“Don’t worry about being the most interesting person in the room, just try to be the most interested person in the room.

• The interested person asks about others and leaves a good impression because people like talking about themselves.

• The interested person is genuinely curious about someone’s craft and learns a lot about how things work.

• The

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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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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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