The Best Questions to Ask Your CEO in Different Situations

by Jason Evanish, CEO Get Lighthouse, Inc.

Regardless of the size of the company you work for or you're interviewing at, getting a chance to ask the CEO a few questions is a unique and special opportunity. 

That's why we want to be sure you make the most of it, no matter what the context is.

No matter how big or small their company is, CEOs are busy people. They've got a lot on their mind and have to deal with countless pressures. One of their most important tasks is the responsibility to their employees: their welfare, their compensation, and the stability of the company.

Today's post gives you a bunch of great questions to ask your CEO when you have the chance. These questions will reveal more about the company culture, the motivations behind it, and other valuable insights to help you understand the company you work at, or decide if one you may go work for is a good fit for you.

How to ask great questions to your CEO: Use How and What, not Why

When it comes to asking great questions to your CEO, you should try to use "How" and "What" questions as much as you can. We previously wrote about the power of "what” and "how” from the book, Never Split the Difference, because it’s so powerful and effective. 

The best part about What and How questions is that they can just as easily be applied to town hall discussions, round tables, all hand meetings, and strategic planning sessions. 

The key to asking them is that they can't be answered with a simple "yes" or "no". Instead, a good What or How question will have them telling a story, or explaining a process. It gives you helpful nuance and detail you wouldn't hear from a simple yes or no question.

What & How Beats Why Every Time

Another great thing about beginning with What or How is that it's a way to spark a conversation in a non-judgemental way. Unlike them, Why questions can make it seem like you're finger-pointing or attacking the person you are asking the question to. It can also feel like you’re demanding an explanation rather than opening a discussion. (i.e.- "Why did you do that?!?” vs. "How did you arrive at that decision?”)   

A why question can immediately put people on the defensive, which you especially don’t want to do with your CEO. When you ask an aggressive Why question, any hope of your CEO opening up, or sparking an engaging conversation goes out the window. It also is less likely to make it through any filters and screening that happens before questions are presented in a company-wide meeting.

With this in mind, you’ll understand why so many of our questions we suggest start with What or How.  Keep in mind, whether you ask some of the specific questions we suggest, or use them to inspire one of your own, try to avoid using Why, and instead use What or How to start your question on the right foot.

Great Questions to Ask a CEO in 3 Different Contexts

Today's questions fit into a few different categories for different situations, so if you're pressed for time, jump to the one that fits your scenario best:

Each situation warrants a different set of questions based on both the audience (is it just you and them, or a small or large group?) and the circumstances (are you interviewing or already work there?), so we'll help you understand those nuances. 

Let's begin...

Questions to ask your CEO

Questions to Ask a CEO in a Town Hall or Roundtable

Town hall meetings or roundtables are meant to give everyone at your organization a voice. Their aim is to provide more transparency and give people the freedom to ask questions about the organization's performance, vision, goals, and other similar topics.

Since this is an all-hands-on-deck event and involves large groups, the questions are usually screened. This means asking something that can get perceived as too aggressive or impolite will never get asked. 

So that’s when the power of What and How questions kicks in. Here are a few examples of the questions to ask a CEO in a town hall meeting or roundtable:

  1. What are some of the most exciting projects on the horizon for us right now?
  2. What is our next big milestone? How do you see us getting there?
  3. What are the biggest challenges you think we're facing at the moment? What is the plan to address them?
  4. What do you think makes us stand out the most compared to our competitors?
  5. What do you think are the key ways we can improve as an organization this/next year?
  6. What can each of us do to help with the challenges our organization is facing right now?
  7. How do we grow and take the next step forward as a company?
  8. What was the reasoning behind [recent decision X]?
  9. What is the most important value we have as a company?

By remembering to start with "What” and "How”, you can significantly improve the questions you ask in town hall meetings. 

They will spark more interesting discussions and engage the CEO, rather than it feeling like you're questioning their authority or putting them on the spot.

Next time you want a more detailed, honest answer, think about how you can use a few "what” or "how” questions to get them to open up.

