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 question would you ask?) A deep question asks people to talk about how they feel. Sometimes this is easy: “How do you feel about…?” Or, we can prompt people to describe specific emotions: “Did it make you happy when…?” Or ask someone to analyze a
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