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?”

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

How do we ask more expansive, generous questions that invite people to feel truly seen, fascinating, attended to ? What a gift to feel the genuine curiosity, presence, and attention of another.