20 Questions

Questions to Ask Senior Executives

Strategic questions to ask senior executives to gain leadership insights, understand organizational direction, and learn from their experience and wisdom.

1

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

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Why this works

Understanding current challenges helps you assess the organization's priorities and how you might contribute to solutions.

2

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

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Why this works

Learning about their vision helps you understand the organization's direction and how you might fit into their long-term plans.

3

What are the key values and culture you're trying to build within the organization?

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Why this works

Understanding organizational values helps you assess whether the culture aligns with your own values and work style.

4

What are the biggest opportunities for growth and development in the organization?

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Why this works

Understanding growth opportunities helps you assess the organization's potential and your career development prospects.

5

How do you approach decision-making and what role do employees play in it?

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Why this works

Learning about decision-making processes helps you understand how the organization operates and how you might contribute to strategy.

6

What are the biggest opportunities for innovation and improvement in the organization?

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Why this works

Understanding innovation opportunities helps you assess the organization's potential and your role in driving change.

7

How do you handle change management and what support do you provide to employees?

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Why this works

Learning about change management helps you understand how the organization adapts and supports employees during transitions.

8

What are the biggest opportunities for diversity and inclusion within the organization?

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Why this works

Understanding DEI opportunities helps you assess the organization's commitment to creating an inclusive and equitable environment.

9

What are the biggest opportunities for professional development and learning?

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Why this works

Understanding development opportunities helps you assess the organization's potential for your career growth and learning.

10

How do you approach performance management and what support do you provide to employees?

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Why this works

Learning about their performance approach helps you understand how you'll be evaluated and supported in your role.

11

What are the biggest opportunities for leadership development and advancement?

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Why this works

Understanding leadership opportunities helps you assess the organization's potential for your career advancement and growth.

12

How do you approach communication and transparency within the organization?

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Why this works

Understanding their communication approach helps you assess the organization's culture and information sharing practices.

13

What are the biggest opportunities for collaboration and cross-functional work?

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Why this works

Understanding collaboration opportunities helps you assess the organization's potential for teamwork and knowledge sharing.

14

How do you handle crisis management and what role do employees play?

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Why this works

Learning about their crisis approach helps you understand how the organization responds to challenges and involves employees.

15

What are the biggest opportunities for technology adoption and digital transformation?

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Why this works

Understanding technology opportunities helps you assess the organization's potential for driving innovation and modernization.

16

How do you approach work-life balance and what support do you provide to employees?

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Why this works

Understanding their work-life balance approach helps you assess whether the organization supports your personal well-being and priorities.

17

What are the biggest opportunities for mentorship and knowledge sharing?

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Why this works

Understanding mentorship opportunities helps you assess the organization's potential for learning from others and sharing your expertise.

18

How do you handle conflict resolution and what role do employees play?

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Why this works

Learning about their conflict resolution approach helps you understand how the organization maintains harmony and involves employees.

19

What are the biggest opportunities for process improvement and efficiency?

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Why this works

Understanding process improvement opportunities helps you assess the organization's potential for driving operational excellence.

20

How do you measure success and what are your expectations for employees?

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Why this works

Understanding their success measures helps you know what's expected and how you can contribute to the organization's goals.

Learning from Senior Leadership

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

Preparing for the Conversation

Research the Executive

Learn about the executive's background, experience, and leadership style to ask informed questions.

Understand the Organization

Familiarize yourself with the organization's mission, values, and current challenges to ask relevant questions.

Prepare Your Questions

Have thoughtful questions ready that demonstrate your interest in leadership and organizational development.

Types of Executive Questions

Strategy and Vision

Organizational vision and direction
Strategic planning and decision-making
Growth and development opportunities
Innovation and improvement

Culture and Values

Organizational values and culture
Diversity and inclusion
Communication and transparency
Work-life balance and support

Leadership and Development

Leadership development opportunities
Mentorship and knowledge sharing
Performance management and support
Career advancement and growth

Making the Most of the Learning Experience

Listen Actively

Pay attention to their responses and ask follow-up questions to deepen your understanding.

Take Notes

Record key insights and information that will help you understand leadership and organizational development.

Reflect on Your Learning

Take time to reflect on what you've learned and how it applies to your own leadership development.

Find Your Perfect Questions

Search our collection of thoughtful questions for any conversation or situation