Podcast
Pearls On, Gloves Off: The Legal Innovation Podcast
Join Mary O'Carroll as she sits down with General Counsel, Chief Legal Officers, and industry pioneers to tackle the debates reshaping legal services and technology. Presented by Practicing Law Institute.
- Management chart
- #179
- Episodes
- 107
- Releases
- Every two weeks
- Typical length
- 54 min
- On air since
- 2022
- Latest episode
- 1 week ago
Episodes
107 episodes, newest first
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51 min
#106 - The Agentic Associate: Mike Schmidtberger and John Nay on the AI-Native Firm
Episode 106
Show notes
Mary sits down with Mike Schmidtberger, chairman of Norm Law, and John Nay, founder and CEO of Norm AI, to get beyond the billion-dollar headlines. They dig into how a law firm and an AI company evolve together, how agentic associates turn four days of drafting into hours, why Big Law is structurally stuck, what 100% fixed fees do to incentives, and why the hardest part of building it all comes down to people.
This episode is presented by PLI.
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1 hr 5 min
#105 - Disrupt Yourself First: How Redgrave Is Rebuilding the Law Firm Model
Episode 105
Show notes
Mary sits down with Erica Zolner, Britney Colton, and Ray Mangum of Redgrave LLP, an information law firm that runs nothing like a traditional firm. They dig into what happens when lawyers and technologists work side by side, how AI turned 600,000 contract PDFs into a risk picture in five days, why disrupting yourself beats waiting to be disrupted, why clients still hold on to the billable hour, and how real-time feedback shapes how the firm rewards its people.
This episode is presented by PLI.
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55 min
#104 - Flight Simulators for Lawyers: The Rise of the Legal Engineer and How the Profession Learns
Episode 104
Show notes
Mary sits down with Stanford Law's Adam Sterling and Irene Liu to unpack the school's new Legal Engineering Academy. They dig into what a legal engineer actually is, why the legal apprenticeship model has been broken for years, how AI-powered 'flight simulators' could compress a decade of experience into months, why AI may be pushing demand for young lawyers up rather than down, and what the legal talent ecosystem could look like ten years from now.
This episode is presented by Workday.
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1 hr 16 min
#103 - The Lawyer Personality Unpacked: What the Data Says After 32 Years of Research
Episode 103
Show notes
Mary sits down with Dr. Larry Richard, psychologist, former lawyer, and the foremost researcher on lawyer personality, for a return visit that goes even deeper than their first conversation. They dig into the seven personality traits that make lawyers uniquely wired for the law and uniquely challenged by everything else, why nine out of ten lawyers are thin-skinned, why empathy has dropped 50% in the last twelve years, what that means for legal leadership in an AI-driven world, and what the science actually says about how to change any of it.
This episode is presented by Workday.
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57 min
#102 - Inside Crosby: The AI Law Firm Rethinking How Legal Work Gets Done
Episode 102
Show notes
Mary sits down with Ryan Daniels, Co-Founder and CEO of Crosby, for a rare look inside one of legal tech's most talked-about AI native law firms. They dig into why Ryan built a law firm instead of a legal tech company, how fixed fee pricing completely changes the unit economics of legal services, why Crosby lawyers are evaluated on speed not hours, how they're building a data moat from every contract they touch, and what it actually looks like when a law firm is designed from day one to hand work off to agents.
This episode is presented by Workday.
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51 min
#101 - Ford's Warning Shot: Adapt or Get Left Behind
Episode 101
Show notes
Mary sits down with Darth Vaughn, Associate General Counsel and Managing Director of Policy and Legal Ops at Ford Motor Company, for a candid conversation about what it actually looks like when one of the world's largest legal departments stops waiting and starts building. They dig into why the billable hour model is structurally broken, what Ford actually expects from its outside counsel, why AI native firms still have a trust problem, and what the legal department of the future really needs to look like - from someone already living it.
This episode is presented by Workday.
