Questions to Ask Your CEO in 2025 (From Simple to Challenging)

​ It is important to know what questions to ask your CEO as it is essential for fostering transparency, trust, and strong organizational alignment. 

Thoughtful questions provide valuable insights into the company's direction, challenges, and opportunities. By engaging with the CEO, employees can better understand strategic decisions, leadership values, and the overall vision for the future. This open dialogue helps build trust between employees and leadership, as it shows a commitment to transparency and inclusivity. Also asking the right questions signals active involvement, encouraging a culture of mutual respect and collaboration. 

Whether seeking clarification on company strategy or learning more about the CEO's leadership style, well-posed questions can deepen relationships and create a more cohesive work environment. 

Ultimately, questions to ask your CEO or questions for the president of a company are not just about seeking information; they are tools for strengthening communication and ensuring that everyone is aligned with the company's goals.

What Makes a Question Powerful?

A client recently introduced me to the concept of the rubber duck theory in software programming, which beautifully illustrates the power of asking questions—and how even the simplest ones can be the most impactful.

Rubber duck "debugging" (a method for solving coding issues) stems from a story about a programmer who kept a rubber duck on their desk. They would explain each part of their code, step by step, to the duck as they worked through it. Surprisingly, the act of verbalizing the problem often revealed the solution hidden within the issue itself. By simply talking it through, the programmer gained the clarity needed to move forward.

This concept extends beyond coding. When you ask basic yet thoughtful questions—like "What are you experiencing? Can you walk me through it step by step?"—with genuine curiosity and without judgment, you create a space for others to articulate their challenges. This process not only helps them talk through their problems but also encourages them to develop their own internal dialogue, empowering them to ask themselves questions and find solutions independently.

As a leader, you can embody the role of the rubber duck. 

By being a safe, curious, open, and non-judgmental listener, you become a powerful guide. You're not the hero who solves every problem; instead, you inspire others to step into their own heroism and discover their own answers.

The Art of Asking and Listening

Effective leadership isn't just about making strategic decisions—it's about fostering genuine connections with employees. A leader's ability to ask the right questions and truly listen can make all the difference in building trust, encouraging open communication, and creating a more engaged workforce.

The Power of Asking Questions

 Asking thoughtful questions isn't just a skill for leaders—it's essential for personal and professional growth. The ability to ask curious, open-ended questions fosters empowerment, deeper connections, and innovative thinking. Whether in the workplace, in relationships, or in personal development, asking the right questions creates space for learning, collaboration, and progress.

When people operate on autopilot, making assumptions and jumping to conclusions, they often feel stuck—like they're running on a hamster wheel but never truly getting anywhere. This cycle can lead to burnout, frustration, and disengagement from the bigger picture.

Shifting away from a mindset of always having to "fix" things and instead embracing curiosity and exploration allows for sustainable growth. Asking questions isn't about proving intelligence—it's about unlocking new perspectives, deeper understanding, and hidden potential in yourself and those around you.

Curiosity fuels progress.

Those who embrace it constantly ask:

• What else is possible?
• How can I approach this differently?
• What solutions haven't I considered yet?

Rather than assuming they already have the answers, they invite collaboration, diverse perspectives, and creative problem-solving. This openness leads to more innovative solutions and stronger relationships.

Asking questions benefits the individual and empowers those around them. Instead of dictating solutions, asking, "What do you think?" or "How would you approach this?" allows others to enter their brilliance. It encourages ownership, builds confidence, and fosters a culture of trust and collaboration.

Actual growth happens in spaces where questions are welcomed, and judgment is left behind. A willingness to ask, listen, and explore new ideas with an open mind leads to better relationships, more intelligent decisions, and continuous learning.

At its core, asking powerful questions isn't just about finding the correct answers—it's about opening the door to new possibilities and creating a path for ongoing growth and transformation.

Essential Questions to Ask Your CEO: Strategic, Personal, and Career-Oriented

Engaging with your CEO can provide invaluable insights into your company's vision, culture, and leadership style. 

With advancements in technology making communication more accessible, employees now have more opportunities than ever to connect with senior leadership. Asking the right questions in town halls, one-on-one meetings, or even casual lunch discussions can foster alignment, strengthen company culture, and provide career guidance.

According to a Gallup study, companies with high employee engagement experience a 21% increase in profitability and a 59% reduction in turnover. Open communication between employees and leadership is a crucial factor in fostering this engagement.

Here's a guide to the best strategic, personal, and fun questions to ask your CEO to gain valuable insights and build a deeper connection with your organization's leadership.

