In this episode, Carl shares a powerful lesson from a conversation with leadership expert Jennifer Garvey Berger about the importance of questioning our assumptions. What sounds like a simple client goal—“I just want a stable future”—turns out to contain layers of meaning that we can easily overlook if we assume we already understand. Carl reflects on the discipline of deep curiosity, the art of asking better questions, and Jennifer’s humbling reminder that she goes to such lengths because she has learned she is “almost always wrong” about her first assumptions.

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