
How to turn "small talk" into Big Talk

Big questions interrupt the daily routines people fall into and prompt them to step back and see their life from a distance. Here are some of my favorite questions that do that: “What crossroads are you at?” At any moment, most of us are in the middle of some transition. The question helps people focus on theirs. “What would you do if you weren’t a
... See moreDavid Brooks • How to Know a Person: The Art of Seeing Others Deeply and Being Deeply Seen
Ask them how they got started, what motivates them, and how they think about navigating their life.
Paul Millerd • The Pathless Path: Imagining a New Story For Work and Life

visited that you hope never to return to. 23. What’s the best surprise you’ve ever received? 24. What’s the neatest surprise you’ve ever planned and pulled off for someone else? 25. Skiing here is always challenging. What are some of your favorite places to ski? 26. Who would star as you in a movie about your life? Why that person? 27. Who is the m
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