There’s math behind that.

But then there was a practical component to this, which was, I remember we would drive out to this warehouse and we would don a welding mask and fire up an arc welder and actually learn to weld steel or lay bricks.

And the expectation wasn’t that we would then graduate and become brick layers or welders, but that whenever we drew lines on paper representing walls, we understood what those things represented in the real world, not in theory.

I’ll give you another story. This one was also very influential to my career.

One of the very first books of design that I ever read, it might be the first book of design I ever read is, a book on video game Design by Chris Crawford.

Jesse: Hmm.

Jorge: I think it’s called The Art of Computer Game Design.

I haven’t read it in many years, but this book is from, I think it’s from 1984. It’s the early 1980s. And I bought this book when I was a kid, programming in BASIC, trying to make video games. And I was disappointed because I was expecting that this book would help me, I don’t know, make better sprites. Like I was a, like a pixel- based designer at that point.

But what this book was actually was a conceptual manual of what good design for games is. And one of the points that Crawford made, and I’m gonna have to paraphrase because it’s literally been decades since I last read this, but I remember him talking about the constraints of the systems he was working with.

Keep in mind these are early 1980s, 8-bit computers.

And I remember him talking about understanding that he only had a certain amount of RAM to work with in these computers. And because he was not just a designer, but also a programmer, knowing the computer’s constraints allowed him to make creative choices that he would not have made otherwise.

Concrete example, he was working on this war game and he realized that with a very small memory footprint, he was able to tweak one parameter and allow the game to indicate the passage of time by shifting colors so that it reflected the seasons. And he would argue that a non-creative programmer probably wouldn’t have spotted the opportunity, and a non-technical designer would not have spotted the opportunity either.

Like he was this Venn thing where it’s, I’m a technical person and I’m a creative person. And because I understand the capabilities of the system, I can make better creative decisions.

Jesse: So what are the implications of that insight for AI and digital product design?

Jorge: The most obvious implication is you have to be involved with the technology. Like you have to work with this stuff hands-on and you can’t just read about it. I think that at this point most people who are working in any kind of professional capacity have at a minimum fired up ChatGPT or Claude or one of these chatbots and had the experience of interacting with it. I do think that it’s important to not stop there and really grok what is going on underneath the hood. And I think that once you do, you’re quickly dispelled of any magical thinking…

Jesse: mm.

Jorge: …that might be instigated by this technology.

It is a technology, it’s not a magical entity that all of a sudden is gonna solve all your problems. It’s a technology that you have to work with and it has capabilities, perhaps unparalleled capabilities, but it also has constraints. And you have to understand both.

Jesse: What are the risks? What are the traps that designers and design leaders might need to watch out for as they are engaging with these technologies in design processes?

Jorge: Uh, Wishful thinking,

Jesse: Oh, yay! The problem is solved!

Jorge: Yeah. It’s, “Hey, we got AI now,” you know? We read news about all these companies laying off people because AI, right?

Most recently there was a thing about Block, right? Where they laid off something like 40% of the company, and the messaging, if not necessarily the reality, behind that decision was that we’ve been working with AI and we have all these efficiencies now, right?

I think that you have to be really careful when parsing news like that because there’s a lot of hype. This technology can do a lot of things.

One of the things that it can do is it can be used to excuse a lot of decisions that are being undertaken for other reasons. So don’t think that you’re going to be able to replace humans in the short term with AI, especially for a lot of complex processes.

Like maybe in the long term, a lot of roles will go away. In the near term, we’re just at the very beginning of this. And so I would say avoid buying into the hype that you’re going to be able to replace humans in the near term and still get the same results.

On the flip side of that, avoid the temptation to think that this is a nothingburger. This is a burger.

Peter: You mentioned, Jorge, in your conversations with Harry on the podcast Traction Heroes, and I gather your practice with Greg now, your consulting practice, you’re trying to help the organizations you’re working with be more intelligent about how they’re embracing these tools. And I’m wondering how you are doing that.

What are the points of articulation for intelligence? And just to maybe kick this off, I recently wrote a post for my newsletter that in turn was somewhat inspired by something that an organization designer named Clay Parker Jones, who works for Airbnb, wrote, which is we need to move past role clarity.

It’s not about roles, it’s not about designers and product managers and engineers and really defining those well and then that will solve the problem. We need to move past roles and towards teams. We need to actually be okay that roles are getting blurred, and we need to then figure out how do we just get the right four or five, six people in the room.

And his insight was, provide them clarity. He talks about team clarity over role clarity in order to take advantage of the potential of these new technologies.

I’m wondering if that is the kind of thing that you’re seeing that you’re working on. Are you focused on roles and teams? Are you focused on process? Are you focused on strategy and making sure that the leadership has clarity and is prioritizing appropriately? Like where do you see these points of articulation, at least at this point when it comes to companies or the organizations you’re working with behaving more intelligently.

Rethink Many Things

Jorge: Everything that’s old is new, right? And this is what I was saying earlier in our conversation, that this new technological disruption is an opportunity to revisit first principles and to think about, hey, you know, what is the work really about? If we thought that the work was, in my case, about, if you take the most superficial read of what information architecture is, right, it’s like the work is about structuring website navigation systems, right? Or taxonomies for people to find products in a catalog more easily or what have you.

If you thought that was what the work was about and all of a sudden you have systems that can do that, that forces the question, what is the work ultimately about?

And when you step back and think about we’ve been doing as designers for a long time. It’s about trying to make sense, trying to help move towards addressing some kind of challenge in a skillful way, right?

Obviously this is not the only discipline that does that, but design has this particular abductive way of reasoning where you try to get a sense of what the challenge is about. You explore a bunch of different alternatives, hone in on one, and then put it out there. You put it in contact with reality so that you can start iterating toward good context-form fit in the Alexander sense, right?

And I think that that’s perfectly valid. The risk at stake here, Peter, and the reason why leadership needs help with this right now is precisely what we were talking about earlier, that we’re so distracted by the capabilities of the technology that we can lose sight of the fact that it’s very easy for us to expedite or automate the wrong things.

I’ll tell you what the wrong way to go about this is. The wrong way to go about this is to look at our current processes and then start trying to automate everything without taking a step back and understanding what the ultimate outcome is, right? You want to make sure that you are using the technology appropriately, and that requires understanding the technology, but it also entails understanding how your business or business unit or what have you is creating value.

You know, you need to step back and… it’s like service design, right? And our mutual friend Craig Peters has written about this, this idea that, hey, you start by understanding the flow and you all at Adaptive Path, you published the journey map thing, right?

Like, which was so influential for us. It’s like you’re trying to understand how people move through these changes to come to some outcome.

So you still have to do that. AI is not gonna do it for you. You still have to do that. If you do that now with the understanding that you have these new capabilities, then something interesting can emerge.

I would say the wrong thing to do is to keep doing what we were doing only now faster and more cheaply, which is what you were talking about earlier, Peter. It’s not about start running faster. You might be running in the wrong direction.

This is an opportunity for us. It’s like we’re at an inflection point. We’re being gifted this incredible opportunity to take a step back and say, how are we really helping people here? And how can we do it better now that we have these new things?

Jesse: So I’m curious about how all of this manifests for you in your own practice as a consultant, as an advisor to design teams and to design leaders or just business leaders more broadly. What does this look like in terms of how you actually get things done?

Jorge: It manifests on two levels, and I think that we have to approach it on two levels.

On one level, it’s what we’ve been talking about, which is understanding the technology hands-on so that you can know what it can and cannot do well in the spring of 2026, and I usually don’t do this, I won’t, like, date the podcast, but it’s very important to acknowledge that these technologies are changing very fast, right?

So it’s very important for you to be up to speed with how the technology is currently working so that you can, when advising people at this very high level, how are we creating value thing, so that you have a good grasp on what the technology can and cannot do well, and which approaches work best.

So that’s one level. The other level is the actual doing of the work yourself changes as a result of these technologies.

I, myself, work a lot more these days with Claude and ChatGPT than I do with Figma, right? So…

Jesse: hmm.

Mm-hmm.

Jorge: That’s a transformation in my work.

In some ways, it’s kinda weirdly regressing that I’ve become very chatty and verbose just because the tools that I’m working with are very chatty and verbose. But I also have to become more skillful at describing what I need help with.

Using the tools on myself, maybe this is something we can drop in the notes for the show, but I’ve been doing experiments that I’ve released publicly around things like conceptual mapping. This is a long running experiment for me. It’s like, how can we use these tools to help us make really good concept maps? And I have a tool that I’ve been building over time. The latest release, I packaged it as an agent skill that you can fire up within Claude and you can feed it a text or point it to a webpage, and ask it a framing question and it’ll draw a diagram of the main concepts and how they relate to each other.

So, highest level, how can these tools help us create more value in new ways, not just in the old ways, but at a lower level? How can these tools help me as a practitioner deliver more value?

Because there are things that it can do much faster than I can, and it behooves me to make myself obsolete in those things because if I don’t, someone else will, right?

The Role of Language and Different Intelligences

Jesse: Right. And then you get into all kinds of internal tensions within organizations. I think one of the interesting questions that comes to mind for me is that for design leaders, they’ve got to be looking at their teams and asking themselves, so I’ve assembled this community of visual thinkers, people who can puzzle out problems of pixels and widths and grids and so forth.

But then, now, the challenge is how many of these people are actually also verbal thinkers? How many of these people are actually also people who can use language to describe what they want in a way that they can elicit the correct result from the system that we’re all now being asked to step up to and engage with.

Jorge: And that’s a characteristic of the current state of the technologies, right? And this is where the, like, understanding the constraints comes in. The word language is in the middle of large language model, right? These systems are very oriented to the kind of conceptual thinking that can be best expressed symbolically through language.

And to your point that’s not the only way of thinking, right? There are other ways of thinking. There are some people who are more visual. There are people who are more maybe like kinesthetic, like people who can express themselves through movement, through, I remember at one of the IA Summits seeing people do these workshops on body storming

was

Peter: Bodystorming!

Jesse: Yes. Yeah.

Jorge: Right. Like that kind of thing.

So we are embodied beings and our intelligence, the intelligence that people bring to the table, sure, language is a big part of it, right? It might even be the biggest part of it, but it’s not the only part of it. And I think it’s very important for us to remember that.

This is one of the ways that we can get wrapped around the axle with these technologies. Like we can end up under the delusional impression that because they’re so masterful with language, that means that they are somehow, like, smarter than us, or all powerful or what have you.

It’s like we bring to the interaction a lot more than we give ourselves credit for.

You might flip the equation and say, one of the great lessons for us, one of the big takeaways for us from this transformation we’re going through, it might expose us to the realization that we have capabilities that we weren’t even aware of, just because we had located so much of our value in the stuff that we could language. And now we have systems that can language pretty good, but we are still really good at other things.

Maybe this is an invitation for us to become really good at the intelligences that can’t easily be expressed using words.

Peter: I can, I know I language pretty good.

Jorge: Really good.

Peter: As you were reflecting on it, actually behind me from some client work I’m doing, is Jesse’s elements. Because I was working with a client, relatively small team, about 10 folks that started as a design team.

And so the people on the team were product designers, and then they decided to add what they call design engineers, which can also be thought of as creative technologists and prototypers and that kind of role. And along the bottom on my whiteboard, product designers and design engineers in the middle next to each other.

And then to the right of design engineer, front end developer, right? Because something that they were distinguishing is a design engineer doesn’t do production ready code. That’s where your front end developers are. And then I have to the left of product designer, the first item I put SD.

And that S was purposeful. It could either be, like, a strategic designer or a service designer, and the idea that there’s a spectrum of work happening here, but that the roles are blurring, right? The “who is exactly doing what?”

You have product designers who can prototype and maybe even do production ready code. So what does that mean for the roles? But, getting to the intelligences, I then use Jesse’s elements, right? Strategy at the bottom, then scope, structure, skeleton and surface at the top. Because there’s this question, what does the design team work on?

If we can automate the stuff up top, and there’s a lot of UX that’s not automatable, at least not yet. But to get meta about this, Jesse’s insight required a visual vocabulary, a visual thinking to be able to see this in two dimensions and to recognize the abstraction at the bottom to the concrete at the top. And the left was in the original document. the left was software. The right was hypertext, right?

There was a logic to it that is probably outside the ability of any LLM to have produced a conceptual model with this kind of clarity.

Jesse: This is not where I saw line of thinking going. Okay. Could LLM reproduce the elements of user experience? Is that your question?

Peter: That’s part of where I’m going with this, right? No, but to, Jorge’s point, right? If we are having to identify what is the intelligences that we bring, as I was reflecting on Jesse’s model behind me, I’m like that’s perhaps a direction or an indicator.

Now maybe at some point LLMs are able to do that as well, but that kind of, it’s not just visual thinking.

But to your point, Jorge wordses, and promptses, is only one of many intelligences that we should be considering as we’re thinking about where things are headed.

What Is the Story You’re Telling?

Jorge: You’re a movie person, Peter. I always remember that scene from Blade Runner where Deckard is sitting in front of the computer display and he’s asking for the system to zoom into a particular part of the photograph. You remember that?

Peter: Oh, of course.

Jorge: I remember, like, even when I first saw that movie a long time ago, I remember thinking, God, that’s a really inefficient user interface, right? Wouldn’t it be faster to pinch and zoom?

But I can totally understand why Ridley Scott would have it there, because you wanna convey like, this is a really advanced society and this is a much better narrative device for what we’re doing with this film, right, if he’s actually talking to it so that we can tell the audience what’s going on with this picture.

As a designer of systems, you need to understand what goal you’re serving, are you serving some kind of narrative goal like Ridley Scott was, or are you actually producing a system that is meant to be usable for humans? In which case, I would argue that’s not a good design, right?

I’m just saying that because we were talking earlier about the things that you can probably be misled by by this technology, and one of them is to assume that the wordy interface is its natural hunting ground, right? Like, just because it is a large language model, the most naive possible approximation of the thing is, like, you slap a chatbot onto the product and it’s, like, now with AI, it’s like new and improved.

Now with AI, that’s a way to do it, but that’s not necessarily the best way to do it. What’s the best way to do it? You have to really grok what the product is trying to do, and you have to grok what the technology brings to the table, what we were talking about earlier.

Peter: You need to have a pretty firm sense of what you want to accomplish.

Jorge: Right. Well, exactly. This is the point…

Peter: People approach these tools and then are like, now what? I don’t know I want to do.

Jorge: Are you trying to help make this experience easier for the user so that they can check out faster? Or are you trying to bump the share price by saying “now with AI”?

Those are different goals and it might be that there might be a way to, like, synchronize them so that hey, we’ve made it better for people and we’ve communicated to the market effectively that we are now using AI or what have you.

But you have to be clear on what goal you’re serving, before you start like investing resources in moving in that direction.

Jesse: Even if AI resources are the cheapest resources, and most plentiful available, right?

Jorge: I would argue that they’re not, because if you’re implementing them in a way that leads you down the wrong path, that may end up being costlier than doing it the old fashioned way.

To Peter’s point, it’s like you can start running very fast in the wrong direction.

Jesse: Yeah. And I think it’s interesting the ways in which people invest in the AI a kind of sense of a source of universal truth. An all seeing Oracle to be consulted about the correct way to do anything at all.

That, I think people don’t build into their processes enough of a sense of teaching the robot what good actually looks like, and teaching it the constraints of your business problem, the constraints of your design problem, the constraints of the problem space that you’re facing more broadly.

I have talked about this in the past, as fundamentally being a skill set of iterative problem framing, because you’re gonna frame the problem. The robot’s gonna get it wrong. You’re gonna reframe it, it’s gonna get it wrong again. But you’re going to refine that down to a problem frame that the robot can actually understand.

Jorge: This might be a good place to like start bringing this together.

Both of you have talked for a long time about the need for a language of critique for the things that we do. And I think that’s becoming ever more pressing now that we are forced to… well, forced. Let’s say we are invited to ask these languaging systems how to work with them and how to create effective experiences.

Our mutual friend Peter Van Dijck has been teaching designers about AI evals, right? That’s a big phrase in the AI space, evals. It’s like, what do you mean by evals? It’s like, basically is the outcome matching up to your expectations, right?

And I think that we need to circle back to that now, more pressingly than ever because we are on the verge, if not past the verge of creating systems that will do it at scale in ways that humans can’t.

Giddy up.

Defining Quality

Show Notes

About the episode:

Dan Saffer—designer, author, and CMU professor—joins Peter and Jesse to take stock of design education at a moment when everything is in flux. What’s worth teaching when the tools change weekly? How do you define quality when AI can spin up a passable prototype in minutes? And what are today’s students teaching their professors about where design is headed?

Special Announcement:
Jesse and Peter are excited to announce the launch of the Intentional Design Leadership Circle, a six week cohort for director and above design leaders who are ready to move beyond surviving and toward leading with purpose. Each week we’ll facilitate discussion on a different facet of leadership, and by the end you’ll have new strategies, frameworks, tools, and a community of peers who understand exactly what you’re navigating.
Find out more and register.

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, our Adaptive Path colleague Dan Saffer joins us. He’ll share some of what he’s learned on his journey from design book author to Silicon Valley design leader to his current work training the next generation of designers as a professor at Carnegie Mellon University. We’ll hear his perspective on what it takes to prepare the next generation for the age of AI, as well as what they’re teaching him about design process, design’s value, and where that value is headed.

Peter: Dan, thanks for joining us.

Dan: Hello. Thanks for having me. this is fun. Unusual seeing you all so far away.

Jesse: It feels so natural, doesn’t it?

Peter: For those listening, we have with us Dan Saffer. Jesse and I have known Dan for over 20 years now. I believe I met you, Dan in 2003 or 4 at a Designing Interactive Systems conference where you were talking about metaphor in design, and you were getting your master’s at CMU, the very program similar to what you’re now teaching.

We’ll get into that in a moment. You worked with us at Adaptive Path for a number of years, and then you went off and had your own journey including through Silicon Valley, and now have found yourself… are you a professor at CMU? What is Dan Saffer doing now?

Dan: My official title is Assistant Professor of the Practice at the Human Computer Interaction Institute at Carnegie Mellon University. Say that three times fast.

And what that means is I worked a lot in the industry and now come back and teach students how to go be industry professionals mostly in design.

I mean, I teach design in the school of computer science. I teach people that want to be UX designers, product designers, AI designers, product managers, user researchers, kind of a wide gamut of folks that come through the program.

And that could be anything from our PhDs to master students and people that are doing stuff at the business school, like people that wanna be PMs or people that are just interested in design and want to come find out what that’s all about, and data scientists, and really, you name it, like we are one of the most popular undergrad, second majors in the entire university.

So it’s really fun. A pretty wide variety of people come through, some of whom it’s, like, this is what design is, and some of whom have worked, you know, in the industry for years.

So it’s been a very interesting three years to convert from practitioner, design lead to design professor. And yeah, speaking of a journey and speaking of finding our way.

Peter: Well, we’re gonna get into that, but you said the phrase, I teach design. What does that actually mean? What does it mean to teach design in this HCI program?

Teaching Design at a University

Dan: Wow, this is a super long topic. So HCI has got a number of different disciplines that are a part of it. So there’s computer science, there’s psychology and sociology, there’s learning sciences. There’s engineering and there’s probably one I’m missing. But there’s also design.

So, in the design faculty, is kind of where my subclass is, is all about teaching a number of different things. We teach service design. We teach interaction design fundamentals. We teach advanced interaction design. I teach a lot of design and AI and we also teach some kind of entrepreneurship, like getting a startup out and those kinds of things.

So that’s kind of what teaching design is currently. So I do a lot of the kind of advanced and AI type stuff, although I have taught pretty much everything else that I just mentioned at one point or another.

Jesse: So in addition to the work that you’ve done over the years, you’ve also written a bunch of books, right, where you have explored different facets of practice within design, interaction design, digital product design. And I’m curious about the threads that you’ve seen that are influencing the way that you engage with students now around those fundamentals.

Like, you wrote one of the classic books on interaction design, Designing for Interaction. You were talking about gestural interfaces before other people were, you were talking about microinteractions before other people were. I’m curious about how all of that work around establishing the deep patterns of how humans interact with these systems is playing out now as we’re seeing, really, this wave of radical change as you are engaged with that leading edge and these AI technologies and how they fit in.

Dan: How I like to think about it is that there’s really only two things right now that are really worth teaching.

One is the fundamentals, and one is the stuff that’s kind of on the cutting edge.

And the stuff in between is really kind of up influx, like the design process is right now kind of in flux. And different methods are in flux. User research is in flux. There’s lots of stuff that is kind of in flux right now.

But there are certain things that never change because human beings never change. So there are certain rules and principles and foundational things like typography and what looks good and how things act, and getting a product sense and reframing and problem finding and meaning making. All those things that are kind of the core, basic, super-skills of design, I think are a really important thread to maintain that connection to Henry Dreyfus and George Nelson and all the people, you know, all the designers that came before us many, many years ago, but now we also have this, like all this new stuff that’s coming and that is just something that, yeah, we are trying to kind of keep up with, figure out what is worth teaching.

So that students can use that to generate things, to generate concepts, generate ideas, to help them you know, do kind of the old school production work. But what we’re trying to keep is the judgment and the thinking part of it. The solving the right problem, the strategy part of it.

So trying to keep those things that are really important about design, while still saying, okay, there’s this new technology. We’re all fumbling around with it. It’s clearly nascent, it’s clearly important, and what do we do with it? And so those two things are the real pillars of what I’m trying to teach and imbue students with my pearls of wisdom these days.

I mean, it’s funny ’cause, like, the original books were meant to be… the Designing for Interaction book was meant to be a textbook. It was meant to be a standard book for design students because there just wasn’t anything out there like it, you were cobbling together all these different articles.

And so the idea was, let’s put it together as a textbook that can be taught. And I’m assuming, because I still get like a dollar or two a month in royalties from it, that somewhere somebody is still teaching it.

Peter: Since you just mentioned the book and maybe whether it’s Designing for Interaction or Microinteractions, what, given what you are working on now, and what you’re witnessing and experiencing, what do you look back at what you have written and think, oh, that no longer holds, that was somehow inaccurate or inappropriate, or you were able to successfully kind of establish some foundation there that does still feel relevant today.

What’s Relevant, What’s Not

Dan: Some things you really have to question, like, is it worthwhile to be doing wireframes now? I mean I spent a lot of time in the book talking about wireframes, and we’ve kind of talked about them for years as being a great way to get people to look at your designs without focusing on the visuals,Right? That’s the whole purpose of wireframes.

Jesse: Right.

Dan: Is that valid now when I can spin up a whole, basically a whole branch, a whole prototype of something that kind of works or looks and kind of feels like… Should I bother teaching wireframes now?

I do, because of exactly what I said,you know, I’m trying to give students a lot of things that are in their toolbox that they can pull out and use when it’s appropriate. That’s the hope where they’re like, oh, wait, if, people keep getting stuck on the visuals here, maybe we should just do the wireframe version so that they can go back and kind of backfill or, pull this dusty old tool out of their toolkit and blow the dust off of it and be like, here, let’s try this old thing and see if it still works.

There are definitely things that I have found that are becoming more relevant. Things like task analysis now is incredibly important when it comes to thinking about agents, for example.

Before you remove an entire person’s workflow or change their workflow by adding in an AI agent to it, you should probably understand that workflow and all the decision points and what’s happening and what the different nuances of that workflow are before you just plow through it with an AI agent and push the button and have it try to do everything at once.

So there’s lots of stuff like that. I mean, remember when prototyping was incredibly hard? it was almost impossible to get something that looked and felt like it worked. I mean, but that’s the olden days now. Like now in an afternoon you can get something that looks and works pretty well.

Jesse: So what are the implications of that for designers and design as an activity?

Dan: I mean the, biggest implication of that is I do no thinking upfront, and I just am like, type, type, type, type, type, prompt, prompt, prompt, go, oh, look, here’s the app. It’s finished, it’s done. Here’s the prototype.

That’s the big drawback to it, right? Where you are quickly prompting and then you are not reviewing to see if it’s good, if it’s valuable, if it actually works the way that you think it should.

Now the bonus to it is that you can spin up four or five of these in the time that it used to take to do a piece of one, and you can then test them all and play with them all and try them all out and see which one really works.

That’s the holy grail of this whole thing is that you can have these things that look and work really well and you can test them and you can get them in a week or less.

Jesse: I think it’s interesting and exciting to think about this as part of an individual designer’s creative process in fine tuning because it seems to me like, why would you need a robust, fully built out, fully detailed, fully realized prototype?

Hopefully it’s because you’re asking some pretty fine-grained questions across those different prototypes about what is the most valuable design process.

What I wonder about is how this plays out in a cross-functional environment, where the designer isn’t the only one coming to the meeting with a prototype. And in fact, it starts to look a little bit like High Noon, like, you know, show down at the O.K. Corral, where it’s like, I got my prototype. You got your prototype, let’s shoot it out, and let’s see whose prototype takes the day.

And I wonder about the implications of these tools for collaboration, not just for individual ideation.

Dan: Yeah, absolutely. I don’t think this is also anything that’s super new. I remember way back in my career that PMs would show up with screenshots of what they wanted to be designed, and it’s a similar kind of thing. Now though, it just looks great. I mean, it looks real in a way that a marked up screenshot for me to design never did.

And I agree. There is this weird, now, tension kind of between PM, design, engineering. It’s like, how do we work on these things together and make sure the right idea wins?

That I think is what is really important. And that is also the thing that AI does really badly, again, which is, are you solving the right problem? Are you going about the right way? Are you framing the problem correctly?

That is something that AI does not do well. If you come with your prototype and it is for this problem, and I come to it with a better framing, then, probably, hopefully my idea will win out because it’s like, oh, I see how you thought about this. This is a different, a better take on this, ’cause it’s solving the real problem, not the problem that we thought we had.

Our classic old consulting problem. You come to us with something that you think is the problem. We find out what the real problem is.

Jesse: Right.

Peter: Yeah, RFPs often had the solution inferred, and we would have to try to back out of that and probe that.

Dan: But I have been talking to a lot of industry leaders, many of whom don’t want me to talk publicly about kind of what they’re doing, but that’s fine. I’m gonna genericize it. But a lot of it is that there is really this merging and blending of the teams, where a lot of the time that designers used to spend in their silo making mocks and prototypes is now spent alongside the PM and the engineer working to refine a prototype or multiple prototypes together.

And, to me, that’s a pretty great solution. I think that to have that kind of close collaboration where you’re working that closely rather than often doing kind of waterfall kind of stuff, where then you toss it over the wall to the engineer.

But again, you have to make sure, just like with our old friend Agile, that you have the time upfront to actually think about what is the right problem? Are we doing this the right way? Are we solving the right things? Is this worth our time to actually spend, to refine?

And I’ve also heard that on certain teams, there are definitely designers who are now shipping production code because it is in places where there’s not enough engineering talent to really handle those, or it is stuff that engineer’s don’t have time for, or don’t have much interest in. So like, final, like, production polish. A lot of times the designers are now doing that and I love that.

I was like, ding, ding, ding, ding, you know, like, ’cause you used to have to file ’em as like a bug report or something like that. Trying to get people to actually work on some of these polish things and being able to go into the code and do little tweaks and ship. Wow. Amazing.

Working in Design Teams

Peter: When you were talking about teams, I understood it to be a designer working with cross-functional product manager and engineer. Something I wonder about is designers working in design teams.

When we collaborated at Adaptive Path 20 years ago, all of our projects were done by teams of designers that had complimentary skill sets, you know, range of experience and it wasn’t just us. Most design agencies would staff teams of designers because that led to better design when you have more brains tackling a problem.

Over the last however many years, 10, 15 years as design’s moved in-house, you tend to get the lone designer, even pre-AI, right? The lone designer working on a Scrum team, in their silo trying to make stuff.

Part of the reason I co-wrote the org design book was to see if there was a way to team-ify design in-house, ’cause, again, I believe designers not just work best, but do their best work, like deliver best when they can work with one another.

I’m curious what you’re seeing either in your observations in industry or college contexts. Usually you have the students working together on projects, and so there’s a teaming there. How does this supplant, support, change the dynamic of, collaboration within a design team when adopting these tools?

Dan: There are two things that I have heard about this.

One is that in a lot of these organizations, there’s still a design organization and then teams are still formed, like they have been for the last you know, however many years.

Someone gets lent out to the onboarding team or the safety team or the transaction team or whatever it is, but they still live in the big design org. I don’t think that that particularly has shifted very much.

And because it seems so easy for one person to be able to spin up these things, the concept of a team is completely lost. That you have people that are doing everything and there’s no one over their shoulder, there’s no one alongside them who is doing the plusing work, as we used to call it, at Adaptive Path, making things better. There’s no one doing that.

And the AI certainly isn’t gonna tell you, Hey, this is a dumb idea. You shouldn’t be doing this. So I think some of that diversity of opinion and diversity of ideas is going to get lost.

And I do worry about that as we start to move to these single person being able to do the PM role, the engineering role, and the design role all at once in one thing, is it just going to be everyone doing everything poorly?

So that’s what I do worry about.

Jesse: It is an interesting question because it’s almost like, you know, isn’t this where we came in?

Dan: For sure. Yes, time is a flat circle here.

Jesse: Yeah, exactly. When we entered this industry in the nineties, what you had were software developers or maybe software engineers who were expected to manage their own projects. They were expected to conceptualize user experiences. They were expected to make the technical, architectural decisions about the components and the modules and the technologies and all the bits and bobs that would need to go together to create that experience.

And then they would be expected to write the code that put all that stuff together. And that was the job for decades before the advent of user experience design as a discreet discipline within the product development process. And, you know, along the way we got product managers and we got, you know, growth hackers and all the other kinds of variants that we got.

Peter: Barnacles.

Jesse: Yeah. Well, but that’s the thing is, like, if it’s all kind of coming back to this idea of the creative contributor who can think on multiple levels at once, what does that mean for the mandate of a design team within an organization? And what does that suggest about the actions that a design leader needs to take in order to activate and realize whatever that mandate turns out to be?

Dan: Now I have heard that in these organizations that I’ve spoken with, and they are all fairly large, have pretty good sized teams in them, that they’re still doing things like design crits. So that is why they still live in a design department. They do have like weekly crits and those kinds of things that are still part of design practice.

And I think that is good because if you are a solo designer working on a single team with a PM and an engineer and maybe a data scientist, you’re not getting that kind of design critique that you might get in larger organizations.

But at a smaller company or a startup, are you gonna get any of that? Probably not. You’re probably just going to be expected to do it all as yourself. And frankly, the tools are not ready there yet. And most of the people that I see get sucked into startups, particularly young designers, they’re not ready for that kind of overall responsibility yet. They don’t understand it.

And so it is, it’s a concern. Now that being said, I know and have worked with people that could rock this, could really like just take this tool and do, like, amazing things with it on their own because they have a great product sense. They have a little bit of a coding background. They’re methodical, they have really good ideas.

They actually bother to think through problems. They do thinking upfront.

So there are a certain set of people that I think this will really, really ignite. But I don’t think that’s everybody.

Jesse: Mm-hmm.

Peter: I’m curious in the context of your classroom, I’m assuming students are doing projects, and I’m assuming they’re doing them in teams. How are you seeing your students navigate collaboration with these tools, that can so much encourage everyone kind of doing their own thing, right?

These are not collaborative tools, usually. Figma is, but the various LLMs are very much like me and the machine are having a dialogue and getting anyone else involved is awkward.

And I’m wondering what dynamic is emerging that you’ve witnessed, if any?

Dan: It depends on the class. So in the advanced interaction design class, it is very kinda one-on-one. But we do have crits with the other designers in the class because that is a, traditional design studio class.

In the designing AI products and services class, we deliberately set up the teams in that class to have technical people, business people, and designers on them.

And so we deliberately try to make a simulacrum of what it’s actually going to be like to work with people of other disciplines. And that is always one of the biggest highlights of the class.

And one of the things that the people love the most about the class, because they come in and they’re like, especially if they’re coming from like the design school or the engineering school or the business school, they’re like, I have been trained to look at things through this very narrow lens. And having to actually discuss and debate even when they are using the tools to put together an agent or a gen AI product or those kinds of things, they are all debating and talking about it as a group of people with different backgrounds.

That’s kind of the best we can do, because you’re right, the tools are not currently set up to do collaborative work.

Peter: Does someone end up, like, owning the keyboard and the other two are talking to them…

Jesse: Whoever controls the prompt controls..

Dan: Yes. I, I, think it does end up like that honestly, I think it is like…

Jesse: the product.

Dan: There is someone who is the designated AI lead when they are prototyping, and that is the person who is in charge of that piece of it.

Now, I will say that before anyone starts to prompt, we force them to spend a week or two trying to figure out what exactly it is that they’re going to build. We don’t let them just run off and just start prototyping. We really force them into doing some ideation, some ranking, some consequence scanning, thinking about what could go wrong. Thinking about things like the business, like the financials. Like, is this gonna be actually valuable to the business? And then, like, do people want this? Is it actually a real need that people have?

So we really force them to go back to design process. We kind of force them into like doing the upfront stuff before they ever touch the keyboard.

And I think that is a great practice for them to have going out in the world.

Jesse: Do you think they see the payoff, the benefit of that?

Dan: I do actually. I think a lot of them really do think that it is valuable, that they just haven’t wasted their time building prototypes that no one wants or that no one will pay for or no one will buy.

And we especially get a lot of designers who are like, oh, I’ve never thought about the business side of things before. I’ve never thought about how much this might cost. And that’s great.

And then we’ve get a lot of engineers who are like, well, I’ve never thought about whether somebody wants this or not. So, it is eye-opening from a lot of different sides, and I think that they do find value in it.

Now, whether they are continuing this process out in the real world, I’m not sure. We lose them after they launch, but I think it is a valuable practice for them to have in their lives.

And certainly in the advanced class, we definitely spend a lot of time talking to them. Like we give them a product brief that sucks and have them try to figure out why it sucks, where it sucks, how to fix it, how to reframe it, all of that before ever again doing any kind of concepting or prototyping or those kinds of things.

Although, I will say sometimes we do have them use the given crappy brief to make the prototype of what is being suggested and see how terrible it is and be, like, is this, what, is this real? Is this really what you want?

Jesse: Right. Right,

Dan: So that alone is an actual valuable tool ’cause you can spin up a really crappy prototype based on really crappy requirements really fast and see immediately like, Ooh, I can see some real problems here. It really blows holes in the PRD, which is great.

Is “Taste” a Skill?

Jesse: Yeah. I love the idea that the reason you’re getting crappy results is because you haven’t been specific enough about what you’re asking for. Or there are inherent contradictions in what you’re asking for that have to ultimately be resolved.

Which kind of comes back to what you were saying before about what design actually brings to the equation, which is problem framing and this kind of taking problem framing as a process, really to shoot a frame over at the machine and see what the machine comes back with and say, okay, is this actually what we wanted? And creating space for that human judgment in the process itself.

And I think that the fear, and for some people, the promise, is that that first one that comes back is gonna be exactly the right thing. And I wonder about not just the process implications, but the mindset implications for for designers, other creative people involved in this creative process who have to be able to look at what came back and actually say, you know what, this isn’t good enough. This isn’t ready for production. This isn’t what we wanted.

And whether there’s a skill set there. I mean, you referenced taste, and I wonder about where that fits into how we frame the value that the human on the human side of the keyboard brings to that interaction.

Dan: I think that we should think about taste in a broad sense. I think there is a lot of design copium happening right now. Where it’s like, well, my brilliant aesthetic judgment will save me from the AI machine, and I don’t think that that is true.

I think these things are gonna be able to present pretty good looking things in short order soon.

And I do think that there is actually a lot of underlying taste about UX that I think is getting lost here. Like, does the flow make sense? Does the information architecture make sense? Does the problem make sense? Are we making it too difficult to do these things? Are we making users do too much work? Is this wrong for our particular context? Can we do this thing because we have compliance issues or regulations that we have to follow?

So I think there’s a lot of taste questions that are really like a lot of judgment questions that have to fall into the big taste category. I think it’s taste broadly in terms of both look and feel. Does this work for our users, our organization, our context, and I think that is really important.

Now, I will say, caveat, that there are times when that push the button, the first thing that comes out is gonna be fine, is gonna be fine for certain basic tasks.

Jesse: Right,

Dan: If I’m making a thing for myself and, I’m the only one who has to see it, well, I don’t care about things like accessibility, does it make sense to a broader audience? Does it make sense at scale? No, it doesn’t. It just has to work for me. And so something that the machine cranks out that’s 80% fine is fine and I’ll just use it.

Now, that just does not work when you’re talking about working at scale, working for lots of other people. People still want good designed things and will always, I think, want good designed things.

But there are these situations where good enough is good enough and we see this all the time with, you know, just to take an old school example… My restaurant site does not have to be the most cutting edge website in the world. It just has to be clear and see things. And a template is perfectly fine for that.

And I think we will see the same thing with AI, that it’ll create a little app for us. That’s fine. It’s based on best practices and a kind of perfectly okay looking generic user experience and UI and it’ll be fine.

Defining Quality

Peter: You’re mentioning concepts of good and good enough, which are, part of a definition of quality.

Dan: Mm-hmm.

Peter: And I’m curious how that conversation is going on in school or with some of these companies you’re talking to. I don’t recall if you were at Adaptive Path when I tried to define quality inside the company, and caused some… you do, okay.

Because it caused some consternation because where I landed was that quality was defined through a conversation with the client. Like it was an agreement, was quality. And if the client was happy, then the design was good or good enough.

And there were people internally who were like, no, ’cause our clients aren’t gonna have the same standards that we do and we should be aspiring for something greater. Fair.

But when then pressed on how do you know when something’s better, it was all, you know it when you see it, which to me doesn’t hold water, right?

And so I’m wondering, as you’re talking about taste, and I know you’ve talked about discernment and you’re in a design school where the goal is to help people develop their craft, and the only reason to develop craft is to make things better, right? Is to deliver higher quality stuff.

How does that quality conversation happen? Or what is that conversation around quality that you’re taking part in or leading with, whether it’s students or, again, the kind of relationships you’re having outside of school.

Dan: It is definitely a very hard thing to define and try to wrap your head around, particularly for students because it’s like, well, this is good, good enough. And I actually last semester, I came up with like a metric or a rubric for myself, which was that this is better than it needs to be.

And for me, that is, that is the mark of quality. Like it didn’t have to be this good, but goddamn is this good? This makes doing this, whatever, this thing is so much better.

Jesse: That is literally word for word what George Lucas said about The Empire Strikes Back. He was disappointed in the production team because it was better than it needed to be. They spent so much of his money on it.

Dan: Yeah, I mean, to me it’s, like, it is that deep understanding of the goals, the task, and solving that underlying problem that I think really sets something apart as being high quality. And again, it’s really better than it needs to be. And that is a surprisingly hard concept to convey to students.

Peter: Well, yeah. How do you teach that? Or, you mentioned crits that you say your advanced program is part of. Like, how are you helping them understand that perhaps what they are showing is not good enough and that it can be better? What does better mean? Is it simply better because it solves the problem better that we have defined, or are there standards of quality that you are trying to help them appreciate and understand? Kind of more common standards of quality.

Dan: Yeah, some of this is a lot of the kind of tacit understanding that you get when you’re doing the kind of one-on-one crit, I guess there’s a number of different things that I’m looking for and trying to get them to see. And some of what I think I’m trying to teach is getting them to see their product through my eyes, how I’m seeing it, and the things that I think are off.

Not that my level of quality is insane, but getting them to notice the things that I do that they don’t. I remember two years ago I was like, that thing is off by one pixel. And the student was like, how did you see that? And I’m like, well, I’ve been doing this a long time. Like I can tell when something’s not aligned, even, you know, even a little tiny bit. It feels off, it feels like it is not quality.

Now, something like that I would not even consider. That’s not quality. That’s like baseline craft, like make things align.

But you would be astounded in the fundamentals class, how many people are just like, what do you mean grid? We don’t need a grid.

Jesse: Well, I think it’s interesting how this applies to where AI tooling comes into play, because it comes back to that same thing. Can you tell that it’s off by a pixel or not? And can you tell that the results that you’re getting are off in some way or not? And it’s interesting the way that what you describe is the honing of awareness and the sharpening of one’s ability to detect the stuff that you wouldn’t have detected early in your career.

And to detect the misfits.

Dan: Right. ‘Cause so much of it is like, it’s all nuance, it’s all small stuff. And it is just getting them to be like, well, why is this three steps instead of two? Can you put these two things together? Or you know, are you making users do too much work here? That’s a huge one for me right now, where it’s like, well, we’ll just have users when they get to a spot, they’ll log in and they’ll do all this other stuff for free.

And I’m like, no, they will not, they will not do that for free unless there is a big payoff for them, unless there’s this value exchange from doing all this work. And trying to get them to see, like, don’t make the users do unnecessary work.

Trying to figure out ways to streamline the flows or make things that are invisible clearer. Like, you know, how the rules work. So one of the problems that we have them work on, that they just turned in, is, like, working with a dating app, trying to figure out how to add this new feature to a dating app and then they have to start thinking about, well, how does this work for people that have paid for the dating app and people that have not paid for the dating app?

And trying to figure out what the rules for that kind of system is, is pretty challenging in some of their cases. And that would be something that would be really hard to try to describe and put into an AI right now.

You can do it, it’s just, there’s a lot of complex thinking that has to go into that and trying to get them to, A, think about it in the first place, and then B, figure out what those rules should be. And then C, how do those rules manifest in the system and where do they manifest is a big kind of journey that they go through.

But yeah, teaching quality is extremely hard. And especially, you know, you get a semester, you get three or four months to do this. And I always am like, well, I hope that wherever you land after this will be your finishing school. Where you will have, I mean, just like I did at Adaptive Path and trying to finish kind of like what you’re starting the kind of education journey through an apprenticeship

Peter: Let’s talk about that.

Dan: Finding our way,

TM.

The Plight of the Junior Designer

Peter: Almost a month ago I did a guest lecture at a grad school course at Berkeley’s I School. And I don’t get a lot of opportunity to engage with the youths. And I was kind of taken by the challenges that they foresee as they consider that next step.

I’m wondering what you’re seeing, what you’ve seen from your graduates and how they’re faring, what you’re hearing from your students or hearing from those graduates as well in terms of, right now there’s a lot of commentary, you know, there’s that Figma report that said that hiring managers are even less likely to hire juniors now than perhaps they have been.

And I’m just wondering kind of how that’s playing out in your context.

Dan: Yeah, I mean, it used to be that most of our grads would be hired before they left school. Like, and that doesn’t happen now. I’d say maybe, 25%. I’m actually just kinda guessing here. You know that it’s a small portion of them that actually have jobs right as they leave.

Peter: I remember, when things were nuts, that there were… a significant portion of students at CMU had a job for them before they started school. The fact that they got accepted into CMU meant that the Googles of the world were like, go to school, but know that, you know, you have an offer from us.

Maybe not a job, but at least an offer when you graduate in two years.

Dan: Yeah, that’s exactly right. they would come in fall and interview you and give you a hire Before you graduated and then they just hoover you in when you were done, which is incredible. And that stuff never happens now, except for maybe some really technical roles. Obviously if you were, an AI computer science person right now,

Peter: Sure.

