conversation

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

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“Say more” and “care to elaborate” are magical phrases. You can also repeat what they said. “Work has been crazy lately.” “Work has been crazy lately?” That can do a lot. The question “why is that important to you,” while more intense, can get you really far, really fast, if you sense a mood of openness, especially if you learn to ask it casually.

We too often think that deep conversations have to be painful or vulnerable conversations. I try to compensate for that by asking questions about the positive sides of life: “Tell me about a time you adapted to change.” “What’s working really well in your life?” “What are you most self-confident about?” “Which of your five senses is strongest?”

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