Strategic Questions to Ask a CEO

These questions help employees understand the company's direction and leadership priorities.

• What strategic questions should employees ask a CEO to understand the company's future vision?
• How does leadership decide on the company's long-term priorities?
• What key trends do you see shaping the industry over the next five years?
• What are the biggest challenges facing the company today, and how are we addressing them?
• If you could change one thing about our organization, what would it be?

Questions to Ask Your CEO in a Town Hall

Town halls are a great opportunity to address company-wide concerns and opportunities.

• How is our company staying competitive in today's market?
• What is leadership doing to ensure a strong company culture as we scale?
• What role do employees play in shaping the company's strategic vision?
• What is one thing the executive team wishes employees understood better?
• How does leadership measure success beyond financial growth?

Lunch with CEO: Questions to Ask in a Casual Setting

A more relaxed setting allows for meaningful yet approachable conversations.

• What inspired you to become a leader in this company?
• What has been the most rewarding moment of your career?
• How do you balance work and personal life as a CEO?
• What do you think is the most misunderstood aspect of being a CEO?
• If you could give one piece of advice to employees looking to grow their careers, what would it be?

Fun Questions to Ask Your CEO

Engaging in lighthearted conversations helps humanize leadership and foster connection.

• What was your first job, and what did you learn from it?
• If you weren't in this industry, what career would you have pursued?
• What's one book or podcast you'd recommend to all employees?
• If you could have lunch with any historical figure, who would it be and why?
• What's the best piece of career advice you've ever received?

Questions to Ask a CEO About Culture

A company's culture defines its long-term success. These questions help employees understand the CEO's cultural vision.

• What are the core values that drive our company?
• How do you ensure our culture remains strong as we grow?
• How does leadership encourage innovation and creativity?
• What's one thing employees can do to contribute positively to workplace culture?
• How does the company handle diversity and inclusion efforts?

Questions to Ask a CEO About Career Growth

Employees thrive when they see opportunities for personal and professional development.

• What advice do you have for employees looking to move into leadership roles?
• How does the company support career growth and internal promotions?
• What qualities do you look for in future leaders?
• How do you handle failure, and what lessons have you learned from past mistakes?
• What skills do you believe will be most valuable for employees in the next decade?

Questions to Ask a CEO of a Large Company

Larger organizations often have different challenges and leadership styles.

• How do you stay connected with employees at all levels of the company?
• What's the biggest challenge in leading a large organization?
• How do you ensure alignment across different departments?
• What role does employee feedback play in executive decision-making?
• What's your approach to maintaining agility and innovation at scale?

Interview Questions for CEOs by Employees

If you're in a leadership interview or want to understand a CEO's leadership approach, these questions are valuable.

• What's your leadership philosophy, and how has it evolved?
• What qualities do you value most in employees?
• How do you handle difficult decisions or times of crisis?
• What's the most significant risk you've taken in your career?
• How do you measure your success as a CEO?

Key Questions to Ask Your CEO for a Better Understanding of Company Strategy 

When thinking about what questions to ask a CEO to gain a better understanding of the company's strategy, there are several strategic inquiries that can provide valuable insight into the organization's long-term direction. Employees can ask, "What are the most significant opportunities and challenges facing the company over the next few years?" or "What initiatives are we pursuing to stay ahead of competitors?" 

These questions help employees understand how the company positions itself in the market and what steps are being taken to ensure its continued growth.

Alao, questions like "What role do employees play in shaping the company's strategic goals?" and "How does the company measure success, both in the short term and long term?" help clarify expectations and alignment between leadership and the workforce. 

By asking these questions, employees can gain clarity on the CEO's vision and better understand how their individual contributions impact the broader company strategy, fostering a stronger sense of purpose and direction within the organization.

5 Key Questions to Ask Your CEO for a Better Understanding of Company Strategy

• 1.What are the top three strategic priorities for the company over the next 3-5 years?
• This question helps employees align their work with long-term business goals and understand where leadership is focusing resources and efforts.

• 2.How does the company plan to stay competitive in an evolving industry landscape?
• Knowing how leadership anticipates market changes and competitive pressures provides insight into the company's adaptability and innovation strategy.

• 3.What key challenges or risks do you foresee for the company, and how do we plan to address them?
• This question uncovers potential obstacles and allows employees to be proactive in supporting risk mitigation efforts.

• 4.How do you see employees contributing to the company's strategic goals?
• Employees gain clarity on their role in the organization's success, fostering engagement and a sense of purpose.

