My guest for Episode #330 of the My Favorite Mistake podcast is Debra Clary, a leadership strategist, researcher, and executive coach with more than four decades of experience at organizations including Frito-Lay, Coca-Cola, Jack Daniel’s, and Humana.

Episode page with video, transcript, and more

She’s also a TEDx speaker, former off-Broadway performer, and the author of the new book The Curiosity Curve: A Leader’s Guide to Growth and Transformation Through Bold Questions.

In this episode, Debra shares one of her favorite mistakes—an unexpected wrong train stop in Italy that turned into a memorable discovery—and how that happy accident helped shape her approach to curiosity, flexibility, and exploring the unexpected. That theme carries through the conversation as Debra and I discuss how curiosity shows up in leadership, why assumptions can derail teams, and why “having the answers” is often the wrong place to start.

Debra walks us through the research behind The Curiosity Curve, including how her team developed a validated diagnostic for measuring curiosity and what they learned about its connection to engagement, retention, innovation, and decision speed. She shares practical examples of how leaders unintentionally shut down curiosity and how small shifts in inquiry can unlock better thinking and stronger team performance.

We also explore how curiosity interacts with psychological safety, how leaders can avoid the trap of reflexive certainty, and why curiosity becomes even more important in high-pressure or high-uncertainty situations. Debra closes by discussing the role curiosity plays in an AI-driven world—why it remains uniquely human, and how tools like AI can actually help people deepen their inquiry rather than replace it.

If you’re interested in how leaders can cultivate better questions, better conversations, and better outcomes, this episode will spark ideas you can put to use right away.