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

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A deep question asks about someone’s values, beliefs, judgments, or experiences—rather than just facts. Don’t ask “Where do you work?” Instead, draw out feelings or experiences: “What’s the best part of your job?” (One 2021 study found a simple approach to generating deep questions: Before speaking, imagine you’re talking to a close friend. What qu

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