Dan: That…

Peter: But it’s not happening out of design anymore though.

Dan: It is not happening out of design anymore. Now I will say in the three years that I’ve been here, it has definitely gotten better. It was pretty bleak the first two years that I got here where it just took students a very long time just to land on their feet, even with a lot of help and support and trying to connect people.

And we do a lot of things like portfolio reviews and I spend, a lot of my time in spring and summer looking at portfolios, trying to help get people ready for school, get ready for post-school, get them kind of launched.

And I’m actually seeing that yes, there is a slight shift that I think is happening and I think that there are people that are looking for new grads, but you gotta be very AI forward, that you have to have those skills to be hired because those are things that a lot of the in-house people don’t have…

Jesse: right.

Dan: …or they are things that at places like Anthropic or you know, at at OpenAI or you know, or Google or any of these kind of big companies that that’s how they work now.

And so you have to have those skills to get in. And so that is weeding out a lot of people on the job market right now who have years of experience. They just don’t have the AI skills. In order to fit into their new process or where they want to or where they wanna be, or they want to get people in who can help teach these new AI skills to their existing…

Jesse: Right.

Dan: …staff.

Jesse: right.

Dan: see glimmers of hope in the hiring world.

Jesse: It is interesting to think about what this means for design leaders. So, you know, we’re closing in on the end of the first quarter. I’m a design leader and I’ve got a certain amount of budget that’s been reconciled. I can can hire four juniors, or I can hire two seniors or, you know, I can create some kind of mix there and trying to figure out how I craft new roles on my team and how do I shape my team for the future.

On the one hand, it feels like the value proposition of design itself is pulling away from execution. It’s pulling away from pixel level delivery, right? It is much more pulling toward the problem framing skillset that you talked about. The kind of thing I would look to seniors to do mostly, but I can’t have a team of all seniors.

For one thing, they’re too expensive, and for the other thing, there aren’t enough of them. So I need to be able to build out my team with a group of people who have a broader skillset. But I can’t look to juniors to do what they used to do for me, which was production and execution. So it almost suggests that there is a reframing of the ladder within design, so to speak, because juniors don’t prove themselves in the same ways.

You don’t prove yourself by your mastery of a tool. You prove yourself by mastery of a system or mastery of a problem space potentially.

Dan: I will say that I do think that juniors are not in Figma pixel pushing as much. Although I still think, for the foreseeable future, Figma will be a tool that people keep using and will continue to use. And I think you’ll be moving a lot of stuff from Figma to code and back again, and eventually there’ll be some kind of merger there.

I do think, however, that juniors will do some of that production work. I think the difference is that that production work will then actually go to production…

Jesse: hmm.

Dan: …will go, out and launch. I think you’ll have juniors who are able to make tweaks and bug fixes for small things.

And that’s how they’re gonna cut their teeth and launch it and see what happens. And that’s what they’re gonna be doing.

Peter: It’s almost… I started doing a lot of qa. It’s almost like, back in the day when, a good way to understand how software worked was to file bug fixes and just to understand kind of those nitty gritty details.

Dan: Right. And that’s how you’ll start to understand the design system. That’s how you’ll start to understand the customer base. They will be put on these smaller things or they will be part of a larger team with more senior people to do some of that kind of work.

Now they probably won’t be doing as much Figma e stuff. They’ll be doing a lot more building kind of stuff. So I think if you are a design leader right now, I think starting to get people in and starting to see how this generation works with things, I think even having one or two of them on your team is gonna be really valuable.

Not that I am a hundred percent biased and I will, and I will be, I mean, it is sometimes shocking to me how this works because I’m like, what do you mean you built an agent to do this thing and you built your own design tool to do this little thing?

Like that stuff to me is, like, mind blowing. I’m like, wait, you’re able to do that? And so that stuff is really super cool and super interesting.

What Are “AI Skills”?

Peter: Earlier you used the phrase “AI skills” and I think you just explained a little bit of what you mean by AI skills. And my org design brain kind of stood up because I think a lot when it comes to how we define roles, right, those roles are often built on skills.

So a product designer will have interaction design skills and visual design skills and information architecture skills. And those skills are basically tool agnostic, right? We are using the same skills for the last 20 years. We just, first, we used ’em in Photoshop or in Visio or in OmniGraffle, and then we migrated to Sketch or Figma and et cetera.

You said AI skills, and I’m wondering what you mean by that. Like what does it mean to develop skill nimbleness, familiarity, comfort, competency with AI in a way that is maybe analogous to developing skills with interaction design or information architecture?

Dan: I think there’s two ways to look at it. One is familiarity with the technology itself. Understanding what AI is capable of, understanding what is required to make it, understanding what is the risks, understanding like just basic stuff like, hey, this is gonna be really challenging because we need a particular kind of data to get this, and we don’t have that data in order for AI to make this kind of inference.

So it’s just understanding AI as a material, I think is one half of it.

The other half is what my colleague Nick Martelaro calls the “AI augmented designer,” where it is the use of AI tools in the design process.

So these are things like being able to do certain kinds of prompts. These are things like being able to create an agent to do certain pieces of the design production work that you may want to do. This is being able to set up a technical environment that you work in, and being able to talk to engineers about how to work with the tech stack that’s there and in order to push stuff to production.

So all those kinds of things, and being able to kind of work fluidly between a tool like Figma that gives you an overview that lets you see the whole system. That’s where your design system is. And then a tool like Claude Code or Figma Make or something like that in order to actually prototype and bring this thing to life in a way that would’ve been impossible five years ago.

So those are the two big skills. One is an understanding of the material, the way that AI works, the probabilistic nature of it, the risks of it. And then the other is how do I work with that as part of my design process?

So having those two things, I think, is what is really valuable to design organizations.

And then of course having the other skills we’ve been talking about, the foundational things, judgment, being able to understand when something is good, being able to figure out what is quality. The combination of those things, I think is a really valuable asset to have on your design team.

Jesse: Well, and another thing that came to mind as you were speaking with all of this is the ability to be, well, adaptive in how you approach things. Not to be too wedded to a particular tool set, not to be too wedded to a particular process, but to be experimental in your approach.

We were talking about the 25th anniversary of Adaptive Path and the experimental nature of how we approached things there, and I wonder if there’s something similar that applies here.

Dan: Yeah, absolutely. I mean the tools change every couple weeks. You know, I mean, it’s pretty funny.

I keep telling the story, but I’ll tell it again, which is, I was teaching my class like, oh look, you can take stuff from Claude Code and put it into Figma. and they’re like, oh, that’s interesting.

And then of course the next question was, well, can you take stuff from Figma and put it back into Claude Code? And I was like, absolutely not. You cannot do that. And then a week later I was like, remember when I told you you couldn’t do that? Guess what? Now you can.

And so there is definitely this idea of, yeah, being willing to be like, oh, now I can do that. Now my process can shift a little to accommodate as the tools get better and better and more sophisticated.

But always knowing that like with any new technology or any new tool, it’s a bumpy ride. it’s not gonna be fully baked all the time.

I mean, the stuff is still buggy and the stuff changes and if you’re doing releases every couple weeks, as a lot of these places are, there’s just unexpected stuff is gonna happen.

So right there is this idea of experimentation, of playfulness and the ability to like throw stuff out and luckily, as designers, we need to be used to that. We need to be used to having a prototype that we’re like, eh, nope, this doesn’t work. And you know, the kill your darlings mindset really helps when everything is in flux. For sure.

Peter: I have to imagine though, it makes it so difficult to teach when the sands are shifting, right? Because usually teaching, right, is built on a corpus of knowledge that has been honed over decades, and now it’s just… all this change is occurring. And so how do you develop the confidence that what you are communicating is worthwhile, right?

Dan: I mean, it’s humbling. And you have to caveat everything when you are talking about this cutting edge stuff like this. This is true.

Now, it may not be true by the end of the semester. I remember my first semester teaching the design for AI products and services class.

That March, every single day of that March, there was a new AI release or big update. Every single day.

And I was like, how do you keep up with this? I mean, you have to be changing things on the fly. You’re adding in new readings, you’re adding in new exercises, new projects.

Like right now, like our final project for that class is all around AI agents, and that is a space that is really up for grabs and the technology is really not ready for prime time. And so how do you teach students to work with a technology that is kind of janky but is gonna improve?

And some of that is, how do you go back to fundamentals? How do you tie it back to basic things that we know?

And so that’s why, for example, task analysis becomes really important again. ‘Cause it’s like, what are we trying to replace here? Can we make sure that the AI can actually do those things? Or what is the point where the AI should intervene in this system? And what are the places where the AI should absolutely not intervene in this system?

And so having those kind of discussions is really important. Even as the top of the ocean is extremely frothy and tumultuous, down at the bottom is, yeah, is very settled.

And so the more you can kind of tie those two things together, the better off you’re gonna be. But it is not easy.

Peter: Well, and something we haven’t really touched on that I think you’ve written about, is AI not as a means in your workflow, but AI as a material that you are shaping for others to use.

And you’re discussing process. When I think about this, I think back to working with Jeff Veen, speaking of Adaptive Path, right?

Who, even before Adaptive Path, would argue for designers letting go of pixel perfect delivery in favor of a more rules-based mindset, ’cause you never knew what browser people were going to have.

Dan: Right. I remember Jeff’s famous dictum, which I always tell my students, which is, if you’re not embarrassed by it, you waited too long to ship it. And so I always talk about that.

Peter: But over time, whether it’s web browsers or mobile, designers were able to get pixel perfect again and really control it.

But now with this new world, it feels like there’s the possibility for things to emerge. And I mean that literally from an emergence standpoint, kind of the evolutionary theory standpoint of a lot of local things happening and then something comes up and you don’t quite know what it’s gonna be.

And I’m wondering if that’s something that you’re seeing or teaching, or how are you helping your students be okay with not specifying to the nth degree what the final output is, but instead setting up conditions that lean towards desired direction but aren’t, you know, putting real firm stakes in the ground of this is what the experience has to be.

AI and the Double Diamond

Dan: Right. So there’s a couple, couple ways to think about how AI is being additive to the classic double diamond process.

Which is that, yeah, at the beginning when you’re doing strategy, you have to think of things like data. You have to think of things like risk, you have to think of things like, if you know upfront that this is an AI project, is this appropriate for AI?

So things like that in the like design strategy portion, thinking about those kinds of things.

But then once you get to that second diamond where you’re talking about design execution, making the thing, right? There’s a lot of kind of new pieces that are starting to fall into place there.

And by new, for some of them, I mean old, in that it is things like designing for intent, trying to figure out what someone’s intent is, which was something that actually came out of conversational UI stuff that those folks have been working on for years. Trying to figure out what is it that people are really asking for here. What are they trying to say and what are they trying to do?

So for example, if I type into a chatbot and say, What’s the best coffee in Pittsburgh? I could be asking for a number of different things. I could be asking for, find me that, I could be asking for, is there a place that will ship it to me? I could be like, is a place near me?

There’s a number of different intents I could have with something that generic. So trying to figure out what intent is and then what is the AI output that best matches that intent?

And what is the best AI input for that too? Is it a chat box? Is it direct manipulation? Is it working behind the scenes to do things like you know, like finding a face in your camera image that it’ll focus on. That’s not something I wanna do manually all the time. That’s a really nice AI trick that can happen in the background.

So figuring out so you’ve got: no AI, you’ve got AI kind of chatbot, and then you have like generated or temporal UI that like, hey, the pieces of whatever you need start to appear. And that’s kind of like what is starting to happen right now.

So is there like a GUI portion of it as well? So there’s that chunk and then there’s the chunk about, like, what is g

Show Notes

When the ground is shifting and the destination isn’t clear, how do you lead? Peter and Jesse explore the mindset and skills required to navigate the liminal moment—when old ways have dissolved but new ones haven’t taken shape. From core mindsets of maintaining situational awareness and striving for balance, to core skills around communication, persuasion and connection to build lifelines, this is a conversation about what it actually takes to lead through uncertainty.

More about Jesse: https://jessejamesgarrett.com/

More about Peter: https://petermerholz.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

This is Liminal.

Change is hard. Leading others through it is harder. In this episode, Jesse and I probe what it means to lead through a liminal moment. The mindset you need, the skills and behaviors that will carry you through. Designers have spent decades pushing organizations to embrace change. Turns out that’s easier to advocate for when you are not the one being disrupted.

Jesse: Hello, Peter.

Peter: Hello, Jesse. So last time you used a metaphor of surfing. Uh,talking about how when you are surfing, you cannot set it and forget it, that it requires this total presence, total attention, constant awareness of what’s going on, constant adaptation to the signals in order to stay on board.

And you were saying that as a parallel to the mindset that leaders need in this liminal moment or the liminal circumstances that they find themselves.

And I wanted to pause there and then pick it up now, because I think, you know, in that last conversation, we, we set up a lot of the context of why we think we’re in this liminal moment and what it means to be navigating liminality.

The Liminal Mindset

Peter: But I think there’s an interesting conversation to be had around, I guess two areas, maybe more. The liminal mindset, which I think is your surfing metaphor, addresses, and kind of a liminal skillset, right? What are the practices that you can undertake that enable you to succeed when things are liminal?

And so one of the things, you know, you’re pointing out with the liminal mindset is that, vigilance, right? That, that need to maintain alertness, awareness…

Jesse: Yeah.

Peter: To not be rigid, right, and, and stuck in a particular mode or mindset, but to recognize the context in which you’re operating, the seas on which you’re bobbing up and down and, and to act accordingly.

That actually puts me in mind of Ed Catmull’s book Creativity, Inc.

Jesse: Mm-hmm.

Peter: Where he argues against rigidity and stability in favor of balance and equilibrium, right? He credits Pixar’s success as not doing the same thing every time and not being really rigid around how they do things, but always being able to return to a equilibrium. But, but allowing themselves to bob and weave a bit, and to go with the flow, again, to continue to use that metaphor.

And so, yeah, I’m, I’m curious, as I reflect that back on to you where this is taking your brain.

Jesse: Yeah. Well, I think that you point out a few important pieces of the puzzle.

So first of all, just to think about it as a mindset rather than as a skillset. What that entails is an attitude, a stance, a way of setting your own priorities within your own mind about what you pay attention to, what you give focus to, what you give energy to, and what you don’t.

And so that first piece of it, the mindset piece of it, I think is really critical.

And then layered on top of that, you have, you used the word vigilance, which sounds to me a little, perhaps a little harsh because vigilance can sound like taking a defensive posture, which I don’t think this is actually what this is.

Peter: I’m talking Charles Bronson, Death Wish, here, yo.

Jesse: Yeah. But rather, in our conversation with Colt, he talked about the concept of situational awareness, which is very commonly applied in military context, where it simply is about, are you on top of what’s going on right now? Not what was going on five minutes ago or an hour ago or yesterday, but are you on top of what’s going on right now?

And are you paying attention to the things in the present moment that are actually the most relevant things. And that is this notion of maintaining situational awareness that I think is really critical.

A lot of it is about operating in real time, being able to be in a real time, tight feedback loops, you know, between perception and action. Allowing yourself to kind of iteratively refine your judgment as you go, rather than, you know, committing to the master plan front and then driving that forward no matter what the waves do, because then the waves are just gonna put you under.

The Liminal Skillset

Peter: Yeah. And it’s, it’s interesting because I always forget exactly how the phrase goes, but, you know, plans are useless and, but planning is essential, right?

So you mentioned the liminal mindset, and I agree there is a state of being, a state of showing up that’s important. But I think there’s also a liminal skillset.

Jesse: Oh, yeah. Mm-hmm.

Peter: And I think designers, design leaders can embrace a set of skills that they are good at, or should be good at,

Jesse: Mm-hmm.

Peter: And apply them to navigating liminality.

And so when you talk about not being beholden to plans, there’s something around the value in having a vision, you know, in these liminal moments, the value of, like, having some sense even in the confusion of where things might be going and, and being able to lean into that.

But it’s, I guess it’s not having a vision, it’s having visions.

And…

Jesse: Well, and it’s interesting for design because of the way in which this kind of pulls against this auteurist view of the designer as the master planner, as the architect, as the orchestrator of every detail, in that the liminal moment doesn’t permit that. It requires you to respond in designerly ways, but not in ways that look like delivering against the master plan.

Peter: That reminds me of, you know, a challenge that some designers have and have had for decades working in digital media where you can’t specify to the nth degree exactly, you know, your layout and your typography and your color scheme and all that. And the frustration that many designers would have.

But instead to recognize that the role of a design leader is more one of orchestrating elements in a context towards a desired goal or outcome, as opposed to fixing some presentation you know, in some kind of snapshot of time.

Jesse: Form, right? Yeah.

Peter: I guess a lot of this is getting back to this notion of fluidity, of feedback loops of, well, flow.

But, but you want it to be directed, right?

And that’s where I think even if you don’t want to be beholden to a vision, a specific point on the horizon that you are death marching to, come hell or high water, I guess what I’m realizing is a lot of the leadership practices that I discuss, you know, generally are highly applicable here.

And the one that’s coming to mind is having an agenda, right. You know, having a point of view, having a perspective of, Yes, I don’t know where this is going, but I have a sense of where it should head, based on my experience, my perspective.

And just knowing, I’m having a hard time articulating this clearly, right?

But, like, by having an agenda, having principles, having a sense of purpose, having a sense of your own value.

I think you talked about this last time, the difference between values and value, really, like, having your own value system as a foundation upon what you’re standing, will help you make better decisions as you’re trying to figure out how to navigate this uncertainty, this ambiguity.

Jesse: Yeah, yeah. As a leader, especially, because of the volume of information you are consuming and processing and making decisions based on, you have to have rubrics. You have to have heuristics. You have to have rules of thumb that can guide you through these situations where the data is imperfect and the picture is ambiguous.

And if you don’t have that, you are very easily led astray by red herring signals.

So you need to know what you’re kind of listening for, especially as a leader, because of the multiplier effect that you have in your role, because of the ways in which, not just the levers that you have your hands on that other people don’t that influence the way entire organizational structures move, but also because, when it comes to mindset, the leader sets the tone for the entire organization. And the mindset that you instantiate in your role ends up becoming what the people on your team model themselves on, and what you end up creating.

AI Tooling Forcing Change

Peter: Since our last discussion, I’ve had a few conversations with design leaders around embracing AI tooling…

Jesse: hmm.

Peter: …that feels relevant here. Well, and it feels relevant here, especially as you’re talking about modeling the mindset, because I think, you know, this uncertainty is opportunity.

And it’s a positive opportunity. This is a, you know, we can charge into this breach and come out the other side having made a positive impact. But only if we approach it with some spirit, if we have an agenda, have that point of view of what to make, how to make sense of, of the mess that, that we’re maybe currently operating in.

Whereas I was talking to one design leader and, and reflecting on how, you know, in a near term future, her team might no longer need Figma, right? Put a design system inside an LLM and, and design right out of that in production-ready prototypes that use live data that collapse the distance between what design is doing and what engineers receiving.

And as I said this to this design leader, they reflected how it was triggering them to think about how their team would not be working within that tool. Even though this particular design leader is rarely themselves in that tool, right? The team’s identity has been aligned with this tool. And, you know, what does it mean when this thing that has been our identity is taken away from us.

Now, on the other side, was this other design leader I was speaking with, I told this last time, where it took two to three months to get this design team comfortable not using Figma and going straight to the AI tools.

And it was two or three months of misery for this design team where they’re like, we don’t like this, this isn’t what we signed up for, we didn’t expect this to be our job. But then once they came out the other side,

Jesse: Yes.

Peter: They, they embraced it.

And I think in part that leader, because again, they weren’t a craft leader, they were this ops leader, there was something about that relationship that allowed this leader to see these people through this challenge, without getting caught up in their own identity getting caught up in it as well.

Jesse: Right, right. Well, I think that this is one of those situations where success requires optimism about change. It requires the leader especially to go, You know what? We don’t know what we’re doing. We don’t know how we’re going to get there. It’s a mess right now, and it’s going to get messier. But I believe there is a place that we can get to, that is a more positive place for everybody.

And you know, as we talked about last time, I think it comes back to, what do you think the value of design actually is in your organization, and how do you optimize for that with this new tooling and with these new processes and new ways of thinking about what a designer’s job is day to day?

Because again, if you think your designer’s job is to be hands-on with a mouse in Figma every day, you might be looking at a really different future.

Peter: Well, and it was funny ’cause that first design leader I was talking about we, we had this conversation ’cause on, on one side, there’s this expectation to embrace AI in their workflow.

Jesse: Sure.

Peter: And then this kind of, resistance or almost dismissal of that within the design organization.

But then, as we were talking about what we were going to cover in our session, another topic was how do we elevate design, and how do we help design really be seen as a force to be reckoned with within the organization? And I’m like, these two things are connected.

Jesse: Yeah. Yeah, exactly.

Peter: Right, right. And one of the places we ended up was, like, you need to define design on the impact and the outcomes it’s driving, not on the artifacts it’s producing.

Jesse: Yeah.

Peter: That’s going to be how you elevate it, but that’s also how you’re going to then be comfortable embracing, you know, other kinds of tools to solve these problems because you realize it’s not about the tool so much is about the nature of the change that you’re trying to drive.

Jesse: Right. Yeah, I think that’s really true. And I think that also it points to something, going back to having an agenda and taking a stand, which is that these things are gonna get defined for you because of the collaborative nature of your work.

So if design teams are not, and design leaders are not, taking the initiative to define for themselves what a design process looks like, that both leverages these tools and leverages the value of what the humans bring to the process, if they are not able to put forward ways of doing this, that advance the human-centered values that they, as teams, say they stand for, they’re gonna get lapped by product, by engineering.

If you continue to define what you’ve done in the terms that you always have, you’re gonna stay in the box you’ve always been in.

Responses to Liminality

Peter: Well, right. Getting back to this concept of liminality, right, there’s maybe three, kind of, outcomes.

What you’re talking about is, is people who, when they engage in the liminal moment are like, oh, hell no. And just back out. They’re like, not for me, don’t wanna deal with it. It makes me uncomfortable, makes me uneasy. And those folks are gonna be the ones left behind, right?

I suspect a significant number of the designers who have found themselves disempowered these past few years, you know, who had maybe been in executive roles, had been promoted, had been given opportunities, and who are no longer, I think many of them it was a self-induced circumstance because when offered this way potentially through, they’re like, Nope, not me, and, you know, maybe unintentionally inadvertently, but found themselves getting rolled back, ’cause they did not embrace that moment.

There’s a second response, which is you kind of remain in the liminal moment…

Jesse: mm-hmm.

Peter: And, I think there could be a type of, like, chaos adjacent design leader who doesn’t mind the discombobulation or maybe they are just getting, it’s like they’re in the clothes dryer. They’re just getting tumbled around and, like, every time they try something, they’re just getting kind of knocked around and knocked around and knocked around.

And that’s a space to be in for a period. You don’t want to dwell there. That’s, that’s gonna lead to burnout. That’s gonna lead to, as I’ve heard from some friends of mine, heart troubles or other kind of, you know, problems as they can’t figure out

Jesse: Just sort of

Peter: kind of how to, how to na-, how to, how to surf it.

Jesse: boiling pot. Yeah.

Peter: Yeah. I mean, to use your surfing metaphor, they’re just getting tossed repeatedly by those waves. They, they can’t get on top of it.

And then the third, right, is surfing that liminal moment such that you’re finding yourself on top of the wave and leaning into a bit of that chaos, but in a way that that ends up being, I don’t wanna say productive, but positive, you know, with some positive outcomes.

You mentioned the positivity earlier. This is something I think a lot of design leaders actually struggle with, is maintaining positivity for, for many reasons.

But, you know, it’s a non-negotiable for a leader to have a positive affect. It doesn’t mean wearing rose colored glasses or being pollyannish or saying things are fine when you know they’re not.

But it does mean having a relentless optimism, having a point of view that there is a way forward. It’s James Kirk-ian, right?

Like there is a third way, you know, the, the, the, the, the, the, the Kobyashi Maru is telling you the only result of this is death. But you have to help people, you have to believe, and then you’ll bring people along by being able to articulate potential positive outcomes that you all can move towards, right?

And having…

Jesse: If you don’t believe that, if you don’t believe that, then that just becomes a self-fulfilling prophecy for yourself and the team. Like you, as the leader, have to be the one, even if you’re the only one, who can see a path forward toward some elevation of the team’s value I think is probably what’s the long term result of that, right?

Peter: And kind of perhaps to that point, something that I’ve, you know, thinking about the liminal skillset, right? So you have a liminal mindset of positivity, [garble], liminal mindset of, if not vigilance, at least awareness and, and iteration and, and you know, kind of checking your priors every

Jesse: Yeah.

Peter: so often.

Liminal Skills are Leadership Skills

Peter: The liminal skillset, as I’ve thought about this separate from our conversation here…

One of the keys to liminality is, is the same as, as keys to leadership. Two really come to mind actually.

Relationship building, right? You are going to get through this liminal moment by having advocates throughout whatever organization you’re in.

That there are people that you are connected to in different places in different functions such that as these seas are roiling, you have lifelines or however you want to think of them, to someone in finance, someone in HR, someone in product, someone in marketing, that, that you’ve set up your own shadow network, support network, whatever, of folks who you’re aligned with, who have similar thoughts in terms of where things can go, and through those relationships, you can better together, as a collective even…

Jesse: right.

Peter: …make your way through to the other side.

And to that something I find myself returning to, and it’s one of the skills, leadership skills that I’ve let go of when I do my teaching, that I think I need to bring back, which is communication.

Being a really good communicator. The leaders who will be followed during these liminal moments are those who can articulate a compelling story of where this is going, right? And then getting people excited by that compelling story to then help you realize, actually realize this story, right?

Jesse: Mm-hmm.

Peter: It might start as a story, but that story is what’s gonna capture interest and engagement and want them to come along to make that story real.

And so to really hone those communication skills that in a way that allows you to communicate a compelling narrative that people are excited by.

Because they’re looking for it, right? And when you’re in a liminal moment, it’s all chaos. It’s all confusion. People are looking to hold onto something that feels real and exciting, energizing.

Jesse: Yeah, yeah. And this actually connects back to something from the surfing metaphor that I wanted to call out, which is, you might be really good at reading the wave. But you’re still gonna fall off the board if you don’t know where you stand.

Which is to say you have to feel a sense of connection to the board that’s holding you up. And in that case, it’s the leader and the team.

And the sense of how you position your feet and how you, you know, maintain your center of gravity, and all of those kinds of things on the board are choices that you’re making moment to moment, but they’re all based on your internal sense of who you are and where you stand.

And so if you wanna get your team excited about a vision, it has to be something that they genuinely believe in, which means it has to be resonant with their values. It has to be resonant with their intentions. It has to be resonant with their own dreams of what this product could be, what their own careers could be.

And if you can’t connect any of those things, you’re trying to get people excited about a bunch of things because they’ve got a whole bunch of important business outcomes attached to them, that’s probably not gonna go far enough.

What If People Don’t Want to Liminal?

Peter: I am wondering, as you were talking about the team, I’m wondering your thoughts on what to do when team members just aren’t getting on board.

They’re the board, but now I’m gonna have them get on board.

Jesse: Yeah.

Peter: Right. You’ve done the work. You’re articulating a positive future. You’re trying to provide some space so that they can get from wherever they are to this future in terms of, you know, maybe some re-skilling, new tools, we’re gonna try different ways of working.

You’ll likely face some resistance within your team, you know, that’s not what they thought they were setting up for. They don’t believe in it for whatever reasons. It doesn’t align with their individual value systems that they’re bringing into this conversation.

What do you say to the leader who’s, who’s, I’m now thinking, so you were talking surfing. I’m now thinking rafting, right? And I’m thinking rafting because the raft is made up of a set of pieces of wood and maybe not everyone in your raft is aligned. You’ve got a piece of wood that’s not willing to be quite tied together to the others to create the raft.

Like how do you just jettison that piece of wood? What do you, what do you do with folks?

Jesse: It’s really hard. It’s really hard and it’s not yet the crisis that I think it will be in 12 months, 24 months.

I think that as these teams processes continue to evolve… Right now, there’s a lot of permission to do things a lot of different ways. So again, I’m talking about AI transformation here specifically, but I think that the example is more broadly applicable to other kinds of liminal moments where what you have is: new technology comes in, everybody looks at it, and it’s very clear that this is going to be in some way useful to how we do our work.

And I think about other kinds of major workplace transitions that happened in the late 20th century when PCs came into the workplace. And all kinds of processes suddenly were done on screens in ways that they previously were done with paper and pencil, and sometimes a knife and a bottle of paste, right? Like, we continue to keep those metaphors because that was the work that was being replaced, the cutting and the pasting.

And so similarly, I think that we’re in this space now where maybe not right away, but somewhere down the line, you’re gonna find yourself in the same position, as a designer in 2026, 2027, as an accountant might’ve found themselves working inside an accounting firm in 1979 or 1981.

Where, you know, this new technology is rolling out that is going to vastly change how you do your work. You gotta decide whether that is something that works for you.

And then to compound that we have the particularly problematic history and ongoing practices associated with this technology. As we talked about in our conversation with Christina. Where, like, there’s no like good guys in the AI space, there are only degrees of malfeasance.

And the question for you as a practitioner is, like, can I still use this tool and feel okay about who I am and what I’m contributing to the world? And on some level, ultimately that has to be a personal decision and a personal choice. Meanwhile, the processes are going to continue to evolve around you.

I imagine that there will continue to be this overlap period. I worked in publishing during the overlap period where publishing was partly done digital and partly done through manual paste-up work. And so I got exposed to both of those practices back in the nineties.

I’m imagining that this is gonna be a very similar kind of thing where there’s gonna be some overlap, and teams that continue to produce results on the timelines that are expected of them are gonna continue to be able to do things their own way. But that is going to continue to evolve.

And for leaders, I think it is a matter of hearing those concerns with genuine sensitivity and grace, while also acknowledging where the whole raft ultimately has to go, in your metaphor.

Peter: Yeah, the reason I ask that question goes back to the conversation we had with Kaaren Hanson a few years ago now when, shortly after she had started working at Chase Bank, and when we asked her order of operations when she inherits a team…

Jesse: mm-hmm.

Peter: When she moves into a new executive role,

Jesse: Mm-hmm.

Peter: At the very top of her order of operations is getting the team right.

Jesse: Mm-hmm.

Getting Your Team Right

Peter: Because as a leader it’s really difficult to advance whatever agenda you have and to see through your plans if the team isn’t capable of that, right? Isn’t ready for it, isn’t skilled for it, et cetera.

And it calls into question, what does it mean to have a “team right,” when you’re in these liminal moments, right? When she was talking about it, at the time, she joined Chase Bank in 21. And it was just at the end of that, just, like, we kind of had a sense of where things were going, right?

And so you knew what the team looked like that you wanted to grow because it’s the same kind of team you would’ve been growing for the last 15, 20 years.

Whereas right now, it’s unclear… you know, as a design leader, and we’re now primarily talking about kind of on the management track. So, you know, hiring managers, design executives, people with responsibility for recruiting and hiring and resourcing and all that, what does it mean to be a design leader in a liminal moment when the role that you’re hiring for today,

Jesse: Right,

Peter: the nature, the shape, the work of that role could be quite different in definitely two years, possibly one year.

We talk about the blurring of roles between design and product management, and do you need designers who are more product-y or not? There’s still this weird, on many leaders part, kind of, fetishization of craft.

Where is that going? Is that actually valuable, increasingly valuable, come what may, because there’s a longevity to craft, right? Craft has been with us for hundreds of years.

Like, is that actually the right thing, or is it part of that rigidity that creates a kind of brittleness that, you know, you get somebody who’s really good, I mean, kind of, to use the metaphors, that maybe they were really good at paste-ups and mechanicals. They were the high end of their craft there, but, you know, they couldn’t translate it into a computer paradigm when the desktop publishing revolution came.

So yeah, how, what are we looking for as we’re staffing up teams that can be resilient through these liminal moments?

Jesse: Yeah. So the people who are gonna come along are the people who are already embodying some elements of that liminal mindset that we talked about.

They demonstrate a kind of an ability to maintain a broad awareness of a situation and not just kind of, like, execute against a brief. They demonstrate an ability to, honestly, to be fluid with their tooling, to be flexible in their approaches, to have more of a tool kit than a rote process that they follow in the work that they do.

And who embody that optimism that, like, whatever the change is, we together are the right people to see it through.

Peter: That’s interesting. ‘Cause that’s, I guess, not necessarily difficult to hire for, but it’s a different process, I think, to identify those types of candidates, then, at least, what I see most teams are using to figure out who to hire,

Jesse: Hmm.

Peter: …right? They’re doing a lot of looking at case studies and portfolios and what did you do on this and what was your process?

And it’s a different set of questions and a different set-up…

Jesse: mm-hmm. Mm-hmm.

Peter: …to understand how someone bobbed and weaved.

I think so often, like, the portfolio presentation skews towards what sounds like a happy path. Like you don’t often hear of the blind alleys that someone went down, especially when they only have 30 minutes to talk about it or whatever, right?

They’re gonna give you the high notes, they’re gonna give you the highlights, and it’s gonna sound like one thing just led to the next, that led to the next, and it was all good.

Jesse: Right.

Peter: Whereas what you want to hear from your candidates is how many blind alleys they went down, how many difficult conversations they had,

Jesse: show me the failed concepts

Peter: What it took to overcome,

Jesse: Yeah. Yeah. Yeah.

Peter: …obstacles, resistance on the way to get to a solution that was good. Might not be the best, but that was pretty good. And, given what was thrown at them throughout the process, that they got to a generally positive outcome should be seen as like a huge success.

But I can tell you for certain our recruiting and hiring processes would filter out someone whose end result was good, not great, but that they got to good, given the process they had to go through is a sign of their…

Jesse: competence.

Peter: fortitude, alacrity, ability, right?

But that’s kind of, you know, thinking about it, that’s the reality that, that so many people, so many designers are operating within.

Jesse: Yes. Yeah.

Peter: Along with some of the stuff that we talked about when we did the conversation about organizational health, my research and report that I did, where so many senior designers, probably even lead designers, are operating from a stance of disempowerment, right?

They are one or two levels below the people that they are partnering with and all that kind of stuff. So, so any success they have should be, you know, confetti should be thrown if they’ve made it out the other side with something that’s good.

Jesse: Yeah. Yeah. Yeah.

It’s interesting to think about the skillset separate from craft.

So, like, just asking the question, what is the non-craft skillset that, ’cause if we assume that the craft is a bit of a moving target in this liminal moment, then what do people bring if the rug is pulled out from under them and the organization suddenly goes, you know what, we don’t need Figma anymore. We’re covered with Gemini or Codex or this or that, or whatever the thing is.

How many of your people can adapt to that circumstance, and what did they bring that isn’t their ability to find a particular command in a particular menu that continues to deliver some value?

Foundational Skills

Peter: Well, when I’ve thought about liminality and in my frame as an org designer, and thinking about how we define roles and responsibilities and skills, it feels to me like we’re getting very fundamental when it comes to skill sets.

Like, like the skill sets that matter most are communication.

Jesse: Mm-hmm.

Peter: You know, that ability to connect with others to clearly articulate what’s in your head in a way that other people can receive it.

Kind of related to that, some persuasion. How do you bring them along towards a direction that you think matters, right? So very basic communication skills.

Relationship skills, as we were saying before. How do we connect with others? Bring them along, demonstrate care? Demonstrate that trust or build that trust that allows us to connect with and align with a group of people.

So, trust building skills, communication skills.

Some, for lack of a better phrase, business skills, right, strike me as foundational.

You know, a little bit of what Leslie Witt talked about. You know, just what are the fundamental business mechanics in the space that you’re operating in, and some awareness of that, and how they work, the knobs and dials that your particular company cares about, and that you can be able to speak to that, because that will be kind of the lingua franca, thinking back to communication, right?

The common language of that organization will be likely rooted in some probably simple business realities. But still, whether or not they’re simple, you still need to have some familiarity and a nimbleness with them.

And then when I think about it from, okay, so, those are like, everything I’ve been saying is just kind of like core professional skills. And I think there’s a lot of value in design and user experience people bolstering those core professional skills.

Not Taste, but Discernment

Peter: What makes design and user experience interesting is we think about those craft skills. It’s not can I choose the right item in a menu in this tool? You know, this is something we talked about, I think, when we were first thinking about AI and its impact on design and user experience. And sometimes the word taste is used. I’m not a huge fan of taste ’cause there’s a, not just subjectivity, but a luxury quality to that that…

Jesse: It’s is a snobby word, isn’t it?

Peter: It can be a little snobby.

Though the word I’m about to say also can be construed as snobby, but there’s a snobbiness to it. The word that comes to mind is, and I think this is something that you talk a lot about, yeah, when you gave your talk on AI and IA, is discernment, right?

I don’t know if that’s a skill. It’s a bit like what Christina talked about. She gave one of the best explanations of product sense of anyone I’ve heard, right? And it’s, you’ve done a lot of reps, you’ve seen a lot of things. You’ve witnessed what works and what doesn’t over the course of career…

Jesse: A highly informed intuition that you apply…

Peter: And, and that gives you this informed intuition that allows you, regardless of tool, whatever that tool is producing, you have an ability to understand and appreciate how that tool will perform, in a heightened way and better than those around you.

So again, is that a skill? It’s hard to articulate that as a skill. But it’s, it’s something you can develop, right?

It might not be a skill, I was gonna say a manual skill, but, you know, it might not be something with like process and methodology and practice and whatnot, a craft behind it that you are developing in a very conscious way, like you are piano playing, right? Or, or something like that.

But it’s something you can get better and better at.

Jesse: Yeah. It’s interesting because I do think this comes back to one of the things I said in that elements of UX AI talk which is that by definition, because it is a probability machine, what it will always be best at is mediocrity, which means that you cannot rely on the system itself to tell you what good enough looks like.

You have to be the one to say what good enough looks like, which means you have to have a point of view on it. And that point of view needs to be informed.

And as we talked about last time or the time before that, a lot of the bad stuff that gets out there in the world right now, in terms of people’s AI projects, is bad because the person who was doing it didn’t know what good looked like.

And the more people we have who know what good looks like, who are working with these systems, the better the quality of the results we’re gonna get.

Peter: Related to that, because what bad and good look… bad and good are subjective-ish. You can create assessment frameworks that help you understand what bad and good are, but in order to tune those frameworks, I think another skill would be, I’m trying to think of a way to, to put it that isn’t wonky, but it’s, it’s, okay, understanding humans.

Jesse: Mm-hmm.

Peter: Right? From a sociological, anthropological, psychological standpoint. Having a robust understanding of people, how they behave, what motivates them, their abilities, how they process information, all those things, will be useful regardless, right, of whatever’s coming, right.

Because, at least until it’s just robots talking to robots, you know, the things we are involved in, there are humans using them.

It does, you know, beg a separate question, which is, if what I’m saying is true, why is it that UX researchers continue to, it feels like they continue to be increasingly marginalized.

Jesse: Yeah, we’ll have to see how that plays out.

I mean, I think the question of, to what extent UX research has proven itself in a lot of these organizations, I think is a big one. They may be producing all of the insights in the world, but unable to get traction around them because of the way they’ve been set up.

But, you know, all of that notwithstanding, I agree with you.

I think that it does come back to the ability to bring a level of discernment that the robot can’t bring, right? So if it’s always trying to hit the middle of the bell curve, you gotta go upstream if you want to deliver some additional value.

And so that’s what this is gonna turn into.

What I’m imagining in the future, is much smaller design teams in which most of the production work is being done by one kind of a robot or another. And you have humans who are engaged in setting up those requirements as robustly as they can, and reviewing the results to fill in those gaps in terms of actual human behavior and actual human psychology and the things that the robot doesn’t know.

And then, you know, those things eventually finding their way to the light of day. But I think that that gap will always be there to close.

Many Possible Futures

Peter: So you, you are putting forth a hypothesis, maybe a speculation, right, of much smaller design teams. And I want to, I don’t know if challenge is the right word, but maybe interrogate it in the context of the conversation around liminality…

Jesse: oh, sure.

Peter: …right? Because a supposition of liminality is that we don’t quite know where this is going.

Jesse: Yeah. That’s fair.

Peter: Right. And, and I don’t mean to say you’re wrong. I’m just like, you, you put forth a, this is where things are headed..

Jesse: Trajectory…Well, I didn’t say that.

Peter: And, something that we’ve discussed and I feel is likely of use, and I guess it’s a skill. It’s definitely a practice.

There aren’t that many liminal practices, and one of the few that I could identify is scenario planning.

There’s a company from ye olden times called Global Business Network that created an approach to figuring out where the future was going, that they called scenario planning.

There’s a book called Art of the Long View by this guy Peter Schwartz. They tended to work with, like, oil and gas folks who need to make 30 year plans, often involving geopolitical uncertainty because oil and gas is in places that are uncertain themselves. At a crossroads.

And so this practice of scenario planning is born to help companies think about what are, you know, I think usually around three potential futures, right.

And the word scenario, meaning you’re telling stories, right? You’re like gathering a bunch of information, all the wisdom that you can. And then you’re looking at three futures, n number of years out, 10, 20, 30 years out, where different things are kind of dialed up and down, you know, in going back to the oil and gas, right?

And one you might have oh, that’s, anything I say is gonna be politically fraught,

Jesse: Ooh. Yep.

Peter: right? But you know, what if there is a war, you know, a, a war is in play. And that would be one turn of the knob. But what if peace is in play? That would be another turn of the knob, right? Like, it doesn’t have to all be doom and gloom.

But you want to prepare yourself for these various exigencies and unknown outcomes.

And then when you do that mapping, when you do that scenario planning, sometimes what you can find is like, oh, there’s a way that we can behave today that will kind of set us up come what may…

Jesse: right.

Peter: …and that’s what I’m trying to get at is, like, you made a hypothesis of small design teams.

You can make a different hypothesis theoretically of larger design teams, or you can make a hypothesis of the evaporation of product management and its designers and engineers working together, and tooling is doing what most people who have the title product manager or product owner are doing. What is that future?

You could make a future of no designers, or people with that title, and instead, you know, it’s product managers working with engineers.

And so, what does that mean?

I guess, given these possible futures, I’m curious, as I’m reflecting on that, what does that suggest to you, in terms of the moment we are in now, not knowing exactly where this is…

Jesse: Yeah, yeah. No, you’re absolutely right. I don’t think it’s inevitable that every design team is gonna get boiled down to three people.

I can see situations in which you’ve got design teams getting larger, potentially a scaling up of certain kinds of design activities that involve more customer engagement, design activities that involve deeper exploration, design activities that involve other kinds of things that design teams don’t have the time or space to do right now because they are on the hook for production work. So I think all of these possibilities are on the table.

Coming back to what this asks of leaders, I think it is about keeping the possibilities open and not letting yourself be paralyzed by that.

You know, when you were talking about the leaders who find themselves kind of tossed about on the waves stuck in the liminal moment, I was thinking about how, you know, the animals have the instinct when under threat to fight, flight, or freeze. And that freeze response is often, you know, a, a natural place for people to go when there’s nothing to fight and nowhere to run to. So what do I do? And just kind of like sit still until something changes in a way that I feel like I can take action on.

