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Ten Infrequently Asked Questions
How did you….
What’s it like….
Tell me about…
Where did you grow up?
That’s a lovely name. How’d your parents choose it?
What is the best way to grow old?
"What crossroads are you at?" At any moment, most of us are in the middle of some transition. The question helps people focus on theirs.
"What would you do if you weren't afraid?" Most people know
“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?” “Have you ever been solitary without feeling lonely?” or “What has become clearer to you as you have aged?”
David Brooks • How to Know a Person: The Art of Seeing Others Deeply and Being Deeply Seen
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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