Unique Questions to Ask Leaders
Thought-provoking and unique questions to ask leaders that go beyond typical interview questions to reveal their true character, values, and leadership philosophy.
1What's a decision you made that you initially thought was wrong, but turned out to be right?
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What's a decision you made that you initially thought was wrong, but turned out to be right?
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Why this works
Reveals their ability to learn from mistakes, adapt, and shows humility in acknowledging when they were wrong.
2If you could eliminate one meeting from your schedule permanently, which would it be and why?
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If you could eliminate one meeting from your schedule permanently, which would it be and why?
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Why this works
Shows their priorities, efficiency mindset, and ability to identify what truly adds value versus what wastes time.
3What's something you believe that most people in your industry disagree with?
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What's something you believe that most people in your industry disagree with?
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Why this works
Reveals their independent thinking, courage to stand by unpopular opinions, and depth of conviction.
4If you had to start your career over knowing what you know now, what would you do differently?
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If you had to start your career over knowing what you know now, what would you do differently?
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Why this works
Shows self-reflection, learning from experience, and willingness to share wisdom gained through mistakes.
5What's the most important lesson you learned from a failure?
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What's the most important lesson you learned from a failure?
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Why this works
Demonstrates resilience, growth mindset, and ability to extract value from difficult experiences.
6If you could have a conversation with your 25-year-old self, what would you tell them?
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If you could have a conversation with your 25-year-old self, what would you tell them?
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Why this works
Reveals their personal growth, wisdom gained over time, and ability to reflect on their journey.
7What's something you're currently struggling with as a leader?
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What's something you're currently struggling with as a leader?
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Why this works
Shows vulnerability, self-awareness, and ongoing commitment to growth and improvement.
8If you could change one thing about how your industry operates, what would it be?
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If you could change one thing about how your industry operates, what would it be?
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Why this works
Reveals their vision for improvement, understanding of industry challenges, and desire to make meaningful change.
9What's a skill you wish you had developed earlier in your career?
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What's a skill you wish you had developed earlier in your career?
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Why this works
Shows self-awareness, understanding of what's truly important, and willingness to acknowledge gaps.
10If you had to describe your leadership style using only three words, what would they be?
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If you had to describe your leadership style using only three words, what would they be?
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Why this works
Forces concise self-reflection and reveals how they see themselves as a leader.
11What's something you've changed your mind about in the last year?
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What's something you've changed your mind about in the last year?
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Why this works
Shows intellectual flexibility, openness to new information, and ability to evolve their thinking.
12If you could give one piece of advice to someone starting their career today, what would it be?
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If you could give one piece of advice to someone starting their career today, what would it be?
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Why this works
Reveals their values, priorities, and what they consider most important for success.
13What's a book, article, or idea that fundamentally changed how you think about leadership?
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What's a book, article, or idea that fundamentally changed how you think about leadership?
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Why this works
Shows their commitment to learning, intellectual curiosity, and sources of inspiration.
14If you could solve one problem in the world, what would it be?
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If you could solve one problem in the world, what would it be?
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Why this works
Reveals their values, priorities, and what they consider most important beyond their immediate work.
15What's something you're proud of that most people don't know about?
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What's something you're proud of that most people don't know about?
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Why this works
Shows humility, depth of character, and ability to find satisfaction in quiet achievements.
16If you had to choose between being right and being kind, which would you choose and why?
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If you had to choose between being right and being kind, which would you choose and why?
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Why this works
Reveals their values, decision-making framework, and how they balance different priorities.
17What's a habit you've developed that has had the biggest impact on your success?
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What's a habit you've developed that has had the biggest impact on your success?
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Why this works
Shows self-awareness, understanding of what drives success, and willingness to share practical wisdom.
18If you could have dinner with anyone (living or dead), who would it be and what would you ask them?
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If you could have dinner with anyone (living or dead), who would it be and what would you ask them?
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Why this works
Reveals their interests, values, and what they consider most important to learn or understand.
19What's something you wish you had known when you first became a leader?
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What's something you wish you had known when you first became a leader?
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Why this works
Shows reflection on their leadership journey and willingness to share hard-won wisdom.
20If you had to describe your ideal team member, what characteristics would they have?
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If you had to describe your ideal team member, what characteristics would they have?
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Why this works
Reveals their values, what they consider most important in people, and their vision for team dynamics.
Getting to Know Leaders on a Deeper Level
Expert tips and techniques for getting the most out of these questions.
Creating Meaningful Conversations
Be Genuinely Curious
Ask questions that show you're truly interested in their perspective and experience, not just going through the motions.
Listen for Depth
Pay attention to not just what they say, but how they say it and what it reveals about their character.
Follow Up Thoughtfully
Ask follow-up questions that dig deeper into their responses and show you're engaged in the conversation.
Natural Conversation Flow
The Reflection Zone
The Values Explorer
The Challenge Zone
Common Pitfalls to Avoid
Don't Ask Generic Questions
Avoid questions they've heard a thousand times. Focus on unique, thought-provoking questions that reveal character.
Avoid Being Overly Personal
Keep questions professional and appropriate for the context. Don't pry into private matters.
Don't Interrogate
Let the conversation flow naturally. Don't rapid-fire questions or make it feel like an interrogation.