But then you have to be able to take that action. So it comes back to our old friend “strong opinions, weakly held,” right, that you want to have a point of view that you feel really confident about, that you feel is the most informed point of view you can muster at this moment, and then be willing to shift it.

The Liminal Leader

Peter: I’m curious what you think of the responsibility of the leader, ’cause they have some usually greater influence, authority, and leverage. What’s their responsibility to define that future? To put shape to the ambiguity, to be the engine of de-liminalizing, right, and bringing clarity.

Or is the liminal moment outside of their control, right? Is it about navigating forces beyond your ability to have that kind of impact? And so it’s about readiness and resilience. And then as things become clear, being able to lean into that.

I’m, I guess I’m trying to, I’m curious your thoughts on, on the responsibility of leaders and their agency in this moment.

Jesse: Right, right. Well, yeah. So last time I talked about how I felt like for a lot of leaders, this was kind of the shoe on the other foot, in that instead of being the instigators of change and the creators of disruption within their organizations, they now find themselves having to respond to change and respond to disruption from outside.

But you’re absolutely right. It’s a balancing act. It’s a dance.

You know, you can’t necessarily shape the wave, but you can shape the trajectory of your board on the wave, and that’s where the surfer’s agency comes into play.

Otherwise you’re just floating.

It is I think, an ongoing question for leaders as to what they can push, and how far and how hard they can push, their own agenda within the liminal moment, because it always has to respond to the liminal moment, so…

Peter: There’s a Heisenberg Uncertainty Principle. Like, like as you push on it, it’s going to affect it and you have

Jesse: Yeah. You can’t measure the velocity and the position at the same time, so Yeah.

Peter: Your action on it will have some effect on the system.

Jesse: Yes. Exactly. Exactly. And needs to therefore be responsive to the system. And this might bring us to what might be actually an interesting stopping point for this conversation, which is, how do you get out of the liminal moment? How do you know you’re out of the liminal moment? What is the leader’s responsibility to try to drive the liminal moment toward closure? And how do you set yourself and your team up for what comes after the uncertainty, you know?

Peter: Hmm. I like that. Let’s see where that takes us.

Jesse: All right. Fantastic. Thanks Peter.

Peter: Thank you, Jesse.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Show Notes

When the old ways no longer hold and the new hasn’t taken shape, you’re in a liminal moment. Peter and Jesse explore what it means to lead through that in-between space—navigating uncertainty without retreating to the past, letting go of what defined you, and finding opportunity in the chaos rather than being consumed by it.

More about Peter: https://petermerholz.com/
More about Jesse: https://jessejamesgarrett.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: This is Liminal.

When the old ways no longer hold sway, but the new have not yet taken shape, you find yourself in the Liminal Moment. On today’s show, Peter and I build on some of the themes in our recent conversations to ask, what do you do when you’re caught in between the past and the future, and how do you lead others through it?

Peter: So Jesse,

Jesse: Hello Peter.

Introducing “Liminal”

Peter: I wanted to have a conversation… and the conversation starts with an episode that we recorded about a year and a half ago now, maybe a little more called, The Phase Shift, where we recognized that changes are afoot in how design is showing up in businesses and how leaders are able to lead.

There had been this set of assumptions around design and it’s kind of steady growth for quite a while. And then a few years ago, those assumptions have been convulsed, even before AI. Things like layoffs and other discombobulation. AI has further exacerbated that, such that it’s not clear where things are headed.

I was just at an event last night with a bunch of design leaders and that’s still the conversation we’re having. It’s like, where is this all going?

And everybody has their own thoughts on what’s next for design. And then, you and I, three months ago, gave a keynote for the Service Design Global Conference that was drawing from our experiences on Finding Our Way, where we were exploring this thing that we had called “The Phase Shift.”

And we talked to a bunch of people and we distilled those conversations. And coming out of that, we had identified a set of, like, conditions that we’re moving from and heading to as design leaders: moving from kind of an over-reliance on craft and towards things like a business readiness, moving from being so rooted in our identity and towards, a multidisciplinary engagement.

And then this concept just kept not going away. And in fact, I had an insight.

I was teaching my masterclass where I have this idea of “mediate the membrane.” And the concept there is that design leaders sit in between these two spaces.

One of the design team that they’re leading, which is a very generative, creative, ambiguous, emotional, human-centered space. And then the rest of the organization that they’re operating in, which tends to be bureaucratic, tends to be very corporate, tends to be business-centered, tends to be data-driven and business-oriented.

And I realized there was a parallel in my mind between that kind of navigating this uncertainty between how design has been and where design is going, and then navigating these spaces as a design leader.

And I said to you, there’s something about this idea of “liminal” that feels right. We’re operating in a liminal moment, and we’ve then off-mic, but now on-mic, been unpacking that.

And I’m curious, I’ll stop my little monologue here, but hand it over to you to pick up, kind of as we’ve been having these conversations, what have you been picking up on in terms of these threads?

Jesse: Well, I think there’s the practical reality of the liminal moment that we find ourselves in now. And then there is the kind of the broader concept of how we approach liminality generally.

So if the liminal space is the space between contexts, it is the corner that we turn from one way of seeing things to a different way of seeing things, in a lot of ways, this hearkens back to some of the ideas in the book that you and I worked on many years ago for Adaptive Path called Subject to Change, where the subtitle was “creating great products and services for an uncertain world.”

And in a lot of ways the thesis of that book had to do with practical guidance for managing uncertainty when you don’t know what’s going to change and when.

And I think that this space that design leaders have found themselves in over the last couple of years has been this kind of lingering liminality, where it’s clear that the old paradigms are kind of falling away. That the ways of thinking about and structuring and approaching and valuing this work that used to hold sway, don’t hold sway anymore. And we are at a bit of a loss for what replaces that.

But in the meantime, we’re just kind of swimming toward the new together. And I think that one of the things that comes to mind for me in this is the particular stress, strain, burden that this places on leaders specifically.

Obviously you and I talk a lot about leaders and their needs and the challenges of that role, and I just notice how for the leaders that liminality is felt at an extra acute level because of the scale of their responsibility, because of the people under their stewardship, under their care that they need to take into account in their choices.

They’re not choosing for themselves the way that an individual practitioner might be, in the face of changing expectations, changing value propositions, changing tool sets, and so forth.

Hunkering Down

Peter: Well, I mean on that front I’ve actually heard from a few folks recently, the conversations with design leaders where one of their primary objectives right now is to quote, protect their team, save their team. Primarily in the face of potential layoffs or other things, right?

And they’re losing sight of whatever it is that the business they are part of is trying to achieve, which might be why layoffs are happening, right? There might be some broader business challenges or a different strategy or whatever. And they’re finding themselves almost like hunkering down and like, how do I protect this group, you know, that they feel some responsibility to, they’ve hired them up, they’ve been working with them.

It’s their team. It’s their it’s guys and gals or whatever, which is, as I think about it, not a healthy kind of approach to this. You start to sacrifice yourself. You start to twist yourself in knots, often around forces larger than your control.

Jesse: Martyrdom complexes.

Peter: Exactly. You’re kind of taking on your team member’s burden as your own or something in this martyrdom way. None of which is healthy.

I think one of the things, as I’ve been poking at this concept of liminality, it evidently causes anxiety, right? There’s a lot of people we talk to, there’s a lot of dialogue out there that folks are…

Jesse: Stressed.

Uncertainty is Opportunity

Peter: Stressed. Upset. Angry. Whether they are responding directly to the circumstances, or you can read it into however they’re talking about whatever it is they’re talking about, whether it’s AI or the job market or other things. And understandably so.

But, you know, you mentioned the Adaptive Path book, And, where the thesis of that book is, Hey, when you’re in these moments of uncertainty, there’s a set of tools that you can use that we in design have developed to help navigate, make sense of, even perhaps take advantage of or thrive in this uncertain space, right?

Design tools are great for de-fuzzing uncertainty and bringing clarity and navigating ambiguity. Like, sit with that ambiguity, but don’t just wallow in it.

And one of the themes of that talk that you and I gave in Dallas, right in the middle, was “uncertainty is opportunity,” right?

We often feel as uncertainty is a negative, is this thing that… A lot of people retreat from uncertainty. Like, when they approach that liminal moment, when they realize liminality is happening, they try to go back to the way things were and they’re hunkered down and try to not move forward.

Whereas the opportunity in this liminal moment is to figure out how to use the tools you have at your disposal, how to be resourceful, and how to make sense of this uncertainty that’s coming.

Because, I guess the other thing is, it’s not just designers, right? Many… Everybody seems to be in a moment like this.

And again, I think designers, when they’re not operating from that stance of fear or anxiety, can actually be leaders, can be facilitators. I don’t wanna say guiders, I don’t wanna suggest we know the answer, but we can bring people along towards whatever that new reality is.

Jesse: Well, design ideally has a different stance, a different relationship to uncertainty than a lot of other functions, because design’s role in many ways is to drive clarity and to drive cross-functional understanding of what’s actually going on with users and what actually constitutes the patterns that lead to product success.

One thing that I find interesting within this is the way in which for design leaders, you know, it’s kind of like the shoe is on the other foot now, because, you know, you and I have had a lot of conversations with design leaders on this show over the last several years in which they talked about the need to advocate for change and the need to push organizations beyond their current ways of thinking, beyond their current ways of doing things to introduce new paradigms, to create liminality for their coworkers and for their stakeholders and for their cross-functional partners.

And now when that liminality is coming from outside, suddenly it’s a leadership challenge. So I mean, there are some ways in which, yeah, what we’re talking about is kind of change management, but it’s also change management from the perspective of someone who maybe doesn’t have as much direct control over the change as designers are used to having in terms of what they advocate for inside organizations.

Transformation Management != Change Management

Peter: Yeah, we’ve talked at length about change management in the past and something that helped me understand perhaps a bit about what’s going on now and what mindset to bring actually comes from work I did a number of years ago at Kaiser Permanente and, a colleague, I had Sami Packard who studied change management.

And something she pointed out to me is there’s a difference between change management and transformation management that I think is perhaps relevant here, right?

Change management is when an organization goes from one way of being or working to a new way of being or working, that is pretty well understood, right?

They call it agile transformation, but it’s really agile change because we know how agile works. We know that structure of the teams and the processes and rituals and behaviors and the tooling and all that. And it’s a matter of kind of getting everyone off of one way of doing things and into a new way of doing things.

Transformation management is more applicable though because it’s what we’re dealing with when you’re dealing with liminality, which is you don’t know what’s coming, right? When you’re transforming, you don’t know into what, necessarily.

You might have some idea of the kind of impact you want to have or something, but the shape, the behaviors, how it works, that’s what you’re needing to discover.

Which again, is one of those areas where design should be a great practice to lead through that because design is about making sense of that opportunity space.

Something else that’s occurring to me when you talked about the shoe is on the other foot. I was hanging out with a bunch of design leaders last night and one of them used to be very active in leading sprints at Google 20 years ago. And something he pointed out in his current experience that he’s witnessed is the degree to which designers have trouble diverging before they converge. Like we have to remind ourselves.

So when we think of the double diamond, right, people have been in the last year or two, to my taste, a little too willing to throw out the double diamond. “Process is over, we’re… new ways of working.”

And to me that was a misread of the double diamond. ‘Cause the double diamond’s very simple. And it basically states before you decide what to do, you give yourself an opportunity to think about a lot of options, and you choose from them as opposed to whatever that first idea you had you ram through.

That’s all the double diamond is about, is make sure that you provide your own optionality. And I think, maybe as a reaction to velocity, as a reaction to pressures, or whatever, we’re losing sight of that divergent step. But when you don’t know what your future holds, you want to give yourself a as many potential futures as possible that you can start trying to choose from. And then identify which seems to be the most enabling, productive, helpful way forward.

Jesse: That’s an interesting perspective because if I reflect back to when we were back in Adaptive Path and we were offering a lot of these things into the market for the first time as consultants…

So, I was the head of our strategy practice, and one of the things that really came to mind for me was that we had to have a way of demonstrating why you would hire a designer to do strategy work.

And for me it always came back to that designers can imagine possibilities to a different degree, to a different depth potentially, across a broader range of possibilities than you might get from somebody who has a different kind of a background.

And as I think about how that applies here, it suggests that design strategy may have more to offer now than it has in recent years because we’re moving beyond the most recent batch of best practices into new territory that requires a return to that kind of exploration.

You know, when I think about the pressure that’s put on these teams to just kind of, like, skip that first half of the diamond and just power through the convergent thinking toward a solution, what that suggests to me is that somebody’s already decided that the front half of that diamond is already a solved problem. That you’re operating in a problem space where you feel like the constraints are relatively known.

And now that we’re moving into these deeper unknowns, especially with AI technology, but also with the evolution of business models and other kinds of things that are going on all around us, design might have a value proposition now that is much closer to what design had to offer in 2005 than it had in 2020.

Is the Time for Vision Over?

Peter: So this puts me in mind of the conversation we had with Peter Skillman, who is the chief design officer at Philips Design, and who in some ways said the opposite, right? And we had this conversation with him about a year ago. It was January of, 2025.

And something he believed is like the time for vision, and you could infer the time for strategy, is maybe… not over, but is diminished. To paraphrase what he said, we’ve done a lot of work developing visions. Now we need to start executing against them and with this new set of AI tools, and the access to execution that is just more prevalent, like, let’s lean in and make and create and, not quite define the future, but deliver the future almost directly.

But, where I’m coming to this now is, and I think it holds with liminality in some way…

What you’re saying about strategy, you know, is in some ways, I don’t wanna say in conflict, but in some opposition to what Peter was arguing around the work of design right now.

And I wonder if we’re in like a bifurcated moment to a degree that we’re not quite recognizing, right?

Because design, and this has been true, you mentioned back at Adaptive Path and people didn’t know that design could be a lever for helping you with strategy or whatever.

But design maybe being a slippery word, a slippery concept that you are always having to define it, because when you say the word design, people have different thoughts in their heads, and perhaps people are talking past each other, where there’s a group of people who are like, yes, it’s about designers working in code, skipping Figma and LLMing their ways to prototypes with live data, and that’s design.

But I think what you’re saying is, well, wait a moment, we don’t know where this is heading. There’s an opportunity for design to be even earlier than maybe we had thought design needed to be, in making sense of the space that we’re operating in, at a much higher altitude.

And these maybe are just two very different things that we happen to label design.

Jesse: Well, I think you’re absolutely right that the digital design field is more heterogeneous than it ever has been in our entire careers. There is a greater diversity of design challenges. There’s a greater diversity of design mandates. There’s a greater diversity of design staffing and process models. It’s just a wider field out there than ever before.

You and I tend to gravitate toward the needs of large enterprises because those have been our clients historically. Those tend to be the spaces that you and I work in. One thing I’ll say about what came out of the Peter Skillman discussion is that I think he’s describing a particular kind of vision work that I agree is behind us, because it is this idea of design as spearhead of a singular vision for a product.

And you know, these C-levels will come down to the head of design and say, show me what my product looks like in five years and give us that North Star and then we’ll build our whole big machine toward that as an outcome.

Whereas the strategic need for design right now is less about, tell me what you know is gonna be true in five years time, but rather help me explore what none of us knows about what’s gonna happen in the next five years. And be a facilitator, a partner, a participant in that creative exploration of possible futures that is going to be necessary for these organizations to be able to make strategic bets.

Because ultimately the change that’s happening is not just happening to design, and it’s not just happening to digital. It’s happening to entire business models and entire competitive spaces.

And that’s gonna continue. It’s gonna get worse. And we’re gonna see some big names go down unexpectedly because somebody got caught off guard by a scenario that they didn’t see coming.

The Work of Strategic Design

Peter: What do you see, though, because you mentioned design strategy, strategic design as a thing we’re tacking back to, but if strategic design is not about articulating a vision of our offering five years from now, which is how it’s often been considered, what do you see as the work of strategic design?

Jesse: I come back to that notion of driving clarity, of answering the answerable, and identifying that which needs deeper exploration.

And, you know, some people would call that product strategy, some people would call that user research. In lots of organizations, design simply doesn’t have permission to even ask these kinds of questions that I’m talking about.

But I do believe that it is within Design’s skillset, within design’s purview to have a point of view on these kinds of questions.

Peter: Well that actually reminds me of a different thing that Peter said that turned into a little, I dunno about argument, but back and forth on LinkedIn, which is whether or not design belongs in the C-suite.

‘Cause something he said on our show, and then he’s reiterated it in LinkedIn is that he thinks design doesn’t belong reporting directly into the C-suite, because that ends up getting design involved in a lot of conversations where design doesn’t belong, around strategic investment decisions. You know, we’ve got billions of dollars to spend, what are we spending it on?

Whereas I thought, and I think maybe what you’re suggesting is, why isn’t design involved in that conversation?

Or rather, why isn’t someone with a design background, a human-centered comfort in ambiguity, exploratory, generative point of view, don’t we want someone with that point of view in that room? When if they’re not in that room, literally everyone else in that room is, going to have a very narrow point of view on how to approach solving that problem.

Which suggests maybe, I dunno if this is liminal, but I guess it’s part of the liminality of a potential path forward for design is to be not quite, you know, the CFO, the CPO, something like that, but closer to it.

Where your, at least, certain design leaders or, very senior design teams helping companies figure out how to expend their resources, right?

Which is kind of the fundamental thing that the C-Suite does, right?

The C-suite has a bunch of resources at hand, and they’re placing bets on what makes sense for them in terms of their future.

And that would be a different role for design, and the designers in that room would need to augment their skillset so that they could be credible.

But I also think their point of view, given all the confusion and discombobulation, I would hope that it would be welcome because they can help that other group of people make better decisions with the toolkit that they can bring into that discussion.

The Value Proposition of Design

Jesse: Yeah, so what that brings me back around to is where the liminality is actually happening in the digital design space. And honestly, I think this applies in the product space as well.

The areas that we’re talking about, what you and I would define as design strategy, a lot of people would call product strategy. And a lot of people would say, this stuff should live in a product organization, and product people should be driving these kinds of processes.

That aspect of it is much less interesting to me than the forces that these teams find themselves subjected to now.

So one of the big shifts that has happened is we went through this massive wave of layoffs following the pandemic. As interest rates changed, as corporate priorities changed, as the ways of measuring the value of this work changed in a lot of organizations, design became seen as a time sink, a cost center, a friction point in a development process that needed to move more fluidly than that.

In those contexts, you’re looking at one way of evaluating what design is and what design has to offer that may be entirely valid and relevant within that context. You’ve got people thinking about these other parts of the challenge.

But then I think it does become about the value proposition of design as a function itself and what design is there to do.

Again, so what we’re looking at is reduced team sizes, reduced budgets for professional development, reduced tolerance for exploration and experimentation within design process. Fewer opportunities for design leaders to move up in organizations, and ceilings over them that previously weren’t there or weren’t apparent.

Where you have… head of design is not gonna ever be higher than a director level at certain organizations, so there’s a cap on that power.

And then on top of all of this stuff, we’ve now got AI.

And as you know, for the last year, I’ve been doing a lot of work around AI transformation and supporting teams with understanding how to make sense of this new tooling and how to bring it into their processes in ways that are meaningful.

And this is what it comes back to, meaningful to the value that they see themselves delivering to the larger organization.

So the liminal moment then becomes much more than a moment. It becomes a process. It becomes a journey of exploration, reexamination, and potentially reeducation of your cross-functional partners, your executive leadership, your stakeholders about what design actually is and can bring to the table.

Because if they continue to put you in that delivery box, that is increasingly looking like a commoditized offering that doesn’t, to your point, have a lot of strategic traction.

Peter: Two thoughts based on what you were just talking about.

Which actually touches on something we discussed when we had the Phase Shift episode.

Which is, people in design will inhibit their ability to navigate this liminal moment if they are unwilling to let go of their identity as a designer.

And so when you were talking about the ceilings that some folks are hitting, which is happening, it’s not universal.

In some places there’s new VPs of design and in other places where they had chief design officers, now all they have is like three directors reporting into product people. It’s a mixed bag.

But let’s talk about those three directors now reporting into product people. If that design director is willing to sacrifice their identity as a designer in order to advance… Okay, you can’t advance as a designer, but perhaps like Leslie Witt at Headspace when we interviewed her, right? You start showing up as a product person and designer, you start demonstrating that you belong…

Jesse: Claim a larger scope.

Peter: …in a certain set of conversationsm and you’re okay letting go of that designer background.

Does that let you grow? Right? I think that’s key.

How is your relationship to your identity potentially tethering your ability to navigate this liminality and come out the other side?

Better, faster, stronger.

But when you were talking about big organizations, it struck me that there’s another aspect to the liminality that these leaders are facing that’s similar to mediate the membrane, but different, which is that designers, design leaders in particular, have to be able to function both horizontally and vertically in these large organizations.

And there’s a liminality there. I just literally this morning on a Slack with a design leader who’s new in their organization was having this conversation because, and it’s one I’ve been having recently, a lot of companies, I think in an effort to embrace this velocity moment, are getting rid of the head of design and having design directors report up through product teams and having those product leaders have more direct control…

Jesse: Yes.

Where Peter says, “Integument”

Peter: …in some effort to, like, keep the decision making closer.

Some organizations are doing that, but keeping design centralized which I think leans into the power of design, right?

Design is great for thinking through a coherent experience across a bunch of organizational silos.

But, and I faced this problem myself as a design leader, right, when literally every other part of your organization is thinking vertically, but you’re this thin layer trying to create an an integument that coordinates and organizes all this effort, even with encouragement from your leadership that this is what it’s about, you run up against heads of product and heads of engineering, and even your own designers who are IC designers who are all thinking very vertically, and they’re incentivized vertically, and they’ve got these blinders on.

But one of these liminal challenges that we’re navigating is, particularly in scaled organizations, navigating between this recognition that end-to-end experience matters, right?

There’s a reason that a company has built out these silos or acquired other companies or whatever, they think that there’s a whole greater than the sum of the parts. That’s the only logic behind it.

But there’s these practices in place that thwart that, and design finds itself square in the middle of trying to make sense of that and getting pulled in all these directions.

Which I think if you don’t have a certain resolve, you’re just gonna get drawn and quartered, right?

Jesse: Yeah, yeah. Knowing what you stand for.

You know, when I talk about the evolving value proposition of design, there was a time in which you could have framed design purely in terms of asset delivery. You could have said the way that I measure the success of a design team is in terms of the volume of PSDs shipped for slicing and, you know, rendering out to production.

And that’s not to say that that was ever wrong because in some organizations that was exactly the right thing that was needed.

But if the tooling is changing under your feet, you can’t define your value in terms of your tools. You have to define the value that the team is delivering against some larger influence that it’s having on the organization.

And I think part of that does have to do with value delivery, but part of it also has to do with values and the values that a team advocates for, or that a leader advocates for within the process that creates guidance through uncertainty for a group of people.

For somebody to go, you know what, we should lay low when the sun is high in the sky, and we’ll wait until late afternoon to cross the desert because we don’t wanna, you know, give the whole team heat exhaustion. Somebody’s gotta be thinking about that kind of stuff.

And that is actually what I think of as being more of the liminal skillset, as it were, for a leader, is to see the opportunity in the chaos, to be able to assess alternatives and choose a direction and advocate for a direction and advocate for that according to some kind of underlying principles that are gonna guide ongoing action that will eventually turn into best practices.

Design Beyond Figma

Peter: Thoughts here resonate with a different conversation I had last night with a different design leader whose design team, which is about, I wanna say, 30 some people, has, in the last four months, basically gotten off of Figma and all into their design system is basically baked into some tool, some LLM-y tool.

And they just kind of build designs directly through the tool. They don’t need Figma. To the degree, if they use Figma, it’s to do some like wireframing, sketching, but they’re not doing the detailed design work anymore in Figma. There’s no value in that.

And one of the things that I asked about, because I’ve gone to Config and there are a lot of designers whose identities aren’t just as a designer, but as a Figma user. They wear Figma swag ’cause that’s who they are. And as we were talking about this, I asked like, what was that like getting these designers to adopt this new approach?

And she’s like, oh, it was miserable. they fought it every step of the way.

But there had been an executive mandate, as many companies have, in terms of embracing AI tooling. So, they needed to demonstrate it.

And I wonder though, because the person who I was talking to, the person who led this organization through it, was not a typical design leader, was not a designer, but was the head of design operations.

And I wonder, someone having a slightly removed point of view, someone who can see the process, see how it all works together, isn’t invested in the practice through a tool, was able to bring, maybe, a clarity to this change that would’ve been hard for someone steeped in the tools to bring, stuck with it, wasn’t thrown by the pushback that they received, but also as an ops leader, knew how to guide people through this.

So made sure everyone got the training, like, created a space for the team to get to the other side, such that now the way this person was talking about it, the designers in their org would never go back.

But had to go, you know, you talk about the desert. Like this was not quite a death march, but no one died, but there was months of uncertainty and misery where they don’t quite know where this is going to lead, that someone needed to shepherd this group through to get to that other side.

And I find myself wondering if, all of my connection to the design ops community notwithstanding, not that ops will be the ones to necessarily see us through, but being able to approach this with some degree of remove, as opposed to woven investment in how things currently operate.

Jesse: That’s interesting to think about. We’ve talked a lot on this show over the years about how one’s craft background can influence prejudice, sometimes put blinders on you as a leader and cause you not to be able to see possibilities that might be right in front of you, because you’re so steeped in your own craft that you had to hone in order to get to that leadership place that you’re bringing your own sense of what design is there to do and what design delivering value at its highest level looks like.

Again, like if you had defined your team’s value in terms of Photoshop files shipped, you need to really rethink things.

Peter: Definitely. Yeah.

Another conversation I’ve been having, and it came up a little bit last night, but is a general theme in the last, I don’t know, few weeks of discussions I’ve been having with folks, is how, in many organizations, design has been reduced to production, to, you know, if not Photoshop files shipped Figma files maybe not even shipped, right? Collaborated on.

And you know, we primarily operate in digital product design, but both of us are old enough to have worked in a kind of design, in a before times.

And I remember my first job at a design agency. I was a web developer there. This was an agency that still did a lot of traditional graphic design, print and packaging and that kind of stuff.

There were the designers, but then there were the production artists. And these were two different roles. In an architecture firm, you’ll have the architects and you’ll have the draftspeople, where you distinguish between the more conceptual thinky systems-y work of solving the design problem, and then there’s another role that’s like, how do I take that solution and make it work in detail. That’s the production artist, right?

And so production artists would take the designs that a graphic designer created and figure out how are we going to get printers and Pantone and all that to ship, to produce what the designer intended.

The designers were not the ones having to do that. That was a different function.

And I think what we lost, in digital product design particularly, you know, in the years say, between like 2005-ish and 2020-something-ish, is the concept of those two roles. And instead we’re assuming all the designers are going to be producing their final assets in order for people to build those.

And then what’s happened is the work just kind of kept moving farther and farther right, ’cause that was the obvious output. And all the left work, you know, was getting lost.

Left, as in shifting left or first diamond or whatever type of work, was getting lost.

And now, in a world of generative AI, that production work is the first to go, right? That just evaporates. As it probably should, right? In the same way that desktop publishing meant we didn’t need certain professions anymore. And that’s okay.

Jesse: Yeah. I mean, you shouldn’t have an army of people solving crossword puzzles with your design system all day, you know?

Peter: One of the things it does is it shines a light on how, for many teams, many in-house teams, because their value was seen as their ability to produce comps, when that value is now captured by machines, many of these teams don’t have the understanding, wherewithal, the muscles, in terms of how to do, I think what you were referring to earlier when you were talking about kind of the more design strategy, strategic design, that different kind of thinking to help an organization navigate that ambiguity.

They just don’t even know where to begin.

What AI Transformation Reveals

Jesse: Yeah, and one of the big things that has come up in the AI transformation work I’ve been doing over the last year is there’s this dimension to it that has nothing to do with process, has nothing to do with tooling, and has everything to do with what people think their value is in the process.

And I think it’s going to be a period of evolution, especially for these larger scale teams, to reframe what a designer does, and what the voice of the designer means in here.

I think that in a lot of these situations where you’re built on layers of internet best practices, you’ve got layers of industry best practices, you’ve got layers of some of these companies have had live apps in the field for 20-plus years now at this point, right? They’ve got their own internal best practices to draw on.

And it feels like the problems are pretty well solved in a lot of ways. And so then the value that you deliver as a designer, it necessarily is about how you work within those layered sets of constraints that define the problem that you’re there to solve.

This shift means that that value proposition no longer really applies because a great deal of that mapping the constraints and working within them is going to be able to be done programmatically. So then, kind of by necessity, the designer’s role in the process has to be to address the ambiguity that the system can’t, that the larger processes and organizational systems that you’re a part of can’t address, and the pieces that the new tooling can’t address, and to be the one to kind of fill in the gaps that make it all still human somehow.

Peter: interesting. As you were talking about the value that you deliver what it made me think of is the book Team of Teams by General Stanley McChrystal, which is, have you read this, Jesse? Are you familiar with this?

Jesse: I’m familiar with the ideas, but I haven’t read the book.

Peter: Okay. So I can’t say I’ve read every word in the book, but I did read it early on in my kind of organization design journey, and it’s actually an appropriate book for thinking about the liminal moment because the insight that the book addresses is McChrystal being a general at the beginning of the global war on terror, and realizing that the command and control, top-down ways of the American military were not working in the face of a essentially networked resistance, where it’s a lot of small cells and pockets doing very small focused attacks. It wasn’t one coordinated army operating against another coordinated army.

But the rules of engagement had changed.

And what he talks about in the book is this recognition, the reason it’s called Team of Teams, is that instead of having one superstructure that just operates, you’ve got a bunch of little nodes. I mean, it’s, a book that’s very much a source of inspiration for things like Scrum in the Agile community and Spotify squad models and all that kind of stuff in terms of how do you create wholly self-sustained teams that are able to be effective on their own. Two-pizza teams at Amazon.

But to the point that you were making about the value you deliver, one of the key issues, and it was a journey that he had to go on, is, he’s like, but my value as a general for however many years, 20 years or 30 years, was to be a decision maker and was to know, and now that can’t be how it works anymore.

And he had to reframe his value is that of a connector, of an informer, of a motivator, of someone who made sure that everyone had what they needed in order to succeed, but that the decisions are gonna need to be made by people closer to the problem than someone back at command.

And so, you know, this questioning of your value, given the moment we’re in, is probably a healthy sign, right?

Like, again, it’s another one of those things like, don’t fight it. That’s not going to do you any good. But instead wrestle with it, and think really hard about what is it, what is that distinct thing that you bring in the environment you’re operating in to address the challenges that you and your team are facing?

And it might not be what it has been for the last however many years.

Jesse: Right. And you know, for years we’ve seen people in design circles on social media who’ve been adamantly advocating for an old value proposition, a classical view of user experience design that they’re all out there going, you know, we have to go back, we have to go back to the ways that we were doing things 10, 15, 20 years ago, to reclaim something that, in their view, has been lost.

But at the same time, every liminal moment represents moving towards something new, which also necessitates letting something old fall away.

And that difficulty that we have releasing old ways of framing our challenges, old ways of framing our value, old ways of framing the nature of the work that we do itself can be limiting our ability to engage the liminal.

We Can’t Go Back

Peter: It is funny because I’m sympathetic to some of that intent of going back, because I think there are valuable practices that for no good reason have been, if not lost, at least, again, kind of atrophied or, downplayed, that would be relevant today.

I think about this in terms of some strategic design and ways of vision setting or whatever, but I think you’re right, it’s not about doing things the way we used to do them in the grand old days when, well, I don’t want to get into that.

There’s a lot of people our age who liked it better when they had a full head of hair and you know, didn’t have the mortgages or whatever hanging over their heads. And they think that life was better then.

But I think some of those practices warrant being brought forward. Probably, I don’t wanna say repackaged, but, integrated in new ways, right?

Like, some of those ways of working are perfectly fine. We don’t have to abandon them, but the overarching assumption of how to do things, you’re right, is probably worth calling into question in favor of adopt, adapt and improve. Adopting and adapting to whatever that context is you’re operating in.

And I mean, this was something we used to think about a lot at Adaptive Path, which… we never had a, a process. We never started at the same place and ended at the same place from a process standpoint.

We had a big methodological toolkit.

You were a director of strategy or whatever. I was kind of the director of practice and I thought a lot about all the kit of parts that we used to do the work and how do you assemble them in this context to solve that problem, which would be different for a different client and different in a third way for another client.

Actually this is reminding me of something that has been burning my britches, which is some talks I’ve seen where people are like, we’re throwing out the design process and doing things the new way. As if there is one design process.

And what I realized is, I think, for many people, again, who’ve maybe been doing this 10, 15 years, there was an orthodoxy of how to do design that they were taught that they are now having to free themselves of in order to be more relevant to current context.

But, and this is gonna sound, I don’t know, self-aggrandizing or something, but I think for folks who’ve been doing this for a longer period of time, in the pre-orthodoxy, before we knew what we were doing and we were figuring it out, I never assumed there was one way to do design.

And it always surprised me when I would hear that people thought there was one way, and I think maybe we’re, just revisiting some of that kind of late nineties, early two thousands vibe of…

Jesse: Nobody knows anything.

Peter: Nobody knows anything. We know little things. We know a lot of little things.

We don’t know how they add up. So we’re gonna try combining these processes together or those two things together, how about that? And that’s fine. Like, that’s healthy.

Jesse: Well and I think that’s the skillset. If we think about what a designer, what a product manager, what a design or product leader might take away from this conversation, I think one of the big things is that ability to assess and make choices. And not to assume that the whole process has been laid out for you already, but to embrace the experimentation and embrace the improvisation that’s necessary here.

You know, one thing that’s been coming up for me a lot in this conversation, you know, I grew up on the Atlantic coast. I spent every summer out at the beach surfing and a lot of time out on the water. And one of the things about surfing is there’s nothing about surfing that is set it and forget it.

You know, it requires total presence, total attention, constant awareness of what’s going on, and constant adaptation to all of those signals in order to stay on top of the board.

And I think that for leaders as well as for the members of their teams, it’s that kind of ability to stay flexible and not get too attached to any particular course that ends up serving them in these liminal moments.

Peter: Well, I think this is a good place to hit pause in our conversation because I do want to explore broadly the skill sets that can allow you to navigate liminality, but I think that that’s a can of worms, that will take us into another episode.

But I like your talking about surfing, because I think a way to think about it is as you are approaching this ambiguity and operating in this liminal space, how can you be riding the wave instead of being kind of overtaken by it or have it crash upon you? And let that be the tease for the next episode of this little liminal… I’m trying to think of the…

Jesse: exploration…

Peter: …liminal exploration, liminal side path, liminal mission.

It’s like a side mission, side quest

The liminal side quest within Finding Our Way.

Jesse: I love it. Peter, thank you so much.

Peter: Thank you, Jesse.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

If you’re looking for help with AI transformation or you just need a private advisor to help you solve your hardest leadership problems, visit my website at jessejamesgarrett.com to book your free one hour consultation.

If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Show Notes

Stanford professor Christina Wodtke joins Peter and Jesse in exploring the real contradictions of AI in design and product work: revolutionary prototyping speed versus the need for critical thinking, efficiency gains versus cognitive loss, and loving the technology while hating the exploitative companies building it. She shares exactly what designers and PMs must vigilantly protect.

Christina’s blog: https://eleganthack.com/

Peter’s website: https://petermerholz.com/

Jesse’s website: https://jessejamesgarrett.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, founder, author, tech industry veteran, and Stanford professor Christina Wodtke, joins us to talk about the sweeping impact of AI on design and product management, including shifting team roles, shifting creative processes, and shifting definitions of value in our work.

Peter: Hi, Christina. Thanks for joining us.

Christina: Hi Peter. Thanks for having me. And hi, Jesse.

Jesse: Hi, Christina.

Introducing Christina

Peter: So, in preparing for this conversation, I’ve been thinking about how I believe I’ve known you since, I want to say 1998 when I believe you were at Red Envelope as…

Christina: Nope. E-greetings. We were…

Peter: E-greetings, sorry, upstairs from Red Envelope, back in the late nineties when there was all kinds of tech going on in San Francisco.

Sorry, E-greetings. And I’ve known you as an in-house UX practitioner, a consulting UX practitioner, a product manager, a game designer, a teacher, an author. you’ve had a multi-layered, multi stage career. But what I don’t know is how you think of yourself today and how you introduce yourself.

So please…

Christina: [laughs]

Peter: Who is the Christina Wodtke of today?

Christina: You missed a couple. General manager and of course founder. Multiple time founder. But, you know, I keep busy. What can I tell you? Most of my time is spent at Stanford teaching. I’m a core lecturer there, which means I have a full-time appointment in which I teach product management and design, interaction design mostly, and game design as well.

So describing myself is never easy. I contain multitudes. But other than hanging out at Stanford with the kids, I write books on the odd occasion. I think I’m up to five now. And I also blog like a maniac, still.

You and I are some of the original bloggers from back in the day.

And then I help companies every so often when they come by and say, help, help. And I say, what you got? So the helping companies have been interesting. It tends to be a type of coaching that’s less life coaching and much more about how do I get my business sorted out. I work with CEOs mostly helping them figure out what’s my product strategy, what’s my business strategy, what’s my hiring strategy?

The word strategy tends to come up a lot.

Peter: Are these startups or more mature companies or all kinds of companies that you’re working with?

Christina: All kinds of companies. When it comes to the OKR work, I get a lot of big companies, you know, your Pepsi’s, et cetera. But for the more hands on coaching, those are almost all startups. I’m a startup person. I always have been. I always feel funny when I’m talking to a company and they’re like, we can’t do that because we’re cross-matrixed in these 15 different ways, And I’m like, Ooh, that sounds unpleasant.

So I’d much more prefer, the startups.

Stuck in the middle with AI

Jesse: So we were interested in having you join us because I’ve been reading a bunch of your writing lately around the topic of AI, and you’ve been doing some interesting explorations, and it’s been really interesting to see you sort through the implications of this stuff in your writing. And I’m curious where you would place yourself right now on the sort of skeptic-to-booster spectrum when it comes to AI.

Christina: Yeah, the doomer versus the booster. I like to think I’m stuck in the middle with you guys. There’s clowns on the left of me and jokers to the right.

Peter: Sure.

Christina: Yes, indeed.

Jesse: I’m keeping my ears covered.

Christina: Sorry, But it’s really maddening because it feels like if you say anything critical about any of the current generative AI companies, you’re somehow an idiot and backwards and a Luddite.

And if you say anything positive, you’re a lunatic, an overhyped, bubble loving fool.

So I say both things and I can be all those things at once.

If I was gonna nail it down and say, this is an extraordinary piece of the technology. I kind of doubt it will change the world the way the internet did. It doesn’t seem to me to be as deep as the internet, which really did change how we do almost everything.

But it is incredibly powerful and it’s amazing when you use it. You just become supercharged.

It also is not easy to learn. Everybody makes it sound like you just spend five minutes and all these amazing things happen. And I don’t find that to be the case at all.

I would say I was using it for six months before I got my head around starting to get value out of it. But of course I do have a day job, so maybe that might’ve been faster. But the hardest part of AI is that the companies suck so hard. It’s very, very painful.

Like, to use AI is to be complicit in this way that’s intensely unpleasant. I’m currently trying to stick only to Claude, but that puts me in a place where I don’t necessarily know what’s going on across the board. So occasionally I’ll use, OpenAI’s offerings, or I’ll use Gemini, but I can’t bring myself to touch Grok or Meta because I feel slimed if I do.

So I’m kind of trying to find a path forward through that. And I think the piece that I’ve written that most people are most familiar with is the one where I said I love AI, but I hate the companies who make it.

And of course I hate them. I’ve written five books. They have literally built their business on the back of mine, right?

I would say that I sell fewer books now. I will say, that I get less consulting engagements now, which in a strange way, I don’t mind.

When I go into do OKRs, people all have the same problems and I kinda wanna just go, just do a close reading of the book. But I love the really hard problems that I get from the people who want me for my mind instead. That’s really fun.

But how can I like a technology that’s built on my effort without paying it for it? It’s kind of, difficult in its heart.

And then of course, it’s the fact that they’re acting like colonizers as Karen Hao says in her wonderful book, The Empire of AI.

They’re exploiting people in poorer countries for both their work.

I didn’t know until I read Empire of AI that they were doing the same mistakes, … mistakes… the same cruel, active choices that Meta made around content moderation. They’re doing it all over again, causing deep trauma in people who can’t afford to get food. And so if you choose between trauma and food, you tend to pick food.

And of course there’s the energy contribution, which isn’t as bad as concrete, but it’s still kind of bad. I can go on for a really long time, the lack of any oversight.

Gee, you think if people talk to AI that maybe suicide might come up? Oh no, that would never happen.We don’t have be prepared for any negative consequences.

But two days vibe coding with Claude Code and then all of a sudden there’s an app and it’s working and it’s beautiful and it’s magical. And I’m like, yay. And then I deploy it and I’m like, I haven’t, yelled deploy, deploy, in such a long time. Maybe not since my startup, and it just feels good.

So yeah, it’s hard. Anybody who thinks it’s simple is somebody who doesn’t need to have AI in their life. And I don’t really have a choice because now it’s going to be a standard technology, so I have to figure out how to teach it, or I’m not a good teacher anymore. It’s hard.

Peter: I want to, I guess, kind of start with where you just ended off with teaching, but I’m going to, perhaps take an unexpected route, which is: you teach at Stanford, which means you are in the heart of the belly of the beast of tech and some of the bad acting that you were just identifying.

Christina: And I’m in computer science. I’m not over in the D School. I am in the heart of the AI planet.

Peter: And I’m curious from that point of view, I mean, many of the people who are these bad actors are Stanford graduates, but I’m curious what you’re hearing from your students. And if you teach undergrad, grad, that would be helpful to understand as well.

What are you hearing from your students around some of these things that you’re talking about? What is your sense of how are they seeing things?

What the students say

Christina: Absolutely. I mean, the first thing to realize is that Stanford is not a monolith. It’s sort of like when people talk about Google, Google’s like a bunch of city states. Stanford’s a bunch of city states.

The people in the business school, GSB, they’re very different than the people in the design school, which is not a truly a school,but we won’t go into that. But the D School folks are very different from the people who are in HCI inside of computer science which is where I’m living.

So what I find is my students are not as fiercely bottom line, money, money, money as some of them. And when they do tend to care a lot about money, it’s usually because they’re first generation low income students who have never had any money and would like to eat.

Once again, eating comes up a lot.

But I’m lucky because I became part of a program, oh gosh, I wanna say, four or five years ago, that was started by our chair Mehran Sahami called Embedded Ethics. And I decided to be one of the first pilot projects in which we work with a philosophy postdoc to put in ethical questions that tie into the topics that we’re covering.

So each of my class always looks at things through the design lens, through the technology lens, through the political lens, from the ethical lens. And I feel like because I teach mostly upperclassmen, I tend to teach junior seniors and master students. It’s sort of a odd middle ground. But they’re very influenceable at that age, which is really wonderful.

And so the things I can say, I can make them go, oh, they’re human beings that my stuff will be touching and do I wanna touch them inappropriately? No, we really don’t want to. We wanna do a nice thing. We’re gonna be thoughtful, we’re gonna think about the end possibilities that happen.

