Leadership in Beta

What if some of the leadership advice we repeat the most deserves a second look?

Kelly talks with Josh Harris, Director of Educational Technology and Assessment, about what he’s learned over 27 years in education and multiple leadership roles. They dig into why understanding how an organization actually works matters, what leaders can learn from the people doing the work every day, and why you should never assume someone else’s job is as simple as it looks.

The conversation also takes on some familiar leadership ideas, from “remember your why” to building relationships before getting to the work. Josh and Kelly explore whether trust might actually be built through doing the work together, and what happens when good intentions become a substitute for examining actual impact.

It’s a candid, funny, and occasionally skeptical conversation about leadership, accountability, trust, and being willing to question the things we’ve always been told good leaders are supposed to do.

Keep leading. Keep learning. Stay in beta.

Kelly talks with Brian Whitmore, CEO of Studio W Architects, about growing a business, building trust, developing future leaders, and learning when good is good enough. Brian shares the realities of being a sole owner, the challenge of succession planning, and why relationships can matter just as much as technical expertise.

A candid conversation about the risk, responsibility, and work behind leadership that people don’t always see.

Keep leading. Keep learning. Stay in beta.

What happens when you stop thinking of leadership as a title and start thinking about it as something everyone can practice?

Kelly talks with Dedrique Taylor, head men’s basketball coach at Cal State Fullerton, about how his approach to leadership has evolved over his career, including why he moved away from naming team captains and what he’s learned about creating an environment where everyone has an opportunity to lead.

Their conversation moves well beyond basketball, exploring vulnerability, feedback, communication, learning from what doesn’t work, and the importance of aligning what you say you want with how you actually show up.

It’s a candid conversation between two longtime friends about getting better, staying open to being wrong, and continuing to evolve as a leader.

Keep leading. Keep learning. Stay in beta.

What if great leadership isn’t about having all the answers, but knowing when to step back?

In this episode of Leadership in Beta, I sit down with Corinna Osborne, Chief Operating Officer of Edgewood Companies, for a conversation about culture, empowerment, and what it takes to lead people well.

Corinna shares how her leadership has evolved from trying to control everything to surrounding herself with talented people, trusting their expertise, and giving them room to learn, even when that means allowing mistakes to happen. We also explore why treating people the way you want to be treated may actually be overrated, and why effective leaders have to adapt to the people in front of them.

From building culture across a large hospitality organization to navigating different personalities and generations, this conversation is a reminder that leadership isn’t about the power of your position. It’s about how you use that position to empower and lift up others.

Keep leading. Keep learning. Stay in Beta.

Watch a quick outtake of my conversation with Coach Dedrique Taylor as he talks about the vulnerability of admitting when you're wrong.

No leader has it all figured out. Good thing.

Leadership in Beta is a podcast about what leaders are still learning, testing, changing, and figuring out along the way.

Short, candid conversations with leaders across industries about leadership as a work in progress.

Keep leading. Keep learning. Stay in beta.