• 5.What investments is the company making in technology, talent, or infrastructure to support future growth?
• This question provides insights into resource allocation and whether the company is preparing for sustainable long-term expansion.

Questions to Ask Your CEO About Company Culture and Values 

Questions to ask your CEO about company culture and values are essential for employees to understand the leadership's commitment to fostering a positive, inclusive workplace environment. 

A great starting question is, "What are the core values that guide our company, and how are they reflected in day-to-day operations?" This helps employees connect their work with the company's larger mission.

Another key question could be, "How do you ensure that our company culture evolves in response to changing employee needs and expectations?" This inquiry explores how the company maintains relevance and adaptability. Asking, "How does leadership ensure transparency and open communication within the organization?" allows employees to understand the role of management in shaping a communicative and supportive culture. 

By asking such questions, employees can gauge whether the CEO's vision aligns with the company's cultural practices, ensuring a work environment that values trust, inclusion, and employee well-being.

Key Questions to Ask Your CEO About Company Culture and Values

• 1.How would you define our company culture, and how do you ensure it stays strong as we grow?
• This helps employees understand leadership's vision for culture and how it evolves over time.

• 2.What are the core values that guide decision-making at all levels of the company?
• Understanding the company's foundational values ensures alignment in day-to-day operations and long-term goals.

• 3.How does leadership ensure that company values are reflected in employee experience and daily work?
• This question reveals how values translate into actionable policies and workplace behaviors.

• 4.What initiatives are in place to promote diversity, equity, and inclusion within the organization?
• Employees gain insight into the company's commitment to fostering an inclusive and equitable work environment.

• 5.How does the company encourage open communication and feedback between employees and leadership?
• Transparency and feedback are crucial for a healthy culture; this question assesses how leadership supports two-way communication.

What Questions to Ask a CEO During an Interview 

When considering what questions to ask a CEO in an interview, it's important to ask insightful inquiries that help gauge the company's values, culture, and growth potential. One great question is, "How do you define success for the company, and what are the key milestones you're hoping to achieve in the next few years?" This shows your interest in the company's long-term goals and vision. 

Another question could be, "How would you describe the company culture, and what steps do you take to ensure a healthy, inclusive environment for employees?" This helps you assess whether the company's culture aligns with your values. Additionally, asking, "What opportunities for growth and development does the company offer to its employees?" can give you insight into career progression and internal opportunities. 

Key Questions to Ask a CEO During an Interview

• 1.Questions About Leadership and Vision
• What inspired you to take on a leadership role in this company?
• How would you describe your leadership style, and how has it evolved over time?
• What are the key qualities you believe make an effective CEO?

• 2. Questions About Company Strategy
• What is the company's long-term vision, and how do you plan to achieve it?
• What do you see as the biggest challenges for the company in the next five years?
• How does the company stay ahead of competitors in a rapidly changing market?

• 3. Questions About Company Culture and Values
• How do you foster a strong and positive company culture?
• What values do you prioritize most in employees and company operations?
• How does leadership ensure that employees at all levels feel heard and valued?

• 4. Questions About Employee Growth and Development
• What career growth opportunities does the company provide for employees?
• How do you encourage professional development and learning within the organization?
• What advice would you give to employees looking to move into leadership roles?

• 5. Questions About Work-Life Balance and Personal Insights
• How do you personally manage work-life balance in a demanding role?
• What's the best leadership advice you've ever received?
• If you could change one thing about corporate leadership today, what would it be?

These types of questions can help you better understand the company's environment and your potential fit within the organization.

Questions to Ask Executives About Business Operations and Performance ​

When preparing questions to ask executives about business operations and performance, it's essential to inquire about the company's efficiency, metrics, and long-term goals. Start with a question like, "What are the primary operational goals for the company this year, and how do you measure success in achieving them?" This will provide insight into the company's key focus areas. 

You can also ask, "What strategies are in place to drive growth and innovation within the company?" to understand the initiatives designed to ensure sustained success. Another important question is, "How does the company ensure that its business operations remain agile and adaptable in the face of market changes?" 

This will help you evaluate how the company handles challenges and remains competitive. 

Key Questions to Ask Executives About Business Operations and Performance

• 1. Questions About Business Strategy and Performance Metrics
• What key performance indicators (KPIs) does the company use to measure success?
• How do you ensure the organization remains agile in a competitive market?
• What major operational challenges does the company face, and how are they being addressed?

• 2. Questions About Operational Efficiency and Process Improvement
• What strategies are in place to streamline business operations and improve efficiency?
• How does the company approach automation and technology adoption to enhance productivity?
• What efforts are being made to reduce costs without compromising quality?

