20 Questions

Good Questions to Ask Executive Leaders

Strategic questions that help you understand executive perspectives, leadership philosophy, and organizational direction while demonstrating your strategic thinking and interest in the company's future.

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

Shows strategic thinking and reveals the executive's vision, goals, and strategic approach to achieving the company's objectives.

2

What are the biggest challenges facing the company right now and how are you addressing them?

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Why this works

Demonstrates understanding of business challenges and reveals the executive's approach to problem-solving and strategic decision-making.

3

How do you define leadership and what qualities do you look for in leaders?

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Why this works

Shows interest in leadership development and reveals the executive's philosophy on leadership and what qualities they value most.

4

What is your approach to innovation and staying competitive in the market?

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Why this works

Demonstrates strategic thinking and reveals the executive's approach to innovation and maintaining competitive advantage.

5

How do you handle difficult decisions and what factors do you consider?

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Why this works

Shows interest in decision-making processes and reveals the executive's approach to complex decisions and problem-solving.

6

What is your philosophy on company culture and how do you maintain it?

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Why this works

Demonstrates understanding of organizational culture and reveals the executive's approach to building and maintaining company culture.

7

How do you approach talent development and succession planning?

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Why this works

Shows interest in human capital and reveals the executive's approach to developing talent and planning for future leadership.

8

What is your approach to risk management and how do you balance risk with opportunity?

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Why this works

Demonstrates understanding of risk management and reveals the executive's approach to balancing risk and opportunity.

9

How do you stay informed about industry trends and market changes?

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Why this works

Shows interest in continuous learning and reveals the executive's approach to staying current with industry developments.

10

What is your approach to stakeholder management and building relationships?

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Why this works

Demonstrates understanding of stakeholder relationships and reveals the executive's approach to managing key relationships.

11

How do you measure success and what metrics do you focus on?

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Why this works

Shows interest in performance measurement and reveals the executive's approach to measuring success and tracking progress.

12

What is your approach to change management and how do you lead through change?

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Why this works

Demonstrates understanding of change leadership and reveals the executive's approach to managing and leading through organizational change.

13

How do you approach diversity and inclusion in leadership and decision-making?

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Why this works

Shows interest in inclusive leadership and reveals the executive's approach to diversity and inclusion in leadership roles.

14

What is your approach to crisis management and how do you prepare for potential crises?

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Why this works

Demonstrates understanding of crisis leadership and reveals the executive's approach to crisis management and preparedness.

15

How do you approach strategic partnerships and alliances?

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Why this works

Shows interest in strategic relationships and reveals the executive's approach to building and managing strategic partnerships.

16

What is your approach to technology and digital transformation?

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Why this works

Demonstrates understanding of technology leadership and reveals the executive's approach to technology and digital transformation.

17

How do you approach sustainability and corporate social responsibility?

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Why this works

Shows interest in responsible leadership and reveals the executive's approach to sustainability and social responsibility.

18

What is your approach to global expansion and international markets?

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Why this works

Demonstrates understanding of global business and reveals the executive's approach to international expansion and global markets.

19

How do you approach talent acquisition and retention?

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Why this works

Shows interest in human capital management and reveals the executive's approach to attracting and retaining top talent.

20

What is your approach to board relations and governance?

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Why this works

Demonstrates understanding of corporate governance and reveals the executive's approach to board relationships and governance.

Best Practices for Executive Conversations

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

Best Practices

Show Strategic Thinking and Business Acumen

Demonstrate your understanding of business strategy and your ability to think strategically about the company's future and challenges.

Focus on Leadership and Organizational Development

Ask about leadership philosophy, talent development, and organizational culture. This shows you understand the importance of human capital and leadership.

Demonstrate Interest in the Company's Future

Ask about the company's vision, strategic direction, and future plans. This shows you're thinking long-term and are committed to the company's success.

Question Sequences

The Strategic Vision and Direction 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 and how are you addressing them?
3
What is your approach to innovation and staying competitive in the market?
4
How do you measure success and what metrics do you focus on?

The Leadership and Culture Sequence

1
How do you define leadership and what qualities do you look for in leaders?
2
What is your philosophy on company culture and how do you maintain it?
3
How do you approach talent development and succession planning?
4
How do you approach diversity and inclusion in leadership and decision-making?

Common Pitfalls

Don't Ask Questions That Show Lack of Preparation

Avoid questions that could be answered by basic research about the company. Show you've done your homework and ask thoughtful, informed questions.

Don't Ask Questions That Are Too Personal

Avoid questions about personal matters or private information. Focus on professional and business-related topics that are relevant to the role.

Don't Ask Questions That Are Too Narrow

Avoid questions that are too specific or narrow in scope. Ask questions that are relevant to the role and show your understanding of the business.

Conversation Templates

The Strategic Vision and Direction Approach

1
Step 1: Start with: "I want to understand the company's strategic direction..."
2
Step 2: Ask: "What is your vision for the company's future and how do you plan to achieve it?"
3
Step 3: Explore: "What are the biggest challenges facing the company right now and how are you addressing them?"
4
Step 4: Connect: "What is your approach to innovation and staying competitive in the market?"

The Leadership and Culture Approach

1
Step 1: Begin with: "I'm interested in understanding your leadership philosophy..."
2
Step 2: Ask: "How do you define leadership and what qualities do you look for in leaders?"
3
Step 3: Explore: "What is your philosophy on company culture and how do you maintain it?"
4
Step 4: Connect: "How do you approach talent development and succession planning?"

Further Reading

"The Art of the Interview" by James Storey
"Cracking the Code to a Successful Interview" by Evan Pellett
"The Interview Playbook" by John Lees
"Interview Like a Pro" by Rob Yeung

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