20 Questions

Questions to Ask President

Strategic questions that help you understand the president's vision, priorities, and approach to leadership while building a meaningful professional relationship.

1

What is your vision for the organization, and how do you see it evolving over the next few years?

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Why this works

Understanding their vision helps you align your work with organizational goals and assess if their direction matches your values and aspirations.

2

What are your top priorities for this year, and how can I contribute to achieving them?

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Why this works

Understanding their priorities helps you focus your efforts on what matters most and identify ways to add value to the organization.

3

What do you see as the biggest challenges facing our organization, and how are you addressing them?

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Why this works

Understanding their challenges helps you appreciate their leadership approach and identify opportunities to contribute to solutions.

4

How do you approach decision-making, and what factors do you consider most important?

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Why this works

Understanding their decision-making process helps you align your approach and know how to present information and recommendations effectively.

5

What are your thoughts on innovation and change, and how do you encourage it within the organization?

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Why this works

Understanding their approach to innovation helps you assess if the organization supports creative thinking and continuous improvement.

6

How do you measure success, and what metrics do you use to evaluate organizational performance?

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Why this works

Understanding their success metrics helps you align your work with their expectations and know how your contributions will be evaluated.

7

What are your thoughts on leadership development, and how do you support the growth of your team?

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Why this works

Understanding their approach to development helps you assess if the organization will support your professional growth and career advancement.

8

How do you handle communication and transparency within the organization?

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Why this works

Understanding their communication approach helps you know how to share information and feedback effectively and assess if the organization values transparency.

9

What are your thoughts on work-life balance, and how do you support it for your team?

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Why this works

Understanding their approach to work-life balance helps you assess if the organization values employee well-being and supports sustainable work practices.

10

How do you approach diversity, equity, and inclusion, and what initiatives are you implementing?

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Why this works

Understanding their DEI approach helps you assess if the organization values diversity and creates an inclusive environment for all employees.

11

What are your thoughts on technology and digital transformation, and how is the organization adapting?

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Why this works

Understanding their technology approach helps you assess if the organization is forward-thinking and prepared for future challenges and opportunities.

12

How do you handle crisis management and unexpected challenges?

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Why this works

Understanding their crisis management approach helps you assess their leadership capabilities and how they handle difficult situations.

13

What are your thoughts on sustainability and environmental responsibility?

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Why this works

Understanding their sustainability approach helps you assess if the organization is committed to environmental responsibility and long-term thinking.

14

How do you approach stakeholder relationships, and what is your strategy for managing them?

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Why this works

Understanding their stakeholder approach helps you assess their relationship management skills and how they balance different interests and needs.

15

What are your thoughts on the future of our industry, and how is the organization preparing?

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Why this works

Understanding their industry perspective helps you assess their strategic thinking and how they're positioning the organization for future success.

16

How do you approach risk management, and what is your strategy for mitigating potential threats?

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Why this works

Understanding their risk management approach helps you assess their strategic thinking and how they protect the organization from potential threats.

17

What are your thoughts on collaboration and partnerships, and how do you approach them?

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Why this works

Understanding their collaboration approach helps you assess their relationship-building skills and how they leverage partnerships for organizational success.

18

How do you approach performance management, and what is your philosophy on feedback and development?

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Why this works

Understanding their performance management approach helps you know how to work with them and what to expect regarding feedback and development.

19

What are your thoughts on the role of data and analytics in decision-making?

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Why this works

Understanding their data approach helps you assess if the organization values evidence-based decision-making and how you can contribute to data-driven insights.

20

How do you approach succession planning, and what is your strategy for developing future leaders?

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Why this works

Understanding their succession planning helps you assess if the organization is committed to developing talent and preparing for future leadership needs.

Best Practices for Engaging with Presidents

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

Best Practices

Show Strategic Thinking

Ask questions that demonstrate you're thinking strategically about the organization and its future. This shows you're aligned with their vision and goals.

Understand Their Priorities

Ask questions that help you understand their priorities and how you can contribute to achieving them. This shows you're focused on adding value.

Demonstrate Leadership Potential

Ask questions that show you're thinking about leadership, development, and the future of the organization. This demonstrates your potential for growth.

Be Respectful and Professional

Ask questions in a respectful and professional manner. This shows you understand the importance of the relationship and are committed to building it.

Question Sequences

The Vision Explorer

1
What is your vision for the organization, and how do you see it evolving over the next few years?
2
What are your top priorities for this year, and how can I contribute to achieving them?
3
What do you see as the biggest challenges facing our organization, and how are you addressing them?
4
What are your thoughts on the future of our industry, and how is the organization preparing?

The Leadership Developer

1
What are your thoughts on leadership development, and how do you support the growth of your team?
2
How do you approach succession planning, and what is your strategy for developing future leaders?
3
What are your thoughts on work-life balance, and how do you support it for your team?
4
How do you approach performance management, and what is your philosophy on feedback and development?

Common Pitfalls

Don't Ask Personal Questions

Keep questions focused on professional topics and organizational matters. Avoid personal questions that might make them uncomfortable.

Avoid Controversial Topics

Don't ask questions about controversial topics or issues that might create tension. Focus on positive, forward-looking topics.

Don't Make Assumptions

Don't assume you know their answers or make judgments about their responses. Listen with an open mind and ask follow-up questions.

Conversation Templates

The Vision Explorer

1
Step 1: Start with: "What is your vision for the organization, and how do you see it evolving over the next few years?"
2
Step 2: Follow with: "What are your top priorities for this year, and how can I contribute to achieving them?"
3
Step 3: Deepen with: "What do you see as the biggest challenges facing our organization, and how are you addressing them?"
4
Step 4: Connect with: "I want to understand your vision and how I can contribute to achieving it."

The Leadership Developer

1
Step 1: Start with: "What are your thoughts on leadership development, and how do you support the growth of your team?"
2
Step 2: Follow with: "How do you approach succession planning, and what is your strategy for developing future leaders?"
3
Step 3: Deepen with: "What are your thoughts on work-life balance, and how do you support it for your team?"
4
Step 4: Connect with: "I want to understand your approach to developing talent and supporting your team."

Further Reading

"The Leadership Challenge" by James Kouzes and Barry Posner
"Good to Great" by Jim Collins
"The 7 Habits of Highly Effective People" by Stephen Covey

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