Questions to Ask a Smart Person
Insightful questions to ask intelligent, accomplished, or wise individuals to extract their mental models, decision-making frameworks, learning strategies, and hard-won lessons—maximizing the value of your time with them.
1What's a belief you held strongly that you've completely changed your mind about?
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What's a belief you held strongly that you've completely changed your mind about?
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Why this works
Reveals intellectual humility and how they update their worldview.
2How do you approach learning something completely new outside your expertise?
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How do you approach learning something completely new outside your expertise?
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Why this works
Uncovers meta-learning strategies and how they build competence.
3What mental models or frameworks do you use most often in decision-making?
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What mental models or frameworks do you use most often in decision-making?
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Why this works
Surfaces the thinking tools that guide their choices.
4What's the most counterintuitive thing you've learned in your field?
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What's the most counterintuitive thing you've learned in your field?
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Why this works
Identifies insights that challenge conventional wisdom.
5What questions do you ask yourself when facing a difficult decision?
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What questions do you ask yourself when facing a difficult decision?
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Why this works
Reveals their decision-making process and values.
6What book, person, or experience has most shaped how you think?
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What book, person, or experience has most shaped how you think?
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Why this works
Traces intellectual influences and formative moments.
7What do you know now that you wish you'd known 10 years ago?
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What do you know now that you wish you'd known 10 years ago?
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Why this works
Distills hard-won wisdom into actionable hindsight.
8How do you separate signal from noise when evaluating information?
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How do you separate signal from noise when evaluating information?
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Why this works
Shows how they filter for quality and truth in an information-saturated world.
9What's a widely accepted idea in your field that you think is wrong?
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What's a widely accepted idea in your field that you think is wrong?
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Why this works
Reveals contrarian thinking and where they see blind spots.
10How do you balance confidence with intellectual humility?
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How do you balance confidence with intellectual humility?
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Why this works
Explores the tension between conviction and openness to being wrong.
11What habits or routines contribute most to your effectiveness?
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What habits or routines contribute most to your effectiveness?
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Why this works
Identifies practical behaviors that compound success.
12What's something you're still trying to figure out or struggling with?
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What's something you're still trying to figure out or struggling with?
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Why this works
Humanizes them and shows ongoing growth areas.
13How do you evaluate whether you're making progress on what matters most?
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How do you evaluate whether you're making progress on what matters most?
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Why this works
Reveals their metrics for meaningful success.
14What's the best advice you've ever received, and why did it stick?
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What's the best advice you've ever received, and why did it stick?
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Why this works
Surfaces timeless wisdom they found transformative.
15What questions should I be asking that I'm not?
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What questions should I be asking that I'm not?
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Why this works
Invites them to identify blind spots or important topics you've overlooked.
16What's a skill or area of knowledge you think more people should invest in?
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What's a skill or area of knowledge you think more people should invest in?
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Why this works
Highlights undervalued competencies or disciplines.
17How do you think about risk and making decisions with incomplete information?
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How do you think about risk and making decisions with incomplete information?
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Why this works
Explores their approach to uncertainty and calculated bets.
18What's the worst advice you've ever received or followed?
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What's the worst advice you've ever received or followed?
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Why this works
Offers cautionary tales and lessons from mistakes.
19If you could go back and give advice to your younger self, what would it be?
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If you could go back and give advice to your younger self, what would it be?
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Why this works
Synthesizes lessons into guidance you can apply now.
20What are you optimistic and pessimistic about for the future?
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What are you optimistic and pessimistic about for the future?
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Why this works
Reveals their worldview, concerns, and where they see opportunity.
Maximizing Conversations with Brilliant People
Expert tips and techniques for getting the most out of these questions.
Best Practices
Ask About Process, Not Just Results
How they think is more valuable than what they've achieved—focus on mental models and decision-making.
Follow the Energy
Notice what they light up about and dig deeper there—passion reveals insight.
Take Notes and Reflect
Capture key ideas immediately and review later to extract actionable lessons.
Question Categories for Deep Learning
Mental Models
Learning & Growth
Worldview & Philosophy
Common Pitfalls
Asking Generic, Googleable Questions
Don't waste face time on facts you could look up—ask for experiences, insights, and wisdom.
Turning It Into a Debate
You're there to learn, not prove yourself—be curious, not combative.