Caroline Webb: Deliberate Wisdom in the Age of AI [013]

Episode summary

Caroline Webb wanted to be an astrophysicist, took an economics class at sixteen, and never looked back. From the Bank of England to McKinsey, where she was told repeatedly to please just relax, she carved out a leadership practice that most people thought was a career-ending detour, and then made partner anyway. Her new book, Leadership Intelligence, draws on behavioral economics, neuroscience, and psychology to give leaders science-backed strategies for the everyday management challenges that no one teaches you how to handle. She was introduced to Ron by Rita McGrath, and the conversation they have is exactly the kind Rita tends to set in motion.

The heart of the episode is the distinction between experiential wisdom and deliberate wisdom. Experience is valuable, Caroline argues, but the more of it you have, the heavier your blinkers, and the smartest leaders in any room are often the ones most at risk of missing what is right in front of them because they already know how it ends. Deliberate wisdom is different: a set of thinking habits anyone can build at any age, centered on one question: what could I be missing? Ron brings his own version of the same idea in the 51% Rule, and the two of them spend the back half of the conversation mapping it all onto AI, why the tool does the grunt work but the judgment still has to come from you, and why the human skills are not a consolation prize but the whole point.

Watch the full conversation on YouTube.