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.

• What’s your favorite mistake?



• Were there similar moments in your career where a “missed stop” led to an unexpected opportunity?



• Was starting as a Frito-Lay route driver a deliberate development path, or was that unusual?



• Where did your passion for curiosity begin?



• Is there a way to gauge curiosity in a team or organization?



• How do you measure something like curiosity in a meaningful way?



• How do you help leaders learn to be more curious instead of just telling people to “be curious”?



• When hiring, is it better to select already-curious people or rely on the culture to develop curiosity?



• Is there such a thing as too much curiosity—can it slow execution or decision-making?



• From your research or coaching, what’s an example of curiosity being missing and causing problems?



• How do you help leaders understand that curiosity and psychological safety are building blocks for innovation—not optional extras?



• Do you see leaders struggle with the difference between knowing, assuming, and figuring things out?



• In urgent or high-pressure situations, does stress make it harder for people to stay curious?



• Do you have examples where curiosity helped prevent a small mistake from turning into a big one?



• Have you seen situations where people used questions in unhelpful or critical ways while claiming they were being “curious”?



• How do you think about Ed Schein’s idea of humble inquiry?



• Can AI replace curiosity—or does curiosity still give humans a unique advantage?



• Can interacting with AI actually help people strengthen their curiosity?