• 3. Questions About Customer and Market Insights
• How does the company gather and use customer feedback to improve operations?
• What market trends are currently shaping business decisions?
• How does the company ensure customer satisfaction while scaling operations?

• 4. Questions About Employee Productivity and Workplace Optimization
• What initiatives are in place to improve employee performance and engagement?
• How does leadership ensure cross-functional collaboration between teams?
• What role do employees play in optimizing business processes and driving innovation?

• 5. Questions About Future Growth and Business Sustainability
• What are the biggest risks to the company's long-term success, and how are they being mitigated?
• How does the company plan to expand or scale operations in the next five years?
• What investments are being made in technology and infrastructure to support future growth?

Also, asking, "What metrics or KPIs are most critical to tracking the company's performance, and how do these influence decision-making?" can help you understand how data drives operational and strategic choices. 

These questions help ensure transparency and align the company's operational strategies with its overall objectives.

How to Ask Thoughtful Questions That Drive Productive Conversations with Your CEO ​

When considering questions to ask your CEO, it's important to frame them in a way that encourages thoughtful, productive conversations. Start by making sure your questions are clear and specific, which ensures that the CEO can provide a well-informed response.

For example, instead of asking a vague question like, "How is the company doing?" try something more focused, such as, "What are the top three priorities for the company this year, and how do they align with our long-term goals?" It's also essential to ask questions that invite further discussion, such as, "What challenges do you foresee in the upcoming quarter, and how can employees contribute to overcoming them?" This helps show engagement and encourages a deeper conversation. Lastly, always ask your questions with respect and openness, allowing your CEO to share insights without feeling defensive. 

• 1. Be Clear on Your Purpose
• Before you ask a question, define your objective. Are you looking for insight into company strategy, leadership philosophy, career growth, or operational improvements? A well-thought-out question should be relevant, specific, and tied to the bigger picture.
• Example: Instead of asking, "What's next for the company?"
• Ask: "What are the company's top three priorities for the next 12 months, and how can employees contribute to those goals?"

• 2. Do Your Homework
• CEOs appreciate well-informed questions. Research company reports, strategic initiatives, and recent announcements to ensure your questions are timely and relevant. This shows initiative and prevents asking something that has already been addressed.
• Example: Instead of asking, "What's the company's biggest challenge?"
• Ask: "Given our recent expansion into new markets, what challenges do you foresee in maintaining operational efficiency?"

• 3. Keep It Open-Ended and Insightful
• The best questions encourage deep thinking and discussion rather than simple yes/no answers. Open-ended questions help spark meaningful conversations and provide richer insights.
• Example: Instead of asking, "Do you think we are growing?"
• Ask: "What key growth areas do you believe we should focus on to stay ahead of industry trends?"

• 4. Align Your Question with the CEO's Perspective
• CEOs think about long-term strategy, market positioning, and organizational success. Frame your questions in a way that aligns with these priorities while also considering how it impacts employees.
• Example: Instead of asking, "Why don't we have more perks like other companies?"
• Ask: "How do you see our company balancing employee well-being with financial sustainability?"

• 5. Be Concise and Respect Their Time
• CEOs are busy, so get to the point quickly. Avoid lengthy preambles and complex wording. A well-structured question should be short, direct, and impactful.
• Example: Instead of saying, "I was thinking about how our competitors are handling remote work, and I feel like we could be doing more, so I wanted to ask what you think about our current approach to hybrid work?"
• Ask: "How do you see our remote work strategy evolving to stay competitive?"

• 6. Follow Up with Active Listening
• A great question is only half of a productive conversation—the other half is actively listening to the response. Avoid interrupting, and show engagement through follow-up questions or summarizing key points.
• Example Follow-Up: "That's a great insight on our growth strategy. How do you see employees at all levels contributing to these goals?"

• 7. End with an Actionable Takeaway
• To maximize impact, translate the CEO's response into an actionable step for yourself or your team. If relevant, summarize their key points and ask how you or your colleagues can support the strategy moving forward.
• Example: "That makes sense—so for my team, would prioritizing [X initiative] be the best way to align with this vision?"

By carefully crafting your questions, you can foster meaningful and productive conversations with your CEO.

Common CEO Interview Mistakes: When CEOs Talk Too Long 

In many CEO interviews, one common issue is CEOs talking too long, which can lead to a lack of clarity and reduced engagement. CEOs talking too long during interviews examples include situations where they provide overly detailed responses without addressing the core of the question. For instance, a CEO may go off-topic or elaborate excessively on past successes without directly answering how current challenges are being handled. 