Melanie Whelan quote about leadership

Questions to ask Your CEO During Lunch 

Having lunch with your CEO offers a much different backdrop for asking questions compared to the previous two scenarios we've covered. 

If you're having lunch with them, you're either 1 on 1, or at a table with a small group. This much more intimate environment means you have the chance to accomplish a few unique things:

  1. Make an impression: If the CEO remembers you in a positive way, that can be huge for your career. However, your behavior has to be genuine, as only toxic leaders like a suck-up, and no one likes a jerk. 
  2. Answer burning questions: If there's something you're really hungry to find out, then you can ask more pointed or specific questions than would be filtered out in a large group (town hall) session.  Just remember what impression you'll be making by asking.
  3. Get deep context: In a small group, you're likely to get a chance to ask multiple questions, including follow ups to something you ask. This can provide priceless context, allow you to elaborate on your ideas, and get them to do the same.
  4. Get to know the CEO on a more personal level: Like all of us, CEOs have hobbies and interests. Since you're having lunch, they'll likely be up for discussing things that aren't just business related. You may just be able to build valuable rapport with them, which allows you to build a long term connection. 

With all of this in mind, what should you talk about? Here are a few ideas:

  1. What are the greatest challenges you've faced as a CEO? How did they change the way you lead?
  2. What motivates you to keep going in your role?
  3. What's your favorite or least favorite part of the job of CEO?
  4. Who were your biggest role models at the beginning of your career? Who do you look up to now?
  5. What do you find the most stressful as a CEO? How do you manage the stress and pressure?
  6. What book or article have you read recently that has had an impact on how you think?
  7. Looking back, what, if anything, would you do differently in your career?
  8. What do you think of our company values? Which values do you think we are we doing the best or worst with? 
  9. What would be your advice to someone looking to become a better leader?
  10. What are some of the misconceptions people have about being a CEO?

Remember Dale Carnegie's one rule for success in business and in life, especially during these less formal events: Be genuinely interested in people.

Encourage the CEO to tell his or her story, and you'll be able to strike up an interesting conversation with them at the very least. You'll also likely learn some valuable things about how they think and what they believe is important.

Questions to ask your CEO During Strategic Planning

Some companies from time to time have strategic planning sessions. These meetings play a crucial role in charting the course of the organization for the short (next quarter) and sometimes long term (next year or more).

As an employee, if you’re invited to such a meeting, you can have great, positive impact, and make a good impression by actively participating and engaging with your CEO by asking good questions. 

Your CEO has a unique perspective that is invaluable to understand better; often, the CEO is a founder or long time employee, meaning they have a ton of historical knowledge of your company. They also spend a lot of time interacting with your market, competitors, potential acquirers and more, which can help inspire key strategic decisions. You can best learn about their perspective by asking great questions. 

Here are some insightful questions to ask your CEO during strategic planning:

  1. How does [initiative X] help us be better positioned in the market?
  2. What do you think our competitors will do in response to this? How do you see our competitive landscape changing?
  3. How does this change our position in the market?
  4. What makes this [new initiative] take priority over [current initiative competing for resources]?
  5. How would you describe our company's vision in the next three to five years? How do our new initiatives help us get there?
  6. What are the top three priorities you believe we should focus on in the next quarter/year?
  7. Where do you see the most opportunity for us to innovate and differentiate in the market among these priorities?
  8. What are the biggest challenges you expect we will face as we tackle these new priorities? How do you think we can overcome them?
  9. How do you see resources being shifted based on these new initiatives and goals?
  10. How do we measure success for these projects? What are our KPIs for these initiatives?
  11. What are the biggest risks you foresee as we begin to execute on these plans? How can we mitigate these risks?

As you can see, What and How questions can be quite versatile. They can get your CEO talking about a variety of topics in a way that will deepen your and your coworker’s understanding of their thinking and strategies. Try some of these questions in your next strategic planning meeting, or use them to inspire your own similar versions.

Conclusion: The right question at the right time makes all the difference. 

