Revealing Questions
“Who are you?”
…is not a question you can really ask someone. Not just because it tends to be socially unacceptable, but because it wouldn’t be very useful. Most people don’t speak clearly about themselves. So the best way to learn useful things about people might be counterintuitive: it’s to ask them about themselves indirectly.
The list of questions below can tell you a lot. They’re especially handy when you are deciding whether to work with someone, or whether to trust someone. Many of them are designed to get past the barriers and the scripts that people set up when you don’t know each other very well. Below each question is an additional bullet point about exactly how we think the question can be useful.
- Who do you admire? Why?
- See the qualities that people may strive for.
- What’s the hardest thing you’ve ever done?
- See people’s definition of hard.
- What are you great at? How do you know you’re great at it?
- See how people define great. Which may tell you about their overall bar for quality.
- What is the most impactful thing you’ve been responsible for?
- Understand what people have really accomplished.
- What are you proud of?
- Learn how people define good.
- Do you believe in a god? Why or why not?
- Their answer to the latter will tell you something about how thoughtful they are.
- What do you think your friends/coworkers would say about you?
- If they answer honestly, it’s an easy way for them to tell you some of their flaws.
- What would smart people disagree with you about?
- Learn people’s best (or worst) counter-narrative ideas.
- What do you do for fun?
- Better understand someone’s priorities and personality.
- What have you changed your mind about in the past year?
- Tells you a bit about how reflective they are and mostly if they’ve ever thought about this.
- What is your best case scenario?
- Figure out what somebody cares about most.
- What was your lowest point? What happened?
- Learn what they consider bad or difficult.
- What book or essay that you read in the past year had the biggest impact on your life?
- Learn if they read and, based on the book, you may get insights about them as a person.
- What were you wrong about most recently?
- The point is not their actual answer, but whether they have one ~readily accessible.
- What questions do you have for me?
- These questions, or the lack thereof, can be quite revealing.
Know that there is a bad, fake way to ask these questions. Don’t rapid-fire them at the start of an interview or after meeting someone for the first time. Pick the ones you care about. Work them in naturally. If you give the impression that you are a person who only asks these oddball, unique questions, people may start to think that you’re doing it for show and not because you care. You should care. Probably.
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