So I like my job ’cause it’s a little bit of a mission is to help them do the hard thinking through the complexity of what they’re facing.

And every once in a while I get the, you know, money, money, money types. And then we, yeah, enjoy lots of fine arguments about, you know, how much of your soul do you really wanna sell when you’re thinking through this and what does that mean? And I always enjoy those conversations.

I think I answered most of your questions. Did I? Oh, what do they think? What do they think?

Honestly, it could be a self-selection bias, but most of them are struggling with the same thing that you and I and most reasonable people are struggling with, which is, do I go all in in AI?

You know, because it will get them jobs. And there’s no question about that. And because they’re from Stanford, they shouldn’t be worrying about getting jobs, but they still do.

They care deeply about doing good. They often come to me, especially in my game design classes, they come to me and say, how can I be making a game when climate change is going to destroy the earth in the next few years? You know, how can I spend my time thinking about these unimportant things? We need to work on hard problems.

They’re very hungry to create meaning and make a difference. And that makes me really happy. And of course then I can say to them, well, you know, games can make a difference too. You can learn a lot from games, right now.

So I think most of them are really worried about the state of the world, and I don’t blame them. I’m worried.

Jesse: Despite your worries, you’ve chosen to jump in with this technology anyway, and I wonder what has helped you get to that place where you can sort of reconcile yourself to it?

Christina: Well, I tried to figure out who was the least evil. I ranked companies by how much harm are they really doing to the world. I could have gone even further, I suppose, and I could have gone with small models.

I haven’t quite got myself all the way up to running a local model, which is where I’d like to be, ’cause then I can get even more in the world of least evil. But this is the world I work in. This is where I live, you know? And I don’t think that you can ignore AI tech as a viable choice.

And the fact is that my students who I adore are gonna go work in tech and they need to know what AI is. They need to know what it doesn’t do. They need to know how it works. They need the answers to the same questions that I need.

And so helping them think through it, first I had to do the thinking myself is really the short answer to that. Yeah, it gives me some cognitive dissonance.

I realized I’d gone too far in the booster side when one day I was on LinkedIn and there’s a post by Timnit Gebru, who’s this amazing ethicist who’s kicked out by Google for being honest about what she thought in public. Don’t do that.

And she shared a really interesting article about the effect of AI, like I said, in the global south. And my first instinct was like vague nausea. And I said, oh, I know this, this is cognitive dissonance. I need to change what I’m looking at and reading.

And so I started following all the doomers, and, not the people who think AGI is gonna take over the world, but the people who are very worried about the real harms that we’re experiencing right now.

And I got myself to a place where I can look at the boosters and I can look at the hype and I can look at the dark side and I can look at the problems. And neither of them makes me wanna throw up any more than any normal person would wanna throw up, I suppose.

And the tech itself is, it’s just so remarkable too.

I mean, the reality is all three of us started in this world at the same time, and then it was the internet. It was making web pages, you know, you could kind of poke at it and you could throw something together, and you got that joy of seeing something go live. You got that joy of seeing people use the things you made, and that’s heady stuff.

And I have to say, I haven’t had this much fun making stuff since, you know, the early two thousands, I think. To sit here and fiddle, paddle around and be able to launch something is just profoundly satisfying for people like us who are makers. So, it has its cost and it has its pleasures.

Peter: You’ve been teaching for about a decade now, like focused on teaching. Is that right?

Christina: A little bit longer, I think, if you count CCA and General Assembly.

AI in the Classroom

Peter: You’ve been teaching for a while, and right now you’re teaching, it sounds like, both a kind of design class and a product management class. And I’m curious how embracing AI has caused you to evolve your syllabus, your curriculum.

What did you used to do? What did you let go of? What are you embracing? What are you recognizing is, like, essential that is not changing? Like, how has that happened for you?

Christina: Well, I started watching AI when ChatGPT first launched, and I didn’t do anything with it for a long time. I was just like, I’m gonna wait and see if it arrives. ’cause you have to remember, we’ve been waiting for AI to arrive for 20 years or longer. So seeing if it was actually gonna be a real thing that made a difference in everyday life and I think this last year was when it really went super mainstream, which is when I started to do with my deep dive, and it was with the desire to bring it into my classroom.

And so this is my first AI enhanced or AI embedded class which is the product management class. Actually, I guess you could argue, I started doing it last spring where I, just said, guys, you can vibe code, you can use AI to make assets for your games. You can use it to make music. You can use it to make images.

Do not steal other people’s work. If you could hire someone that would be better. If you can draw it yourself, that would be better. I built in some extra credit for people who are willing to do the creative work themselves, but…

The quality of the games went through the ceiling. It was just amazing. I was blown away. And they were just much more finished. And I think part of it is they didn’t have to spend a lot of time thinking about Unity and what was Unity gonna do.

They could spend more of that time thinking about how does this game have interesting pacing? How does the game mechanics work together? They were just able to get a lot farther along.

And then this fall, this is when I’m like, okay, you can use AI for this. You cannot use AI for that.

The rule of thumb is, first, what level of accuracy are you going to get? People don’t talk about hallucinations enough. When you realize that it’s 30 to 60% hallucinations depending on your setup, and that you have to do a lot of work to bring it down into single digits.

And there is no such thing as zero hallucinations. Being willing to make business decisions based on an AI “summary,” and I use scare quotes with summary is a scary premise for a business.

So a lot of what we had to do is go, okay, now how are we gonna generate this information? How are we gonna validate this information? When do we do our own research?

I became really interested in product sense, which I think a lot of people are referring to now as taste, which, you can’t fight language, but boy, it makes me want to.

So, I think it’s just really important to remember that when they’re using the ai, they’re not using their brain. And when they’re not using their brain, they’re not creating memories. When they’re not creating memories, they’re not gonna get it better at product sense.

And that’s what I explained to ’em. I just opened it up in the very first class and I said, here’s where you’re gonna use AI. Here’s where you’re not gonna use AI. Here’s why. If you wanna cheat, go ahead, because I don’t wanna play cop, but I will grade you on the quality of your results.

And if you use AI to do the writing, the results will be mediocre. And you’ll get a grade that reflects that because that’s kind of the nice thing right now is AI produces mediocre writing and they do a lot of writing in my class.

And I said I would rather see typos than have to read something boring.

And so far it seems to be going pretty well. I’m enjoying it. So almost everything has some AI and, in fact, this Thursday we’re gonna do a whole class on vibe coding.

The other thing I changed this year was I brought in a lot more guests than I usually do. People who have been doing PM and working with AI for a while, and that’s been really powerful as well.

Actually, it’s nice too, ’cause then I can sit down.

Peter: Ha.

Jesse: I wonder about where the taste issue comes into play in terms of the way that we interact with the technology itself. Because, you know, one thing that has come up for me over and over again in looking at what people get excited about and looking at what people are putting out in the world, is that the stuff that’s not very good that gets out, gets out because the people making it couldn’t tell that it wasn’t very good.

And so I find myself wondering about as practice evolves, how does that intuition get built in a practitioner? And how does the process potentially have to evolve to make sure they have the opportunities to leverage that intuition and not have all the decision making being taken away and given over to the technology.

Maintaining vigilance in the face of AI

Christina: Yeah, well, I mean, we’re at war with our own brains. As you guys I’m sure know, our brains have been evolved to be incredibly efficient because they’re huge calorie eating monsters when they’re being used to do thinking. And so there’s always a part of us that really wants to take the easy way out always. And you have to actively fight against that.

I really think that you have to be active in your care and feeding of your brain, so to speak.

So I’ve been referring to the product sense exercises as product sense pushups. So here you’re going to analyze the onboarding flow of these three different companies in three different sectors and write about what you see the differences are, and why do you think the choices they made were made? Those are the kinds of things that you have to do.

I mean, it was the same for me. I started writing a novel and my first instinct was, wow, this is so fast. This is amazing. This is interesting. And then it was like, well, this is sort of crappy. Why is it doing this? I don’t understand. It’s boring…

Oh, okay. Now I wanna go edit it. Oh wait, because I didn’t write it in the first place, I can’t hold the whole plot in my mind. What am I gonna do now? I’m gonna have to rewrite things. It’s been like this ongoing back and forth between, oh my God, it’s so fabulous, Oh my God, I’m not getting smarter.

And that’s part of it, is you have to commit to your own brain. So just like you wanna listen to good podcasts and you wanna read good books because you wanna make sure your brain is in a good shape. You need to do the same thing with AI. You have to be careful what you outsource.

Peter: You’ve used the phrase product sense a few times, which is a phrase I’ve heard since I left UX consulting and went in-house and found myself exposed to product managers who would use this phrase, but no one has ever defined it for me. And I’m assuming since you’re teaching it, you have a definition.

And I would love to hear how you define product sense. Is it a framework, is it a set of tools? Like what, what is that thing?

Defining “product sense” vs “taste”

Christina: So just like when you’re learning an instrument, you’re going to want to listen to lots of music, get a feeling of what makes a good piece, a bad piece, spend a lot of time practicing and doing repetitive activities. It’s all the same.

And what are we really building up? I think we’re building up an intuition about what’s good and bad. Like we often talk about the iPad is really intuitive and all it means is we know how it works and when we pick it up, we recognize the patterns that we’ve learned elsewhere, on our iPhone perhaps.

So I read this book a long time ago called Working Knowledge and they define intuition as compressed experience. And I think that’s what product sense is, is it’s compressed experience. You’ve seen lots and lots of products and you’ve seen lots and lots of data. You’ve seen lots of user tests. You’ve read about the financial changes in a given business.

And out of that body of work that you’ve taken into yourself, your brain has turned it into patterns and you can quickly reach into yourself and plot those patterns when you’re testing something new.

And so the reason I don’t like the word taste as much is because I think taste gets conflated with being a tastemaker, having, I guess, it’s also a feeling for what’s interesting, but that feeling seems to be…

Jesse: fashionability.

Christina: …yeah, it’s, it is too much about fashion and I think taste worries me that way. It’s like, hamburger menus are cool, but do they actually work? And when you look at the stuff that goes down the runway at a fashion show, is that something a real person would wear most of the time, no, but it’s very, very interesting.

So I feel like taste can become experience on steroids where you’ve become so deeply experienced that you’re bored with ordinary things. And I think in our particular business, product management, design, what have you, we can never get bored by the ordinary because ordinary people like ordinary things.

Blurring of roles

Jesse: I’d like to talk about product management, design, what have you, and especially the what have you, and the blurring of these roles that more and more people are speculating about, projecting is going to happen, as a result of this technology. And I’m curious about your point of view as somebody who has been a designer, has been a product manager, has taught design, has taught product management.

Like what do you see as how the interaction between these roles evolves with the introduction of these technologies?

Christina: Yeah, because I have my feet in multiple different spaces, I have sort of a sense of how people are reacting towards them. And the short answer seems everybody thinks their job’s going to go away which I’m not very convinced of. And actually it’s probably engineers who are in the most danger at this particular moment, especially at the, sort of, crappy low level ones. The very senior ones will be needed ’cause they’re the only ones who know when the AI is lying to them.

But with design and product management they’ve become more and more alike over the years. When I first started, the product manager was firmly in the business space and the designer was firmly in the experience space, in the “how does this software behave?” How do we organize the information that it holds? How do we present it to a user in a way that they can understand and find pleasurable?

But it’s been interesting to see how product has shifted much closer to user experience in that they do their own research and they, they do more research than we used to. I talk to any good product manager here in the Valley and they’re like, yeah, we talk to users every single week, period. We do research, we do testing, we do product discussions. We write, and I can’t think of the word, but quick prototyping exercises with them. Participatory design, that’s my word.

And these are product managers doing this. In fact, we should ask what’s going to happen to the user researchers who seem to be the ones who are probably in the most danger right now. And we often forget to talk about them. I saw something interesting, I saw that there was a new survey they looked at all these job listings across all the different job boards.

And it turns out designer is one of the most highly sought after one. And every time I go on LinkedIn, everybody’s like, nobody listens to me and there are no jobs. I’m never gonna get a job. And then I see a survey like this that says people are looking for good designers and I wonder what’s going on here.

This is an interesting little mystery. I think design and product have always had a tumultuous relationship because they both own the same thing, the user’s relationship to the product. And they both think they own it, and they both think that means nobody else gets to own it, which is problematic.

So the way I think of it is, I love Theresa Torres’ product trio, where you have an engineer, you have a designer, and you have a product manager. The problem I have with that when it’s drawn as a Venn is product managers like to put themselves in the middle.

And I disagree with that. I think that everybody wants to be in the middle, right?

I think that they need to remember that they’re representing the business first and foremost, and a happy customer makes for a good business. Unless you’re United. And then making people profoundly unhappy means rising profits, apparently. But we won’t go into enshittification just now, I don’t think.

But I think that you really wanna think about, as a designer, what do I bring to the table? And it should be your years of training. It should be your experience. It should be whatever product sense or designer’s intuition that you’ve been developing over the years. And the product manager needs to respect that the designer does have a body of knowledge that they do not own.

The best people like Marty Cagan and Theresa Torres talk about how much they adore working with designers and how critical working with a good designer matters. But not everybody is a good product manager. Sturgeon’s law applies everywhere. 90% of everything is crap if you don’t know it.

When the team includes AI

Peter: Well, I’m wondering if either as part of your teaching or, your consulting, or maybe going back to when you were more active, like directly leading teams, the concept of team. In fact, I think you wrote a book about teams, and that seems to be relevant to this. Now I’m remembering “The Team That Managed Itself”.

Am I remembering the title right?

Christina: Yes, the book that didn’t want a title.

Peter: Yeah. Well, but that I think reflects on this, right? Because I think something that’s often missing in the development of our practices, design, product, et cetera, is this recognition that you don’t do it alone and that you’re likely going to do it with people who are explicitly not like you, and that you need to figure out how to engage with them better.

And some schools, in some contexts try to do, you know, like, let’s have the business school students work with the I-school students. But whenever I’ve actually been involved in those things, like as a, you know, some type of sage, a graybeard, trying to help them out, it’s clear that no one sat them down and helped them figure out what it means to work together.

With this evolution of these roles, teaming seems even more important because we can’t rely on what we thought we knew about these roles. How do you approach that? How do you help coach or guide people through being better teammates?

Christina: Well, product management is my youngest class. I think this is the fourth year I’ve taught it. And I had to think about a lot of this stuff when I offered to start teaching product management because there were no product management classes for undergrads. I think there still aren’t, at Stanford, you have to be a grad to be able to get into a product management class.

And we were having a bunch of students who were graduating and becoming product– PMs. So the HCI group and I agreed that there should be a product management class and I agreed to teach it. And so I had to ask myself really, what is the unique value within design and what is the unique value of product management and how do I make sure I’m not turning out more product managers who think they’re designers.

I mean, I don’t know how many product management conferences you go to like Mind the Product or Product At Heart or whatever. But they resemble design conferences.

Business is incredibly important, right? You really have to understand pricing, you have to understand marketplaces, you have to understand go-to-market approaches. There’s like some very incredibly important business concepts that you have to understand as a PM.

There’s interpersonal dynamics. I have always taught a little bit about how to effectively team in my classes. Everybody works in teams and I figure if you’re gonna work in teams, in my class, I’m gonna teach you something about how to work in teams. How do you give feedback? How do you hear feedback? How do you create norms around the work you’re doing? And how do you decide how you’re gonna work together?

Just like a bunch of really sort of basic, I’d call it interpersonal hygiene, where you’re trying to figure out how not to get into unnecessary fights so you can save yourself for the really good and juicy ones.

And then the last piece was execution strategies. Like they should know what Agile is and they should know what Scrum is and they should know what the lean startup is and they should understand what it means to bring a product to market.

And it’s very different, ’cause when I went to design, yeah, there’s definitely a lot of user research and some of my students do go on and become user researchers. But starting to learn things like you don’t come up with one idea. You come up with 15, you embrace bad ideas, you generate wildly, you refine them, you think with your hands, like there’s just, once again a bunch of skills that I think are profoundly important for design.

And so that’s pretty much how I approached the differentiation and really tried to focus on the thing that brings your unique value forward.

Peter: It is almost reminiscent of Cooper’s paired design where you have one is the generator and the other is the synthesizer.

And they were, yeah, they were, this locked pair. what you’re talking about in terms of design and product management, designers generating and product managers kind of sifting through and synthesizing and distilling and there being a feedback loop there.

Christina: Yeah, a little bit. I like the product trio because I think that engineers are often overlooked for how creative they are. It’s gotta be one of the most creative professions out there. They literally make something out of nothing. The ability to figure out how to bring things into the world using only ones and zeros, I don’t know how we could not say that’s creative.

So when you have these three people together, you could do almost anything. Somebody who knows how to make enough money to keep the thing going, somebody who knows how to make it desirable enough that people will wanna use it, and somebody who knows how to make it actually work. It’s kind of ma– it is magic. It’s something that’s wonderful.

And I think one of the hardest problems about teaching is it’s really, really hard to have a class that isn’t all the same, like designers take design classes and engineers take engineering classes and product manager take, which means if I put together a team for an activity, I’ve got five PMs.

The very first year I taught it, I tried to get them to pick a role. You know, okay, who’s gonna be the designer and who’s gonna be just, it didn’t work. Everybody wanted to do everything. And that could be maybe, ’cause they’re Stanford students and they’re all good at everything as far as I can tell, which is kind of terrifying when you try to go in and teach them.

But it just doesn’t work. So I’m still trying to figure out how to do interdisciplinary training because I don’t think we have enough of it.

Jesse: I wanna come back to the question of what happens to the magic created by the product trio when they adopt a new robot pal. And the implications for how each of those disciplines continues to deliver against its value proposition with this new player in the mix.

Prototyping

Christina: Yeah, I think we’ve identified the first truly valuable use case, which is prototyping. I mean you know, you hear people say, oh, AI can’t do production code, but just the idea that no one ever has to sit there and manually hook together pages in Figma. So you could have some vaguely clickable prototype where half of it doesn’t work and the data is wrong.

And now you could spend that exact same amount of time and have a completely interactive prototype with good data. And of course everybody’s gonna say, oh, it’s done, let’s ship it, which it isn’t. But that’s always been true for every prototype. That seems to be the nature of prototypes, is the higher fidelity they are, the more people think it’s ready to launch.

I can’t believe how much better a designer it makes me, I’m sitting here, like I said for the last couple days, prototyping a new app in Claude Code. I’m a design… ex-sdesigner. I guess, I’m a guess, ex-everything. But I’m an ex-designer making a prototype in a command line interface. It’s like, what, who am I, what is this world I’m living in?

And I can quickly launch it and play with it and say, okay, I see that doesn’t feel right, I’m gonna change these. I remember reading How Designers Think, which I really love, by Brian Lawson. It’s an HCI classic. But it’s really more architects he is working with.

And he talks about how a designer while drawing is in a conversation with themselves. They’re not drawing to explain things, although sometimes they are, but as they draw out these ideas, and you know this very well, Jesse, with your love of diagrams, me too, you’re diagramming as a way of going, does it fit like this? Or does it fit like this? Is it more like that? More like that.

And so if you’re able to prototype something natively in the material that it will eventually be in, which is code, you can get such a good sense of what works. And I think that’s gotta be the biggest winning use case of all. It’s not as scary as trying to synthesize user data where you have problems with getting it wrong.

Like I said, you don’t make decisions off of hallucinations, but you’re not losing anything either. Like if you never planned to learn to code, which I haven’t coded in well over 20 years, then I’m, didn’t think I was gonna start now, but apparently I was wrong.

So, it’s just so satisfying.

And we’ve seen it, like we have all these coding Lovable and Bolts and everybody talk about vibe coding. When people say vibe coding, just replace it with the word prototyping and you can see the value and it’s more testable. You know, if you have something that has more links and real data, you get significantly better feedback from your customers because that you can have them act naturally.

Jesse: I wonder about the implications of that for the skillset of the person sitting at the prompt and what they need to bring. Because like we’ve talked about what a product person brings, we’ve talked about what a design person brings, and we’ve talked about what an engineer brings. And I wonder what the potential mix of those value props might actually be required to be really good at this thing that you’re talking about, the prototyping work.

Christina: It makes me crazy that everybody on LinkedIn, which is probably a terrible place to figure out what people are talking about. But…

Peter: it’s the best we got.

Christina: Ever since I rage-quit Twitter over Elon Musk, I’m kind of lost in good places to have conversations. So I still held a hope Blue Sky will finally get fun.

Peter: Maybe we can bring mailing lists back. That’s where we all met originally.

Christina: I miss mailing lists. Don’t even get me started. I never feel so old as when I talk about how much I miss mailing lists.

But I think that when people say vibe coding means we don’t need a PRD anymore, or stuff like that, I’m like, no, no, no. Let’s talk about the importance of figuring out who your target audience is, of figuring out what the market is like right now. Figuring out how should it look and how should it feel and how should it behave.

These are things that vibe coding… can’t be done until you get your head around that problem. I think that what’s exciting to me is I can go straight from a piece of paper, which is incredibly fast, to an interactive prototype, without having to work with all these klugy things that we’ve put in between it.

Like, let’s be honest, in a lot of ways Photoshop can be kind of klugy. Figma can be very klugy when you’re trying to do interactive stuff with it. Or you could argue, no, I’m fast with Photoshop, I’m faster with Photoshop than I am with a piece of paper and some colored pencils, and I’d rather do it that way.

But you can do either one and then you can upload it into the vibe code tool of your choice, and then it can make you an interactive prototype without spending hours of putting things together. So I think the thing that made people valuable is not going away even a little bit. I think the way that we realize that value is changing radically.

Team norms with AI

Peter: Jesse asked a question about this robot member of your team, and it kind of builds on what we were talking about earlier in terms of team dynamics and how teams learn to work with one another. And it made me think about norming.

What does it mean to norm with a robot buddy? Which then made me think about something you wrote recently about context engineering.

And I’m wondering if you could talk about that maybe in the frame of norming, like how you set up your robot buddies to better work with you and extrapolating that to what does it mean to work with the team?

Christina: Well, you know, it’s always a little bit dangerous to talk about robot buddies when we’re really talking about something that’s a probability machine, the most amazing, incredible probability machine that anybody’s built so far. But still, it is, it’s not a human who has feelings.

But on the other hand, the context engineering is a great way to talk about norming because when we come together and we talk about norming, norms are, of course, the often unspoken values that we share.

We have an understanding of, do we interrupt each other? Do we not interrupt each other? Do we raise our hands or do we just speak out? Like there’s a million tiny social decisions that different cultures have come up with different ways to solve for them. And so by spending some time when a team is first assembled to write down those norms, what are we gonna do?

What happens when you and I disagree? Do we take it offline? Do we argue with it right in front of the team, right then, there? If I have a problem with you, how do I handle that? With how we’re interacting? Like these are all the norms.

So the question then becomes, when I interact with Claude, which is as I’ve said, my favorite, I wanna tell Claude, how are you gonna interact with me?

I wanna say, please do not blow smoke up my butt. I’m not interested in your sycophantic ways. Stop using all those exclamation points. You sound like a damn cheerleader. If I wanted that, I’d go to ChatGPT.

You know, I really feel passionately about, here’s how I want you to talk to me. So I went ahead and I put in at the system level the norms of how do we talk to each other. I want you to challenge me.

I want you to, I went through a whole period where I was like. I’m very much a one shot prompter. I just like to write something in the chat box and go and hope for the best. So I had it always asking me questions. I said ask me questions before you do something. And then it would just ask me questions endlessly. So I got to ask me questions when you’re about 70%. You think with 70% confidence that you understand what I’m talking about.

And that seemed to solve the problem for me. So now I do one shot and ask me all these really useful questions, and then it just builds something and it’s really pretty perfect.

And in a lot of ways when we’re working with a team, we design our norms, but then we check in on them every week. We say, okay, are they still working? Do we need to come up with a new rule? Do we wanna get rid of one of our rules? Is it silly? And I think that’s the same thing as you have to think about context as sort of something that you’re continually refining as you work with these.

And it requires a lot of metacognition as a human being. You have to spend a lot of time thinking, what works for me? Do I like the blunt honesty or do I like a little compliment here and there? And be self-aware enough to be able to make those choices. And I think a lot of people aren’t. But it makes a huge difference to have that context there.

The robot buddy. Yeah. I think, I feel, I feel more like a cyborg. It’s like an exo-suit. I put it on and I can do all these things I couldn’t do before. Rather than a different individual, even though maybe it’s like Jarvis, you know, if you think about Iron Man, where there’s a voice there, but it doesn’t really belong to a body, it belongs to the suit.

Jesse: That’s quite the image.

Christina: I love it.

I love putting on my Claude suit and going out and conquering the world.

Jesse: Well, so much of the talk is about efficiency, right? And so much of the talk is about using AI to do more with less and being able to kind of get the most out of your teams and stuff. And I wonder about how you see the tension between kind of efficiency and quality, because you were talking about how AI really raised the quality of your students’ work. And at the same time when we talk about AI processes relative to other kinds of processes, it’s not necessarily that they’re making you more efficient, you’re just spreading your energy around in different ways, right.

Christina: Maybe I think that the question we should be asking ourselves is how are we gonna spend that time? You know, it’s just daylight savings time and everybody got an extra hour and there were endless newsletters going, what are you doing with your extra hour? Which is kind of silly because. We still sleep eight hours a day or eight, eight hours a night and or awake 16 hours a day.

But anyway I think with AI we really are getting back hours. Like something that would’ve taken me three days to write, took me three hours to write. I mean, it is, quite a large jump in certain types of tasks and all tasks. So now that I’ve gotten time back, what am I doing with that time?

And I fear that a lot of executives are going to say, “More, just do more.” But I think the real value would come if we did nothing with that time. Like we need to use that time to go for a walk and think about strategy. We need that time to leave the house and touch grass, to be healthier, to spend more time with our family because it’s been shown over and over again that when we go to a four day work week, that productivity goes up, not down, and that’s before AI.

I was talking to one of my students, my students are so frigging smart, it’s just such a delight to have hard conversations with them. And I said, Hey, it looks like, you know, inference is getting cheaper and cheaper. What do you think they’re gonna do with it? You know? And he goes, oh, they’re just gonna spend all that energy that would’ve been used on bigger models. And I feel like that’s the instinct. And capitalism is just to consume every single thing it can as opposed to stop and take a pause.

And it’s a very shortsighted version of capitalism that’s not science-based. It’s mythology based, I think, where if you leave the office, the, I can’t believe 9-9-6 is back. It’s, it’s, it’s nuts. It’s like, if you’re gonna be successful in AI, apparently you have to work from 9:00 AM to 9:00 PM six days a week.

And I’m like, no, no. If you’re successful with AI, you’re working four to six hours a day and you’re spending the rest of the time like reading and thinking and exploring and napping. All of these things have been shown to increase productivity. So I think the question is what are we doing with those hours?

And I would say it’s don’t use your common sense. Use the science instead.

Peter: Big fan of napping.

Christina: Napping is beautiful.

Jesse: He is a big fan of napping.

Peter: I, I am.

Jesse raised again, the work you do in game design and that was a thread I wanted to pursue a little bit, you’ve been working in game design for decades now.

Not necessarily full-time, but you’ve definitely had a foot in it. You’ve attended the Game Developers Conference. That’s a space that you’ve continued to attend to.

Christina: I worked at Zynga. I’m working with some game design companies on and off.

Peter: And I’m wondering, you know, I think Jesse and I have benefited in conversations with folks who are operating in spaces adjacent to the kind of digital product design, UX design, maybe even service design space that we tend to find ourselves in.

We had a great conversation with someone from the consumer packaging goods world and talking about brand and packaging design and those experiences and the challenges that community is facing. And I’m wondering what you are seeing in game design, what trends or realizations are occurring in that space that would be of interest and relevant to, a more kind of UX or digital product design practitioner or leader, like, just breaking us out of our kind of typical modes and, how might we learn from others’ experiences?

Christina: Yeah. Well, I mean, you know, I was saying earlier how AI and actually also VR and AR have been arriving for a very long time and never seemed to actually arrive, but they arrived in game design ages ago, like GDC quickly had an AI summit. Before ChatGPT was launched. And that’s where most ordinary people think of AI as beginning.

And AI has fully taken over all the other tracks as well, there’s a summit beforehand, and then there’s the main conference. And AI is everywhere. Because it’s such a useful tool to allow you to do the onerous work of making a game.

Also games are a hit business. A lot of things fail. People don’t wanna spend much money on creating them because it’s a huge risk every time you make a game. So having AI that can, you know, make your animation go faster, make more sprites more quickly, is valuable.

Then you have things like procedural generation, which is always super interesting. Like how do you automatically create levels or challenges? AI is just very obviously applicable to game design the way it isn’t as clear within UX.

There are many, many winning use cases in game design and it’s often hard to bring that back to UX. Because I think that UX is sort of problem obsessed, but not all opportunities are problems.

And game design is not solving the problem of boredom. It’s instead speaking to a certain longing that’s inherent in us to play. Playing is probably one of the most fundamental human activities that exists. Because through play we develop new technologies. We learn how gravity works and how the world works.

Play is how children learn. And it’s how adults learn too. It’s not just the province of children. So, it is hard to talk about what is game design doing that we should learn from? ‘Cause I did a bunch of that when I was very first, you know, doing my Mechanics of Magic talk, which you were kind enough to host me when you were at Groupon.

Peter: That’s right. That’s right. Well, 15 years ago or something.

Now, one thing I’m picking up on is, and it’s something that we don’t maybe talk enough about in the space of UX and digital product design, which is production.

The three of us have been doing this long enough that UX design, even the production aspects of UX design were innovation. We were creating stuff. We were the first to make shopping carts or checkout flows or, you know, whatever things that are now very beyond rudimentary.

And I think there’s still a little bit of that mindset that like every designer on the team should be doing–like, we need designers to be doing production art and production level stuff.

And we haven’t yet figured out how to gracefully hand this off to a tool the way that it sounds like game designers are like, yes, if you could just like, figure out all the in-betweens between, you know, this version of this character and that version of the character, great. Oh my God, that would be amazing.

Whereas we would be like, no, no man, a human’s gotta draw every single one of those in order for me to feel validated. And, there’s probably some type of production opportunity that’s untapped in the spaces we’re operating in that tools like this could help with.

Jesse: Well, so for our audience, you know, we’ve got a lot of folks who listen to this show are in-house leaders of design teams. They are, in some cases working inside large organizations with a million constraints. They’ve got product partners and engineering partners breathing down their necks, and they’ve got the executives telling them to figure out this AI thing. What would you advise those design leaders as to how to think about and approach this challenge?

The Power of Variations

Christina: One particular thing that I think AI is incredibly useful for, everybody just goes, AI is good for brainstorming, and they kind of wave their hands around.

But what AI is incredibly good at, because it doesn’t get bored, is variations. So if you wanted to see 20 versions of a certain page, all with a slightly different shade of teal, you could do that in 20 seconds, you know? And immediately go, oh, okay, I think this one’s better than this one. Or this is more on brand for us.

I love going, give me 20 ways that x, y, z you know, give me 20 titles for my blog post. Or things like that. So it&#

Show Notes

Peter and Jesse discuss findings from Peter’s survey of 750 UX pracitioners on organizational health. Designers feel good about their work but struggle with quality standards, staffing, and career growth. Senior practitioners are the unhealthiest group. Reporting structure predicts team health. Consulting teams outperform in-house teams, where visionary design capabilities have atrophied and empowerment remains elusive.

Read the 2025 State of UX/Design Organizational Health report, including access to the survey data for your own exploration.

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, our very own Peter Merholz shares with us insights and perspectives from his 2025 survey on the organizational health of digital design teams. We’ll look at where designers feel they’re delivering value, where they’re struggling, and the key indicators that your team might not be set up for success.

Hello Peter.

Peter: Hey, Jesse.

Jesse: Welcome to the show.

Peter: Glad to be here.

Jesse: As always. Today…

Peter: Do I have a choice?

Jesse: Hey, this was your idea.

Peter: The podcast was your idea…

Jesse: No, you’re right, you’re right. This episode was your idea. We’re gonna talk a little bit about the survey that you did last year around organizational and team health for design teams.

And I wonder just to kind of set things up what were you hoping to learn by doing a survey of design practitioners out there in the world?

Organizational Health Survey

Peter: So this survey, this research, has been brewing for me for years now. I had created a version of the survey that was specific to individual design organizations to be used to help clients a number of years ago, just as part of my practice.

And I’ve realized, particularly, I think, in that 2023-ish timeframe, as things started getting confusing and discombobulated and disrupted, that it would be interesting to take a snapshot of the state of the industry, and that this survey that I had been using to help specific design teams understand their organizational health, like, how, how well are they performing and, how healthy are these organizations, and organizational health means things like the mindset of the people on the team, how motivated and engaged are they, how supported are they feeling? Are they able to do good work? All those types of things.

I thought, oh, this could be helpful industry-wide, just to get a sense, pulse check. But I’m just one guy. And it laid dormant for about two and a half years until Lenny Rachitsky did his survey of product development teams, one of the findings of which was around burnout.

And within that finding around burnout, that designers are the most likely to be burned out within a product development org, more likely to be burned out than product managers, engineers, et cetera.

And that caught a lot of attention. There was a lot of commentary about it, primarily on LinkedIn.

And so that was the trigger to be like, okay, I gotta get this thing out there. And we need to, by we, I mean kind of the UX design community, we’ll benefit from a look within, right?

The Lenny study was broader. It was not about design, though it included designers.

I wanted to really take that snapshot of what the UX and design industry is feeling about the organizations they’re part of. And so that’s what spurred it. Like, literally weeks after Lenny’s survey, I published mine, which in some ways was perhaps unwise because I did it right at the start of summer.

Like had I, done it in the spring, I probably would’ve gotten, it would’ve been easier to get a, good feedback, but did it in the summer. But I was still able to get nearly 750 respondents from around the world to share what their experience is inside their various organizations.

And I think come up with a decent, informed perspective on the state of the health of the teams that UXers and designers are part of.

Jesse: Got it, and it would seem from the survey results that that health would be approximately 3.28 out of five.

Peter: Yes. Solved. It’s pretty mediocre. Or middling is probably, maybe a better kind of word for it.

You know, there’s some kind of demographic questions just to try to get a sense of the size of the organization you’re in and where is your organization within a larger company? Are you reporting through product and engineering? What kind of industry are you in? Financial services, professional services, retail.

So there’s, a set of demographic questions and then there’s a set of, they’re not questions, they’re statements. Likert statements, right? Where you put a statement out there and then you have someone say whether or not they strongly disagree, disagree, neither disagree or agree, agree and strongly agree. And you can assign those a value from one to five in that order.

And it’s those Likert questions that are really getting at the organizational health. Whether or not people have the tools and resources they need, do they feel good about the work that they’re doing? Are they adhering to quality standards? Are they supported in their professional development?

Whatever it is, writ large, when you look at the industry as a whole, it turns out that the answers are basically, on average, they’re very, or ,like, in the middle. They’re just in the middle.

Which to me actually suggests that the tool is pretty well tuned to get a result like that. it also suggests that, you know, things aren’t great. Things aren’t terrible, but, and I’m sure we’ll get into this, there are circumstances where results shift one direction or another, and it does start pointing to certain environments that are healthier or less healthy.

Certain contexts that correlate with healthier environments. And then you can start inferring why.

Jesse: Yeah. I actually am curious about something a little more granular than that, which is really when you were digging into the data, I’m curious what the process was like for you as you were going through it and what you maybe discovered along the way that caught you off guard, or were there any aha moments in your own journey with this?

The Internal Contradiction

Peter: One of the things that became clear very quickly and kind of bore out regardless of how many people answered it, was this interesting dichotomy, this internal contradiction.

By and large, people feel good about their own work and their ability to do good work in their organizations. I have a set of statements: “The work I’m asked asked to do matches my level of experience and expertise,” “I take pride in the work I deliver,” “the work I do has a positive impact.”

Those all ranked very strong. They were among the most positive responses that people had. And that kind of surprised me…

Jesse: hmm,

Peter: The strength of that positivity because in a lot of conversations I have with folks, I find that people are often frustrated by their ability to do great work or, put work out there that has the kind of impact that they want it to have.

And the internal contradiction is you have on one hand people saying, I take pride in the work we deliver. And the work I do has a positive impact on users.

But then when you ask questions that are a bit more, say, systemic…

Jesse: hmm.

Peter: You get what were the strongest negative responses. So that includes a statement, “We only ship experiences that meet our standards of UX and design quality,” ” Our staffing levels are sufficient to deliver on the work expected of us,” and “I have the time and focus to do my work well.”

Those three statements had the strongest negative reactions, which feel in conflict with the statements that had the strongest positive reactions. And it’s one of those results that I would follow up with, if, I were doing this for a client and really wanting to unpack that, I would follow up with like a handful of one-on-one interviews with a range of designers.

You know, try to get maybe 20 designers to see if I can unpack why those two things

are…

Jesse: …telling different stories,

Peter: …so divergent when they seem to be talking about the same thing, which is like, what we’re able to get out in the world.

Jesse: Yeah. I’m curious about this one about quality because it is such a topic of conversation in the design community, and you have a lot of people responding in the negative about their ability to maintain standards of quality in what they ship.

I noticed that the, question about, having standards of quality is much closer to that average. But the gap between having the standards and being able to enforce or implement those standards seems to be one thing that the survey is highlighting here.

Peter: Yeah, and I think that was a surprise that the statement, “we have clear, explicit standards of quality,” ranked, you know, greater than three, because at least in my anecdotal engagement with a bunch of design organizations that are otherwise somewhat mature, they actually rarely have clear, explicit standards of UX and design quality.

And so that leads me to want to better understand what people think that phrase means. What, in their mind, is a clear and explicit standard of UX design quality. Just because I see teams struggle defining quality. Some of the biggest, most mature teams struggle defining it in any clear, systematic explicit fashion.

But even if we assume that yes, we’re doing a little better than middling on teams having these clear and explicit standards of quality, it’s not surprising to me that they’re not shipping to those standards. That tracks with most of the conversations that I have with whether, again, clients or just industry peers, that the quality standards of design are not appreciated or understood by people outside of the design team.

And so teams ship work that the designers are not happy with, though, that then conflicts or contradicts that phrase of, ” the work I do has positive impact on our users, and “I take pride in the work I deliver.”

So I, struggle with, some of this.

Jesse: Yeah. I think it might be a matter of degree. I mean, I think that it is possible to feel like you’re having an impact and feel like that impact is constrained by the environment or the context that you find yourself in. And I wonder about whether there is a story within here, which is basically, it’s not me, it’s you.

You know, that design knows how to do design well. We have standards of quality. We feel like we’re making an impact. We feel a sense of pride in our work, but I don’t have the necessary tools to do my work well, or the time and focus or the staffing investment isn’t there. Or the partner expectations aren’t there. The value alignment isn’t there to actually activate on.

We all know we are good. We’re just waiting for everybody else to give us a chance to show it.

Peter: Right. Right. And I think that’s where I have landed is, that in those very specific areas that design controls, designers largely feel pretty good about the state of things. But the moment they start interfacing with the broader system that includes the elements where they lack control, that’s, where you start seeing the scores tank.

Jesse: I wonder though also about the trap of self aggrandizement in this for designers and design teams to basically.

Peter: You think?

Jesse: Well, well, like how does that play into this you see it, you know, the ego attachment to again, like, we’ve got everything figured out. It’s all of our partners who are the problem.

UX/Design Less Satisifed Than Other Functions

Peter: I mean that’s probably true of every function, right? Functions are tribal. Those tribes feel like they know what they’re doing and often, I think, feel like the people outside of their tribe don’t know what they’re doing.

I think the part of what’s at issue here is a matter of power, and I think designers tend to lack the organizational weight to insist on, say, standards of quality that perhaps the other functions do or are able to abide by.

And so, you know, long ago I wrote about another trend that I’ve seen, which is when you do internal surveys of product development teams, and then you analyze the results by function, like product manager, engineer, design, data, whatever the functions within the team, designers almost uniformly are, like, 10 points behind the other functions.

And so to the point you were making, I think there’s some greater disconnect between designers and design practice and design expectations, and an organizational reality relative to other functions, where it seems like engineering and product, that disconnect is non-existent or much less.

And there’s just something about, I think, how those functions are better attuned to the broader company that they’re a part of than design is.

Jesse: Is that a gap that design can bridge? Does design inherently need to be a little bit separate?

Peter: So that gets back to the concept you and I have discussed around, this idea of design… I’m wary of the phrase “in a bubble,” and I’ve, something six months ago, seven months ago, or maybe more now, where I refer to it as the membrane, right? Because it needs to be permeable.

But this idea that design is a meaningfully different function than other functions within the organization. Engineering, marketing, sales, finance, HR have, in many ways, more in common with one another in terms of how they approach their work. A more analytical approach, a more spreadsheet-driven approach, easier tie to clear value, than design.

It’s harder to measure. Design’s impact is mediated often through other functions, or it’s realized through collaborating with other functions or facilitating other functions and design effort, instead of being as analytical and as operational as some of these other functions, right?, is more generative and creative and exploratory.

And so design as a function is kind of a misfit in most organizations. That it’s not aligned with whatever the dominant kind of cultural values are, whereas other functions have an easier time aligning with those more, kind of, business-centered values.

And so, yeah, I struggle with this. I don’t want designers to always be frustrated and upset that they can never achieve their ideals. And I don’t want design to think like it needs to operate in a black box in order to protect its work.

But there is something distinct that is worth nurturing with design in these environments that means it’s being treated differently in some ways than the other functions.

Jesse: Well, I guess I’m wondering if it’s having an impact on organizational health, things like burnout, things like people wanting to, to stay in this career then.

I think the question then becomes, how far can we go toward bridging that gap? And honestly, this comes back to leadership and the choices that leaders make in how they structure and organize their teams.

I think also there is something about the cultural expectations of design and designers that may be at play here because of the ways in which those squishily defined standards of quality actually become safe spaces to play in.

You know, if you’re not being held to a metric.

Peter: It feels more than just a dichotomy, of what it means to perform as a designer, and I mean this somewhat broadly–design research content–these practices that are often lumped together.

Creative practices, humanistic practices, social science practices, that just, again, tend to have an engagement mode that is different than other functions.

The Schizophrenia of Design Leadership

Peter: I think a lot about the challenge that leaders of those functions have, right? When you’re in it, when you’re a practitioner in it, you can kind of keep some of that noise at bay and just focus on the process in the work.

But the leaders are… they can’t escape it. They’re living in two worlds. And that’s where that’s kind of schizophrenic, kind of concept comes from, right?

They’re spending half their time or whatever in design, being generative, being creative and nurturing this exploration, and that way of working. But then they have to turn around and interpret that mode of working to a broader organization that is more calculating, more business centered, more spreadsheet oriented, whatever. And vice versa.

They then also need to be able to speak that language of the dominating business values, and bring that into their team so that their team is maintaining relevance.

The risk of when you create a bubble as opposed to a membrane, right? The risk of a bubble is that you’ve just become irrelevant. And I’ve seen that again and again. Where design teams kind of just get so disconnected with what’s happening in the organization that they kind of get flushed out.

But the solution isn’t for the design team then to just dissolve itself into the fabric of the organization, ’cause then you lose what makes it interesting and distinct.