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59 min
#100 - The Future of Legal Is Already Here - A Conversation with CLO Eric Greenberg
Episode 100
Show notes
Mary sits down with Eric Greenberg, EVP, Chief Legal Officer, and Corporate Secretary at Cox Media Group, for a milestone 100th episode conversation about what it actually takes to lead a legal department through transformation. They dig into why AI governance is really an anthropology problem, why buying software is the beginning not the end, the future of big law and outside counsel relationships, and why the most important leadership skill right now is making it okay to be wrong.
This episode is presented by Workday.
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54 min
#99 - Who Is Sandstone? Inside Legal Tech's Most Talked-About Company
Episode 99
Show notes
Mary sits down with Nick Fleisher, Co-Founder and CEO of Sandstone, to pull back the curtain on legal tech's fastest-rising company. They dig into why great software still matters in the age of AI, how Sandstone is solving the permissions and context problem that's plagued in-house legal for years, why law firms will never out-build tech companies, and how an AI-native team is redefining what it means to build lean.
This episode is presented by Workday.
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51 min
#98 - Anna Richards
Episode 98
Show notes
Mary sits down with Anna Richards, Head of Community at Brightflag, to catch up on what's actually happening on the ground in legal ops right now. They dig into the shifting skill sets legal ops leaders need, how to think about building a tech stack from scratch, and why the job keeps getting harder even as expectations keep climbing.
This episode is presented by Workday.
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Thank you to our sponsors for making this show possible.
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53 min
#97 - The Senior Talent Problem Nobody Wants to Talk About
Episode 97
Show notes
In today's episode, Mary sits down with James O'Dowd, CEO and founder of Patrick Morgan, to explore what legal can learn from the PE and AI disruption already reshaping accounting and consulting. James breaks down why governance is the real unlock private equity brings, how compensation models are shifting away from legacy profit-sharing, and why cultural buy-in ultimately determines whether any of it sticks. On AI, James unpacks the concept of "talent debt" and closes with a bold prediction: a major technology player acquiring a large professional services firm may not be as far off as it sounds.
This episode is presented by Workday.
Join Mary's Substack Community
Rate and review on Apple Podcasts
~~~
Thank you to our sponsors for making this show possible.
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54 min
#96 - Curating AI Tools for a Global Law Firm
Episode 96
Show notes
In today's episode, Mary sits down with Ilona Logvinova, Chief AI Officer at HSF Kramer, to talk about what it actually takes to turn a global law firm into an AI native organization. They cover why the Chief AI Officer title means something different from innovation, what it takes to build a forward deployed legal engineering function, and why the real edge isn't buying technology - it's the people and incentives behind it.
This episode is presented by Workday
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Thank you to our sponsors for making this show possible.
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1 hr
#95 - Legal Will Lead The AI Revolution
Episode 95
Show notes
In today's episode, Mary sits down with Aine Lyons, Senior Vice President & Deputy General Counsel and Chief Strategy Officer at Workday, to talk about what it actually takes to build a modern legal department. They cover why Aine deliberately designed Workday's function without a traditional legal ops silo, what it means to reskill every lawyer in the department, and why guardrails and governance matter just as much as the agents you're building on top of them.
This episode is presented by Workday
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Thank you to our sponsors for making this show possible.
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54 min
#94 - Who Needs Associates? Pierson Ferdinand's Partner Only Model
Episode 94
Show notes
In today's episode, Mary sits down with Michael Pierson and Joel Ferdinand, Co-Chairmen of Pierson Ferdinand, and Christina Wojcik, their Chief Innovation Officer. Together, they break down what it actually takes to build the law firm of the future and why buying AI tools without rethinking your structure, culture, and compensation model is the wrong place to start.
This episode is presented by Workday
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Thank you to our sponsors for making this show possible.
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1 hr 5 min
#93 - Harvey CEO: Individual Productivity Is a Trap
Episode 93
Show notes
In today's episode, Mary sits down with Winston Weinberg, CEO and Co-Founder of Harvey.ai, to talk about what it actually takes to transform legal - and why buying AI tools without rethinking how your entire organization operates is the wrong place to start.
