By Jill Romford on Wednesday, 29 January 2025
Category: Blog

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.

Leaders don't need to ask complex, business-centric questions to break communication barriers. Instead, thoughtful questions about employees' well-being, challenges, and aspirations can foster a more supportive and collaborative environment.
One executive, John, shared that he shifted his leadership approach by asking, "How can I improve the lives of my team members?" Rather than focusing solely on his own performance and company goals, he prioritized the needs of his employees. This change in mindset transformed the workplace dynamic, strengthening team morale and productivity.

When leaders approach conversations with genuine curiosity and empathy, they demonstrate that they care about employees beyond their work output. This helps build relationships based on mutual respect and trust—a key factor in workplace satisfaction.
Engaging with employees means more than just asking questions—it requires active listening. Instead of isolating themselves in executive offices, leaders who spend time in their employees' workspaces create an environment where employees feel comfortable sharing their thoughts and concerns.

Listening without interrupting, judging, or rushing to provide solutions is essential. Employees need to feel heard and valued, particularly when they're addressing challenges within the company. Leaders who cultivate this ability encourage a culture of openness, where employees aren't afraid to speak up when something isn't working.

When leaders consciously try to be approachable, visible, and receptive, employees feel empowered to communicate honestly. A workplace where leaders listen first and lead second fosters collaboration, innovation, and long-term success.

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:

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.

Questions to Ask Your CEO in a Town Hall

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

Lunch with CEO: Questions to Ask in a Casual Setting

A more relaxed setting allows for meaningful yet approachable conversations.

Fun Questions to Ask Your CEO

Engaging in lighthearted conversations helps humanize leadership and foster connection.

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.

Questions to Ask a CEO About Career Growth

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

Questions to Ask a CEO of a Large Company

Larger organizations often have different challenges and leadership styles.

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.

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






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





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






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






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. 








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? 

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

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

  • What are the company's top priorities for the upcoming year?
  • How does leadership plan to address employee concerns and feedback?
  • How is the company staying competitive in a changing market?
  • What are some ways employees can contribute to innovation and growth?
  • Q4: What are behavioral questions for a CEO?

  • Can you share an example of a time you had to make a tough business decision?
  • How do you handle setbacks or failures within the organization?
  • What's your leadership philosophy, and how has it evolved over time?
  • How do you balance short-term business goals with long-term vision?
  • Q5: What strategic questions should I ask a CEO? 

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

  • If you could have dinner with any historical figure, who would it be and why?
  • 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 every employee?
  • Q7: What questions should an employee ask a CEO?

  • How can employees align their daily work with the company's long-term vision?
  • What leadership qualities do you value most in employees?
  • What are some ways employees can have a bigger impact within the organization?
  • How do you personally stay motivated and inspired as a leader?
  • Q8: What are good lunch with CEO questions to ask?

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

  • What skills or qualities do you think are essential for career growth in this company?
  • How do you approach decision-making when faced with uncertainty?
  • What can I do to contribute more effectively to the company's success?
  • How do you define success, both professionally and personally?
  • Q10: What questions should I ask a CEO about career growth?

  • What advice would you give employees looking to move into leadership roles?
  • How does the company support professional development and skill-building?
  • What common career mistakes do you see employees make, and how can they avoid them?
  • What qualities do you look for when promoting employees?
  • Q11: What questions should I ask a CEO about company culture?

  • How would you describe the company culture in three words?
  • What steps does leadership take to maintain a strong and positive workplace culture?
  • How do you ensure employees feel heard and valued?
  • What role do employees play in shaping and improving 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.

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