Jesse: Right, and potentially, the additional value that can come from unified approaches to process and design principles and stuff like that.

You mentioned how the needs of the leaders or the concerns of leaders might be really different from the concerns of ICs, but you didn’t just hear from leaders in this survey.

You actually hit a pretty broad range of kind of levels in organizations. And I’m curious if there were really any strong divergences that you saw by organizational level.

The Plight of the Senior Practitioner

Peter: I touched on it in the health report, the primary thing that I wrote for my newsletter. The people who are feeling organizations to be their least healthy are senior practitioners.

And there’s an irony there because the senior practitioner, senior designer, senior researcher, whatever, are also often the most sought-after level.

People aren’t hiring juniors. They wanna start by hiring seniors because you can hire a senior and then you don’t have to manage them. They can kind of just get the work done.

But if you look at the data, the senior levels across the board on the Likert questions are anywhere from like… i’m seeing like five to 10% below the average, regardless of what the statement was. And this is a decent population, 135 out of the 740 or so, right?

So these numbers hold water, and they’re just struggling the most.

Whereas what you see is when you get over the hump and you become kind of lead level or staff level, you know, kind of go beyond that, and the more senior you are, the healthier things appear to you.

And I think what happens is it’s essentially survivorship bias. Where those who have made it through some crucible, and come out the other side, and have kind of figured it out, are feeling better about the organizations they’re a part of. And those who are earlier in their career, don’t quite understand how things work, and aren’t being probably coached all that well, are feeling pretty negative about the state of things.

And I think that’s a real concern. Something that I believe to be true, and I’ve seen it ’cause I work with a lot of directors, senior directors and VPs, is that over the last few years we’ve seen a lot of people who hit director level and then just left the industry, right?

There’s something about the organizational realities, the trends that have been occurring, the challenges in finding jobs, whatever it is, that a lot of folks who were like 15 to 20 years in to being a UX design type person are just like, not for me. I am out. This is not working anymore.

Something I am hypothesizing based on this research is that there might be a wave of that happening at that senior moment. You know, someone five, eight, maybe 10 years in who before they’re able to get over that hump into more kind of active leadership roles are evidently feeling frustrated and disconsolate about the state of affairs and might be leaving sooner than I would’ve expected, because it’s just not working out for them.

And, perhaps they’re early enough in their career that other paths available to them, and it’s not as colossal a shift. I do just find myself wondering, what talent are we sacrificing at these earlier stages…

Jesse: oh, for sure.

Peter: …by not enabling the growth and development of these earlier folks.

We’re Not Supporting Professional Development

Peter: And on that front, something we haven’t touched on, but, like, the most negative scores in this entire survey we’re in response to the statements, ” I have a clear growth path for my practice and career,” and “I’m given support in achieving my career goals.”

And given that those are the most kind of negative statements…

Jesse: Was that across all the populations?

Peter: That is across all the populations.

In particular is, I have the statement, “I have a clear growth path for my practice and career,” might have gotten the single lowest score of any statement. It’s tied with the statement, “Our staffing levels are sufficient to deliver on the work expected of us,” which I think actually shows the severity of, that, right?

‘Cause we all know about how no team is staffed to do the work, that is asked of it.

Just as equally, individuals are not being given a path for what it means to grow in their practice and career.

And I would imagine if you’re at that senior practitioner moment and you don’t have that clarity, like, that’s hugely problematic, right? Once you get over that hump and you’re kind of lead level or getting to you know, manager, director level, like, you’re able to, in some ways, kind of make that path in front of you.

But we are doing a terrible job of helping earlier stage professionals understand how they can grow doing this type of work.

The Importance of Empowerment

Jesse: Well, I wonder if another piece of it is the way that these roles are currently construed. In that it feels like there is, like, this hump that you describe, it’s like this empowerment cliff that you have to scale from the bottom to get to a place where you are actually empowered.

And at these senior IC levels and below, there is increasing competence, but not increasing empowerment.

And so you get to a place where you’re eight to 10 years into your career, you have demonstrated over and over again your ability to do more and take on more and to deliver more sophisticated and, more impactful results. And none of it has translated into any additional empowerment because of the way that these teams are structured and set up.

Peter: Yeah, I mean, so are you saying it’s, not just a matter then of health, but…

Jesse: i’m saying It’s not just a matter of, like, giving people a path up the ladder, but rather pushing empowerment downstream so that they have more in the roles that they’re already in, and they’re not burning out where they are.

Because the truth of it is that for every VP level role in an organization, there might be, you know, potentially like a dozen director level roles available.

So there’s gonna be a natural sort of cutoff when you go from director to vp. And there’s a similar kind of thing, like for every director there are gonna be n number of senior managers and ICs underneath them.

And so while there are never going to be enough higher level roles for people to move up into, there are always more opportunities to drive empowerment down the stream.

Peter: Right, right. And yes, I see what you’re saying. And so those senior practitioners, yes.

Typically, we hire them because they have the craft skills. They’re usually quite competent in doing the work. They’re self-directed. They don’t need a lot of management. You can give ’em a problem and they can figure it out.

But, yeah, so we’ve got these requirements for their ability, but then we’re not matching it with, the word you put was empowerment, or an agency or that ability to have a say in the work equal to their ability, and particularly relative, I would think, to their cross-functional peers, right?

Also, you know, one of the things that often happens is that design is one level lower in an org chart than product and engineering, right? So you’ll have a VP of Design, but their peers will be SVPs of product and engineering, or you’ll have a director of design who is working with VPs throughout the organization and that cascades down.

And if we think about it at that senior level, that means that your senior designers are likely working with manager level, senior managers. And I know some of them are probably working with director level PMs or engineer.

And they’re just not gonna win those arguments, right? They’re asked to show up as peers to be a three in a box, to have that kind of standing. They’re hired in a process that has required them to demonstrate a level of craft and ability, but then when they are placed in the work, yeah, they find themselves just being told what to do.

Jesse: Mm-hmm. right, right.

Peter: I think that’s, I think that’s fair.

Jesse: So, you know, you touched on something earlier on that I think it’s time for us to get to, which is what did you notice in terms of patterns for what sets teams up for success, for health?

What Condition is Healthiest

Peter: So probably the strongest signal coming outta this entire report was that the more senior your head of design is, the healthier your organization is. And the proxy for that is, how many levels is your head of design from the CEO? Are they reporting right into a CEO? Are they two levels, so, reporting into someone who reports to the CEO. Three levels, four levels, et cetera.

And you can chart just kind of the lower down that the senior most design person is, the less healthy their organization is. So that was, again, the single most salient result.

There’s an interesting correlate to that that I was actually just looking at, which is related to reporting structure.

So if you’re reporting to the CEO, your organization is the healthiest, but we know that design often reports through other functions. And so I had a question, are you reporting up through some type of digital function? Are you reporting through IT? Reporting through product management, which was the most common reporting. Through engineering, or reporting through marketing.

And those signals were, to me, surprisingly strong in that, again, if you’re reporting right into a CEO or I said kind of a GM of a business unit, if it’s a really large company. And so, you know, imagine… I’ve worked with Chase Bank. Chase Bank has business units that have like mini CEOs that lead them. If you’re reporting right into them, that’s the healthiest.

One of the things that surprised me is that the next healthiest reporting line was digital. So you see this in, these legacy enterprises where they’ll have a digital function, a chief digital officer, and that digital team will be responsible for websites and mobile apps and that kind of thing.

And it’s interestingly different, it can be a little bit confusing because there’s digital and then there’s IT and then there’s engineering, all of these sound very similar, right? IT is reporting up through information technology because, oh, look turns out we’re building things that are distributed through computers.

A very legacy structure is to put, Design in IT, often with product people as well. I still see that in some organizations.

And then you have engineering functions. Sometimes design is reporting up through engineering.

Now I have a hypothesis is that the reason digital is ranking stronger than any of these other reporting lines is that digital is seen as a business channel, right? And so there’s a more strategic kind of business-aware…

Jesse: Yeah. It seems to sit on the other side of a line. Somehow in terms of that business orientation as opposed to a sort of delivery or product building orientation.

Peter: IT and engineering are typically more delivery functions that often aren’t, and I’m gonna use the word, empowered again, but I mean it in the Marty Cagan sense, written this book Empowered, right?

But IT is often, and teams within engineering are often not empowered.They are getting requirements from the business that they have to execute on.

Digital is a business and so it’s generating its own requirements. And so design in that context can have a bit more of a business flavor to it and inform the strategy.

Perhaps the biggest surprise, I dunno if it’s a surprise, but just something worth noting was that product, which is the team that more designers report up through a product management function than any other, almost half, it was like 300 I think in the survey. Yeah. 335.

Product trends slightly negative. So that probably, because it’s so many, needs some unpacking, right?

Because there are product teams that are delivery teams, that are feature factory teams, and then there are product teams that are empowered.

I guess I would hypothesize if you were able to distinguish between those different types of product teams, you would probably see something similar to what we discussed with digital being healthier because they’re more strategic and more empowered and things like IT and engineering being less healthy because they are just seen as service functions and delivery functions.

Jesse: So what this brings to mind for me is the notion of almost like cascading value propositions where the value proposition that you’re able to fulfill as a design function has to nest within the value proposition of the next level function up…

Peter: yes.

Jesse: and so on, right?

Peter: How Saarinen of you. Chair in a room? Room in a building? Building on a street? Street in a city. Sorry.

Jesse: Yeah. Design team in a product team. Product team in an engineering team. Engineering team in an IT organization. Yeah.

Peter: Totally.

Jesse: I’m wondering, it may not be so much about levels from the CEO as it is about that cascading value proposition. I think levels from the CEO is potentially a proxy. Obviously, once you get to the highest levels, it’s definitely a proxy for a higher level value proposition.

Peter: I see. So, yeah. There’s gonna be some conflation because if you are multiple levels from the CEO, it’s interesting… If you’re second or third level from the CEO and then reporting up through what function…

Jesse: exactly.

Peter: That intersection is going to be very important.

Jesse: Yeah. So, yeah, exactly, because if you have a chief product officer and you’re reporting to that person, that’s gonna be a different story than if you have a VP of product who reports to a CTO or something like that, right?

Peter: Mm-hmm. I think that’s right.

Jesse: is there anything interesting about industries?

The Joy of Consulting Services

Peter: There was. There was.

In the initial report, that was one of the areas I highlighted because I had one of my biggest surprises.

Now, you know the respondents to the survey were those that are in my network and I didn’t, you know, try to find people myself and spend a lot of money identifying survey respondents. I posted it to LinkedIn and then just kind of kept hammering away on it and asked people to, you know, spread the word.

But,so, it kind of, it’s sciencey, it starts with me and ripples out.

And because of that, the two industries that were most strongly represented were enterprise software and services and financial services and insurance services because that’s just kind of been the space I’ve been playing in. I think they frankly do dominate a lot of design and UX hiring. You know, I worked with Chase Bank. There’s a thousand UXers on the team that I worked with, right? So, these industries have large teams.

Or enterprise software and services think, you know Salesforce or, whatever, right? We know these types of companies have sizable design organizations. Microsoft, even Google, much of it is now enterprise software and services, right? And they have thousands of UXers.

And, you know, perhaps to be expected, those industries were kind of in the middle. They were average when it came to organizational health. And probably kind of like what we were talking about with product, you know, you could do some unpacking in there and find some interesting, like two or three variables that would suggest like, oh, you know, enterprise software mixed with these things is gonna lead to a great health. Well, enterprise software mixed with those things is gonna lead to poor health.

The industry that came out strongest and kind of with a bullet, and it aligns with something I believe to be true, is that the industry that had the healthiest organizations was professional services.

So consulting, design firms, management consulting.

Now, I don’t know what kinds of professional services, but I’m expecting some combination of consulting services and design firms. Yeah.

But where design is a thing sold to clients and where design has some, frankly, if it’s a design firm, right, like, special standing, obviously.

And, what intrigued me about this is that it actually aligned with some research. There’s this gentleman, John Knight, who did some research and I linked to it in my report. He had done some research on his own that found that designers operating in these consulting contexts have much greater job satisfaction and engagement than designers who are working in-house, right?

And that kind of tracks because if you’re a designer working in a design firm or even a management consulting or it consulting firm, but where they’re selling your design services, you are getting to practice design.

That is the value that these companies are selling to their clients is good design.

And so they are set up to enable good design, which is not true of many in-house teams.

A change that has occurred for me in the last just two or three years…

For the longest time, I was largely encouraging people coming out of college to go in-house. That seemed to be where the energy and the juice was. And it felt like the state of design agencies and consulting services was precarious and at times perilous.

But in the last couple of years, not that the business has been super healthy for design firms, but if you, as a designer, especially coming out of school or earlier in your career, if you as a designer can get a job in a consulting environment you will feel better about your work.

I just think that has now become true again. You’ll feel better about your work. You’ll be able to do better work. You’ll be able to engage in your practice with more depth and rigor. On the flip side, you’ll probably get paid less,

Jesse: Hmm.

Peter: right?

There’s a reason a lot of designers go in house. Salaries tend to be better. The economics of consulting are such that practitioners in those environments tend not to get paid as well as practitioners in in-house teams.

But if you’re getting paid enough, you will feel better about the work you’re doing in those environments.

Jesse: You know, you and I, you and I ran an agency together for a long time, and I actually wonder what this whole turn potentially means for design agencies and their value propositions.

You know, the thing that you’re talking about, about depth and rigor and looking at the way that the respondents to the survey have struggled with quality and feeling like they can be successful in those environments, I wonder if this suggests an opportunity down the road for design agencies to make a different case for the value that they bring to client engagements.

Peter: it’s a good, not just question, but subject to investigate, because there’s, there’s something amiss, broken when it comes to design in a lot of organizations and, the word that comes to mind is reckoning.

I think about that… it’s a Judd Antin article about user research reckoning, but I think we’re seeing reckonings all over the place, and there’s some reckoning that is happening with design and it’s relationship to business, to capital, to the organizations.

I think you’re right. I think there’s an opportunity for external design agencies to, I was about to say recast, reorient, reframe the value that they’re delivering.

You mentioned Adaptive Path. I realized sometime around the time that Adaptive Path was getting acquired by Capital One and there was this existential time for Adaptive Path, like, do we get acquired? Do we figure out a way forward?

We couldn’t figure out the way forward if we stayed as is. And we felt a little stuck with Adaptive Path. And I wasn’t an employee at the time, but based on the conversations I was having, Adaptive Path was who it says it was, and as it was, could not bloom again.

And so the path of acquisition was a way for Adaptive Path to evolve.

And I actually think from what everything I heard and witnessed around Adaptive Path and Capital One, it did get a chance to evolve.

That said, if the path not taken potentially, was for adaptive path to say, you know what, we’re not an experienced design firm, but we are a management consultancy, right?

And there’s some companies that have gone that path. SY Partners kind of notably, I think some other design firms, went that path.

And it would’ve been a fundamental reframing, half the team probably would’ve left, it would’ve caused a fair bit of emotional fraughtness.

But I believe that it could have worked, right? It could have found a way forward and remade itself.

Now, it wouldn’t be a design firm. It would’ve lost touch with a certain set of things, et cetera, et cetera.

But could it have found a way to bring a human-centered approach to doing work through this Trojan horse of management consulting? ‘Cause the value, and I believe this to be true of many design firms I interact with today, the value that these design firms are offering is commensurate to the value that management consulting offers at three times the price.

So there’s an opportunity there.

But yeah, I wonder what it looks like to take advantage of it while still maintaining some, somethin; somethin’ about design, and not just, again, kind of dissolving into looking just like a boutique management consultancy, which wouldn’t be the goal.

Jesse: Yeah. Well, I guess I find myself wondering if it is a bit of a reversion to where we were when Adapted Path started, which was that organizations didn’t know how to build internal design teams. Most of the organizations that we engaged with had very limited internal design functions. They were used to partnering for design and it took them a while to figure that out to start building their own teams.

Now, 20 years later, those teams are reaching a certain sort of plateau, a certain ceiling in their effectiveness and their ability to deliver against the promise of having an in-house team in the first place way back when. And so then I start to wonder if that gap that you identified in the survey data between the health of in-house teams and the health of consulting teams points to an opportunity for design firms to deliver a different kind of design or a different level of design than organizations can achieve on their own internally.

We Forgot How To Do The Future

Peter: Well, that puts me in mind of a client organization of mine where they, they brought on a new head of design and that new head of design realized that what his team needed to deliver was a vision of a future state experience.

You know, kind of a very classic, like what do we look like three to five years from now, as a way to rally not just the design organization, but a broader product development organization.

And this new head of design looked around at their team and realized that no one in their current organization had the capability to do that work. That was not what these folks had been developing over the last 10 to 15 years, as they were focused on incremental improvements, and shipping, and not to suggest that wasn’t what they should have been focused on, but that imaginative visionary muscle had atrophied.

And so this head of design, brought in a consultant, you know 25, 30 years in industry person who knew how to do visionary design work as an individual, right?

Didn’t bring in a consulting team, brought in this individual to drive doing some vision work, and then handed over one or two team members to this person to create a small team.

But, the head of design realized they needed an external person to kind of teach and train this group how to do this type of work.

And it’s the kind of work you’re not gonna do a lot of, you’re not making visions all the time.

I think back to our conversation with Peter Skillman, where he’s like, the time for visions is passed, now we’re on execute, execute, execute. And there’s some truth to that, right? Like, like you make your visions and then you gotta deliver on those visions.

But I think we have a generation of in-house designers who don’t know how to do…

Jesse: …they’ve never been asked to…

Peter: …a kind of valuable design work, a more strategic, a more visionary design work that doesn’t feel unrooted.

Like, anybody can, like, do a concept car type thing. And it’s kind of shiny and glossy.

It’s important that these visions feel achievable. There’s a rationale behind ’em.

And I think we have a generation of digital product designers for the last 15 years, yeah, they’ve never been asked to, and now they’re being asked to, their leadership is being asked to, and, no one knows quite how to do it.

They just don’t know the process by which you develop a coherent, practical vision.

I think there are opportunities like that for design firms to elevate certain aspects of internal team’s practices.

Less, maybe, from a project standpoint, is kind of one of my takeaways from this. And more in a very hands-on, not even coaching or mentoring, I mean, the person was doing the work,

Jesse: Right.

Peter: but through the work was also coaching and mentoring.

Jesse: Mm-hmm. So I think one last question for you, which I’m curious what you see within this data that gives us some reason for celebration or perhaps even some optimism.

Peter: That’s a tough one. Not because it’s so dour, but just because the results were so in the middle.

Jesse: Hmm.

Peter: And part of me wants to believe the reason for optimism is a little bit of that, you know, name it to tame it, right? Like, I think there’s a lack of awareness of how these elements that are called out in the survey contribute to health.

And by highlighting those and by being aware of them, we can encourage investment, right, and investment in that which needs investment in, right?

So we need to figure out how to better invest in articulating growth paths and professional development. We need to figure out how to teach designers and design leaders how to advocate for and defend quality standards.

I guess a positive lens on this is, I think, with applied effort at a few key points of articulation, you can get a pretty significant gain. You don’t have to try to solve all of it at once, but focus on these few areas and you’ll get a kind of an outsized return relative to if you were to focus on other areas.

Something else, again, however much I scratch my head at the positivity based on some of the commentary that’s out there, just around the frustration that designers have, some foundational or fundamental core of satisfaction that UXers and designers are bringing to their work, that I think if appropriately nurtured and cared for, is an energy, a momentum that can be capitalized on.

I think most people who do this work do it because they love it. They love this work, they want this work to be great.

And, again, around the things that they can control, they’re feeling pretty good about it. And, how do we enhance that, elevate that, maximize that so that they can then feel, I’m gonna go back to the word you used, empowered.

‘ Cause I think that power and empowerment is probably a hidden theme underlying a lot of this, I don’t ask any questions about power. Power is not mentioned at all in this organizational health survey, but I think your insight that empowerment is a condition that is affecting how people are responding to this.

And I think you see that when you look at things like the reporting functions, right? And, those who are reporting into functions that have more agency and power are feeling better, and those who are reporting into marketing and engineering, where you tend to do what you’re told are feeling worse…

Jesse: mm-hmm. Yeah.

Peter: …and now I want to do a follow up bit of research and try to unpack the power dynamic and see how that plays out in this. So, I think there’s that opportunity then to taking, again, that core that is healthy and good, empowering those folks to do the things we’ve hired them to do and allow them to do them well, and we will realize even greater health, the conditions are almost there to enable it. But we need to activate it to make it happen.

Jesse: Can we look forward to more surveys from you in the future?

Peter: I have nothing planned specifically in that regard. Though, I do think given the response to this one I would like to field it again this year and, see what the difference is. I think there’s value in it.

Maybe work with others. So anyone listening to this who wants to collaborate, I did it all on my own this first time around and it’s why it took months to publish the results and stuff like that. But yeah, I think there’s value to field, to have this awareness. So I would like to keep it going.

Jesse: Peter Merholz, thank you so much for being with us.

Peter: Jesse, thank you for having me. Thanks for, humoring me or engaging me in this.

Jesse: So if people wanna read your report or get a look at your survey data themselves, how can they do that?

Peter: I’ll put links in the program notes for that. So if you’re listening to this podcast in your reader or go to the website and I’ll put links to it. The report I published it as part of my newsletter, The Merholz Agenda. It’s a free subscription, but I do ask that people subscribe to read it.

Usually you can read my newsletter without subscription. This is something I am asking people to subscribe for. And with that, you’ll have access not just to the report, but to the Survey Explorer and all the data. You can go ham and come up with your own insights and findings.

Jesse: Right. Thanks Peter.

Peter: Thanks, Jesse. Take care.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

For more about my leadership coaching and strategy consulting. Including my free one hour consultation, visit jessejamesgarrett.com. If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Show Notes

Product leader, author, and civic tech veteran Christian Crumlish joins Peter and Jesse to discuss his transition from UX to product management and his experimental AI product manager, Piper Morgan. The conversation explores how product and design roles can be natural allies rather than adversaries, where AI truly adds value versus hype, and how practitioners can thoughtfully adopt new tools while staying grounded in fundamental UX principles and maintaining agency over their practice.

Find Christian on LinkedIn: https://www.linkedin.com/in/mediajunkie/

Find Jesse at https://jessejamesgarrett.com/

Find Peter at https://petermerholz.com/. Peter has just published the 2025 State of UX/Design Organizational Health Report, available to all of his newsletter subscribers.

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show: Could you replace your product partner with a robot? That’s the question we’ll be exploring with longtime Silicon Valley and civic tech veteran Christian Crumlish, design leader turned product leader, and author of the book, Product Management for UX People. He’ll share with us learnings from Piper Morgan, his hobby project, to build an AI product manager, what he’s learned from that process about both product work and design work, and how AI can enable new creative possibilities for seasoned practitioners.

Peter: Christian, thank you so much for joining us.

Christian: Thanks for having me.

Peter: Our pleasure. As we were just discussing before we hit the record button, Jesse and I have known you for going on 20-some years in this field of user experience, information architecture, interaction design, et cetera. But in the year 2025, who are you, how do you introduce yourself? What are you up to?

Christian: Yeah, that’s a great and very unfair question. Um, because it’s always too much or how to know what’s relevant to the person I’m talking to. But I’d say to normal people, I generally nowadays say I work in tech or I’m a technologist. I don’t go straight to saying that I’m a product manager unless, they really want a job title kind of thing.

And because I’ve been doing civic tech and I’m still doing it, I’ll probably lead with that these days. It’s the kind of technology I’m involved with that’s focused on public service. And I’d say broadly, probably in a category of… later career, having the privilege to choose more what you wanna work on and tending towards things that feel more purposeful than like selling more apps with hats on cats or whatever.

No shame in like anybody who’s making a living doing that but I’m framing it as a kind of privilege to be able to say… Whitney Hess like advised me once when I was trying to make some choices that, like, the amount of money more than you actually need to live on is often hazard pay.

You often earn it through doing things you don’t really need to or want to do necessarily.

Peter: Right.

Civic Tech Product Person

Christian: So I’m a product person. I’m currently working for a company called Kind Systems, which is based in Irvine, California, but pretty much remote. We do civic tech, but also we have some private sector clients.

And I’m leading a project at the VA right now, helping veterans who are disputing claims or who want their claims for disability to be reviewed, helping them kind of navigate the very complex set of pathways for doing that. And you know, tackling that kind of stuff is exactly the in-the-weeds enterprise scale work you do in government that doesn’t necessarily sound, like, you know, Silicon Valley tech, but is consequential enough to be very interesting to me.

Kind also does, you know, we work with other kind of large data type client projects, and we have a product of our own called Open Laws, openlaws.us, which is, it’s a data source for up-to-date legal code.

Peter: Hmm. I think if our audience does know you, they’ll probably be most familiar with a book you wrote and a transition you made from being a UX practitioner to being a product manager. And I’m wondering, kind of, I’m sure you’ve told the story plenty, but what precipitated that transition?

What enabled you being ready for that transition and, what has it been like? You’ve now been in product, I think for about a decade, if not longer. Like, what has it been to remain in that mode with that UX background that you have?

Christian: Yeah. it’s the going over to the dark side, that’s the cliche, I think. And I think also I would say for people who know this podcast and know your all, like, work and thinking in this space, I think folks are probably familiar with the idea that Peter, you’ve made a strong case that the central concerns of product, quote unquote product and quote unquote UX, are basically the same concerns.

You know, the customer experience, the value of what’s being built, the purpose of it, whether it’s meeting people’s needs, a lot of things like that. And yet the way the business is structured, the person with a product title and the person with a UX or design title often do very different day-to-day tasks or have very different oversight responsibilities.

Not necessarily in a bad way, but if you’re gonna make do with the way things are structured right now, potentially in a very complimentary way, that’s my angle. That you can be allies in that thing rather than like somehow eternally fighting twins, you know, who become a constellation eventually or whatever.

You know, I think I was motivated originally probably by some of the wrong motivations for people who are in UX and think that the grass is greener in product management. Like, I will have more power. I’ll finally get to decide. I’ll be in the room, I will be strategic.

You know, the other things was like, it’s fun to draw. I like to use Figma. Like, I’m a designer. That is my identity. Like you don’t get to have any of those things over in product management. Unless you want to be that Willem Defoe meme who’s like, I’m something of a designer myself, guy, you know, which no designer likes.

I mean, I very clearly… coming into the room as a person, even with my design colleagues who might have a bigger design reputation than a product reputation if they know who I am at all, or know, any of my background, I have to say I’m not the designer on this project. I’m a product manager who has opinions about design or questions about it.

But like, if I start talking about what the design should be like, shut me up. That’s not my job anymore.

Jesse: So it’s been this interesting sort of collision course that product and design have been on for a while now. As you have alluded to, you’ve been part of the group of people who’ve made the transition from one side to the other, and I’m sure there are some folks who have found themselves going back the other way as well, right?

Marker

Christian: Although I’ll say it’s hard to go back the other way. Yeah, I mean there have been junctures in my career when I’ve been saying, oh, I’d like to now take a senior design job again. And you know, I don’t fit the turtleneck anymore.

Jesse: And we’ve talked about on this show, we’ve talked about some of the ways in which these overlapping mandates between product and design roles and between product and design teams have led to a lot of confusion about ownership and responsibility and a lot of confusion about where the value really lies in each of these roles. And I wonder, from your perspective, having been on both sides of the fence, how would you characterize the value that product brings to the table versus the value that design brings to the table in the here and now given, you know, all of the evolution that we’ve been through.

From UX to Product

Christian: Yeah. And I think that’s an important distinction because I think we all have our, like, well, if I were king or if, on the ideal team I would set up, you might divide responsibilities a certain way and hire a certain way. I know people like Wendy Johansson, who has a both a design and product background, and is also an entrepreneur, and in her current company she has roles that combine the design and product role, ’cause that’s her vision and mental model.

And she just empowers people to do that. But I think if you don’t have that in place, you can’t just wish that into existence on your own. So I think the value that the product manager is supposed to bring to a team is focus on goals.

And, I mean focus in the sense of sharpening a pencil, like, choosing, making sure the team does not spread its attention too broadly across too many so-called goals and therefore not succeed in any meaningful way.

So there’s the taking the punch bowl away. You know, the person who says we can’t have seven goals this quarter, we can only have one number one goal, which you have to be that person a lot.

And you know, a lot of the things I say, I think UX people will sometimes say, well, I do that, or I sometimes do that, or, that’s been part of my job at times. And of course, if there isn’t a product manager or the product manager isn’t doing that, it frequently is the strategic senior UX person who’s gonna do those things, or the person with the magic marker who can like facilitate the right conversation at the right time.

So none of this stuff is necessarily alien, but I would say that that’s the main thing a product manager is supposed to do. And the techniques they use, though, usually aren’t design techniques.

They usually use things that are, like, if you take the fancy framing about outcomes versus outputs, et cetera, they’re mostly like project management techniques, or at least organizational techniques.

Figuring out the right process for the team. Being a, un-sticker, you know, tracking stuff down, gluing, making sure the communication is working, quote unquote glue work.

And again, UX people often do a lot of that, but they usually don’t do it across the domain of the whole thing. They’re not necessarily given privy to the whole thing.

They often do it in a way that’s design centric or UX centric and somewhat less involved and even like less wanting to be involved in some of the other dimensions of the work.

So when the division of labor works well, and I maybe haven’t said what the value of the design leadership or design team brings and, I think it’s, you know, meeting the user’s needs and figuring out how to achieve the outcomes.

I think the product manager is not the one saying we should have a feature that looks like this, it should be on this page and stuff like that. But they should say, that thing you’re designing, how is that gonna help people no longer hassle our customer support so much as we’re supposed to be trying to do this quarter?

You know, like you have different conversations and you kind of are measuring or looking at different dimensions of the same thing. And when that works well, it’s sort of a binocular vision, you know? And if you have respect for, like, you’re gonna decide the design points, but I’m gonna still be a customer of your design like a client and go, ” Tthat design, I don’t know how it meets my needs now. I’m not gonna say make it more yellow, make it pop, you know. Make the logo bigger,” it’s gonna be a, hopefully, a more intelligent conversation than that.

I think that the UX side doesn’t always have the same understanding of what should they ask for product to do or how to step in and when to back off.

And both in my consulting work in the past, and I’d say anytime I step in and have to run product, or even set rules for how products should work in a situation, there’s a whole norming, storming, whatever, like one of those cycles where the actual people on the actual teams have to have the real conversations, get all their assumptions, all the baggage they’ve carried in from past teams and how they worked and all the unspoken assumptions about what I own, what you own, what it’s called, get that up on a whiteboard, get a discussion, figure out that 60, 80% of it is fine.

Everybody’s, oh, yeah, yeah, you totally do that. I don’t do that. Oh, I don’t ever wanna look at a spreadsheet, you know.

And then you get this like, juicy gray area around design, around discovery, around strategy where everybody’s like, no, no, that’s me. I wanna do that, you know.

And then you have to have the sometimes difficult conversations, sometimes not so difficult conversation about who does what, who decides who’s the owner versus the interested party on some of these things.

And even you sometimes have to say, okay, we don’t a hundred percent agree, so on these jump balls, we’re gonna flip coins, we’re gonna try it your way, whatever. But we’re gonna track. And maybe after a while we’ll try it the other way, if we don’t love the way it’s going.

I think any smart team is constantly retroing how they work in a much broader sense all the time and going, okay, this whole thing where you decide, and then I do what you say isn’t working out, let’s try it my way, where we talk about it first.

Or it’s not that trivial, but I’d say that’s where you often get to. So, there isn’t like an off the shelf recipe of product, you know, product drives like this and UX drives like that. You know, it’s, often like, which mix of concerns and which other mix of concerns, and the way that they’re kind of jiving.

I find that when I do product the way I do it, which is not the way everybody does it, and the way I think of it, it’s very much a service job. If there’s leadership, it’s the leadership of facilitating that the team figure out the right thing to do, have the right conversations.

It’s not telling people what the answer is a lot of the time. And it’s a lot of like emptying people’s waste baskets, like conceptually figuring out that they’re stuck and getting them unstuck. Tracking down, like, at the VA, what’s the policy for this? I’ll go research those voluminous documents and bring it back to you. You can keep designing.

So like with designers, I used to be a designer. I’m like, Hey, you want me to write those GitHub tickets for you? Because I’m, that’s all I do all day now. So I’m happy to do that. Designers are like, yes, thank you. I mean, usually they want to make sure I did it right but it, you know, I can enrich them and put the acceptance criteria in and the blah, blah.

You know, like stuff that’s like kind of tedious for a designer who would like to get back to looking at the research or thinking through the solution or something like that. So I think there are very healthy divisions of labor that are possible in these roles that there’s still sharing the goal of, we want the experience to really meet someone’s needs and, you know, be reliably, consistently good.

Product in different contexts

Peter: Something that I wonder, ’cause I know you’ve worked in some different contexts. You’ve been in proper pure tech where what you were building was the product to sell. You’ve worked in civic tech where you’re creating software and systems to help people engage with governmental services.

From what I’ve seen, design and user experience people tend to show up and do pretty much the same things kind of regardless of context. But product people don’t, product people are very much more needing to adapt to whatever their contexts are. And I’m wondering for you how that’s borne out, how do you show up differently when you are working at, 18F than when you were working in Silicon Valley tech than when you’re working now in this kind of maybe hybrid.

And I say this because I find that conversation, particularly in places like LinkedIn, people start talking past one another because, you know, if you read Lenny’s Newsletter, everything is the height of Silicon Valley tech product. But in my experience, 95% of the people doing product aren’t in environments like that.

Christian: Yeah. Not all tech is that. I mean, when I was at 18F, one of the things I was doing was bringing in product speakers and UX speakers, you know, but for my product team, and so John Cutler is one of the people who came and spoke to us.

It was a lot of fun. And he came up with something for us, you know, where he didn’t just go, I’m gonna give you talk number 99. I wrote three talks this week. And, you know, you’re gonna get one of them, whatever.

Peter: John’s output, he is probably writing a talk right now.

Christian: I know. Talk about like, just working with your brain chemistry, you know, like, letting it do what it wants to do. John, it’s so awesome.

And we talked about it and I was like, well what is my team anxious about? What does my team feel? In the public sector you’re like, am I falling behind the private sector? Is the stuff I’m doing gonna be hard to sell if I ever wanna work in the private sector again? Am I not doing the hip cool stuff?

I keep hearing that, you know, in Silicon Valley they now have like donut teams or something and we don’t have them, you know, something like that. And, made a very similar point that like there’s this fixation, the newsiness of like the 5% of tech that’s done in a pure tech and VC, which is just a name for a kind of banking you know, funded tech that has to drive profits in this 10x way.

And that becomes like the model for how all tech should be done in a way that’s super unrealistic. And the story is often that, look, the private sector’s like this and the public sector’s like this, and you’re comparing a little startup that is like gonna break laws because they’re gonna lobby to change the laws if they ever get successful or it won’t matter ’cause they were outta business anyway. And they’re not gonna have HR and they’re not gonna do anything by the book, ’cause they’re just trying to move fast and break things or whatever.

And I’m sure that’s fun. I’ve been adjacent to that world.

And then you’re like, but then look at this sclerotic public sector thing that’s so complicated and slow, but you’re not comparing GE and the government or Procter and Gamble and the government, you know, or, a large health or pharmaceutical concern and the government.

And if you do, they’re way more like each other than either of them are like a Silicon Valley startup. They have regulation, they have lawyers, they have HR, they have compliance, they have sunk costs, they have very complex system.

It’s super fun to make… Look, I know we’re gonna talk about my my hobby project and it’s super fun to make a thing that does not have dependencies. You know, everybody likes to make the new thing, but most useful stuff has to plug into the existing things and they are complicated.

Creating a robot product management associate

Jesse: So you mentioned your hobby project and, yeah, you know, a lot of this stuff is in flux for all of us right now. Especially as new technologies are shifting the way that we look at product development, the way that we look at our roles relative to product development. And you have recently been documenting some work of your own as you’ve been working with AI.

Basically, I mean, I don’t want to put words in your mouth, but it feels to me like you’re trying to build a robot product manager.

Christian: Kind of yeah.

Peter: So you’re trying take product management jobs.

You’re trying to make it so that there’s no room for entry level product managers.

Christian: That’s right. I’m, trying to eliminate those people.

Peter: All these Stanford grads, what are they gonna do now?

Christian: Yeah, and I always like to say that I would rather have an actual human intern or apprentice when I can do that and have people who are quite junior and eager to learn and have broad knowledge, but not specific knowledge, that’s a great kind of person to have on the team, even if just for a summer, and not to trivialize it, but it can be like, go through all our documents and clean them up or make suggestions or like, look at all these long tail of things we kind of have been wanting to do and also shadow these projects and learn and help us formalize our processes better.

You know, there’s all kinds of things that a smart intern can do who doesn’t have to have too much domain knowledge or discretion. Even, like, make a lot of copies of this template and then bring it back and let me see if you did it right can be a good use of an intern’s time, but not a good use of your highly paid staffer who has to bill out or whatever, something like that.

So I don’t have an intern right now or anything, but I was like, my sense of like most people who’ve dabbled in chat-oriented gen AI or LLM type stuff is that, you know, it’s ongoing, but it’s sort of ephemeral and it’s not really focused on your stuff or your priorities.

If it learns about you, it’s usually in a creepy way that’s accruing value to the company, but not in any way that you own or have any mastery of, and ownership of it. And I started to learn a little bit, like most folks, you know, in our field about this, and I should not jump past the part where like a lot of, I think, our colleagues, particularly in the UX world, but in tech in general or in the world in general, I have a lot of qualms about the way this type of AI is being marketed and rolled out and sort of virally engaging people.

You know, when you talk about all how many customers OpenAI has and what a great platform it is, et cetera, et cetera, it just feels like Facebook again, like another everything thing that everybody’s in, but isn’t necessarily the healthy or good way to do that stuff, where that’s just the end in itself to get the engagement.

I worked in mental health, worked for a mental health startup for four years. And we used a natural language NLP-based chatbot at the time. So sort of at least one generation less sophisticated than the LLM chats we use now.

But we put a lot of thought and concern into making sure the chatbot didn’t misrepresent itself as a person or, say something terribly inappropriate, you know?

And it’s not easy and not trivial to do that. So from my point of view, I thought, how could I have something that’s actually, I have some control over what it knows, what it cares about, what its priorities are in a persistent way.

And I began to understand that when I was 18F where I knew some folsks over at 10x, which is another part of the technology transformation service in GSA, in the government where I was, that was more like a kind of Google X type incubator or a place where anybody in the government should say, Hey, we should do something, something like a suggestion box and they could take it on and run a, prototype, or you see if they could get it off the ground.

And they were of course doing AI experiments, some of which have now launched as like GSAI or USAI and things like that.

And typically what you do nowadays is you set up something like a sandbox, particularly if you’re in government, have to deal with PII or other kinds of, you know, sensitive information back when they cared about that kind of thing.

You wanna make sure that you’re not putting that stuff just in the public machine or into Google or into OpenAI’s databases, you have to have a sandbox that makes API calls and can engage, but has rules about what can pass through one way or the other, and things like that.

And so I began to understand that you can make software that uses these tools more programmatically that’s different from, say, just chatting with something and getting advice from time to time in some ongoing way.

And I was like, I wonder if I can maybe make this little kind of intern. What I think of it as like a product apprentice who wants to be hired as an associate. So they’re trying to do a good job, and as they learn to do things that get more sophisticated, maybe they can become an entry level product manager or a PO, maybe they can eventually become more senior.

And then we can of course, abstract ourselves up to higher levels of the work. But even if they could just like generate a bunch of draft GitHub tickets from me or review tickets, see if they’re thorough enough, like, I was, like, that would help. So it just became this thought experiment at first.

And I, you know, started by chatting with the chatbots and saying, how can I do this? What would be involved? And they recommended a stack, a model for doing it and, yeah, I think it was Gemini or one of those tools at first gave me like, here’s a whole bunch of Python files. Here it is, you know.

And I installed them and it was basically just a proof of concept. Like it was a little machine that could call out to an LLM and had a couple canned files, A PRD, a spec, a GitHub issue or something like that. And had like two or three canned queries.

And it did a good job of analyzing the doc or critiquing the issue or making a new issue from the thing. So it proved, but in this very canned way, that such things are possible. That got me like, oh, this is cool, you know, so I started saying, like, well, you know, like, let’s, go beyond the canned stuff.

Can I give it some real docs or can I ask it some real questions? And it was like, sure. You know, they’re always like, yes. Yeah. I call that the rocket to Mars anti-pattern. Like, can I make a rocket to Mars? It’s like, yeah, go to Home Depot and get a big pipe and some dynamite, like something to cap it on one end and we’re going to Mars tomorrow, you know?

So you get a lot of this Yes energy and I started hacking away at it and I got it to the point that I had a UI on it and I could upload contextual docs and I was having it, like, draft or critique actual tickets that I could use in my work in a minimal way. Like still in a, basically like barely, like I’m putting more energy into it than I’m getting out kind of way. But kind of exciting.

But it also started getting, like most things that are vibe coded, it got very spaghetti-ish. It was mixing the different projects. It wasn’t really that clear on what was what part of it was hacked together or mocked, or just like, it wasn’t architectural.

And this is why I started to feel like the shame, the chagrin of a late career practitioner who’s doing everything the wrong way. And like all of my red flags should have been going off.

Like, you’re just building it. You haven’t done any research, you haven’t like talked any users, you haven’t done any design yet. You know, you’re just like YOLOing off a cliff. That’s how you make software. Like, I knew it was wrong.

Jesse: Well, what, how do you respond to that in your own mind? how do you, how do you, you

Peter: And does it involve two sock puppets talking to each other?

Working with AI Tools

Christian: Well, I mean, part of me was, like, oh, this is going nowhere. I mean, I think the way I always do when I’m working and something stops and I realize, oh, you know, I made a mistake. Like I shouldn’t have done it this way or that’s tapped out. Like, we’re getting diminishing returns on this approach. What are we doing wrong? Like that’s, kind of my life, on some meta level.

I mean, that’s probably the thing that keeps coming off of this is that I’m learning stuff about orchestrating and working with AI and I’ve gotten lot further than what we just left off.

But it’s this constant learning curve and 99% of it is stuff I kind of already knew from just working with the other kinds of things that use language that I know called people like, because they’re the same byways, you know, like the language is the whole channel. It’s the carrier of everything that’s happening, is this language layer now.

And by the way, this is, if you’re a UX person and have the ethical qualms I think we all have about the way it’s being done and the challenges around that, I think it’s still impossible not t o be fascinated by this HCI layer, this human computer interface that is so much more language rich and language parsing than before.

And, you don’t have to anthropomorphize it at all to say the manipulation of language has always been an extension of our thinking in our minds.

And it’s now like outboard as well. I mean, if you remember, it’s all you, you know, you at plus generic everything, but like the only personality is coming from you and you don’t start to think it’s a ghost in the machine.

There are some super interesting ways to like, engage with that and to think about what happens now when like, you’re operating computers, but there’s another computer kind of in between that is operating the computer for you, but helping you, figure out what you want to do.

It’s another paradigm. It’s another layer, you know that wasn’t there before, not in any meaningful way.