This episode is presented by Workday.
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Thank you to our sponsors for making this show possible.
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Support the show!
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55 min
#92 - "AI is our Kodak Moment"
Episode 92
Show notes
In today's episode, Mary sits down with Virginia Briggs, CEO and Managing Partner of MinterEllison, to talk about what real AI transformation actually looks like inside a law firm.
This episode is presented by Workday.
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Thank you to our sponsors for making this show possible.
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Support the show!
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56 min
#91 - Wordsmith CEO: 70% of Legal Tech Gone by 2027
Episode 91
Show notes
When Ross McNairn realized his legal career meant reviewing 15,000 documents by hand, he didn't just question the system - he rewrote it. Literally.
In this episode, Mary sits down with the Wordsmith ai founder to unpack what happens when a former lawyer turned engineer takes on legal's biggest inefficiencies and why AI is about to redraw the boundaries between in-house teams and law firms.
From exploding startup valuations to the rise of "shadow legal," Ross brings a builder's lens to a profession in flux. The result is a candid, sometimes uncomfortable look at where legal work is actually headed, and who stands to win. This episode of Pearls On, Gloves Off is powered by Workday. Learn more at http://workday.com.
In this episode:
• The Breaking Point: Ross shares the exact moment he realized private practice incentives reward inefficiency, and why that pushed him to build instead of bill.
• AI's Real Impact on Legal Spend: Why in-house teams are poised to cut 70–80% of external counsel costs, and why no GC is asking for more law firm dependency.
• The Two-Sided Market Problem: Can one product truly serve both law firms and in-house teams when their incentives are fundamentally opposed?
• The Founder Reality Check: Behind the hype of legal AI startups - what building a company actually feels like, and why most won't survive the next wave.
• The Rise of Legal Engineering: The emerging role that blends law, systems thinking, and AI - and why it may become the most in-demand job in legal.
• Who Wins Next: Ross's prediction that up to 80% of current legal tech players won't survive the coming platform shift.If you're trying to make sense of legal AI beyond the hype, this conversation delivers a clear-eyed view of what's changing, what's breaking, and what's being built next.
Thank you to our sponsors for making this show possible.
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56 min
#90 - Clients "Do Their Own Research." That's A Problem for Law Firms
Episode 90
Show notes
This episode of Pearls On, Gloves Off is powered by Workday. Learn more at workday.com.
In this episode, Mary sits down with Claire Hart, Chief Operating Officer, Chief Legal Officer, and Board Member at Groq, to talk about what legal leaders should expect in the AI era - from their law firms, their teams, and themselves. With senior leadership roles at Google, Blizzard, and Genies, Claire brings a sharp perspective from the intersection of law, business, and technology.
The conversation starts with the LinkedIn comment that got people talking: Claire said she would be horrified to learn that some of the law firms she works with are not using AI. From there, she and Mary unpack why adoption is still so uneven, how the billable hour distorts incentives, what young lawyers need to stay relevant, and why judgment, curiosity, and team design matter more than ever as legal moves into an AI-driven future.
In this episode:
• Claire's AI hot take: Why clients should be alarmed if their outside counsel aren't using AI
• The adoption problem: How risk concerns and the billable hour are slowing real change
• Efficiency vs. incentives: Why the tech clients want conflicts with how firms make money
• What young lawyers need now: Judgment, communication, and adaptability over pure technical skill
• The blurring of roles: How lawyers, legal ops, and contract managers are starting to overlap
• What law firms still miss: Why understanding how businesses actually operate is now a competitive edge -
48 min
#89 - AT&T's New In House Law Firm
Episode 89
Show notes
In this episode of Pearls On, Gloves Off, Mary sits down with Bill Ryan, Senior Vice President and Chief Compliance Officer at AT&T, and Ava Guo, Assistant Vice President and Senior Legal Counsel, to talk about leading through the AI inflection point inside a global legal department. As tools evolve monthly and expectations rise, the real differentiator isn't access to technology, it's execution.
