Questions to Ask Smart People
Thoughtful questions to help you learn from intelligent people, gain insights, and engage in meaningful conversations with experts and thinkers.
1What's the most important thing you've learned that you wish you knew earlier?
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What's the most important thing you've learned that you wish you knew earlier?
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Why this works
Learning from their hindsight helps you benefit from their experience and avoid common mistakes.
2What's a common misconception in your field that you'd like to correct?
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What's a common misconception in your field that you'd like to correct?
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Why this works
Understanding misconceptions helps you learn accurate information and avoid common errors in thinking.
3What's the most interesting problem you're currently working on?
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What's the most interesting problem you're currently working on?
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Why this works
Learning about their current work helps you understand their thinking process and what challenges them.
4What's a skill or ability you've developed that you're most proud of?
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What's a skill or ability you've developed that you're most proud of?
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Why this works
Understanding their proudest achievements helps you learn about their values and what they consider important.
5What's the most counterintuitive insight you've discovered?
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What's the most counterintuitive insight you've discovered?
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Why this works
Learning about counterintuitive insights helps you expand your thinking and see things from new perspectives.
6What's a question you wish more people would ask you?
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What's a question you wish more people would ask you?
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Why this works
Understanding what they want to discuss helps you engage them on topics they find meaningful and important.
7What's the most important trend you see developing in your field?
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What's the most important trend you see developing in your field?
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Why this works
Learning about trends helps you understand the direction of their field and what's coming next.
8What's a book or resource that changed your thinking?
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What's a book or resource that changed your thinking?
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Why this works
Understanding their influences helps you learn about sources of knowledge and ideas that shaped their thinking.
9What's the most important quality for success in your field?
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What's the most important quality for success in your field?
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Why this works
Learning about success factors helps you understand what it takes to excel in their area of expertise.
10What's a mistake you made that taught you the most?
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What's a mistake you made that taught you the most?
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Why this works
Learning from their mistakes helps you benefit from their experience and avoid similar errors.
11What's the most important question you're trying to answer?
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What's the most important question you're trying to answer?
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Why this works
Understanding their current focus helps you learn about their priorities and what they find most important.
12What's a skill you're currently trying to develop?
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What's a skill you're currently trying to develop?
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Why this works
Learning about their growth areas helps you understand their learning mindset and what they value improving.
13What's the most important advice you'd give to someone starting in your field?
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What's the most important advice you'd give to someone starting in your field?
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Why this works
Understanding their guidance helps you learn from their experience and get practical advice for your own development.
14What's a concept that took you a long time to understand?
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What's a concept that took you a long time to understand?
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Why this works
Learning about their learning journey helps you understand complex topics and how to approach difficult concepts.
15What's the most important relationship in your professional life?
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What's the most important relationship in your professional life?
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Why this works
Understanding their professional relationships helps you learn about networking and collaboration in their field.
16What's a project you're most excited about?
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What's a project you're most excited about?
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Why this works
Learning about their excitement helps you understand what motivates them and what they find most engaging.
17What's the most important lesson you've learned from failure?
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What's the most important lesson you've learned from failure?
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Why this works
Learning from their failures helps you understand resilience and how to grow from setbacks.
18What's a question you're still trying to figure out?
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What's a question you're still trying to figure out?
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Why this works
Understanding their ongoing questions helps you learn about their curiosity and what puzzles them.
19What's the most important change you've seen in your field?
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What's the most important change you've seen in your field?
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Why this works
Learning about changes helps you understand the evolution of their field and what's driving transformation.
20What's something you believe that others might disagree with?
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What's something you believe that others might disagree with?
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Why this works
Understanding their contrarian views helps you learn about their independent thinking and unique perspectives.
Learning from Smart People
Expert tips and techniques for getting the most out of these questions.
Effective Questioning Strategies
Ask Open-Ended Questions
Frame questions that allow for detailed responses rather than yes/no answers to get deeper insights.
Show Genuine Curiosity
Demonstrate authentic interest in their knowledge and experiences to encourage more detailed responses.
Follow Up on Interesting Points
When they share something intriguing, ask follow-up questions to explore the topic more deeply.