Jesse: In what way would you say you were doing design work in this process?

From vibe coding to something realer

Christian: I mean, I’d say that up to that point I wasn’t doing design work except the thing that I think is actually not a bad thing that goes on in a lot of vibe coding today, which is like bespoke personal custom design.

I just need a little database to keep track of my jogs. You know, I’m shopping for lamps and I need a little lamp optimizing app, you know, whenever.

And, that stuff I think is cool as long as you don’t like try to productize it and then leak everybody’s social security number with your janky backend,’cause you don’t know anything about software. Like, that’s bad.

But that idea that you can whip something up and it just works. That’s super cool. It’s like macros, like anything like that, that’s fun.

But if you wanna do it for a living or professionally or seriously, that’s not the right way to do something.

It’s a nice way to prototype of something, prove the concept. That’s all good.

So that was the point where I said I need to take a step back. But even so, I was still thinking about technical design. I still wasn’t thinking like a UX designer yet. And so partly, ’cause I was thinking this is just for me, you know, it was, number one, a learning project.

I was doing it partly to learn and then I realized about three or four weeks into it that I can also share this with other people. And that’s gonna be a very interesting layer of what I’m doing, too.

And then I thought like third level success would be, this even works for me at all.

And then like fourth level success would be I could productize it. Yeah. I could generalize it for other people, you know, but like, that would be really great.

And along the way I think I started figuring out some things about how to work methodology stuff that’s starting to maybe be potentially more valuable than any product that I could make if true. But you know, I mean if what I’m learning is actually valid, it’s always this question with bots until I see the final proof.

And that’s why I’m always suspicious saying, well, what you’re learning about process is more important than what you’re making because I’m a product person. And I’m like, well, if the thing I’m making never actually turns out to happen or be good, then how do we know my process is good?

Peter: Right. Are you doing this solo or are you collaborating with anyone that isn’t code?

Christian: There’s no other human contributing to this project yet. I have one or two people who agreed to do alpha testing, which I’m trying to get to maybe next month or so. I hate to put time frames on things, I’m usually wrong.

And, another person a person from our world reached out to me recently and said, Hey, I’d, like to kind of copy what you’re doing, maybe even clone your thing. You know, just for myself is that okay? Are you looking for contributors, whatever? And like, we’re having lunch next week. ’cause I, you know, I’d love to have people help me.

Peter: But at this point it’s you.

Christian: It’s me and all these bots. I slip into this first person plural a lot, but it’s me and some bots.

Peter: Yeah, Reading, your, I don’t know what you call it. A blog,

Christian: Newsletter, blog. It’s a blog.

Jesse: Development journal.

Peter: Documenting this experience. You do refer to others, but I figured they were all…

Christian: They’re all roles, they’re all like defined roles that, at least in my process, help separate concerns and kind of focus different conversations or decision making streams.

Peter: Well, and, you started by just hashing it out with an LLM for a while until you got something that proved out a bit of the concept, but then you realized was not workable because it was spaghetti.

Christian: Yeah. I literally said like, Hey, aren’t we just trying to turn a GitHub machine into like a smart agent? And it’s like, yeah, you’re right. That’s what we’re doing. That’s wrong. We shouldn’t do that. You know? So like,

The complexity of what appears to be simple software

Peter: Well what I noticed, and I can’t say I’ve read your entire corpus of work ’cause there’s a lot there, but the amount you’re talking about architecture for something that still seems relatively simple as a piece of software.

Maybe I’m not understanding it, but, right, this is a hobby project. It’s trying to do a fairly straightforward thing, and pretty evidently you need to be thinking architecturally to a degree.

That kind of surprised me as someone, I think all three of us, right? We all have information architecture backgrounds, so maybe I shouldn’t be surprised, but I was surprised how quickly you need to get into architectural thinking, even for something simple.

And I’m curious kind of what your experience was in realizing that and now practicing that.

Christian: Yeah, I mean, I think I have to qualify a little bit of that. First of all, what I’m making is not simple. I mean, it may sound simple, like if it works, it’ll seem simple, but it’s definitely under the hood, not simple. And I think there’s simpler things one could do. All right. I mean, the simpler version of this stuff I already do.

I’m like, I have a Claude chat and I’m like here’s all my meeting notes. Write me up like a weekly report. I’m already doing that kind of stuff. I don’t need like a custom piece of software for that.

There’s like one product I’m aware of for product managers out there already that’s an AI product. It’s called Chat-PRD.

My understanding is it’s a ChatGPT wrapper, essentially, like a lot of products, but a with some custom harness to be… that knows what a PRD is, and so like if you’re gonna be already using that kind of tool and this is your job, that’s a smart kind of product to exist.

And I think that if Piper Morgan, like, meets its goals it’s not gonna be that kind of tool essentially. It may even just be like, yeah, I’m gonna go use the chat PRD model context protocol and make one for you, ’cause I don’t need to specialize in that.

Like the ecosystem already has a thing for that. That’s more behind my mental model. I, think I’ve been working in platforms for too long, you know, so everything becomes a platform in my mind right away, and a microservice, even though it’s got no users and barely any functions yet.

But, so first of all, I think, yeah, I think the complexity is often really there. If you’re gonna make anything, I mean, it’s a hobby project, but it’s a hobby project in, “could I make software that’s really safe, that’s really ethical,” I mean, which is another interesting side note, that could be used but actually not, like break your bank spending LLM token costs or all these things are like making it real in our world, involves a lot of dimensions. It is complex.

And, yeah, I started off with a kind of, I didn’t know where it was gonna go. I don’t think there’s anything wrong with sketching an idea. Getting excited about it and then going, well, whoa, this approach needs some stopping and thinking. I think that’s a very healthy, organic way that a project evolves.

And, you know, there was a phase then where it then became architectural design. In my mind it was like, what’s the right way to build this? And I was asking tools that are more trained on how engineers think than how designers think. Although you can say you’re a, you’re a unicorn UX designer, like, I have a chat helping me design the website that like, is trying to think more like a designer, but one that can code too, you know? Of course. Why not?

And I did this thing where I asked a couple of this… models that were reputed to be smarter. Like, what is the right way to do this? Like, if you’re gonna do this seriously, how, ought you to do it? And they agreed on a couple of things like strict domain models, domain driven design, sort of defining the concepts that go with product management.

And this is where it’s like an IA type of thing, you know, where you’re saying product managers think they have projects, they work on products, they have tasks, they have roles…

Peter: …you have like a data or content model

Christian: Exactly, and, you define them in a layer that is separate from the database layer and certainly separate from any of the integration or orchestration or anything like that.

And you try not to mix concerns. And a lot of my early learnings, because I’m not an engineer or a technical architect, I now had one on demand. I can’t hassle the engineers I work with. I’ve had to learn all my tech by osmosis, by like just listening when they talk and everything all these years ’cause they’re too busy.

But, you know, occasionally people have explained stuff to me, obviously, but I mean, I can endlessly go, like, because it was a learning project, I’d say, well, why, why are we doing that? Why would you wanna do it that… and anytime they’re like, what do you wanna do? This idea or the two other options? ‘Cause I always have to give you two bad options after every good option or whatever.

And if I’m not sure, it’s usually do one or no, do two. Sometimes I’m like, well, for option three, what are the pros and cons? Like, I’m a product manager, I don’t know stuff. You just have to tell me like what’s the good or bad aspects of each choice.

And then it’ll be, oh, good question. And it’ll lay it out.

But I was still lazy about it early on. I was really like, how much can I do without fully paying attention?

And one lesson was, you have to pay attention. You can’t, you know, like the self-driving car, you know, no, still can’t tell a white van from the road or whatever. So you gotta watch.

And the other thing was that, I was still like triangulating rather than being really intentional.

And I got two good plans and then I got a third smart thing to do the Hegelian synthesis and come up with an Uber plan.

And then I just started trying to do it and, you know, it was quite a while, I mean, probably a month or two in before I even said, but I haven’t thought about the UX of this at all. I’m totally not doing this right, you know?

And I’ve even have a concept in my, you know, the semantic universe I’m creating with these assistants that we used to label patterns and concepts and things, that there’s this spiral where like after a while I started to learn the same kinds of things over and over again, but always at some higher level of abstraction or slower pace layer or something where it’s like, oh, I need to write stuff down.

Oh, I need to always write stuff down. Oh, I need to have them write it down. Oh, I need to have them read what they wrote down. Oh, I, you know, and then you do that and you’re like, oh, I need to automate that.

And then you’re like, oh, I need to check it. It doesn’t have errors. You know, it’s like there’s always this like level of like backing up and going, alright, now the chaos is crept in at the next level and I need to now put processes in place to like make that less prone to be me lazy, or the bots cheating or anything else.

Jesse: This sort of iterative entropy control.

Christian: Yeah. And so I always agree. It’s like I’m trying, the chaos will never be gone. I’m trying to like get it fractally down to like, oh, the documents aren’t perfect, you know? Not like, oh, the code is only 70% written.

Wisdom for those just starting out with AI

Jesse: Right. You’ve talked a little bit about how your career experiences have informed the way that you’re engaging with this project and I think that for a lot of people who’ve been in this business for a long time, all this AI stuff came up and it was like, Oh man. Not another thing. Like it was gonna be like NFTs all over again, right?

Yeah, exactly. And trying to figure out, like everybody telling you that this thing is relevant, but you can’t necessarily see the connection. The people who are selling it to you don’t really seem to understand where you are coming from.

And for a lot of people, I think especially, you know, people who are less technologically sort of inclined, they tend to kind of bounce off of it and go, you know what? I’ve got design processes that I’ve been working on for the last 25 years. They are working great for me. I don’t see a reason to change.

Christian: Yeah.

Jesse: And there is this unwillingness to engage with this stuff. And I’m curious about your, I don’t know, advice or perspective for those folks who are kind of standing on the other side of this going like, everybody’s telling me that this thing is coming, but I don’t know how to think about it or engage with it as a creative professional.

Christian: Yeah, I’ve thought about this a lot. It’s definitely what drove me into writing this thing and, not coincidentally, I’d say four or five people who are more or less peers of ours, roughly from the same cohort we came up in, have reached out to me personally at some time or another to thank me for doing it,to say that they’re now trying something themselves.

You know, it’s not just to inspire people. I try to show like, if you’ve read any of the voluminous blog posts, often there are tales of like, Hey, that thing I reported being done, it’s totally not, it’s broken. I was an idiot.

It’s like, there’s lots of like warts in all. Like, ‘ cause I don’t want to be one of those people who’s, like, the best way to make a prompt, you know, like, I figured out.

You know, it’s, it’s like, no, this stuff is, like, new, weird, like, it’s the view source era. I think Christina Wodtke has sort of pointed out that there’s this vibe that feels very nineties-ish to some of us.

I think there’s two ways in which, sophisticated mature practitioners of UX might want to think about whether they should or shouldn’t engage with this technology or to what extent they do or don’t need to do it.

And I think one was the level I think you spoke about of, like, I don’t need it in my tool stack. I don’t need some Figma thing telling me how to lay out my page that doesn’t understand my design system that well anyway. You know, it’s more work than not to fix it.

All the stuff you hear from programmers, like it’s watching the bot is more work and more boring than writing the code. You know, things like that.

And I think that’s legit. Like, I don’t necessarily trust everybody’s pasting AI into their toolkits right now, you know, everything like that.

But I think the other thing, like, I hinted at before is, like, a layer of, the human computer interface, it desperately needs ux people.

Like, chatbots and, like, wrappers around LLMs is not a user experience, does not a user experience make, you know, like there’s plenty of work to be done figuring out how this kind of technology ought to be part of the orchestrated experience we have with all the other kinds of technology that we use.

If that isn’t UX or service design or the broader thing that we all are into, I don’t know what is.

Having said that, I get the qualms about it, you know, I’ll out myself as being old enough that I can remember conversations with the people who were towards the end of their careers when I was entering the workforce, who basically were reluctant to adopt the personal computers.

They didn’t want a computer on their desk. They’re like, I’m gonna be retired before this is a thing. I don’t wanna have to learn how to use DOS or whatever. And if they weren’t really, like, 63, they were wrong, like two years later, they had a PC on their desk and like for the next 10 years of their career, they were typing on a PC, whether they liked it or not.

And I think, a lot of us are doing the same thing with the AI thing. Where, when I was still working for the state of California two or three years ago for Office of Data and Innovation that was running a product unit, the service innovation team we called it, but it was essentially a product unit that had designers, engineers, and product managers on it.

And Gen AI started to explode and the governor was very interested in us being forward on it. And I think intelligently trying to like leapfrog a bit, you know, like, that thing where, hey, there’s a new tech. Rather than being 10 years behind industry, why don’t we in the public sector look into it right now, you know, on our own.

But that sort of meant everything became Gen AI. It’s like, stop what you’re doing. You’re on the Gen AI task force, you know, or things like that.

And I told the very good PM who’s like earlier in her career than I am, that you’re gonna be our AI PM. Like, you go to those meetings, you are gonna be on the task force.

And there was an element of like, I thought she’s got 30 more years in her career. Like this is gonna be a big part of the rest of her career. She ought to get in on it right now. But I was also like, eh, I think I’ll sit back and let the kids figure this one out. Like, I don’t know if I need to really master AI.

I’ve got 10 years myself and I could probably like, wind it up on what I do, you know, and fast forward two, three years later and I’m like, my daily blog about my AI project, you know, so it’s like, like it caught up with me like everybody else, you know, on some level.

And then another friend of mine who I think took a sabbatical, took a break from his work, started playing around with vibe coding, in a less technical way than me, like not interested in looking at the code, doing Lovable, making tools for himself and things like that.

And he was telling me how exciting it was that he could do this, this guy actually worked at LinkedIn and he was saying how LinkedIn has been full for the last year about you gotta get AI skills and all these like experts who are got AI in their title for the last 20 years apparently, and they’re all experts on the very latest AI and they got the best prompts and all the news and everything like that.

And he said, he realized like, oh, all you need to do is like be laid off for six weeks and dabble around and you’ll be like one of the foremost experts in Gen AI. Like, if you think you’re behind, you can’t be behind. Certainly not with the latest models or the coolest new thing because it’s like there’s no time to get behind.

Like you’re not behind. Anytime you start now you’re pretty up to date and all you, and all you need is like, be underemployed or, get laid off or whatever and just like need to spend some time really getting into it and suddenly you’ll… So I’m not recommending getting laid off, but I’m saying that, that sort of view source thing where you’re like, you can at least with the coding-oriented stuff I’m doing–and, a lot of people don’t wanna code as much as I felt like this was like re-empowering me after being abstracted away from the code for so long, I know that’s not everybody’s vibe–but the way it extended or bridged a gap and brought some project I wanted to do, a passion project, into, like being real.

I think that versions of that are happening for a lot of people and it’s been a way for me to explore the texture of the material, to understand it as a material that you work with. And it’s slippery, it’s squirmy, a lot of what I’m learning about orchestrating this stuff is that it’s 80, 90% all the stuff we always ever did with software.

But then some of those API calls or some of those subroutines go to an LLM or go to some other much more volatile, chaotic thing that is quote unquote creative and can do this new stuff, but is error prone. It might not return well structured JSON, so you might have to filter it correctly before, you know, trying to interpret it.

So you actually put these little beasts in cages. You’re like, oh, you demon, I’m gonna, like, put you in this box and you can only admit JSON, whatever crazy ideas you have, you know, whatever. So it’s like, but it’s an interesting idea that you can sort of put these little things that might be a little bit toxic or wild, but at the same time, sparking these abilities that didn’t use to exist.

It’s quite, it feels like magic sometimes. It feels quite wild. And if you like language like I do, it’s quite an interesting playing field if you don’t lose your point of view and start to, you know, kind of get mystical about stuff that isn’t mystical.

Applying your hobby to your day job

Peter: You mentioned how Piper Morgan is a personal hobby project, but you do have a proper job. And I’m wondering how you are using these types of tools in that context. If you’re collaborating with colleagues and how what you’re learning in Piper Morgan is informing how you’re showing up with these tools within your quote unquote day job.

Christian: Yeah. it’s a good question. For one thing, I call it a hobby project, partly because the software, as I said, could never launch. And the overall learning project will have been a success, let’s say. So I don’t wanna set too high expectations for the code base, but it is serious.

I’m taking it seriously and spending a lot of time on it. I’d say it’s something like a 10% time project, you know, like, that kind of Googly idea of like, it’s something that I do partly with the marginal time I can make available from my work serving, you know, the VA and also having some slack time in one week in the average week.

And then I am honestly putting in some of my personal time as well because it’s an obsession and it’s very fun and I get obsessed with trying to like, achieve certain finishings and things like that. So I’m like, I’m gonna keep working after dinner, or, you know it reminds me of other creative projects I’ve done, you know, where you just wanna do it. It’s more fun than other stuff you’re doing and you’re interested in the next step.

But along the way I’ve definitely learned things. So at Kind, we have a Robot Overlord Slack channel where we talk about the use of LLMs and other kinds of AI technology. That Open Laws product that we make is not AI-derived because you don’t wanna be like pulling fiction, hallucinated stuff in the code, but obviously a large data source that could be accessed by API or bought in bulk is a input to other people’s AI layers on top.

And there’s interesting things where like their search isn’t very good, so you might want to help them search better, but you don’t wanna see their PII ’cause they’re a law firm. So how can you have a layer that is anonymized at your end, but is kind of a product for them that helps make their searches? That’s an interesting product problem for me.

Like as a product person, a product manager who wants to bring a thing that mostly has enterprise technical clients right now, a little closer to like a consumer facing or professional facing tool.

That’s where my R & D work, let’s call it, in a business sense building Piper Morgan is helping me think through potential architectures that we might want to explore in our own product. And also while I’m not an engineer, most of the people at KIND are engineers, and so they’re all like all engineers grappling with how to use these tools in a way that doesn’t suck more time than it gives and things like that.

And so not everything I learned is applicable, ’cause again, I’m working in my own little sandbox and I don’t have to like, follow the VA’s rules for committing pull requests and things like that. So I, can’t just say, just do it this way, if, like, their environment can’t look like my bespoke environment.

But I think I am trying to draw larger lessons.

Like, for instance, there’s this concept that technical architects or engineers have called an ADR, an architectural decision record. Which is just a document that you kind of organize, you keep track of, this is why we decided to use a singleton pattern when we implemented da, da, da da.

So later on when you’re like, oh, why do we do that? You know, like, it’s not well commented in the code where you look it up. It turns out things like that are really good

Show Notes

Figma’s Head of Insights Andrew Hogan joins Peter and Jesse to explore emerging trends in design practice as AI transforms creative workflows. The conversation examines how role boundaries are blurring across product teams, where AI delivers real value versus hype, and design’s growing opportunity to lead strategic orchestration in increasingly complex digital experiences.

Find Andrew on LinkedIn at https://www.linkedin.com/in/ahhogan/.
Learn more about Jesse James Garrett and his coaching and consulting at https://jessejamesgarrett.com/
Learn more about Peter Merholz and his digital book “Design Org Dimensions” at https://petermerholz.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, design industry analyst and head of insights for Figma Andrew Hogan joins us to talk about just why Figma needs an industry analyst anyway, how he drives business impact as a researcher and key findings from his research on what’s changing about design and what isn’t with the advent of AI.

Peter: Andrew, thank you so much for joining us.

Andrew: Thanks for having me. Super excited to be on.

Peter: Awesome. So gonna start start with a softball, which is just like, well, you’ve got an interesting role at Figma. Head of Insights, I think is the title. What do you do?

What Does a Head of Insights Do?

Andrew: Thanks for this one. I don’t know if that’s a softball to be honest, but, my job is essentially to analyze the industry, the design industry, what’s happening, where is it going, what sorts of trends are going on. We do that through a lot of different means, whether it’s looking at our product research, whether it’s looking at, big state of design, state of the designer surveys, state of AI and design, a lot of states of, and then to figure out how to get that out in the world so that people have a view of what’s going on.

And so that Figma has a view of what’s going on because you always wanna design for like, the next biggest space, right? You’re designing for the world that you’re in and maybe where the world is going. So my job is to make that work better internally, working with our research team and share that out externally so that people can sort of see and plan and think a little bit with some different kinds of data that are maybe outside of their day-to-day experience.

Jesse: How do the questions that you pursue differ from what a typical UX research team might be taking on?

Andrew: I think ideally they’re extensions of each other. So, let’s take like AI. Obviously Figma wants to know, how are people thinking about AI? What are they finding value in? What do they want to be able to do? And then also, how prevalent is the usage? How might that compare to how across developers, designers, product managers are using AI?

But I don’t think there’s a huge amount of daylight there. Often it’s taking a slightly broader view than like, did people find value in this specific feature? But again, really good experienced researchers, they’re doing that, they’re thinking about it that way.

Peter: Some of what you do could be also considered market research, and I don’t know if it falls under that, Jesse mentioned UX research or if it’s a different kind of research, but I’m also intrigued… you mentioned how the value of the work you’re doing is for Figma as well as for the community.

But if you could share, I’m curious what insights you’ve had or that you’ve helped uncover that have informed what Figma has launched? Are there any through lines between anything you’ve worked on and, something that people have had a chance to use because your insight pointed out an opportunity?

Andrew: Sure. I mean, so there’s a lot of parallels here with what I did at Forrester before, which is where I was for seven years as an industry analyst. You’re always looking at the direction of, people are excited about, where they’re going, what they’re spending more energy on, what they’re spending less.

So I can’t give like a specific feature or anything, but certainly like one of the things we look at is, people feel like they’re a lot more efficient when they’re using AI in their design process, but they don’t always feel like it’s getting better, they’re doing better work. And so we think a lot about the tension between those kinds of things.

And so you can imagine the sorts of features that might lead to efficiency versus the sorts of features that might make people feel like their work is getting better. And so that’s a trend we’re looking at,we’re tracking over time.

And then, ultimately looking to do both, right? You want to help more people to be able to participate in the design process, and then you also wanna be able to make experts faster, better, all of those kinds of things.

Peter: You’re operating in an enterprise software context, which I think people in the design community often forget, right? Like, they just think of it as a design tool, but really you’re enterprise software. Is a role like yours typical in enterprise software? ‘Cause it’s curious to me that Figma would want to have a Forrester style analyst in-house, like, as opposed to just, partnering with Forrester or something like that.

What’s the logic or the intent of bringing that in-house?

Andrew: I mean, you get certainly lots of benefits in terms of day-to-day conversations, right? For like a Forester or an IDC or a Gartner, you have these very like specific engagements and you’re always thinking about exactly what to share and how to share it.

And I think we all would like to believe that those things are free and open, but the reality is you’re kind of always thinking it through, and in-house you can kind of just say like, Hey, are you just seeing this?

It’s a quick Slack and I think that’s the kind of benefit. And then you also have this benefit of, there’s sort of this context that I know about when it’s comes to like, future roadmaps or company strategy, that we can think about when we are designing studies.

Because you often need to have a really long view. And so the ability to partner with our research team and take a long view while also getting answers in the near term and then helping people who are thinking about where should their career grow? What sorts of skills should they try to pick up? If they’re leading a team, what sorts of skills should they encourage people to go do?

Or sometimes I think about it as like, filling out the strategy slides. That’s a sort of a glib way of saying it. You know, here’s the direction that we’re going.

You can often partner with customers to help them sort of fill out the strategy slides because they need to justify why they’re going in a particular direction. And, previously they might have only been able to engage with like a Gartner or only gotten like a Figma product perspective.

And there’s just a little bit more space and data to share. There’s like a broader view that I think you can offer. And obviously it’s a Figma view. I work at Figma. Like, it’s a very specific perspective, but I think people tend to find the triangulation of those perspectives to be helpful.

And I’m sure they take some of it, I’m sure they throw some of it away. But it can be kind of lonely trying to make these decisions and this role offers both inside Figma and outside Figma, like another view. And I think that’s what’s useful.

Then you still go to Gartner. You still go to Forrester, or you still go to IDC. None of those things go away. It’s just one more lens.

Jesse: It’s interesting to think about the investment in your role as really being an investment in supporting the decision making of leaders across Figma, really, because of that vantage point that you bring and that perspective, which is like standing just slightly outside the organization, right?

And I wonder what is the tension between your role as you talk about, like, having a value proposition that is both inside Figma and outside Figma, and what is your role as kind of being the person on the edge who’s gonna bring new things into the organization that maybe aren’t even things that people were asking for?

Agent of Osmosis

Andrew: Yeah, I am always trying to be like an agent of osmosis for information out, information in. You both have given me feedback and shared perspectives that I’ve brought in. That’s always the goal. You facilitate information sharing. And that’s a pretty helpful spot to be in. And it isn’t just helping people at Figma. It’s helping leaders outside of Figma. And I think that’s the unique part. So, often, “Hey, did you see this comment? These people are having this issue. I heard this discussion from somebody at a dinner. Like what do we think about that?”

And it’s a privilege to do that. And also like a big responsibility too, because when somebody tells you those things, that means they’re fired up enough to tell you this is something that they’re thinking about and they want someone at Figma to get back to them. They want someone at Figma to think about it more.

And so sometimes that’s the kind of position that I’m in. And frankly, a lot of people at Figma have those sorts of roles. It’s extremely customer centric in terms of taking feedback, thinking about it, acting on it, and just taking it really seriously.

And so, in that sense, it’s not so different from the other jobs, it’s just a slightly bigger spot. And then, the advantage of having a lot of other data to work with is that you can kind of triangulate: this is something that seems really common; this seems like an uncommon thing, but maybe there’s something else going on at this organization.

And we’re always trying to do that. And then again, the ability to bring things out that maybe people outside of Figma are not thinking as much about, or people outside of the design world.

I think design sort of takes for granted the idea that design is a differentiator for AI. But I don’t know whether the rest of the world always understands that the ability to whip up a screen really fast is not the entirety of design. That’s not it.

And so sometimes helping people understand, oh, it’s also about the information architecture. It’s also about the transitions between screens. It’s also about the fundamental value proposition of it. And so this role can kind of help us do that too. That’s the goal, right? You’re always trying to do these things better, but that’s sort of the goal of it.

Value propositions for design

Jesse: You touched on the notion of differing value propositions for design, and we’ve, in our previous conversations on the show, have talked about the way in which the impact of AI in particular is really a function of whatever that value proposition is for design within an organization.

And I’m wondering about what you are seeing in terms of the range of value propositions for design that are even out there right now. Because in my work as a leadership coach, I hear from leaders who come from a really, it feels to me, like a broad range of different, positions in terms of how the value proposition of design is a function, and therefore their value proposition as a design leader, is perceived in their organizations. And I wonder just kind of taking the broad view before we even get into how AI impacts all of it, what are you seeing from your vantage point there?

Andrew: So when people say design, right underneath that is like brand, visual design, information architecture, interaction, and I think that also broadly separates into like, marketing and brand design and then like digital product design. And definitely within organizations, you might differentiate based on something different within those different spheres.

But I also think that outside of design, not many people think about it that way. And so there is some like risk and danger in sort of like slicing it too thin, the different ways of differentiating. But the thing that you seem to have touched on there is also that it’s like part of the strategic value of the organization or the strategic set of choices.

And, hey, we’re gonna invest in being the best retail logistics, and we’re gonna do an amazing job at that. And we’re gonna design all of our internal software to facilitate incredible logistics. None of that sounds exciting. And yet there are some incredible businesses that create great experiences that are focused on that kind of thing.

And I think what’s really interesting right now is that more leaders are recognizing that that is how you do it. You don’t do it by generating a screen. You do it by thinking about how are we gonna use this to, like, support our strategic decision making and create software that’s incredible for helping us on whatever our competitive advantage is.

And so they do align. And what has been interesting to me is the degree to which outside of design that kind of isn’t… I don’t know… That… that recognition is not always there. And the idea that design is the differentiator is exciting to people. And then you sort of get down to it and you’re like, exactly how are we gonna do this? And what are we gonna do?

And then that’s where the job of the design leader is to say, “Hey, we should really align on this thing because strategically this is where we need to be as an organization.” And that seems like a big opportunity that more and more leaders can step into. That has been an interesting trend as well, because it’s not just about how the screen looks, it’s also like how helpful is it towards the goals?

Peter: I wanna reflect on what I’ve witnessed in terms of Figma’s relationship to design and how it might speak to some of these trends that we’re talking about, right? So Figma launches, it’s very much a design tool. It’s talked about as a design tool.

But then as Figma becomes more powerful, Figma is seen as a means by which designers can better collaborate and interact with non-designers, right? So product people, engineers, reduce the amount of coordination necessary for handoffs, and other kinds of just alignment.

You know in 24, Config was interesting in this regard. So Config, the annual conference, because in 24, Figma seemed to be positioning itself… on the tote bag, I think it read “for people who build products,” right? It kind of was moving away from a designer specific space, and I got the sense it was because it saw itself as part of a dialogue around product development, and design is part of that, but not, the only voice.

In 25, this past year, Figma seemed to go all in on actually no, we’re for designers and all the new tools and everything was, was really about design capability. I found that curious, and I suspect it has something to do with AI and maybe the way that AI is affecting role definition within product development environments, and like leaning more into like design as this activity actually makes sense again, with AI providing a different kind of power, a different kind of agency or capability for the people using the tool.

That was a long question with some threads in there, but, but I’m curious like how that relationship between Figma, at least the commentary, the positioning Figma as a design tool, as a product tool, as a design tool reflects some evolution that we’re seeing in design and design practice.

Design is everyone’s business

Andrew: So the two things I would say is that we have this saying design is everyone’s business. And that’s partially a reflection of what happens where more people want to work in design, on design, who are outside of a specific design role.

We have a stat, 56% of those involved in like the digital product process are doing a major, design, like, macro task, like prototyping as a big part of their job. So design is sort of everyone’s business, and it’s partially because it’s as we just talked about, like strategically become really important. People see it as this really important lever to creating great experience, to building a business that’s really successful.

And I think as part of that, you do have more roles sort of blurring where designers are doing things that maybe engineers would’ve done before. Like maybe they’re working on code, maybe they’re doing things that PMs would’ve done before where you’re sort of writing up a PRD, but you also have other people doing things that maybe designers would’ve done before. Like, here’s this prototype.

And what’s been interesting in this study that we’ve been running, which we’re gonna share shortly, is that it’s born out of a desire to sort of communicate across functions. These become like boundary objects where you’re trying to convey to a product manager, Hey, here’s why I think we should do this. Or the product manager is trying to convey to the designer, here’s why I think we should do this. And so I think you’re right, Peter, that AI tools are driving this sort of shifting and blurring of roles.

But it’s towards generally people trying to do work that they’re really proud of and that, achieves the goals that they’re trying to achieve and, helps their organizations and ultimately helps the people that they’re trying to support.

And I think we see that happening more and more. We see sort of like an acceleration of it, whereas before it was kind of happening. That’s one of the things that was interesting about Figma is more people kind of just got in as it was easier to do it through a URL.

And then more recently, more tools like Make which is our zero to one app creation tool. More roles are doing that kind of thing in an effort to create better products, which is to wind all the way back to your original question. We are always trying to figure out how to help people ship better products get those products out into market, and so they can figure out, are those the right products, should something else happen?

And I think what you’ve seen is an evolution in the understanding of exactly how to do that and who’s involved, and then also in the tools and their capabilities, which have certainly increased over the last couple years.

I’ll just give you one stat. 80 plus percent of designers and developers think that learning to work with AI well will be important to their success in the future. And I think leaders have to figure out how to navigate that because not everybody feels like they have the time and space to work and practice and try to use tools that are different or feel different, have different capabilities, and then also you have to figure out which parts of the process you should keep, which parts of the process you should change.

All while the pace has accelerated and the expectations of shipping have also accelerated. So I think that’s an interesting leadership topic to think about. Because, you’ve gotta provide a lot of air cover for teams right now.

Jesse: I’m glad you brought up the leadership angle because I really see this playing out in a lot of organizations right now where there is this tension between the freedom to experiment and the need to continue to deliver results, right? And the desire to have a strategy, have an answer right away about where you’re going, while also continuing to create the space for the unknown to come in because there’s still so much need for experimentation.

I’m wondering about, really, the big picture of how you think about how these technologies are impacting things broadly. We’ve talked about kind of where it intersects with various aspects and angles of design practice and design leadership. But as someone who has to think about this stuff now all the time on an ongoing basis in order to continue to deliver insights for Figma as an organization, how do you think about, thinking about AI.

Andrew: It’s so meta every time we do one of these reports, you’re like, what’s the best way to, use generative AI in this? Does it have a role? Should we generate something and then look at whether we like it or should we write it and then ask for input or should we just not use AI at all?

And you know, the truth is, I think this is true for designers as well, as the answer is: it depends. The answer is, it depends on what’s useful in that moment.

There’s this quote from one of our AI studies, it’s hard to run a restaurant when the menu keeps shifting. And that’s kind of how people feel. Which model should we be using, which tool is out. All of that is definitely true. And so I think from like a leadership perspective, you’ve gotta create some space for this, whether it’s like, “Hey, show me your latest way that you’re using AI in your process” and you have three or four people demo, that’s a super common thing.

Whether it’s filling out the strategy slide for your CEO, this is how we’re using AI in our process. And then kind of, maybe fudging your way into whether you’re really doing that a lot or not.

And then also trying to create a little bit of extra space for experimentation. The hackathon is very much alive and well. And I think organizations are using those things better than they have before.

But sometimes it also just means conveying to the team that, Hey, if you don’t think AI is really helpful in this, don’t use it. And that’s easy to say, but then someone says, Hey, the engineers are done, what does the next stuff look like? What should we build next? And so trying to create some space when, if it’s easier to generate code than it is to create designs, then you might have to figure out how to change the working process a little bit to make it simpler or to bring more people into the process.

So all that to say, I think my overwhelming thought. Is that it is uncertain exactly how to build all these things in. And so as a leader, you’ve gotta be pulling from a lot of different directions and studies and experimenting yourself at what maybe could or should work. But ultimately towards the goal of whatever your objectives are.

Like the goal isn’t like use AI usually. Actually that’s not true. The goal of many AI initiatives is use AI. That is, that was one of our findings from the study was overwhelmingly it was experiment with AI, or the other catchall is improve customer experience.

So I think that is partially true, but I think it’s creating some sense of, like, sort of stability, it’s okay to experiment. It’s okay to not use it. And figuring out also how to bring people along who are not using it at all because I think that’s a rough spot to be in right now, is not using any generative AI in your process. I think you’ve gotta find some way to do it. And, part of that is probably working with your engineering leadership at, ” What are you guys doing? How is this working? What could we do to make it simpler or plug into your workflow?”

The challenges of Generative AI

Peter: It’s interesting you say that, given, I don’t know, what feels like some of the news of literally the past week or so, where it feels like we’re starting to hear the early results of product development teams trying to use generative AI, and at least publicly, the commentary is not positive, right?

I think a lot of folks have put a lot of time and effort and money and are not seeing… I don’t know what they were expecting, but not seeing gains, not seeing, not seeing impact or results that they were expecting. And so, there’s definitely been a bit of a craze.

Andrew: But this is the opportunity. I’m excited you brought that up because I think this is the opportunity for design and design leadership. If things are not working, that is often a place to prompt a reexamination of, ” Well, what are we doing? Are we just like using this technology just because we could, like what are we actually trying to achieve” and then trying to design something, both internally, right? What is our process like?

There’s sort of this meta design thing that I think both of you are very skilled at and skilled at thinking about, how do we help engineers ship things? How do we ship better things? Let’s examine that. And then there’s also this sort of like, well, did we actually try to solve like a customer problem that they had or a user problem? Did we even conceptualize this thing in the right way at all?

And those are both amazing spots for design to step in and show, show leadership, because I look at that 80% stat and I think that this is not something that is going away. So 80% think that this is critical to their success in the future, and embedded in that is their workflow and AI powered products and a lot of other things.

But in general, these are people who are working with this stuff every day. There are probably quite a few skeptics in there. And so it says to me that we have not found all of the great use cases for this technology yet, and we have not designed things well so that people can accomplish their goals, whether that involves generative AI products or not.

And so it seems to me that in a spot, if there are things that are not working, that’s a great opportunity to step in and say, Hey, Design can help us make sense of this mess, and we have a set of tools or just I can help make sense of this mess.

You don’t even need to bring design into it. You could just say, I have a set of tools and tricks to be able to do this. You know, we saw it with mobile, we saw it with the internet. These things sort of repeat. They go in cycles and then eventually the application layer gets designed well and things become more useful.

Maybe that’s like too optimistic of me. But it seems to me that there’s an opportunity in that if there are areas where it’s not working well.

AI Wariness

Jesse: You touched on the skeptics, and this is an interesting part of it for me because what I hear from leaders inside organizations, when we talk about, you know, how is the experimentation going and are you getting any traction with your experiments? And they often describe a level of kind of a cultural resistance to these technologies that to me feels like it might be particular to design teams, and something about design as a process that makes the practitioners less willing to embrace these tools in the way that their product and engineering peers and partners are.

And I wonder if you’re seeing something similar in terms of cultural resistance to these technologies within design teams specifically and where that resistance is coming from.

Andrew: So the data we have from January is that like about 30% of designers have adopted AI into their regular workflow, and about 60% of developers have. So that’s a pretty big gap that would sort of support some of what you’re saying there.

I would expect that it would’ve changed from January to now, August. I would also expect that, if you put something in a Chat GPT and you ask it some questions about something, do you think about that as part of your design process?

Maybe, maybe not. So there’s maybe some usage that is not quite captured in that, the design process is sometimes just wrangling your collaborators and your stakeholders. That’s part of it, too.

But I remember the early days of both mobile and digital design, which you guys probably remember even better, where, do you remember the phrase above the line and below the line where the marketing campaign, the below the line things were the digital stuff.

And then you had the above the line. That was all the TV stuff. And then, there were people who said like, I’m never gonna make websites. I’m never gonna work on that. And then over time, you get a little more comfortable. You add some skills to your level of understanding and the things you feel good at, and then you start to branch out into things that maybe you didn’t feel as comfortable with to begin with.

And, I think this is always true to diffusion of innovation. There are people who are really early adopters to things. There are people who are early career and they’re just learning a way to do things from the beginning. And then you see it spread and the parts that are really useful tend to really stick. The parts that are less useful sort of fade away. And ultimately at the end, if something is really helpful, that’s a, major general purpose technology,.like many, many of us think that AI is.

Designers are ultimately also part of making that happen. And so I don’t know if it’s a distinct thing with design, but I do think there are sort of patterns that play out here.

Jesse: I think that it’s interesting because the work that we do, as Peter often likes to refer to, sits at the intersection of technology and the liberal arts. And a lot of folks came into this work from the liberal arts side.

And there is a bit of resistance, I think, to embracing too much technology in the creative process itself. It’s fine if we want to build technology with technology, but when we start looking to technology to provide pieces of what we think of as our creative value proposition, that starts to make people uneasy and it starts to make people resistant.

Andrew: I mean the fascinating thing there is if you look at other fields and other studies, there was this MIT study about if, if college students write essays with AI, they like basically don’t remember the essay later, and it gets progressively worse over time. And if you think about that for a minute, it’s because at the end when they’ve done this four times, no one has ever given them any feedback. They haven’t seen anything come of it. They sort of stop trying.

And sometimes you do have to like, try and work and think really hard and fire all your neurons and synapses and pull it in. And it’s like, as, like John Maeda would say, you have to think uphill sometimes.

And I think that’s partly where some of it’s coming from, that you know the answer is not generating a page that looks visually interesting. The answer is creating some solution to a problem, and sometimes you have to think through it and work through it really hard and sketch it out in whatever form you find easiest.

So that part totally resonates. People have very different creative processes, and if you want a novel solution, you might have to pull it out of some sort of generated, here’s a list of 10 possible solutions. But sometimes I think people would tell you they look at 10 possible solutions, they hate them all, and then they know what to do.

Peter: Mm-hmm.

Jesse: I want to come back to the notion of where this technology is best applied because, that I think is part of it for some of these skeptics, that there are places where they don’t see it playing effectively, and there are other places where maybe they might see a place for it.

And I’m curious about those broader patterns of high value use cases teams are seeing in these experiments. I know that it’s still early days and there’s not a lot of great data, but you’ve got, as we’ve touched on, maybe more data than anybody on some of this stuff, and so I’m curious about what you’re seeing about where people are seeing the value of these technologies in these creative processes.

How we use AI

Andrew: So I don’t have survey data that says like, this is it, this is the spot. What I do have are a lot of anecdotes that prototypes and ways of communicating an idea to people have become like a go-to place for generative AI.

And that’s because you can sort of do them quickly. You can think about what works and what doesn’t. And then, you know, a prototype is worth a thousand meetings. That saying is still very true.

And so the place that it’s helping most seems to be different disciplines communicating better with each other about what they’re thinking, in order to lead to a better solution at the end that actually gets shipped.

And that is an important nuance because it isn’t like you prompt the thing and then you get the final and then you’re done, right? You prompt like a potential change to a flow or something important and you get an idea from it, or you share it with someone and they get an idea.

So it’s like a midpoint in the process. That seems to be where teams are finding a lot of value here.

And then in addition, this is totally tongue in cheek, writing emails more quickly or responding to maybe some like feedback or something that seems to be like across every job role. Everyone seems to be using it that way.

And then, sorry, the other one is pulling out research insights and summarizing those things quickly. The risk there is that you don’t actually fully digest the research and really pull out what’s super important. But those summaries are done. And so that is the tension, right? If the summary needs to be done, you can do that very quickly now, but that is not quite the same thing as getting someone to care about it or getting someone to really fully get like, here’s the best answer, but it’s also a faster way to disseminate research insights. Here’s this clip that’s really helpful, you should look at all those things seem to be getting faster as well.

Peter: I’m gonna pull back a bit, and some of my own anecdata, but in my work with design leaders, I’m increasingly seeing, and I’m wondering, Andrew, if you’ve seen this, if you had the data to back up my hypothesis that’s your job is, to be our data repository.

But, there’s, like, been some recognition that the products that we’re creating have gotten complex and perhaps overly complex over time. Companies acquire other companies. Companies keep building things, and what I’m seeing more and more of is a desire for design at the highest level to be a kind of a more horizontal thread to cohere, to create something cohesive that spans an enterprise.

I’m having a conversation, one of my clients, an insurance firm, sizable insurance firm, and I was looking at the opportunities of service design to create something that feels like it’s member driven as opposed to corporate driven. Because members are going across the silos within this organization, and I’m wondering, 1) what you’re seeing, hearing in terms of that, and 2) what role does Figma play in something like that, right? One of, one of my challenges…

Andrew: we will take challenges. I like challenges.

Peter: With Figma is it gets associated with design, but, and I think you would recognize that it only addresses a part of a much larger design process or potentially process.

Now to the degree to which you can use diagramming and visual communication to help explain more than digital product design, and maybe there’s the solution, but, like, I get a little concerned that people associate Figma with design, but then they think of Figma as the thing where I draw screens.

And so two things.

How do we help these leaders with kind of this big tent messy end-to-end service experience? Or are you seeing that as well? And then, How do we think about supporting folks spanning enterprise wide challenges?