This can leave the interviewer, and even the audience, feeling disconnected or unsure about the company's present direction. To prevent this, it's important for interviewers to ask concise, focused questions that encourage CEOs to stay on track and offer clear, actionable responses.

Navigating Sensitive Topics: Questions to Ask Your CEO About Organizational Change ​ 

When it comes to navigating sensitive topics, questions to ask your CEO about organizational change are crucial for understanding the company's direction, especially during times of restructuring or transition. Start by asking, "How do you envision the company's growth after the recent changes, and how will it impact the team's daily operations?" This provides clarity on the company's future and how employees may be affected. 

It's also helpful to ask, "What steps are being taken to ensure employees' concerns are addressed during this transition?" This shows your concern for the employee experience and encourages transparency. 

Additionally, asking, "How can employees contribute to supporting the company through this change, and what role do they play in the transition process?" demonstrates engagement while offering an opportunity to align personal contributions with company goals.

  The Role of CEOs in Shaping Employee Experience: Questions to Ask ​

Questions to ask your CEO regarding employee experience can provide valuable insights into how the leadership views and enhances employee satisfaction, retention, and development. For example, you might ask, "What initiatives is the company currently focusing on to ensure employee satisfaction and engagement?" This helps uncover how the CEO prioritizes employee welfare. 

Another important question could be, "How does the company approach career development and internal mobility for employees looking to grow within the organization?" This question can offer insights into the company's commitment to professional development. Additionally, asking, "How does leadership foster a supportive work culture, and what role do employees play in shaping it?" encourages a discussion about collaboration and mutual respect within the workplace. 

These types of questions give employees a clearer understanding of how leadership views their role in creating a positive work environment, improving retention, and enhancing overall satisfaction.

Real-Life Examples: Impactful Questions Asked to CEOs in Interviews ​ 

Questions to ask CEOs in an interview can significantly impact the relationship between the CEO and employees, as they allow for deeper insights into the company's culture and vision. 

One example is from an interview with a tech company CEO, where the candidate asked, "What do you see as the biggest challenge facing the company in the next three years, and how are you preparing for it?" This question led to a meaningful discussion about long-term strategy and risk management, providing a clearer picture of the CEO's foresight. 

Another impactful question asked was, "How does the company support work-life balance, and what steps are taken to prevent burnout?" The CEO's detailed response demonstrated the company's commitment to employee well-being, strengthening trust between leadership and staff.

FAQ: Essential Questions to Ask Your CEO

Q1: What are some good questions to ask a CEO? 

• What is the biggest challenge the company faces in the next five years?
• How do you see our industry evolving, and how is the company preparing for it?
• What key leadership lessons have you learned throughout your career?
• How can employees at all levels contribute to the company's success?

Q2: What are good questions to ask a CEO about diversity?

• What steps is the company taking to promote diversity, equity, and inclusion (DEI)?
• How does leadership ensure diverse voices are heard and valued in decision-making?
• Are there any company initiatives aimed at increasing diversity in leadership roles?
• How do you measure the impact of diversity efforts on company culture and performance?

Q3: What to ask your CEO during a town hall?

Q4: What are behavioral questions for a CEO?

Q5: What strategic questions should I ask a CEO? 

• What is the company's long-term vision, and what steps are being taken to achieve it?
• How do you ensure the company remains agile and innovative?
• What major risks or challenges do you foresee for the company?
• How do you decide which markets or business opportunities to pursue?

Q6: What are some fun questions to ask your CEO?

Q7: What questions should an employee ask a CEO?

Q8: What are good lunch with CEO questions to ask?

• What inspired you to pursue leadership in this company?
• What's the best career advice you've ever received?
• How do you balance your professional and personal life?
• If you could change one thing about corporate culture today, what would it be?

Q9: What questions should I ask my CEO in a one-on-one?

Q10: What questions should I ask a CEO about career growth?

Q11: What questions should I ask a CEO about company culture?

Wrapping up

Questions to ask your CEO during interviews, meetings, or one-on-one sessions can play a key role in strengthening organizational alignment. By asking thoughtful, targeted questions, employees can gain clarity on the company's vision, strategy, and goals. This fosters transparency, builds trust, and ensures that everyone is on the same page. 

Engaging with the CEO through open dialogue also promotes a culture of mutual respect, where both employees and leadership can collaborate towards common objectives. Ultimately, asking the right questions helps align the entire organization with the company's mission, leading to stronger teamwork and better performance.