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September 11, 2025 41 mins

In this episode, you will learn from Charlotte Jackson, Co-founder of the Candid card deck, Substack writer, and transitions coach, about transforming conversations through better questions. Charlotte explains why "What's the dream?" works better than "What do you do?" You will learn her “pebble vs. boulder" approach to asking specific, disarming questions that invite genuine responses rather than rehearsed answers. You will also learn about finding conversational "trailheads" and how intentional questions can deepen relationships and self-understanding. Excited for you to build and grow your Portfolio Career!

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