Andrew: So a couple things. I think certainly diagramming, storyboarding, a lot of times those things get communicated in decks as well, and Figma Slides is suited for that too. And it’s nice to be able to say, Hey, let’s take this software that’s part of this process and let’s contextualize how it fits into the larger way in which this gets passed from point to point. And so that’s how I would think about that.

Which is not too dissimilar from how it was done before, except now it lives in a URL, which is kind of nice. And you can participate with somebody around the world, different time zones. So probably more to be said there, but certainly you can contextualize the digital product or the software in a way that is I think, really helpful.

And then also you can get interesting feedback on it from people whether that’s fire emojis or whatever else. If that’s the kind of meeting you need to have, you can have fire emojis.

So, and then taking the other part, definitely as a stitcher-together of distinct interactions or products or goals and stakeholders and systems. I think design has probably always done that really well, distinctly well, just because often the people doing it understand the humans involved better, and then, if you understand how the information needs to flow, you can do all that better.

I don’t have any data to support that as something that’s happening beyond the same conversations I’ve had, but I think increasingly it will be really important, as these things get more multimodal, whether it’s input,either an image of the thing you’re trying to do or the text of the thing you’re trying to do, or click a button of the thing you’re trying to do and then, we’ll give you the answer back in audio form or here’s a video of whatever you were asking about.

When you start stitching together all those inputs and outputs, it becomes even more important. And then when you start needing to orchestrate agents to do any of these processes, you have even more inputs and outputs.

And ultimately, there’s still some human that’s responsible for the decision. And again, design is really critical to actually making sure that human can understand the decisions being made, can adjust it.

And so if you take what has always been done, which is the ability to stitch these things together to create a better experience at the end, ’cause you understand the humans and then you expand it to the complexity that is now possible, and then the agents that are also now possible and the new interaction design challenges. I think that our customers are saying design is becoming more important to doing those things well.

And the design, sort of, like, bag of tricks to use like a very, very reductive term, becomes more important.

I think all of that is very true and really happening and will become more important as the app layer and the interactions that we have with LLMs and with the software systems that are being built on top of them, as those things become more important, I think that design skills become more important too.

But, you know, that’s the view of the guy at Figma, right? Of course, the guy at Figma would say that would think those things. But, I don’t know. I’m not sure how else you do this other than diagramming it out and thinking about inputs and outputs to the systems and somebody has to do that.

Jesse: Mm-hmm.

Peter: Well, and that, kind of speaks to something I’ve been feeling and or sensing, which is, and Jesse and I, maybe coincidentally, in a couple months are speaking at the Service Design Global Conference, but service design, has a set of practices, service blueprints and whatnot that I think become increasingly valuable when, I don’t think much about our agentic future, but if there’s gonna be a bunch of things just kind of operating out there, coordinating, corralling, aligning, orchestrating that behavior becomes super important and doing so in a way that is responsive to user needs and…

Agent wrangling

Andrew: Well, then you can understand, just the fact… understanding what did the agent just do, you know? And I think, users, you can very quickly envision how they become like air traffic controllers that need like a set of effective dashboards to be able to orchestrate all of these things so that like they don’t book the $10,000 trip to Bali. They book the $1000 trip to Bali, or, their bill gets paid on time instead of being charged a late fee.

And as the gravity of the decision increases, the importance of the design increases where, you know, it’s kinda like running a power plant. You really wanna make sure the person running the power plant understands what’s going on in the power plant, and then the process by which that happens becomes more important then as well.

Jesse: Mm-hmm. I find myself wondering about the implications of all of this for design’s influence on product strategy, because you’re talking about an approach that potentially really kind of flips the equation in terms of requirements driving design, turning into design driving requirements.

Andrew: I mean, it’s an interesting provocation because if it’s simpler to generate features, which I don’t really mean that it’s simple, but if, let’s just say, it’s simpler to generate features, then how the features fit together towards a certain goal, and the context by which those features are shown, or how they’re shown, becomes more important.

Those things then become really critical and then the rest of it is maybe less critical.

And I think what, we’re talking about is, more of a future state, right? I think for most enterprises, you can’t just like generate and bang out a bunch of features at this point.

But if it is easier to create them, then how you feel using them becomes more important.

And so then the question is, how do we create the right feeling for what people are experiencing, and then how do we make sure that they’re successful? Which is design.

Quality and other standards of success

Peter: Well, we spoke around the same time that the AI report was launching and, you mentioned that insight that you shared earlier, where designers felt like they were getting more efficient, but they weren’t necessarily producing better work. At that point, we talked a lot about quality and defining quality.

Something, I think about it a lot is design organizations need to have more explicit standards of quality that they then can uphold through all this activity.

But then as we were talking about the backlash that we’re hearing in the last, just the last couple of weeks around some of these generative AI engagements, and I think a lot of that backlash is companies went nuts trying things out, but without a sense of direction.

They were just trying out for the sake of trying it so they didn’t have standards of success. And then when they finally took stock of what’s happening, it’s like, well, it’s not doing anything. And it’s like, yeah, it’s not doing anything, ’cause you didn’t have a point of view, you didn’t have a direction you were going and you were just throwing spaghetti against the wall in hope that stuff stuck.

So intent becomes very important. But then this last piece that you’re talking about around the coordination, this orchestration, all this activity that’s going on in the system and the role that design can play in helping manage that. I start now wondering about, what are the design skills, design practices that become increasingly important?

And I’m thinking about that in light of what we’ve seen over the last six to 12 months where every job description for a designer is talking about high craft, but what you were just mentioning is not high craft design in the way we think of it with like high polish, high UI, subtle micro interactions and all that kind of stuff.

it’s a lot of IA, it’s a lot of interaction design, it’s a lot of workflows, it’s a lot of conditionals, making sense of all that, with the interest of delivering value to a user.

I’m curious where you see the intersection of quality, craft, intent, new skilling. What are you witnessing?

Andrew: I mean, it, it’s gotta be both, right? And I think one of the reasons I focused on the product strategy, higher level experience is because that is often under-discussed.

And the point about craft and micro interactions is talked about a lot. And I think both are really important.

You can’t have an experience where, oh, it’s really great. I can see exactly, like, the way that my information got shared and it did this really interesting animation that now I know exactly what it means. But then like ultimately, on the other side, did it actually get action?Did whatever I was trying to accomplish, get accomplished?

You can imagine like an agent, oh, the agent, it’s really great. The agent said it was gonna buy the shoes that I was looking to buy, but like, then it doesn’t buy the shoes or it overpays by, you know, a hundred dollars on the shoes.

Those are like distinct things, and yet you can’t ignore one in favor of the other. But you do have to think about both.

So, I would imagine that some designers would specialize in one part or specialize in another. Potentially if the higher flows are not being thought about, someone will step in and try to think about the flows after the experience doesn’t work or people give feedback.

And so someone will do that, and it’s a question of who is going to do it. Who either feels like they have permission or takes the opportunity to do it. And so that’s kind of how I would think about it. And I do think it’s worth thinking about the definition of craft as helping people have, like, the feeling you’re looking for them to have with the tools that you have available.

I don’t know that that’s like a Figma definition, but that’s how I would think about things like craft.

Jesse: Along those lines, there was one finding from the January study that I found well, you know, almost counterintuitive, which had to do with how organizational scale impacts how these technologies are being deployed in organizations. I wonder if you can kind of recap what you found in the study.

Andrew: I mean the core of it is, really it’s the smallest organizations. So your, like, one to 10 employee organizations and how differently they think about AI to the success of their products, and even how they are thinking about work. And I think that’s not really that surprising, right?

Once you hit two-, three- hundred people, you have like some well-worn paths. And unless like the number of people changes dramatically, you probably would kind of keep going in the same way.

But if you’re a new company and you’re thinking about how to do something and you’re probably starting with the premise that you’re gonna be AI-powered in some way, those organizations are different.

And so then that also has implications for, if you’re a large organization trying to increase use of AI for the express purpose of increasing use of AI, splitting small teams out to go do it, and almost like telling them you’re going to either work this way or you’re going to build an AI powered product.

You might have more success with like a small, small team that is just in the work. That is just building.

And, I don’t know, it’s an interesting finding ’cause I think it speaks to the accessibility of the technology, like, you can do things, has never been greater.

And what we’re all trying to figure out is like the best way to do things. The most effective way to create products for users. Those are the things that haven’t really been figured out. Yeah, just trying them, it’s easier than ever.

The Power of Writing

Peter: Your role is the head of insights. I don’t know if that means you actually have a team that you’re leading, but there’s a leadership component to that.

And I’m curious, so ours is a podcast about leadership, and I’m curious, what leadership skills you’ve been developing, particularly within a place like Figma, right? Because as an analyst you were probably doing your analysis and some consulting.

Now you’re in-house, now you’re navigating organizations. Now you’ve got politics. Now there’s probably people who, if you’re delivering insights, you’re probably finding out things they don’t necessarily want to hear, right? ‘Cause it might go against what they think, what they thought the reality was.

And so I’m wondering what, are the leadership skills you’ve been leaning into to get traction to bring people along to your point of view, your agenda, within Figma and what that journey’s been like of developing kind of that leadership approach.

Andrew: One of the interesting things is the power of writing.

And I thought it would be less important because that was my job at Forrester. Like the core job is like you create insights and you put ’em into a report and then you do a lot of other things. That is not dissimilar to my core job at Figma.

And I think, I thought that writing would become less important because it’s such a visual company, it makes like a tool. And writing things down still has tremendous power. It still creates a lot of reach and then it forces you to think about what you think is really important.

And then ideally, you’re creating some other dissemination mechanism too. You know, you’re making a video, but the video’s gotta be really quick. It’s gotta be really engaging. All that.

And I think I, thought that was less critical. And it turns out that interviewing somebody about their insights can be a really powerful thing to do.

And then writing those things down is really critical. And so, I think leaders have to make artifacts and one of the key artifacts of leadership is writing things that people can then better understand your perspective and then force you to articulate what the perspective actually is and find out whether you are aligned with the people around you.

Jesse: Andrew, as a professional asker of questions, what are the questions you are most interested in exploring next?

Andrew: I am not tired of AI and design and what the interactions will be between those things. I just feel like you keep peeling back the onion and what are the great practices that teams are using? What are people finding success with? What are people excited about? What are people nervous about? Those remain really important questions.

And then I think importantly, what isn’t changing about that is still a really important question, because it still sure seems like getting a team to understand a user’s perspective and actually getting a real user perspective, not like, some version of it that they’re presenting to you, those things still seem really important and incredibly difficult. You know, AI just doesn’t do that. Other than maybe creating some more scale and more interviews, maybe summarizing it.

So what’s changing, what isn’t changing? I’m excited to keep researching it.

Jesse: Fantastic. Andrew Hogan, thank you so much for being with us.

Andrew: Thanks for having me.

Peter: Yeah, this has been great. Thank you.

Jesse: If people wanna find you on the internet, how can they find you?

Andrew: LinkedIn.

Jesse: That’s where it’s at.

Andrew: I am, I am a big LinkedIn fan. I do not engage in the other networks nearly as much. Find me on LinkedIn.

Jesse: Terrific.

Peter: Sounds good.

Jesse: Thank you.

Jesse: For more Finding Our Way, visit findingourway.design for past episodes and transcripts, or follow the show on LinkedIn. Visit petermerholz.com to find Peter’s newsletter, The Merholz Agenda, as well as Design Org Dimensions featuring his latest thinking and the actual tools he uses with clients.

For more about my leadership coaching and strategy consulting. Including my free one hour consultation, visit jessejamesgarrett.com. If you’ve found value in something you’ve heard today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.

Show Notes

Product Discovery coach, teacher, and author Teresa Torres joins Peter and Jesse to explore the messy reality of organizational change and cross-functional collaboration. She discusses why external coaching has limits, how individual contributors can drive change within resistant systems, and what the rise of AI means for blurring roles between product, design, and engineering teams.

Learn more about Teresa Torres and her teaching at https://producttalk.org/
Learn more about Jesse James Garrett and his coaching and consulting at https://jessejamesgarrett.com/
Learn more about Peter Merholz and his new digital book “Design Org Dimensions” at https://petermerholz.com/

Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, Teresa Torres, product discovery coach and educator, and author of the book Continuous Discovery Habits, joins us to look at the changing landscape of digital product development from the product side. We’ll talk about what a coach can and can’t do for organizations and leaders, where product and design leaders get off track in driving meaningful outcomes, and what the new wave of generative AI means for the relationship between product and design.

Peter: Hi Teresa. Thank you so much for joining us.

Teresa: Thanks for having me. I’m excited to do this.

Peter: So I’m gonna start with a very easy question. Well easy to ask. I dunno how difficult it is to answer, which is: just how do you introduce yourself these days? I’ve known you now for 15 years, and so I’m curious how you’ve evolved since we first met.

Teresa: Yeah, I mean, I still introduce myself as a product discovery coach. I’m now an author, so that’s new in the last 15 years. But you know what’s funny is I don’t do a lot of coaching anymore. I mostly do a lot of curriculum design. I still do coaching through our office hours and things like that, but it used to be, my primary mode of engaging with people was I coach teams in depth over time. And that’s kind of changed. I now do a lot of curriculum design and we, our primary delivery mechanism is courses.

Peter: Say a little bit more about that. When we worked together I was embedded within design teams and, you know, you were coaching us through these product discovery engagements at both OpenTable and then again at Snagajob, and there was a curriculum component to it at that time, I remember, but I’m curious how that’s shifted or evolved for you and, why more focus on curriculum than maybe the kind of hands-on coaching?

From Coaching to Curriculum Development

Teresa: Yeah, a few reasons. So yeah, I started out as a coach. What that meant was I worked with a cross-functional product team for roughly 12 weeks, sometimes a little longer for the teams that needed it. But our goal in those 12 weeks was just to build really strong discovery habits. It was everything from: how do we collaborate as a cross-functional team, what does a good customer interview look like, how do we run quick assumption tests that we can rely on, h ow to start with clear outcomes, kind of the all the habits you see in Continuous Discovery Habits.

And I think just ’cause of the nature of my personality, I get bored when I do the same thing over and over again. And so I started creating a formal curriculum behind my coaching practice, ’cause I just got sick of telling teams the same thing over and over again. So then they would basically go through a content module. They would try to apply it in their own practice and then they would come to coaching.

And what I found eventually was that the things that we would cover in coaching were more like, here’s what’s hard in my unique organizational context, and not, here’s what’s hard about the skill of interviewing. And that’s because the content was getting good enough that it was helping them build their skill, but it didn’t help them with the messiness of, like, but my sales team doesn’t want me to talk to a customer.

And so I realized that one of the challenges with coaching is you need a leader who’s willing to invest in it. It’s kind of a high value, which means high cost, service. And I just wanted to get some of the skill development out to more teams.

And so with online courses, you can offer it at a much lower price point. A lot more people can engage. We still do, I say we ’cause me and some of my instructors still do, coaching with some of the organizations that we go a little bit deeper with. But I would say primarily I do curriculum design to support our suite of courses.

The Product Discovery Mindset

Jesse: So tell me a little bit more about what you mean when you talk about product discovery and who you work with inside these organizations to support the development of this practice skillset. What would you call it? It’s almost a mindset, isn’t it?

Teresa: it is a mindset. There’s several mindsets. There’s several skills… I mean, there’s like the academic term of like knowledge, skills, and abilities, KSA. It sort of spans a lot of things. I think the big thing for product discovery, I try to keep this really simple. How do we know we’re building the right stuff?

And every team in order to build something, has to make decisions about what to build. How do we know those are the right decisions? How do we have good feedback loops with our customers to help steer us along the way? I know since your audience is a lot of designers, I will be upfront about a lot of these practices came from design, but came from a particular type of design.

Jesse, I know we’ve talked about like, and both of you… Design agencies and like these practices of research and human-centered design and feedback from customers.

I think what’s changing is, in the early days of the internet, we didn’t have the right people on our teams to do that research. And now companies are starting to invest in cross-functional teams that are building those skills. And so we’re bringing it in-house. Product teams are doing it themselves, instead of going out and hiring research firms or going out and hiring design firms. And so it’s led to a more team approach. It’s led to a more, just, cross-functional approach.

And then I also think the pacing of it has changed quite a bit. So when we outsource something, we tend to hire a company for a big project. When we’re doing it internally, we can do it more continuously because we’re working on a product more continuously.

Jesse: Do you engage with design teams in your practices? Is that a part of what you do or are you really focused on…

Teresa: yeah.

Jesse: …the product management side?

Teresa: So in my coaching, I always coached the cross-functional product trio. So it was typically a product manager, a designer, and an engineer. Trios look different at every company. Sometimes they’re quads, sometimes they’re quints. Whatever the cross-functional team is, what roles you have.

So, like, some teams that I worked with had a user researcher as the fourth person. Some teams had a product marketing manager as the fourth person. Some data products have a data scientist, sometimes in lieu of a designer, sometimes in addition to a designer.

So when I say product trio, it’s really just the cross-functional product team. Whatever roles are involved and however many people that is, once you’re more than five people, it gets hard to move quickly. I would say generally it’s three to five people. And then we see the same thing in our courses. So we have product managers, designers, user researchers. And even lately, more engineers enrolling in our programs.

Peter: I am curious how you think things have progressed, because in my interactions and conversations with my clients and other design leaders, it feels like so many organizations are still struggling to do just the basic blocking and tackling of things like product discovery or dual track agile or contemporary product development, or whatever you want to call it.

There’s still a lot of PMs or POs getting requirements from the business and funneling it out to a group of people and saying, go build that. And I’m wondering if, and maybe now given your perhaps broader perspective, ’cause you’re engaging with more people through teaching than you probably could through coaching, like, are we still bending towards progress as a whole or are we, it feels at times, like, we’re kind of stuck or sometimes we go backwards. Like, what’s your take on, just, like, how things are going in terms of organizations adopting continuous discovery, product discovery, these practices.

The Unevenness of Change

Teresa: I think we’re still making progress. I think it’s uneven and there’s some two steps forward, one step back happening. So it can feel like in a single moment maybe we’re not making progress. But I just think back, like to the beginning of my career, okay, so I took my first full-time job in 1999. At that time, I graduated a very naive student of HCI.

And I really thought this was just how business worked. And as you all know, this is simply, it’s still not how business works. But I’ll tell you, my first job, you wanna know what my title was? It was application software developer. Do you know what I did in my job? I did interaction design.

Peter: Right.

Teresa: People didn’t know what interaction design was.

They didn’t hire designers, they hired people that built applications and software. And so even though I was a full-time designer, my title was application software developer. We have certainly come a long way. I’ll also tell you that, like, at that time, I think I was involved in a year in maybe like two or three usability studies because we had to rent a facility with a two-way mirror and it took all day and we spent a month recruiting the right people, right?

Like if we just remember where we came from, like we have made tremendous progress. Now, I also, like, during that same time period, the web was blowing up everybody and their mom wanted to be a web developer, which means everybody and their mom wanted to be a designer.

And now we say things like designers own research and designers own that. No, some designers have that background. Some designers do not. Some product managers have that background. Some product managers do not, right? And so I think some of this, like, it’s just as messy, it’s way messier than we want it to be.

Here’s what I do see. I see way more companies recognizing if we wanna make good decisions about what we build, the customer needs to be part of that process somewhere. I think it’s hard to find a company that doesn’t agree with that statement. Now, does that mean they’re resourcing their teams to do that? Well, not necessarily. Does that mean when the economy shrinks that their founders, some very famous vocal founders, don’t start talking about we gotta go back to command and control and this is the right way to do things and we don’t empower our teams anymore, right?

Like there’s always false starts, there’s always ups and downs. But I think the long arc, we have made tremendous progress. I’m still blown away when I meet a team that is talking to a customer every week. We have a whole industry of discovery tools. Of unmoderated testing platforms, one question surveys, all sorts of testing tools that like literally would not have been able to exist ’cause there was no market for them. Whereas now there’s a huge market for them.

Jesse: I’m interested in the cross-functional collaboration piece of what you described. You know, I often feel like everything of any strategic significance in an organization usually came out of a conversation among three or four or five people. Tops. It’s rare that it’s a mass of people coming together to actually drive something meaningful.

And I wonder about the different perspectives that you have to reconcile as part of that process, and what it takes to create a sense of being, actually just being on the same team, you know, across these different functions. I hear from so many leaders who feel that they are caught in incentive structures that incentivize different behaviors and different outcomes cross-functionally.

So design’s chasing design’s goals, and product is chasing product’s goals, and the organization doesn’t really have any interest in reconciling those. And so we have to reconcile them on the ground, face-to-face in those three to five person meetings.

And I’m wondering about how you’ve seen that done effectively.

“We suck at collaborat##ing”

Teresa: We don’t, I mean, I think if the outcomes aren’t aligned, they’re not gonna work as a team. The good news is I do see way more companies giving cross-functional teams a shared outcome way more than I’ve ever seen in the past. Like, I think we are making progress there. Now, of course, each functional role has other goals or other health metrics they care about, right?

Like, a cross-functional product squad isn’t gonna have a shared outcome of like site uptime, but your engineers better care about site uptime, right? And there’s probably similar analogies for every function.

I think here’s the reality. We suck at collaborating and we see this like up and down the organization. Like our executive teams are totally dysfunctional ’cause we don’t know how to collaborate across functional roles. Too many of us are taught from day one in business, be territorial, have clear boundaries between your role and the person next to you.

And this ladders all the way up the organization. It’s why the head of sales only cares about closing the next deal, and the head of product only cares about how we’re gonna serve the whole market. And the head of design only cares about, but it’s not delightful enough.

I know these are like platitudes and I’m not trying to dismiss any of these things, but like, it causes a lot of dysfunction and, like, if we don’t let go of those things, we will actually never collaborate.

The good news is, I think, at the individual team level, it’s easier to do this than at the executive level because at the team level, your scope is narrower. You’re just trying to build a thing. It’s three to five humans where you can build strong relationships. There’s not as much at stake, and it really is just like, how do we learn about each other and learn about each other’s strengths and figure out who should do what when.

I think it does require that everybody let go of maybe owning some of the things they think they should own all the time. And so here’s what I mean by that. Let’s say a designer wants to get their hands dirty and like play around with Cursor and implement some of their design. Should a engineer on the team that usually does front end development be threatened by that? I don’t know. Maybe not.

And like when the product manager uses Lovable to like play with the feature before it goes to design, should the designer be threatened by that? I don’t know. Now if we’re shipping it without it going to the designer, I have a problem with that. And like, ideally, all three of these people are like ideating together and playing with some of these things together.

But I think, especially with generative AI, like, the boundaries between our roles are gonna blur even more than they already have. And I personally have always been a boundary spanner. Like I’ve been a designer, I’ve been a product manager. I do some coding. Like, I really think the more we overlap in roles, the better we’ll work together.

But it’s hard because our egos get in the way, right? Like, I wanna own that decision. I wanna do that piece.

Peter: Yeah. Egos get in the way, as Jesse said, incentives get in the way, right? We are rewarded as individuals, not as teams. and I’m wondering on that front, if you’ve identified a set of qualities or conditions that indicate to you that this group of people is more likely to adopt practices in a healthy way. Like what are those things that you look for that tell you these folks are ready to embrace these new ways of working and, and succeed? And what are the, maybe, warning signs that like, yeah, I can teach you new ways of working, you’re, gonna be stuck because the problem isn’t one of process. it’s something else.

Teresa: There’s definitely some organizational stuff that I look for. So like, especially when I was coaching in my sales process, I would tell the leaders that I was contracting with like, do not bring me in to coach your teams. The rest of the organization isn’t ready for this because here’s what I saw really early on in my coaching practice, is I would teach cross functional teams how to do this work, and then the bosses would still say, no, just build what I’m telling you to build. What do you think all those cross-functional teams did? They went and got new jobs. They learned a more fun way to work, right? And the first time that happened to me, it was really painful. I was like, oh man, this company just paid me a lot of money to train their teams and they all left. And so I started being really upfront about that with leaders in the contracting process.

Like, don’t empower your teams unless you’re ready to empower your teams. So there’s a lot on the organizational side, on the team side. We have to break a lot of bad habits and we, a lot of this is just trust. The team has to trust they’re gonna be rewarded for these new behaviors.

And I think that’s the hardest part. Is that, like, if the rest of the organization isn’t on board, all it takes is one middle manager anywhere in your organizational hierarchy that affects that team that can break that trust.

So if a designer is hearing from their design director that they shouldn’t be brainstorming ideas with their cross-functional product team, they should be doing it in a design studio. Or more often what we hear, if the engineering lead is hearing from their director of engineering that they shouldn’t spend any time on discovery because they need to be increasing their velocity of code it’s gonna be a huge problem.

We see the same with the product manager. If the product manager, like is still getting pressure everywhere from the organization to just build what they’re told, then all this stuff we’re telling them feels like a charade. It feels like the flavor of the week, we’re not really gonna do this.

Peter: When I think back on our time together, and more of the discovery coaching mode, it was a lot about process. It was a lot about, kind of, steps along the way. And I’m wondering how your approach has evolved to accommodate these questions of trust and relationships and what do you teach people, or how do you help them better relate to one another and build that trust?

Think ‘habits,’ not ‘process’

Teresa: Yeah, so the first thing is I look at it more as a collection of habits than a process. That’s why habits is in the book. I think that’s an important distinction because there’s a process to how we teach it, but hopefully the teams that we work with take away, you’re not doing every step, every time.

We talk a lot about, we’re putting tools in your toolbox and you have to decide which tool is relevant in the current situation. And that I think is really important, ’cause so many people want a process to follow or a recipe to follow. And we all know life is much messier than that.

Peter: I’m wondering if, as part of your teaching now, right, ’cause you’ve talked about the importance of trust and the importance of the relationships within the team members, are you addressing that dynamic head on in your teaching? And, and what are the things that you found help people better connect with one another?

Teresa: Yeah, we do a lot of this and you know, we, there’s this pattern I really love. So first I’ll explain the problem this pattern solves.

A lot of us in business, we’re taught to advocate for our point of view. Which means we don’t really listen to other people’s points of view. We just go into a meeting trying to win the conversation. And even people that aren’t competitive, like this is what business has rewarded. I’m not suggesting this is like an individual problem. I think this is like the culture of business is that there’s a lot of advocacy going on.

So the first thing we try to do is we try to break that. We try to say, look, in all of our courses, we follow this pattern where people work in groups. So we’re trying to simulate a product trio. We give them a homework assignment that they do individually and then they come to class and their goal is to redo the homework assignment in the context of their team.

And we follow this pattern of: first, share your individual perspectives on the, on the assignment. So they’re each sharing their individual work with each other. And we teach them don’t listen for what you think they did wrong or right, just listen for what’s different. Be curious. This is about exploring the different perspectives on your team.

So try to let go of this idea of like, my version is the best version. I need to win. But listen for, across all the different perspectives,. what you like about it, what’s better, what you can take from it.

And then we have them co-create a team version. And what we find sometimes in week one, they’re not very good at it. It’s hard to let go of this, I need to win. But when they do it four or five times, they start to learn like, oh, our team version can actually synthesize all the best parts of the individual versions.

And this is very different. Even if, like, what we see a lot of teams intuitively do is, they wanna come to the meeting and start the work together, but then we get all this groupthink problems, the most dominant personality dominates the work, right?

So like, it’s really important we start with, do the work individually. Take the time to exploit all the different perspectives where you truly understand the different perspectives. Then co-create a new version. And when we see, when teams practice that, and get good at that, they realize it’s not about, did they have the best option. It’s about collectively, we’re able to take the best of each of us and co-create a great option.

Jesse: I’m curious about how that collaborative dynamic potentially plays out beyond the team level, especially looking at the leadership level. You touched on earlier how if you’ve got dysfunction in your leadership relationships and your leadership collaboration, that’s gonna cascade down into the cultures of those teams.

And the people of those teams are gonna model themselves on, you know, the priorities that are being set by, and the messages that are being sent by the leaders that they report to. And I’m curious about cross-functional leadership collaboration, and creating that alignment in ways that can have a positive cascade effect in ways that can actually help entire teams get along, and not just individuals.

Teresa: Yeah. Honestly, I have no idea. I’m gonna share, like I have no idea how to solve this problem. I’ve been on executive teams. I’ve been a CEO where I was responsible for an executive team. I have coached executives. I’ve done work like alignment workshops with executives. I don’t do that work anymore. I don’t know what the answer is.

I’ve read all the books, like The Five Dysfunctions of a Team, right. Like I, I’ve read the books, I know the theory, like I’ve worked with, I’ve seen other great executive coaches come in. I think here’s the challenge at the executive level, everybody who is an executive has by definition had a lot of success in their career and that success came from what they’ve done historically.

We all know it’s The Who Moved My Cheese book. What got you here won’t get you there. right? Like, it’s really hard for us to let go of what has worked for us in the past. But I think the challenge is, there’s always a little bit of truth to this in every role, but I think especially the executive role, to be a good executive and to contribute to a well-functioning executive team, you have to let go of your needs, if they come at the cost of the whole business’s need.

This, like, skill of thinking across the business and being able to think from the different perspectives is really critical. I don’t even know many CEOs that are good at this, and they’re the ones that like, it’s their job to be good at it. So I think what we’re bumping up into at the executive level is this is a really hard thing for humans to do. I mean, if I had a silver bullet here I would probably do more executive coaching. But I, I, it’s messy and I think it’s hard and I don’t particularly enjoy it, which is why I work at the IC team level, that is a scope that maybe people are more idealistic and more willing to change and, a little more coachable.

Peter: Following a bit of what Jesse was saying, and you saw me flipping through your book, in order to adopt the kind of continuous discovery approaches that you are teaching, people internally would need to embrace some flavor of change management, right? This is a new way of working, thus it is change.

And one of the frustrations I’ve felt, largely on part of my clients who are in these organizations that are going through a product transformation. adopting the product operating model. They’re learning to do product discovery. And, a frustration that I hear from them is, they’re shown how to do it. Like, the glorious future of, just work like this, but they’re stuck in their existing day to day.

And it’s not like they couldn’t get to that point, but it’s a process to get to that point. It’s a change management process to get from where they are today to this glorious future.

And oftentimes the leadership who’s spent on the training or whatever, is just like, you should just be working in this new way. But the teams, feet on the ground, are, they’re not. The product owners aren’t comfortable doing customer interviews, and liked being able to just tell everybody what to do. They don’t wanna work three in a box or whatever.

Like, there’s an evolution that’s required, and I’m wondering how you teach, how you think about, what you counsel your clients or students on, in terms of wherever they’re beginning, the slog, the necessary slog it is to get from that point to this glorious future and, how you help them navigate that change.

The lie at the heart of most change management

Teresa: Yeah, this is a really big question. I’ll share.

I went back in 2011 and I got a master’s in organizational change. Here was my takeaway. Organizations don’t change. People change. That’s like the headline of my takeaway, right? There’s a really great book called Managing Transitions, William Bridges, that really talks about what an individual goes through when they’re going through a big change.

And then he talks about it as like, almost like grieving, like there’s three stages you have to grieve for what you’re losing. Then there’s this messy, neutral zone, and then eventually you step into the new future. And I like Bridges’ writing on this because most change management people, the big names, John Kotter, there’s several other big folks that write in this space, they talk about change management as a process that happens to the organization, but I have literally never seen that work, right?

You can bring in the McKinsey’s and pick your other favorite consulting firm and they’ll create a Gantt chart with swim lanes and tell you here’s where you are in the change.

Like it doesn’t reflect reality. In fact, even Snagajob, Peter, is a good example of this. Snagajob had all the right things in place. They had a product leader and a design leader that supported the change. I actually don’t know who the engineering leader is, which maybe that’s one of the challenges.

They invested in coaching all of the teams went through coaching. One thing I’ve learned since we worked together at Snagajob is maybe we could have done more at the middle management layer, r ight. Like we’d hit the teams, the executives were on board. And even so, even with a lot of the right pieces in place, not all of the teams moved the same amount.

So why does that happen? Well, every individual is going through those three stages very differently. Some people don’t ever grieve, ’cause they’re not willing to let go of what they’ve been doing. They refuse to change, right? Some people step into change, they try it on, and they really struggle with that grief.

Or they get through the grief and they’re in that messy, neutral zone, but they’re struggling to see what the future looks like.

And so I think something we dramatically underestimate is how much work leaders need to do to guide every individual in the organization through the change. This is another reason why I moved from coaching to courses.

So in courses I can teach you skills. Courses Courses are very good at teaching skills. What I struggled with as, a coach when I was an outsider, it’s hard for me to guide you through the change because I’m not your boss. I’m not your leader. I’m not setting the culture. I’m not able to do rituals that reinforce it. I can’t combat a middle manager that disagrees, right?

I think I really believe in something Marty Cagan says, which is, “one of the primary responsibilities of a leader is to coach their teams.” To coach the people that report to them. I saw this as a huge limitation of being an external coach.

I think as an external coach I can help with skills, but there’s so much of this messy internal stuff that if you’re not managing the people you’re coaching, it’s hard to be successful.

I’ll give a really concrete example of this. Early in coaching, we helped the teams get access to customers. This is actually something something Snagajob was already really good at.

When we were working with the teams there, they were already using Ethnio. They’re already recruiting people directly from the product. Actually, still to this day, 12 years later, I still use Snagajob as an example. But I still had teams show up three weeks in a row saying they didn’t do an interview. They just didn’t do it. And I can spend three coaching sessions on where the resistance was coming from and why, and to help them break down barriers. But if they didn’t wanna do it, there was nothing I could do. I’m not their boss. I’m not there with them.

The importance of coaching

Peter: Right.

One of the challenges, that you’re identifying, it sounds like it happens in product, it definitely happens in design, which is design leaders don’t know how to coach. That’s not something that they’re taught, that’s not something that they realize. They know how to direct, but that bringing up is something, is a skill that’s kind of gotten lost.

You almost want, I’ve thought this about this for a while and, what you said is kind of reintroducing it, right? You almost want like a, like a master/apprentice relationship between a leader and their team in terms of really helping them understand the craft.

And I don’t mean it in the designerly way of craft, just like what are the, to use your term, habits, practices, whatever it is that you need to embrace in order for that next generation to be effective. And leaders are rarely equipped for it. And if they are, the other problem is that they’re almost never given the time to do it, right.

I think something that’s not recognized is that kind of coaching. I mean, that takes a lot of time, right? It’s not just…

It

Teresa: does take a lot of time.

Peter: …Yeah, it’s not a one-on-one every other week or so, ” How is it going?” It’s rolling up your sleeves.

But then, leaders are doing more and more IC work, but that’s not coaching, right? Like, that’s, not leveraged. It’s a kind of labor that I don’t think is appreciated because it’s not obvious that it’s driving outcomes, kind of, directly.

Teresa: Yeah, I think is a huge problem. I think most leaders in any discipline don’t know how to coach. Why would they? That hasn’t been a part of the job description. But I think if we’re going to empower teams, now coaching is required and I think, ideally, like eventually because you empowered your teams, you now have more time to coach.

The challenge is the transition I have to coach my team so they can be empowered so that I have some free time. I’ve been thinking about this a lot and I’ve been talking to a lot of product leaders about this very topic this summer. Leaders need better resources for how to get good at coaching and what does that look like and what does coaching their teams even mean?

Jesse: Well, speaking as an external coach, I feel like I have to defend the value of external coaching a little bit here. Just in that the work that I do is one-on-one work. It is also at the leadership level. So in a lot of ways what I’m bringing as a coach is not really about change management or organizational transformation so much as it is helping a professional look at their own practices and supporting them in their own evolution and their own change management, so to speak.

Teresa: Yeah, let me clarify. I actually think that there is a role for external coaches and especially at the leadership level. I think there’s a difference between, I personally have a coach who helps me see my own stuff and helps me get outta my own head and hold space for me and is a sounding board and ask me questions, I think there’s always space for that, and I think all the way up and down the organization, even at the IC level,if we could get to a point where everybody could have a coach, I think that would be an amazing world, because we need way more reflection than we naturally do.

I think what I’m getting at and like what I experienced as a discovery coach is a little bit different. It’s an organization is trying to get from point A to point B, which means all the teams in that organization are saying, you need to do B, you need to get to B.

And so you bring in an external coach and you help them with like, what does it mean to get to B, how do I get there? But if there’s stuff happening in the organization that’s competing with like, yeah, we’re trying to get to B, but we’re gonna do C along the way, we’re not really, not really on the way to B.

That’s when, like, how effective that external coach can be is really limited. ‘Cause there’s so many competing forces, and this is where I think, like, if the leader was coaching those teams on how to get to B, The leader would see oh, C is interfering, I need to go remove that obstacle, right?

And like as an external coach, I tried so hard, I would meet with leaders and be like, here’s what I’m seeing from your teams. Here’s the obstacles. But it’s a little bit like when we tell somebody about our research, they don’t care unless they’re involved. I think with change management in particular, this is where leaders have to be directly involved in coaching their teams. Coaching is a terrible word ’cause it means a lot of different things.

I think it’s different from what I would think of as traditional executive coaching.

Peter: I face the same thing. Sometimes I’ll get a director of design reaching out to me who wants my help, but if their boss is the head of design, I’m like, I need to work with them. Like, ’cause I’m gonna work with you and what I might say to you might be in conflict with what your boss is telling you, and, right? And there’s that dynamic there that I think is what you’re getting at and the risk that we’re setting up by having too much of that kind of directive coaching be external, right? Because the team needs to own it. That leadership chain needs to own it.

Teresa: I even see this at the product leadership coaching level, right? So, would I coach a product leader on how to bring the discovery habits to their organization? You know, the first question I would ask is, does your CEO want this? Right? Because if the CEO doesn’t want it, how effective are you gonna be?

Jesse: Yeah. Yeah. It applies at every level of the organization. What I’ll often say to prospective clients is, the more power you have, the more I can help you activate. And if you are in a position in the middle or the lower middle of an organization, yeah, we’re gonna be, we’re gonna be resorting to some gorilla tactics to get things done, because you don’t have necessarily the latitude or the permission to just make things so.

Two conflicting, competing thoughts

Teresa: There’s something I’ve come around to. It’s gonna sound like they’re competing thoughts, but I think there’s power in the fact that they’re competing thoughts.

So the first one took, I mean I’m probably still learning this, but it definitely took like every day of my full-time employee experience to like, actually, no, I think it took 15 years not being a full-time employee to actually believe this and own this. I think that the only person that can drive change in an organization is a CEO. It doesn’t mean other people can’t influence that change and can’t contribute to that change, but if your CEO is not on board, it’s not gonna happen. This was really hard for me as an employee because I just wanted to change things, right? Like, I thought that this was the right way to do things. And, and even now, like, I surprised some people ’cause they’re like, Hey, my CEO wants me to build this thing. What should I do? Well, clearly you should build that thing. Like, I think we struggle with accepting our organizational realities.

I’m gonna drop one that might annoy a lot of people, a lot of your listeners, but I’m gonna say it anyway ’cause I feel like it needs to be said. How many designers do we know that don’t think they should care about business outcomes? Like, I’m sorry. It’s great that your product is delightful and it should be delightful and that’s good, but if it doesn’t make your business money, you’re not serving the business. We do need to serve the customers. Don’t get me wrong, this is one where I get into deep, horrible arguments with designers about, but like the reality in a for-profit business, the CEO is responsible for growing profit and every single person that works in that organization is responsible for contributing to growing profit.

Everybody. And I think that like we still struggle with this ’cause like we all have our ideals like, and I think design has a lot of great ideals. They also sometimes get in the way of like doing design in a business.

Peter: Mm-hmm.

Teresa: Okay. So that’s the first thing, which, like, still is hard for me to even say out loud because I am such an idealist and I want it to be different.

The competing thing I’ll say is I often tell people you can adopt the habits regardless of how your organization works.

Jesse: Mm-hmm.

Teresa: I think these sound like competing thoughts, but they’re not, because I don’t need the rest of my organization to be outcome focused for me to start to think about outcomes. For me to start to think about the impact of what I might be working.

I might not have access to customers because I might not be allowed to talk to ’em in my organization, but odds are I have some access to them somewhere, whether that’s reading forums online or finding people in my personal network, like with every single habit in the book, there is something you can start with, even if your organization is telling you you can’t.

And so, like, what keeps me sane is holding both of these things at the exact same time. I’m not going to change my organization, but I can change me. It turns out if enough me’s change, the organization changes.

Peter: And you’re tapping into something that I find is part of my work, which is recognizing that nothing happens or very little happens without cross-functional connection and collaboration. There’s this belief that everything you’re doing has to be aligned with all the people around you at all times and needs that support up and down the chain.

And while there’s some truth to that, allowing people, the word that comes to mind is selfishness or self-centeredness, and being, like, kind of to your point, you can do what you think is right. Give that a shot. There’s no one holding you back. Try it out.

Like, you don’t have to always align and connect and integrate with what’s going on around you if you think there’s a different way of working. Now there are political challenges and relationship challenges and you don’t want to just be kind of operating 180 degrees from everyone else around you necessarily, but, providing some permission.

I like what you’re saying because I think more people with the right idea need permission to like, do those things. But I also like your comment about the CEO and that change because yes, you have permission to try some new things, but you also need to recognize the reality in which you’re operating.

You’re not just gonna be able to willy-nilly make change.

Teresa: Yeah. I always tell people, I go, look, you need to rock the boat, but don’t get fired. That’s the reality, right? Like if you wanna work this way, you have to rock the boat a little bit. Just do it within the constraints so that you don’t get fired. And I think that’s these competing ideas of like, I do work in an organization that I don’t control and I barely influence and I probably will never really influence if I’m an IC and I can still have so much agency in what I do all day, every day. Your boss is not looking over your shoulder all day every day and never will be.

So you gotta find what are the safe places that you can start to introduce some of this stuff. And what I love about this is, here’s what I see happen when people do this. They start to do things in weird ways and people get curious about those weird ways and ideas start to spread. And if those ideas happen to work, they spread even more.

And it turns out we do start to influence change just by changing ourselves. And this is why I like William Bridges’ work. We’re all individually changing at our own pace.

Experimenting with AI

Jesse: Speaking of permission to experiment, there’s a lot of experimentation going on in organizations right now, and a lot of folks are not waiting for permission to experiment because they are seeing the opportunity to seize these new technologies of AI to do their jobs and well, in some cases, to do maybe what might be somebody else’s job in the organization too.

And I wonder if you can put on your future forecaster hat. I can see it hanging on the wall there. And speculate with us a little bit about what this technology potentially means for the future of the product trio, future of product discovery, the future of product delivery.

Teresa: Yeah. Okay. I recently interviewed 17 people about how they used Lovable in their work. I will be releasing a blog post about this in August. I also am building two of my own AI products at a depth I did not think I would be at. Like, I just started tinkering and it ran away from me. And now I have a pretty robust AI product.

And both of those experiences have really pushed a few themes for me that I also will be blogging about in August. But I’ll give everybody a sneak peek. I think one of the biggest impacts generative AI is gonna have on how we build is we’re gonna see an even bigger blurring of our roles, and we’re gonna have to get comfortable with it.

And I say this for a couple reasons. I mean, I just talked to 17 people about lovable, most of those 17 people were product managers who were building features that their engineers are shipping without designers. Now, do I want that world? Absolutely not. I want designers involved. But why are these teams doing this?

