20 Questions

What Are Good Questions to Ask a CEO

Strategic questions to ask a CEO about leadership, vision, company culture, and business strategy to gain insights and build meaningful professional relationships.

1

What is your vision for the company's future and how do you plan to achieve it?

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Why this works

Understanding their vision helps you align with company goals and understand the strategic direction they're taking the organization.

2

What are the biggest challenges facing the company right now?

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Why this works

Learning about current challenges helps you understand the context and how you might contribute to solutions.

3

How do you define success for the company and how do you measure it?

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Why this works

Understanding their definition of success helps you align your efforts with company objectives and know what metrics matter most.

4

What is your leadership philosophy and how do you develop your team?

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Why this works

Learning about their leadership approach helps you understand the company culture and how they value and develop people.

5

What are the key values that drive decision-making at the company?

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Why this works

Understanding company values helps you align your actions with what the organization stands for and what guides their choices.

6

How do you stay competitive in the market and what differentiates you?

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Why this works

Learning about their competitive strategy helps you understand the company's position and what makes them unique in the market.

7

What role does innovation play in your business strategy?

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Why this works

Understanding their approach to innovation helps you know how the company values creativity and forward-thinking.

8

How do you handle failure and what have you learned from setbacks?

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Why this works

Learning about their approach to failure helps you understand their resilience and what they value in learning from mistakes.

9

What is your approach to building and maintaining company culture?

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Why this works

Understanding their culture-building approach helps you know what kind of environment they're creating and how you might fit in.

10

How do you balance short-term results with long-term growth?

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Why this works

Learning about their approach to balancing priorities helps you understand how they make decisions and what they value most.

11

What are your thoughts on the future of your industry?

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Why this works

Understanding their industry perspective helps you learn about trends and opportunities they see in the market.

12

How do you approach risk-taking and decision-making?

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Why this works

Learning about their decision-making process helps you understand how they evaluate opportunities and make choices.

13

What is your approach to customer relationships and satisfaction?

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Why this works

Understanding their customer focus helps you know how they value relationships and what drives their business success.

14

How do you handle change and what is your approach to transformation?

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Why this works

Learning about their change management approach helps you understand how they navigate uncertainty and drive organizational change.

15

What are your thoughts on sustainability and social responsibility?

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Why this works

Understanding their approach to sustainability helps you know how they balance profit with purpose and social impact.

16

How do you approach talent acquisition and retention?

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Why this works

Learning about their talent strategy helps you understand how they value people and what they look for in team members.

17

What is your approach to technology and digital transformation?

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Why this works

Understanding their technology strategy helps you know how they're adapting to digital changes and what role technology plays in their business.

18

How do you handle stakeholder relationships and communication?

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Why this works

Learning about their stakeholder approach helps you understand how they manage relationships with investors, customers, and employees.

19

What advice would you give to someone starting their career?

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Why this works

Learning their career advice helps you understand their values and what they think is important for professional success.

20

What are you most proud of in your career and what drives you?

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Why this works

Understanding their proudest achievements and motivations helps you learn about their values and what they find most meaningful.

Best Practices for Asking CEOs Questions

Expert tips and techniques for getting the most out of these questions.

Best Practices

Be Respectful of Their Time

CEOs are busy people. Be concise, focused, and respectful of their time constraints.

Ask Thoughtful Questions

Show that you've done your homework and are asking questions that demonstrate genuine interest and understanding.

Listen Actively

Pay attention to their answers and ask follow-up questions that show you're engaged and learning.

Be Professional

Maintain a professional demeanor and approach the conversation with respect and courtesy.

Question Sequences

The Strategic Vision Sequence

1
What is your vision for the company's future and how do you plan to achieve it?
2
What are the biggest challenges facing the company right now?
3
How do you define success for the company and how do you measure it?
4
What are the key values that drive decision-making at the company?

The Leadership Philosophy Sequence

1
What is your leadership philosophy and how do you develop your team?
2
What is your approach to building and maintaining company culture?
3
How do you approach talent acquisition and retention?
4
What advice would you give to someone starting their career?

The Business Strategy Sequence

1
How do you stay competitive in the market and what differentiates you?
2
What role does innovation play in your business strategy?
3
What are your thoughts on the future of your industry?
4
How do you approach risk-taking and decision-making?

Common Pitfalls

Don't Ask Obvious Questions

Avoid questions that can be easily answered by looking at the company website or recent news. Show that you've done your research.

Don't Be Too Personal

Keep questions professional and focused on business topics. Avoid overly personal questions about their private life.

Don't Interrupt or Dominate

Let them speak and don't interrupt. Ask follow-up questions but don't dominate the conversation.

Don't Ask About Sensitive Topics

Avoid questions about confidential information, legal issues, or other sensitive topics that they can't or shouldn't discuss.

Conversation Templates

The Strategic Overview Framework

1
Step 1: Start with: 'What is your vision for the company's future and how do you plan to achieve it?'
2
Step 2: Follow with: 'What are the biggest challenges facing the company right now?'
3
Step 3: Ask: 'How do you define success for the company and how do you measure it?'
4
Step 4: Close with: 'What are the key values that drive decision-making at the company?'

The Leadership Insights Framework

1
Step 1: Start with: 'What is your leadership philosophy and how do you develop your team?'
2
Step 2: Follow with: 'How do you handle failure and what have you learned from setbacks?'
3
Step 3: Ask: 'What is your approach to building and maintaining company culture?'
4
Step 4: Close with: 'What advice would you give to someone starting their career?'

Further Reading

"Good to Great" by Jim Collins
"The Lean Startup" by Eric Ries
"Built to Last" by Jim Collins and Jerry Porras
Harvard Business Review CEO interviews

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