“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 situation’s emotions: “Why do you think he got angry?” Or empathize: “How would you feel if that happened to you?”


Asking a deep question should feel like sharing. It should feel, a bit, like we’re revealing something about ourselves when we ask a deep question. This feeling might give us pause. But studies show people are nearly always happy to have been asked, and to have answered, a deep question.”