Talking to the CEO of your company is a unique opportunity to find out some crucial things about them and their company. Depending on the context, it allows you to learn (or read between the lines) how the company treat their employees, how stable they are, what motivates them, and golden nuggets of advice you can use to accelerate your own career.

Unfortunately, opportunities to talk to CEOs are rare, and their time is limited. That's why you need to come prepared and know what to ask in different situations.

Use this post as a starting point to think about the questions that you'll get real value from. Avoid schmoozing, as they're probably used to it and will see right through it. 

Remember: CEOs are normal people like all of us. Their experience has allowed them to rise to the highest levels, so think about what you could learn from them in that regard.

Always be aware of the context (the occasion, how many people are listening, how formal/informal the setting is), ask about things that aren't obvious to everyone, and show genuine interest in what they have to say. That way, they'll be much more willing to open up, and you may even develop a relationship with them.

:rocket:Boost Your Management Skills on Your Time!:rocket: Tight on time, but dreaming of becoming a great manager? Lighthouse is your beacon! Our courses, crafted with leaders like you in mind, are tailored for leaders with busy schedules. Spend just 15 minutes a day and watch your management skills soar. Curious to learn more? Click here and step into your potential today!

Are there any questions I should avoid asking my CEO?

Yes. There are certain questions you should not ask when interacting with your CEO. It's crucial to maintain professionalism and respect boundaries. Here are a few types of questions that you should avoid:

  • Personal or invasive questions: Avoid asking your CEO about their personal life, family matters, or any other that are not related to work, especially if you would find the same questions offensive or invasive.
  • Negative or confrontational questions: It's important to frame your questions in a constructive and respectful manner. Avoid asking questions that come across as confrontational or focused solely on criticizing decisions or actions like “why did you do that!?!?”
  • Yes/No questions: These types of questions don’t give you any context or additional information to help you understand their thinking. Instead, consider framing your questions in a way that encourages your CEO to provide detailed and thoughtful responses. Shifting your questions to begin with either “What” or “How” are a great way to positively frame questions that also gets your CEO talking in detail.

Are there any specific strategies for asking challenging or sensitive questions to the CEO?

Asking questions that begin with “What” or “How” are great to use when you're asking challenging and sensitive questions. Doing so gets your CEO talking about their thinking and rationale, without making them feel like they’re being attacked.

There are also a few other strategies to keep in mind when asking tough questions of your CEO:

  • Frame your question with respect: Use respectful and non-confrontational language to maintain a constructive tone. This is where starting questions with “What” and “How” can work much better than a similar question starting with “Why”. 
  • Provide context and examples: When asking a challenging question, provide relevant context and specific examples to clarify your concerns or observations. It can help your CEO to better understand the situation, which can convey why it’s important or context that makes them more accepting of being challenged.
  • Seek understanding, not confrontation: Importantly, approach the conversation with a genuine desire to understand the CEO's reasoning or perspective. Listen actively, without interrupting, and be open to different viewpoints.
Jason Evanish

Jason Evanish

As the founder and CEO of Get Lighthouse, Inc, Jason and the Lighthouse team have helped managers grow their leadership skills in dozens of countries around the world. They’ve worked with a variety of companies from non-profits to high growth startups, and government organizations to well known, publicly traded companies. Jason has also been featured in publications including NPR, the Wall Street Journal, and Fast Company.

Read more

Browse topics

Follow us:

Note: We do not accept guest posts, so please do not email us.

Sign up to learn the essential skills you need to become a great manager:

1 on 1 meeting software, leadership courses, and group training to help you be the manager you always wanted.

Do You Want to Learn
How to be a Great Manager?

Sign up to join over 27,000 managers who get our latest posts to learn:
  • How to motivate and retain your team;
  • How to have more effective one on ones;
  • Lessons from other managers & research that matters to you.
+ Free copy of our E-book: 10 Steps to having amazing 1 on 1s with your team
Learn how to have amazing 1 on 1s today
Sign up now to get your free book to learn how to have motivating, engaging 1 on 1s. Learn from great leaders like Andy Grove, former CEO of Intel, and workplace research from Stanford & Harvard.
Share via
Copy link