Bill and Ava share how they're thinking about urgency, culture, ROI, and outside counsel alignment in a world where everyone has AI. If you're trying to separate hype from operational reality, this conversation delivers.
In this episode:
• Execution is the differentiator: "Vision without execution is hallucination" - why moving from experimentation to delivery is what actually matters.
• ROI has to be measurable: Beyond "time saved," how they track precision, reduced document review, hours, dollars - and build trust over time.
• AI increases volume, not just efficiency: As courts, consumers, and counterparties use AI too, filings and complexity are rising.
• Mindset beats mastery: Why they're hiring for curiosity and adaptability over deep tenure or tool-specific expertise.
• Not everything is a GenAI problem: The continued importance of structured systems, legacy tools, and disciplined workflows.
• Law firm relationships are evolving: What urgency, partnership, and value look like from the client side in an AI-accelerated market. -
50 min
#88 - Big Law: Record Profits… For Now
Episode 88
Show notes
In this episode of Pearls On, Gloves Off, Mary sits down with Mike Abbott, Head of the Thomson Reuters Institute, to unpack the paradox: how can firms be thriving on paper while the ground shifts beneath them? Clients are tightening spend. Work is moving down-market and in-house. AI adoption is accelerating, especially on the client side, yet most of the industry still can't measure ROI beyond "time saved." And the biggest unresolved question hangs over everything: when tech makes legal work faster, who gets the benefit?
Mike brings the data, the patterns, and the historical context, plus a sobering signal: late 2025 showed a sharp dip in M&A alongside a rise in countercyclical practices. If you're trying to understand what's actually coming in 2026, this is your listen.
In this episode:
• Record profits… and warning lights: Why a "great year" can still mask real risk (and why it feels eerily familiar).
• The work is moving: Not just in-house, down-market into the second hundred and mid-size firms.
• AI as an efficiency engine (for now): Adoption is surging, but ROI tracking is still immature across the ecosystem.
• The billing model stalemate: If ~90% of billing is still hourly (with "creative" hourly flavors), what happens when AI collapses time-to-deliver?
• Value gap reality check: The uncomfortable stat: one in four clients say they've never experienced a law firm that delivers value - and what "value" actually means to clients.
• Legal ops as the bridge: Why the legal ops function is more critical than ever, and why it's unlikely to be a passing trend. -
44 min
#87 - Updates & Hot Takes with Alex Su
Episode 87
Show notes
Mary O'Carroll kicks off a new era of Pearls On, Gloves Off - independent, sponsor-curious, and still laser-focused on what's actually changing in legal. Her first guest in this new chapter is the person many listeners will recognize instantly: Alex Su. Former litigator, ex-legal tech sales leader, early "legal influencer," and now Chief Revenue Officer at Latitude.
This episode is a blunt conversation about the gap between buying innovation and actually using it. Mary and Alex dig into why legal excellence by itself doesn't deliver business value, why so much AI adoption is still "innovation theater," and why integration (not hype) is the make or break factor for legal tech, legal services, and legal careers.
In this episode
• The core thesis: Legal excellence alone doesn't cut it. If a lawyer, ALSP, or AI tool isn't embedded in the workflows, it won't stick.
• AI reality check: 2025 was the year of "buying"; 2026 will be about renewals, retention, and ROI.
• CLM is back: "Agents will replace workflows" didn't land (yet). Real SaaS infrastructure still matters, and AI works best layered into it.
• Disaggregation/right-sourcing is accelerating: Big Law moves upmarket, expanding room for ALSPs, flexible talent, and tech-enabled delivery.
• The Innovator's Dilemma for firms: Dropping "lower-value" work can erode stickiness, and invite new providers to move up the chain.
• Training is the looming issue: As work shifts and automates, the profession has to rethink where reps and apprenticeship come from.For those thinking seriously about legal transformation, technology, and where the industry is headed, this conversation lays out what actually matters next.
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