Questions to Ask Company CEO
Make the most of your time with leadership by asking strategic questions that demonstrate your value, gather insights, and build meaningful professional relationships.
1What's the biggest challenge the company is facing right now?
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What's the biggest challenge the company is facing right now?
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Why this works
Shows strategic thinking and helps you understand current priorities while demonstrating your interest in company success.
2How do you see the industry evolving over the next 5 years?
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How do you see the industry evolving over the next 5 years?
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Why this works
Reveals their vision and strategic thinking while helping you understand market trends and future opportunities.
3What qualities do you look for in your top performers?
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What qualities do you look for in your top performers?
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Why this works
Gives you insight into what's valued at the company and helps you understand how to excel in your role.
4What's the most important lesson you've learned as a leader?
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What's the most important lesson you've learned as a leader?
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Why this works
Provides valuable leadership wisdom while showing respect for their experience and creating a personal connection.
5How do you want the company to be different in 3 years?
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How do you want the company to be different in 3 years?
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Why this works
Reveals their strategic vision and helps you understand where the company is heading and how you can contribute.
6What keeps you up at night regarding the business?
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What keeps you up at night regarding the business?
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Why this works
Shows vulnerability and trust while revealing the CEO's biggest concerns and priorities.
7How do you balance short-term results with long-term strategy?
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How do you balance short-term results with long-term strategy?
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Why this works
Demonstrates understanding of leadership challenges while gathering insights on their decision-making approach.
8What's the most innovative thing happening in our industry?
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What's the most innovative thing happening in our industry?
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Why this works
Shows industry awareness and helps you understand cutting-edge developments that could impact the company.
9How do you measure success for the company?
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How do you measure success for the company?
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Why this works
Reveals their definition of success and helps you understand what metrics and outcomes matter most.
10What advice would you give to someone starting their career?
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What advice would you give to someone starting their career?
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Why this works
Provides valuable career guidance while showing respect for their experience and creating a mentoring moment.
11How do you stay connected to what's happening on the front lines?
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How do you stay connected to what's happening on the front lines?
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Why this works
Shows their approach to staying grounded and reveals how they gather information from throughout the organization.
12What's the most important decision you've made recently?
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What's the most important decision you've made recently?
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Why this works
Reveals current priorities and decision-making processes while showing interest in their leadership challenges.
13How do you want to be remembered as a leader?
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How do you want to be remembered as a leader?
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Why this works
Deep question about legacy that reveals their values and long-term vision for their leadership impact.
14What's something you wish you knew earlier in your career?
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What's something you wish you knew earlier in your career?
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Why this works
Provides valuable career insights while creating a personal connection and showing respect for their journey.
15How do you handle failure and setbacks?
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How do you handle failure and setbacks?
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Why this works
Reveals their resilience and approach to challenges while providing valuable leadership lessons.
16What's the most exciting opportunity you see for the company?
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What's the most exciting opportunity you see for the company?
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Why this works
Shows optimism and forward-thinking while helping you understand potential growth areas and opportunities.
17How do you build and maintain company culture?
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How do you build and maintain company culture?
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Why this works
Reveals their approach to culture and helps you understand what values and behaviors are important.
18What's the best piece of feedback you've ever received?
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What's the best piece of feedback you've ever received?
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Why this works
Shows their openness to feedback and provides insights into what kind of input they value most.
19How do you want employees to feel about working here?
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How do you want employees to feel about working here?
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Why this works
Reveals their vision for employee experience and helps you understand the kind of workplace they want to create.
20What's one thing you'd change about how we work?
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What's one thing you'd change about how we work?
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Why this works
Shows their self-awareness and continuous improvement mindset while revealing potential areas for change.
Best Practices for CEO Conversations
Expert tips and techniques for getting the most out of these questions.
Best Practices
Be Strategic and Thoughtful
Ask questions that demonstrate your understanding of business and show that you're thinking at a high level about the company's success.
Show Genuine Interest
Listen actively and ask follow-up questions that show you're engaged with their answers and want to learn more.
Respect Their Time
Be concise and focused. CEOs have limited time, so make every question count and avoid wasting their time with obvious or trivial questions.
Question Sequences
The Strategic Insight Sequence
The Leadership Wisdom Sequence
Common Pitfalls
Don't Ask Obvious Questions
Avoid questions they can easily find answers to elsewhere. CEOs value strategic thinking and unique perspectives.
Don't Make It About You
Focus on the company, industry, and leadership rather than your personal career advancement or individual concerns.
Don't Be Overly Familiar
Maintain appropriate professional boundaries while still being engaging and showing genuine interest in their perspective.