Because their company hasn’t hired enough designers. They’re still shared across teams. They’re limited by resources and the product managers just trying to get something out there,

Jesse: Mm-hmm.

Teresa: right?

What does that mean for design? I don’t know, but it kind of scares the crap out of me. I mean, most product managers are not equipped and Lovable does a pretty good job.

Like if you just want a basic boring design, it does a pretty good job. But for those of us that want delightful products in the world, it’s not gonna get us there. But here’s how I think about this. There’s always been tools that allow us to build mediocre things, and there’s always been companies that choose to build great things. I think AI is gonna make a lot of mediocre things. So for all those companies that are letting their product managers use lovable to do design instead of designers, they probably weren’t hiring designers anyway. Well, there may be more of them. Yes. But I think we’re gonna see with a lot of mediocre products, design is gonna come right back in importance because we’re gonna try to not be mediocre.

Just yesterday I saw a post on LinkedIn that was like, Lean Startup is dead. It’s free to ship now. We don’t have to learn anything. We can just ship things and here’s what… yeah, since people only hear this, I’m gonna point out that Peter is like passing out over here. Here’s what comes to mind.

Have you two seen the Simpsons episode where Homer Simpson gets to design a car?

Peter: Oh yeah, the Homer.

Teresa: This is the most relevant like pop culture reference of all time right now. What happens when we let anybody design anything? There’s no coherence. It’s a nightmare. It’s not usable, it’s certainly not a Lovable product.

Okay, so that’s the first thing I think is gonna happen is we’re gonna see a lot of blurring of rules. We’re gonna make a lot of mistakes. We’re gonna think some rules aren’t needed. We’re gonna see people try to ship products without engineers because delivery’s free. I I mean, come on, is it really free? Is it ever really gonna be free?

We’re gonna see people try to do the same without design. Some engineers are already talking about how they don’t need product managers anymore because ChatGPT can just write a PRD for them. I think we’re gonna see that all three of these roles are critically important and they’re gonna stay critically important.

The second thing I’m seeing: Getting quality out of LLM based products and features is really hard. So I’ve been talking to a lot of people about how they’re building LLM features and products, and here’s the mantra here, over and over again, getting to a prototype that looks like it works is really easy.

You can do it in one or two hours. Getting something that reliably works at scale for thousands, if not tens of thousands, if not hundreds of thousands, if not millions of users is really hard, and we’re just starting to learn how to do it. And the ways that we’re learning how to do it require so much cross-functional collaboration to do it well that I think we’re gonna be forced to work even better together.

So this is what I’ve experienced with my own product. Like I started to get into the world of AI evals. It’s a big, messy topic that most people have not even heard of yet, but it’s basically evals answer the question of how do I know if my LLM feature is good, right?

It’s non-deterministic. I’m getting all kinds of outputs. How do I know across my production system that it’s good? There’s lots of ways to do evals, but the best way to do evals requires the domain expertise of your designer and/or product manager, and most importantly, your customer. And engineering expertise to automate it and get a large enough sample to represent what’s happening in production.

Right now, like, I ended up in this community of like AI and ML engineers, ’cause I took a class with some of them and they’re all talking about who has this domain knowledge and I’m, like, your product managers and your designers and your customers, and they’re like, oh, would they do this stuff?

Like, we’re just learning. Nobody knows. It’s like, it’s literally like 1994. Like, we’re just learning. And I think, like, the little that I see so far, it’s gonna require, like, not two in a box, three in a box. I mean two people at the same desk working together, discussing what’s the right way to do this.

And maybe eventually we’ll get tooling that like support handoffs, so we’re not literally sitting at the same desk doing this. But right now, that’s what good looks like.

Peter: How has building your own product changed how you think about building product?

Teresa: I’ve become an engineer. I’ll tell you, I spent my weekend like configuring VS code and using cloud code and setting up a proper dev and prod environment. Like I am pretty much an engineer at this point. Maybe not a very experienced engineer, but an engineer. Why don’t I just hire an engineer?

Because I don’t know how to separate the engineering work from the product and design work yet. Like I don’t even know what that looks like. Partly it’s ’cause I’m still learning, but I’ll tell you, I’m hearing this from other teams. Like the biggest question I’m getting from other teams about AI products is like we’re arguing over who should do what because there’s parts that are not that fun, but they’re critical to the quality of the product, right?

So right now, I personally am trying to do all the parts because it seems this question of who’s eventually gonna do what seems really messy. So I’m trying to understand all the parts.

Peter: You are your own triad.

Teresa: I am my own triad. It will not stay that way forever, that it’s not sustainable. But generative AI does make it possible. I mean, it’s helping me fill the gaps that I didn’t know how to do myself, for sure.

Jesse: And it seems like that’s the opportunity for a lot of folks, whether you sit on the product side, whether you sit on the design side, whether you sit on the engineering side. If you are one of these people who already naturally has a toe or two dipped in these other waters. You know, if you are a design minded product manager, if you are a product minded design person, if you’re an engineering person with either of those sensitivities, the opportunity is here for you to create a different kind of value than you’ve ever created before.

Teresa: I actually think our boundary spanners are gonna be our most valuable employees. I would argue they’ve always been our most valuable employees. Now, I have a bias. I am a boundary spanner, but I do think when we can speak to multiple roles in our organization, it does increase our value. And I think that’s gonna get exacerbated by gen AI.

Jesse: Teresa, what are you most looking forward to with what’s to come for design and product?

Teresa: I’m actually really excited about what generative AI unlocks, so like I personally have been nerding out on and like the tools that I’m building are all around how do we teach skills? Use generative AI to teach skills and help humans build skill. So like one headline I see a lot, like the founder of Anthropic gave a talk where he said all entry level jobs are going away.

And this like scared everybody, like how are we gonna develop talent? And I actually, I’m not so sure I agree with him because I think we’re gonna be able to level up entry level employees a lot faster because of generative AI. I think people are gonna be able to enter their careers with a lot more experience.

Like in my head, in the back of my head, I have this like Neo in the Matrix, like just downloading a skill. It’s not quite gonna be like that, but I think we do like now have the ability to let people build hours of practice on their own time through interaction with LLMs. I think it’s gonna require that we get really good at designing what that practice looks like. I think like apprenticeship is gonna look really different. And I’m actually really excited about that. And I’m someone who loves to mentor and to teach, but I’ll give you an example. The first tool I built, is I have a customer interview coach, so my students in my interviewing class submit their transcript and they get very detailed feedback on how well they conducted a customer interview and like way more detailed feedback than any of my instructors would ever have time to give them.

And they get this every single time they submit a transcript. It’s really unlocking deliberate practice. This is like version one. I can tailor this to like, oh, it looks like your last three transcripts, you’ve struggled with this particular skill. So you’re only gonna get feedback on that particular skill ’til you get better at it, right?

Like it unlocks personal learning journeys. And for me, what I love about it is now I have visibility into learning outcomes. Like as an instructor, I can go and observe, but now I get concrete data on every single student in my class. This is magical.

Peter: Hmm. Hmm.

Teresa: Now, it’s not like I gave you a certificate because you came to five class sessions.

Now, it’s I gave you a certificate because I saw your interviewing practice evolve and you reached a level of competency and it was all done through generative AI. Pretty cool.

Jesse: I love the idea that these technologies are not just going to replace entry level people, but actually enable people to level up from the entry level more quickly. And the idea that these technologies are not gonna replace anything human so much as they are going to augment and amplify the human abilities that we already bring to this work.

Teresa Torres, thank you so much for being with us.

Teresa: Thanks for having me.

Peter: Yes. Thank you so much for joining us. I know you’re pretty easy to find out there, but, where do you point people to so that they can follow up with you?

Teresa: Yeah, so most of my stuff is linked from producttalk.org. I blog every Wednesday. I might be adding a Monday AI themed post starting in September. That’s a little sneak peek also of what’s coming. And the book is Continuous Discovery Habits, available worldwide.

Show Notes

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Summary: Dr. Lesley-Ann Noel, Dean of Design at OCAD, joins Jesse and Peter to discuss her global journey from Trinidad to Toronto, leading design education through relationships over craft, preparing students for social change, and her vision for decolonizing design while navigating the tension between academic values and industry demands.

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Transcript

Jesse: I’m Jesse James Garrett,

Peter: and I’m Peter Merholz.

Jesse: And we’re finding our way,

Peter: navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership.

Jesse: On today’s show, we’re joined by Dr. Lesley-Ann Noel, the new-ish Dean of Design at the Ontario College of Art and Design, and author of the book Design Social Change. We’ll talk about social change and design’s role in it. We’ll also talk about design education and its relationship to design in practice, and how she uses her design skills to find success in the world of academia.

Peter: Dr. Noel, Lesley, thank you so much for joining us today.

Lesley-Ann: Thank you so much for the invitation, Peter.

Peter: We have some mutual friends in common who have said how impressed they are with the work that you are doing as the still relatively new Dean of Design at OCAD, the Ontario College of Art and Design. And maybe to start off, it would be good just to get a bit of your story.

How did you land as the Dean of Design at OCAD, and what’s this first year been like?

Lesley-Ann: Yeah, so I, I don’t think we have enough time, but I’ll, I’ll take you around some of the twists and turns. Actually I’m gonna go way back to me at 19 , me as a late teenager. I was interested in graphic design first, and I’m from Trinidad and Tobago in the Caribbean, and I was interested in graphic design and applied to all of these fantastic schools like Parsons and Pratt and RISD and Howard and got into a few of them and then just didn’t have the money to go.

And my parents said to me, you can study anywhere in the world as long as we don’t have to pay for it. And actually, that has sent me around the world. So I ended up doing undergrad at Universidade Federal do Paraná. Which is a federal university of Parana in Brazil, where I landed just because I was looking for good free education. And I did industrial design there.

From there I went back to Trinidad. I used to teach at the University of the Western Indies. I eventually took leave from the University of the West Indies and went to North Carolina State University as a PhD student at that point. Then from North Carolina State University as a PhD student, I went to the D.School at Stanford for a year on a fellowship, a teaching fellowship. From there, I went to Tulane University. Spent two years as associate director of design thinking at the Phyllis Taylor Center, I’m, I’m messing up the name, but I love Tulane. I love the Taylor Center. And then from there I went back to NC State as a faculty member. Spent some time there, went up for tenure, got tenure, and then got a very distracting phone call from OCAD that said, Hmm, we have a job here that you might be interested in.

And at that point, I actually did not think I was gonna leave Raleigh again for the rest of my life. And, came up to Toronto for the interview with my partner and my son. And we all looked around and said, wow, this city is actually kind of cool. And this city is everywhere at the same time. So Toronto is Trinidad, it’s Vietnam, it’s Brazil. It’s just everywhere at the same time. And, as I progressed in the interview process, ’cause I really just came up for the trip…

Jesse: mm-hmm.

Lesley-Ann: and as I went further and further in the interview process, I thought, oh wow, this is actually pretty exciting. OCAD is a fantastic university with very clear mission, and so I was very happy that they selected me for the position and I just walked then into this role of Dean of Design and I’ve been learning on the job since August last year.

it’s up and down, up and down, a very interesting rollercoaster.

Peter: It sounds like almost from the beginning you’ve had an academic orientation when it comes to design, teaching others, getting your PhD, and when I think of design, design is, such a craft, it’s such a practice. Obviously most of the people we engage with, they do it for, you know, hands-on design for their job.

I’m wondering what it was, After you got your maybe that first degree in industrial design, what was it that drew you towards more of a teaching and academic path as opposed to a practice, craft path?

The Path to Academia

Lesley-Ann: Maybe it’s that I describe the academic path more clearly because it’s easier for people to understand, right? I, think a lot of us as designers, we learn how to hustle and we, you know, there are designers who get jobs and then there are designers who maybe I’ll use kind of business language, the designers who make jobs, right?

And so, you know, a lot of us really are moving from hustle to hustle to hustle. I started off in furniture design and then really spent there’s a gap in the story that I just told you. I spent a long time doing consulting work as a designer and working for really anybody that I could convince that they needed design, you know, whether it was government ministries, export promotion councils, really anybody, theater production companies, anybody who, who was interested in design or who I could make interested in design, I would do projects for them.

But I ended up being drawn to academia, I’ll have to say, because of the stability, you know, and there was a point where I was like, okay, I need a little bit of stability. I have a child’s education that I’ll have to pay for eventually.

And then there are some countries in the world where there will be fewer stable opportunities for designers. It’s not that design work doesn’t exist, it’s that maybe the stability of a full-time job in design might not exist. So that’s really how I ended up in academia because academia provided some stability when I needed it.

And then what always interested me in academia is that, okay, if you are from a place without design jobs, kinda like what’s the role of design in that kind of space. You know, like having studied in Brazil, going back to Trinidad, those have always been questions that I’ve focused on, you know, what else can we be doing with design? Is it just about graphic design? Is it just about jobs or are there other things that we could make with our design abilities?

Jesse: What do you see yourself creating now at OCAD?

Creating Space: The Dean as Co-Designer

Lesley-Ann: So at OCAD I see myself, this will sound very, very wishy-washy. I see myself creating space.

Jesse: Mm.

Lesley-Ann: So in my last role at NC State, I worked with a lot of PhD students, and at OCAD, like we don’t yet have a PhD program, but I do see myself doing that kind of PhD advisor role almost, with a lot of faculty members who are doing research.

So I, see myself creating that kind of environment at OCAD where people are supporting people to deepen their own practice, creating some additional opportunities for students trying to emphasize that there are many different ways of doing design and, there is space for your design practice in this world of design.

I think of the Dean role as a support role where I am supporting a lot of people to be great.

Jesse: I imagine that entails a lot of context switching as you are shifting from one leader’s needs to the next leader’s needs. As you’re engaging with the leaders of these various design disciplines or programs that are all under your umbrella, how do you manage all of that?

Lesley-Ann: So we have six programs at OCAD. Lemme see if I could count them all. We have graphic design, advertising, illustration, industrial design, environmental design, and material art and design. And these are our undergrad programs. And then we have graduate programs in design, which I have less of a role in.

interestingly, in the undergrad programs, I use this as my entry conversation with people, I’ve had an active interest in all of these six programs. I mean, it’s a coincidence that I ended up here, but, you know, I always, I loved illustration as a teenager. My first job was in advertising. I worked in graphic design for a little bit because that’s where we all find work. I am an industrial designer. I’ve collaborated a lot with architects, and I used to do ceramics and jewelry, and so it’s that I am often drawing on a little bit of knowledge that I might have, you know, I am then this generalist and I’m drawing on some general information that I have on all of the programs.

Then my own knowledge of academia and teaching and learning, and that’s how I’m having the conversations with the different chairs of the programs, or the faculty members, and then my design practice most recently has been about co-design.

And so actually, I’m using those skills because I have to do a lot of listening to understand people’s work. And then sometimes I’m co-designing with them, right? Helping them to co-design their research, practice, co-design new courses that they’re teaching. Sometimes even co-designing experiences with industry. That’s really how I’m navigating all of these conversations. I’m using a lot of my co-design skills, as well as some of my knowledge from design across the disciplines.

And then, because I’ve been around a block a few times, you know, there’s stuff that you end up knowing because you’re old, right? Or you end up knowing how to have conversations with people because of age. And so some of the work that I’m doing is just based on that positionality, right? You know, I, I have a, a design professor colleague. I have to laugh as I say it, but he’s, he is been calling me an elder for a few years, and like would come to me for mentorship.

And now in this role it’s like, okay, I’m taking up that space and maybe assuming that kind of positionality as, okay, I’ll give you support and guidance to get you through the process. So that’s the way I’m doing this work now.

Peter: It sounds like, if I understood the six programs at OCAD, at least the undergrad programs, they’re not particularly digital. But I saw that Ben Shown from Blink UX had visited your class. And, obviously that’s a UX design practice.

What is your relationship to more digital design, UX design? How are you seeing that in the context of your school as well?

Embracing Thing-lessness

Lesley-Ann: Yeah, so now we, we might get into the conversations that might get me in trouble, but that’s fine, right? There are a lot of places where the UX content isn’t explicitly visible in the titles of programs, right?

I visit a lot of design schools and I think that a lot of design schools, we have these legacy titles. We have 20th century names. We might have actually like Bauhaus and Ulm kinds of names of programs. And I think that there is digital content in a lot of the programs, but it’s not always very visible, right? So the UX, UI work is happening primarily in our graphic design area, but also in industrial design.

And I saw this in the last school that I was in as well. We would see UX, UI in graphic design and industrial design, right? Oh, maybe Ben said this, somebody told me that architects make the best UX designers, which I didn’t know, right?

But, you know, so I think that there’s digital content everywhere. I don’t think that the names of the program clearly say where the digital content is. So actually like one conversation I’ve been leading in our program is, I’ve been having people brainstorm around different “what if?” scenarios. So one of the scenarios that I gave people recently is, well, what if we just concentrated less on things, you know, and focus more on a thing-less area of design?

Because our programs have legacy titles, they’re really programs around things, right? And so, you know, if we make the thing-lessness a little bit more explicit maybe that might prepare people for strategy and UX and UI and management and all of these other areas where there are in fact a lot of opportunities for design, right?

But I really just kind of planted the seed for the conversation and maybe ran away. No, I didn’t run away, but I do think that we will continue that conversation. Our masters programs are, I’ll say, thing-less programs. So we have SFI, which is Strategic Foresight and Innovation, Design for Health, and Inclusive Design.

You know, those are our three design masters programs, right?

And even though I’m asking people to think about the thing-lessness, right, I also like things to understand other ways of thinking. So, when I learn to make a chair, for example, I’m learning a process that I then can apply to anything.

And I think when designers can see their work in that kind of abstract way, then they can work anywhere. And that’s really I where wanna push the conversation to at OCAD where, you know, even though people are learning in these initial silos, that they understand, well, actually it’s a process that they’re learning that they can then apply in many different contexts, and we are bringing you here and, making you comfortable with being flexible and then you can take that flexibility in other places.

Peter: This will sound diminishing, and it’s not the intent. To what is OCAD a trade school, like, are students coming there to get skills to get jobs, versus maybe a more kind of classical view of education where they’re going there to engage in a passion and who knows what will come out on the other side, but the journey is the reward.

How are you framing that now as dean?

Lesley-Ann: So we have both conversations here, right? Where we do talk about, you know, what jobs are people going into. And then in some of my work, of course I have to work with industry and the thing is, I am more on the other side where I think education is about people learning to be flexible and learning to address issues and people exploring different paths.

And I do very often lead conversations like that. I’ve just had to remember that I actually have had the privilege of paying for very little education. You know, I studied in Brazil for free, studied in Trinidad for a fraction of the cost, had a, PhD scholarship. And, you know, sometimes when I talk about education being the journey, I do have to also think about the people who are mortgaged to the hilt to try to pay for education.

So, you know, we have to have both conversations at the same time. So we do have some areas in our programs where people are very, very job focused and very focused on what are the immediate rewards of the educational experience or immediate outcomes.

And then there are other people who think about it much more abstractly, and are thinking about the journey and the collaborations and the research that will happen, and then the research outputs. And so I am kind of like moving between both conversations all the time.

And maybe I should say too, then in the way that I am starting to promote collaboration, that’s also on the journey side of it, rather than the specific job side of it, where I’m really trying to promote collaborations across disciplines, where we could be exploring problems much more creatively. That leads to the jobs that people are looking for, you know, and creative experience, the different experiences of school lead to the outcomes that people want.

And actually also my hesitation about talking about jobs so much is that some of us don’t want jobs and that’s okay, right? I actually heard that at undergrad and I felt it was very transformative for me to hear that early, where my professor walked into the classroom and said, ” There are no jobs for any of you,” which is frightening to hear.

But his point was that we make them, we make the jobs. And I found that very empowering. And actually I didn’t really look for a job then for the first 10 years after I graduated because I was listening to what this professor had said and kind of like following different opportunities. And then I had a baby, and then I realized, okay, maybe I do need a job.

Peter: Separately, we can talk about the role of design and its relationship with capitalism.

Lesley-Ann: Yes, yes, yes.

Jesse: I find myself wondering about change, you know, and the relationship between academia and industry being so much kind of dictated by the pace of change in each of these spheres. And often I feel like the challenge for academia, and you referenced this when you talk about, you know, 20th century titles and things like that, the challenge is to stay in step with the current state of industry while also providing the necessary validation and reflection that academia has to offer.

And I’m curious about how you see that tension and how you resolve that within your programs.

The Importance of Relationships

Lesley-Ann: Yeah. I don’t know yet if I’m resolving it. You know, one way that I think about that tension is that there, well, I mean… I’m gonna respond in a few different ways, right?

One conversation that I’ve had with students actually is about relationships and just the importance of relationships. And this is gonna sound maybe a little airy fairy, but it’s real, right? That school context, university context is creating an environment where these relationships are formed and whether these relationships are formed with other students, with faculty, with alumni, with industry, you know, all of these relationships are actually important for students’ growth right now.

If we are faculty that are always just embedded in our work, in our teaching, we maybe can’t keep up with the pace of change of industry, right? We have different areas of focus, you know, we are trying to do different things with the way that we teach.

What we can do is we can continue to build our relationship with industry, right? We can, you know, be bringing industry partners, whether into classes, giving talks. Again, we can be building these relationships with industry partners.

And then I think our job is to keep people flexible and fresh so that, I have to say, industry continues the work, right? I, don’t think that it’s possible for any school to prepare students a hundred percent for a specific job, but, you know, we can have people leave school with the right mindsets and the flexibility and the ability to innovate and all of that, and then they continue learning in industry.

Peter: Relationships is something Jesse and I talk a lot about in the context of leadership, right? To lead is to relate to others and bring them along with you. And the reason we talk so much about it is that designers are rarely taught how to develop strong kind of business relationships, at least.

Lesley-Ann: Mm-hmm

Jesse: The focus is on craft in their development.

Peter: …and we talk with folks who’ve been doing design work for a decade, they get into a leadership role, and all of a sudden they now need to tap into their soft skills. It’s not, soft skills is not a phrase that I like, but it’s, it’s often how it’s labeled.

And so I’m wondering, given what you said, how do you see helping folks earlier on and possibly in school develop these soft skills? Is that something that’s maybe an evolution in what you’re teaching or, how you are guiding students so that they are better prepared when they enter the world?

So often design programs are tailored towards design services, like, agency practice, which is very different than what most of the designers are now embedded in an enterprise. And I’m wondering how that’s maybe changed how you are setting people up as they leave school.

Lesley-Ann: So I am going to take what you just said and use this as a soundbite for everything. You know, just the importance of relationships I don’t know how I ended up learning about the value of relationships, right. But I, think that the relationships are as important or more important than a craft.

And maybe it’s that if you are going into leadership in particular, I changed the way that I thought about design work. Maybe like if I think about my first 20 years of practice as a designer, which has aged me, right? I think somewhere after the first 10 years I was like, oh, it’s not just about me. It’s actually about all of these other relationships that I need. And then started to realize that these relationships also lead to other opportunities or learning,

so that has been a work in progress.

But we have made this a visible challenge as we talk about teaching post pandemic. You know, even though the pandemic was five years ago, we are still feeling the impact of the pandemic on the teaching and learning.

And I’ve been explicit in my leadership role saying that we are talking about relationships and we are going to do what we can to make sure that the students are building relationships, because the pandemic kind of took that ability away from them, right?

Now some of it is my philosophy driving this where I think, okay, like I said, we can’t teach you every single skill, but we can encourage you to have relationships with people who have the skill, or we can encourage you to develop relationships that will lead you to other opportunities, so it’s that the relationships are needed sometimes to maybe backfill.

You only have a, finite amount of time. That sounds so transactional, right. But I mean, you know, you, you have a finite amount of time in school and, in focusing on your relationships, other things can happen even after the school experience is gone.

Jesse: I find myself wondering about the change that is going to be required for the school to create the space, as you put it, for these things to happen, and your role within that as change maker. You’re relatively new in the role. There are clearly some expectations that came along with the chair.

And I wonder about how you make the case, build momentum, get in there and make change happen, as a new leader in an organization like this one.

Lesley-Ann: So let me drop a name now. My friend Don Norman. And, seriously when I became Dean, Don said, alright, you’ll now be a public figure. I was like okay. And then, you…

Peter: So you had known Don already.

Shaping the Future of Design Education

Lesley-Ann: Yes, yes. I have a kind of funny story about… Don probably doesn’t know the first time we interacted, but I think I had a paper out there in the world, that was written even before I started my PhD, like a really badly written paper that he thought was interesting actually.

And I was writing about design education, like Trinidad or something like that. And he emailed me about the paper and then he kind of commented and he says, and your citations are wrong or something. We started off having these email interactions and then our relationship got closer through the Future of Design Education projects.

And then we’ve had quite a few interactions since. He also told me, well, you can’t change everything or you can’t get everybody on board the train and you have to make small wins. And so that’s really you know, the same way I talk about relationships for the students. I am working on my relationships with faculty. We have about 70 full-time faculty. And so I’ve been working on the relationships with them and figuring out in each relationship what’s a small win or a win-win kind of scenario, And how can we then amplify that to do other things? S

So that’s where you hear maybe MBA talking, right? Where I’m really trying to see, well, okay, what is it that people are trying to get to? How does that align with some of our academic and strategic goals? How does it align with trends in the industry or in academia, you know, and how can we get everything to align so that people are thriving.

I really like these words, thriving, flourishing, joy, and I think that despite the crazy context that higher education might find itself in, that I really have to figure out how am I supporting people to do well in the work that they’re doing.

Jesse: So for you as a leader it seems like there’s always the risk that that support going out turns into no time left for anything but line item firefighting with people all the time.

How do you maintain balance between being a support resource for your leaders in the way that they need, and your own leadership?

Lesley-Ann: So I carve out some time for strategic thinking, right? On my calendar, right? I mean, it doesn’t always say strategic thinking. But I do some big thinking regularly. I ask other people to do big thinking as well.

And the first time I did it in one of our meetings, somebody said, we don’t have time for blue sky thinking. I’m like, yes we do. You know, because the thing is, higher education right now feels like it’s on fire. I mean, I’m in Canada we are not dealing with the same issues that you’re dealing with in the States, but you know, everywhere in the world right now, higher education actually is in chaos, right?

And it’s like we can’t only be putting out fires. We do have to think a little bit more long term, and we have to make sure that we have space for that, right? So there’s that. I regularly do professional development. You know, I find courses, go to other people’s events and learn. I make time to learn. That’s what it is.

And then I work with a coach who’s like a therapist and she listens to me and then she says, you’re not crazy, you know? So, so yeah, I think to balance things, we have to create the time to be doing different types of thinking.

And then actually, I hate to say it, I switch it off at a certain time, you know I’m a parent, I’m a partner, I, really try to turn off the workday at a certain time and then go and walk or kayak or whatever, you know, with people who maybe love me a little bit more than um, than the other people I support, right?

And, and then that keeps the balance that, maintains it.

Jesse: Hmm.

Peter: So I should have realized this earlier. You are the second Canadian dean that we’ve had on our show actually recently. In that we had Roger Martin, I don’t know if you know Roger, he had been the dean of the Rotman School at University of Toronto. He’s not there anymore, but we had him on because he was very much about the intersection of design and business.

And one of the things he mentioned is that when he became Dean of the Rotman School, He had a vision for the program and it was actually a very simple vision. He said he wanted the Rotman School to be Canada’s name business school outside of Canada, like to have visibility outside of Canada.

And then it took him 15 years or something to like chip away and make that happen. But he was able to make that impact.

And I’m wondering your vision for the school at OCAD, if you had one coming in, in terms of what you thought it could be, or now that you’ve been there almost a year, you know, what do you see as your vision? What is that change that you’re trying to lead to towards, for the school.

Lesley-Ann: Yeah. It’s nice that you interviewed Roger Martin. I’ve never met him, but I mean, he did what he set out to do because I knew about him and Rotmans before I even knew about anything in Canada, right?

My big vision before I got here was I was like OCAD has decolonizing design written in its academic and strategic plan and goals, and so there is an energy around decolonizing here that I’ve not seen in other places that I’ve worked. And so my big goal when I came in was around making decolonizing design, making OCAD really the visible place around the world for that work. And I imagined us, you know, doing partnerships with people in New Zealand and Australia and South America and, you know, really then bringing this more fringe movement into mainstream design.

And then of course, I would’ve been building on Dori Tunstall’s work before me, right? ‘Cause was the dean before me. And I think there’s still a place for that work. I am now of course recognizing that, okay, Roger Martin took 15 years to do that. You know, deans, we think in five year terms. And so my first five years, I think the goals might be a little bit more conservative, right? When I came in, I found that people wanted more community post pandemic.

Peter: Mm-hmm.

Lesley-Ann: So, you know, some of the work is again, about, actually all of the work is about relationships. So it’s about relationships between faculty and students, relationships with academic partners.

So I’ve been having a lot of conversations with universities in the area about, okay, let’s collaborate some more, let’s do more research. I am, in fact, investing a lot of energy into research because I’m coming from an R1 university in the States, North Carolina State University into OCAD.

So I’m trying to bring in that kind of research mindset as well. So, you know, some of my goals are around research relationships, and then some industry partnerships. So, I mean, little bit more conservative, but it is in fact, you know, they’re tied to what Roger Martin’s goals are. You know, definitely about OCAD’s visibility, you know, making sure that OCAD is very visible globally.

And then that we are doing research, and we are driving industry practices around our values, you know, so OCAD is a very values-driven institution and we are transparent about our values, and I think that we can also transform some of the industries that we are active in, you know, around our values, around decolonization and indigenization and anti-racism and all of these words and philosophies that really drive the work that we do.

And I think that we can impact the industries that our students go into.

Jesse: It’s interesting to think about how this mission carries within it the notion of design as a tool for creating positive change broadly in the world by changing design itself. And I’m curious about the relationship between design and change as you see it, because I know that this is something that you’ve definitely given some thought to over the course of your career.

Design as a Tool for Social Change

Lesley-Ann: Yeah. I think as designers, we are always trying to change the world, right? You know, okay, so let me use some quotes here. So there’s that Herbert Simon quote about design is always the practice of, changing existing circumstances into preferred circumstances, right?

And so if we are thinking in that way, then everything that we do in our work is about imagining this future and thinking about what are the steps to get there, right? So I think that it’s a real superpower that designers have.

You know, working across five different universities, I’ve seen that almost every design student, you know, when they are given the opportunity to create their own projects, their projects are very often about creating social change and campaigns and making sure that the world is better. And I think that we could really lean into that.

So actually, one of the scenarios that I gave the faculty in our brainstorming activity a couple weeks ago was about what if our program was just designed for social justice and maybe we got rid of all the silos, and everybody then is kind of focused on that social change or social justice or, you know, because a lot of the projects that faculty want to work on, that students want to work on, are in fact in that social change, social justice space.

So I thought, well, what if we did that, instead of having an advertising program and a graphic design program and a… right? People have to warmed up to these conversations.

It is what we do as designers. It sounds so airy fairy, you know, we, are always trying to make the world a better place, right? And so, you know, we could actually be more explicit about that too in our education.

Peter: I was thinking back to your MBA, as well as a PhD in design, and your teaching design, but you maintain this relationship with industry, so you’re kind of straddling these, and you’re talking about how designers seek to drive meaningful change, positive change, but designers are also, in my experience, really good at getting in their own way of realizing the change they seek, right?

They don’t focus on relationships, they focus on the thing. When it’s time to speak up and engage and do the work of driving change, which often requires politics and communication, designers are, like, many designers are just back all, all the way off of that. They’re like, no, not me.

But the reason I brought up the MBA thing is, you’re seeing folks early on in their development, and some of it for me is, personality types that gravitate towards different fields and practices, right?

And, you know, you’ve spanned both. So you kind of suggest that it’s not a hundred percent, and I don’t mean to be too stereotyped here, but there does seem to be a personality type that drifts towards design. There’s perhaps a different personality type that drifts towards business and marketing and finance.

How do we help those folks in design embrace what those folks getting an MBA learn about how to show up with others and make change? ‘Cause that change management’s a formal class, right, In an MBA program, that designers are never taught.

But, what would it mean to try to seed earlier on or help those folks, whose personality might encourage a certain introversion or reticence or focus on the work and craft, that if they want to make change, they gotta show up differently?

How is that going from your point of view?

Lesley-Ann: So I used to teach a class, which I call a social studies class for designers. And I’ve actually met more and more people who are teaching that kind of critical education that was absent from design education. So, you know, how do we get designers to think more critically? We definitely have to weave that critical thinking into the education.

So my design education was about pretty things. And that’s not enough. If designers want to change the world or whatever we say we want to do, we need to know more about the world. Like you said, we have to understand politics and current affairs and, you know, we really need to have broader educational experience than designers used to get some years ago.

And so I’ve seen more and more people, you know, like at the academic conferences, reporting on how they’re changing their classes to have more critical discussions in the classroom and then have designers engage with people more.

So I think of the business people as different though. The first conversation about the critical literacy, that’s like getting the designers closer to the social scientists and maybe the humanities people, so that we are seeing the world through a different lens.

And then in my MBA, actually, like, organizational behavior and organizational development. Those were the courses that fascinated me because I could see, again, the designerly-ness in those courses that I had never had to think about before, right?

So, to answer that part of the question, I don’t know that I’ve seen a lot of people doing that early on, you know, having people understand organizations and how organizations work, how people work in that kind of way. I haven’t seen a lot of that in the undergrad training, but I’ve seen a lot more people bringing critical conversations into undergrad.

So I do think that design professionals will begin to change and look different as this kind of education gets a little bit more common. But the thing is, there is always that tension between, let’s just focus on craft and skill, and then let’s get a broader education. And I will always be in the camp of let’s expose the designers to a broader education. Because anybody can learn the crafts or I hate to say, now we bring the AI in…

Peter: That relates a little bit to what I was thinking when I was last in Toronto, I didn’t get a chance to see you in a conversation with Michael Dila, where you were discussing the future of design.

design

Lesley-Ann: Yeah.

Peter: And I wonder when I ask you what is the future of design, right, what are you leaning toward as you look out? ‘Cause you’ve mentioned co-design, right? You’ve mentioned relationships, you’ve just mentioned AI, right? What is your sense of the change and trends that are brewing, and how are you going to, I don’t wanna say maintain relevance, but, you know, stay engaged, appropriately engaged. Not just yourself, but the school that you’re helping lead, so that it, especially in what feels like a time of, I don’t even say rapid change, just discombobulation…

Lesley-Ann: yeah…

Design Will Always Be Relevant

Peter: Just, it’s a weird time right now. So how are you steering the ship through that and toward what’s the distant point on the horizon there?

Lesley-Ann: Okay, so again, this is gonna sound so fuzzy. I, It’s about flexibility and relationships. You know, that’s kind of like the only thing that’s gonna get us through this rollercoaster, right?

I am not afraid of AI or higher education is under threat, I mean, I’ll say that I’m not afraid of that threat, we’ll always be relevant. I think that we will be less relevant if we are fixed and we say things like: This is the curriculum. This is the way we do things. This is…

So, it’s that we have to be part of these conversations and we have to be experimenting with the different trends as they come and go, right? So if the trend now is AI, we all have to kind of figure out a little bit of it, right? We might not have to stay on the trend, but we have to understand what it does.

You know, I think that the core skills that we have will always be relevant, and it’s up to us to also emphasize our relevance to whatever society we’re in.

Jesse: What are some of those skills that you think will keep design relevant in the future?

Lesley-Ann: So, I think that making is important.

Well, actually understanding the agency of making things, you know, just that thing of being able to sit down and even without AI or anything like that, sit down and say, well, okay, this is the idea I have in my head and I get this idea from my head onto a screen or onto paper or whatever.

And then the thing is made, whether I make it with my hands, or whether I’m using 3D printing or, you know, I think that that’s making skill and that making ability will always be relevant.

And not everybody in society, even though everybody makes, not everybody is aware of that agency and that power of making things.

And I, in my own research, I’ve taken that agency, designerly agency, and used it in children’s education, and that’s how some of the work that I do around social change is tied to that thing of knowing, I can make this object, maybe I can make, this will sound so hubristic, I can make the world, right?

But knowing that you can take power of things around you like that, I think will always be relevant. Even if the tools we are using to make things will change.

Jesse: I’m struck by the idea that design is inherently about agency, about empowerment, about the ability to do more with your dreams than just dream them.

Lesley-Ann: Yeah. Yeah. Okay. So I have an industrial design bias, and those of us who do industrial design, we have no idea what jobs we are gonna do, right?

But I think when I speak, ’cause a lot of people just never get jobs in, you know, there are some jobs for industrial designers, but I’d say they’re fewer than graphic design as a matter, but industrial design education, I think, gives you a sense, well, the industrial designers I know think that they own the world. Why? Because they know how to make a chair. They know how the printing press works. You know, they could kinda look around a room and break apart every single object in a room. And, that gives them sometimes this kind of sense of power that maybe makes them very obnoxious.

But I think that that’s, that’s good for people to know that we make this world around us. Well, I, I’ll use language that I use often these days. The world doesn’t just happen to us. We make it. And I think that that’s good knowledge for us to have. So that it creates some action as well from people.

Jesse: Yeah. Yeah. Because inherent in that knowledge that we make the world is the implication that we can remake it anytime we want, and that’s a powerfully optimistic statement, I think.

Lesley-Ann: Yeah.

Peter: You mentioned earlier, OCAD’s values system, or set of values. And some that you inherited around things like decolonizing design, but you also recognize that you’re not gonna like “Decolonized design, check, moving… What’s next?” Like that’s, that’s a process.

But I’m wondering, something I think a lot about is a challenge that designers, but particularly design leaders, face when it comes to values.

And this touches, I think on some of what we were talking about with respect to agency. Design is a humanistic endeavor, right? It’s in the arts and humanities.

We are often, though, designers and design leaders, are working in industry. And industry has a different set of values, a corporate set of values, a more calculating set of values. An MBA set of values, maybe a little more mechanistic, little less about agency and creativity and generation, and a bit more about calculation and deconstruction and analysis, and a different set of tools.

And I’m wondering, navigating these different value systems and your engagement with industry, you’re talking about trying to help bring some of OCAD’s values into industry. Like my country’s on an anti-DEI kick unfortunately…

Lesley-Ann: mm-hmm.

Jesse: Hmm.

Peter: …Canada I know it’s a different conversation there.

But I, I imagine there’s tension in the values that OCAD is encouraging and the values that industry, even your industry partners are willing to receive. I, I don’t know how much decolonizing talk you can bring inside some of these types of corporate environments.

How is that conversation going, and how are you helping designers think about, or maybe even just for yourself, think about living in these different worlds of a more humanistic practice, of care, of ethics, of equity, and then a more corporate industry mindset of business results.

Lesley-Ann: Well I try not to think of it as different spaces. And when I used to teach, we would have conversations about ethics and the students would talk about what do I do if I get a job offer from tech company, whatever.

And I would actually say, I want you to take that job because I would prefer that you are designing my technology than the person who has not had these conversations about ethics. That’s what my hope is, as leader, as an educator, that we are having these conversations about ethics or we are having these conversations that are driven by values, and the graduates will take these values with them into the work that they do.

Interestingly, well, in Canada you can have conversations about decolonization everywhere and indigenization and, you know, so I wouldn’t be surprised if you know, we went into a conversation with RBC or TD Bank and we led with decolonization because that’s the context that we are in, because everybody talks about it all the time.

Maybe in 10 years time in design we’ll see that because really, well, okay, things are complicated on your side of the border because people can’t talk about these things anymore. But if I think about design education, even up to last year, at every single conference I went to, people were talking about these critical issues so much that I would’ve said then in 10 years time, everybody in design would be bringing these values into everything that they would doing, right? And we wouldn’t be thinking in this kind of bifurcated way, right?

Now, I’ve always said to my, like, industry partners, I’m in academia and I know I, maybe I’m in a little bit of a bubble or privileged space where I can lead with these values, but I, also say at least I can do this work and be public about this work.

And that can drive maybe the way some people in corporate spaces have their conversations. So you know, we can lead the corporate world to continue to talk about values and I am in fact hoping that our students and our graduates will go out and take the values conversations with them into the world of work.

Jesse: Speaking of optimism and design, what are you most optimistic about l ooking ahead?

The Role of Design in Positive Change

Lesley-Ann: I’m generally optimistic. I’m a little bit over-optimistic about futures, you know, and equitable futures and I imagine social change in this way where we reach one barrier and we eliminate it, and then we find the next one and we eliminate it and we find the next one.

And so I’m just kind of optimistic that we will be always moving forward and changing the world and it will get better and better and better.

And so 10 years from now, everything is gonna be a lot easier for people than it is now. And maybe I’m thinking explicitly about people with marginalized identities.

You know, I think a lot about accessibility, about homophobia, transphobia, you know, so I, just imagine that life will be easier in 10 years time. Fingers crossed.

Peter: What’s the role of design, in driving towards this positive change?

Lesley-Ann: There’s the role in the movement of, you know, galvanizing people and getting them on board the movement. And then there’s a structural kind of change or structural work that we can also do as designers, right? So if you are in UI or UX, you could be bringing in principles of trauma-informed design from the start, or, you know, principles around accessibility.

You’re bringing that into the work and you’re making sure that bad design doesn’t go out at all. So I, think both in making the movement of people, and then just looking at the individual issues and trying to just break them apart and get rid of them, there’s a lot that we can do as designers and I was prepped for that question because my students ask me this all the time when we did that social studies class.

They’re like, so what can I do as a designer to change the world? And I’m like, it doesn’t matter if it’s big change or small change, we can all do something.

Jesse: Fantastic. Dr. Lesley-Ann Noel, thank you so much.

Lesley-Ann: Thank you so much for this invitation.

Peter: Oh our pleasure.

How can people find you, engage with you?

Lesley-Ann: So LinkedIn should pay me, but LinkedIn is the easiest. The easiest place to find me is actually LinkedIn. Yes, all of social media, LinkedIn and Instagram are easy, but LinkedIn is the best place to locate me. And then I mean my email address is somewhere on OCAD website, but it is lnoel at ocadu dot ca and people can respond.

I’m actually slower on email, but I’m available and accessible to people.

Peter: And anything you want to plug?

Lesley-Ann: So I am, I, I could plug my book.

Peter: Please do.

Lesley-Ann: I’m the author of Design Social Change, because I really have been having these conversations about agency and seeing the world around us and understanding what needs to be changed and then taking action around that change. So I’ll, I’ll definitely plug that.

And I’ll also say to people, if you’re in Toronto, come and visit OCAD. ‘Cause we are in a really cool building downtown Toronto. So even if you just come and take a picture in front of the building, come and do that. Yes.

Jesse: Thank you so much for being with us.

Lesley-Ann: Thank you.

Jesse: For more Finding Our Way, visit findingourway. design for past episodes and transcripts. You can now follow Finding Our Way on LinkedIn as well. For more about your hosts, visit our websites, petermerholz. com and jessejamesgarrett. Com. Peter recently launched The Merholz Agenda, his semi weekly newsletter. Find it at buttondown.com slash petermerholz. And if you’re curious about working with me as your coach, book your free introductory session at JesseJamesGarrett. com slash free coaching. If you’ve found value in something you’ve heard here today, we hope you’ll pass this episode along to someone else who can use it. Thanks for everything you do for others, and thanks so much for listening.