The more experience you have, the easier it is to stop asking questions.

So what happens when your expertise starts answering for you?

Joy Chik and Ana Pinczuk explore how experienced leaders can use pattern recognition without becoming trapped by it, why one honest question can reopen learning, empathy, and humility, and what it takes to pause before jumping to advice.

Ana is President and Chief Product and Technology Officer at SentinelOne, and has served on several public-company and nonprofit boards. Joy and Ana got to know each other through their work on the Board of Trustees at AnitaB.org. From a founder's "$40 million in bookings" that meant something different from what she assumed, to a whiteboard session relearning her own field, to starting over at Cisco, Ana has repeatedly had to set down what she knew in order to see again.

Together, Joy and Ana unpack how experience can quietly turn into certainty, and the one habit that keeps it alive: ask one more question.

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Logo and other art courtesy of Andy Reddout.

This podcast was produced by Tom Larson and Sue Corcoran, and edited by Amy Enser.