The Best Questions to Ask Your CEO in Different Situations

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 a 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.

questions to ask a ceo

Great Questions to Ask a CEO in 3 Different Contexts

Today’s questions fit in 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…

improve your leadership skills by preparing questions to ask your ceo

Questions to Ask a CEO in an Interview

How can you ensure your first impression of a company you want to work for is accurate? How can you tell if their culture is on a good track or not? 

Unfortunately, many people interviewing for a job can’t figure out the answers to these questions. They often rush into new roles, only to end up locked in and feeling disappointed.

The most important thing to do when you’re interviewing is to look for potential red flags, so you don’t take a job at the wrong company. That’s not easy at the start of an interview process, but if you have an opportunity to talk to the CEO, here’s what you should ask to uncover them.

asking about turnover is among the most important questions to ask your ceo

Have you had any voluntary turnover? 

The best leaders take great pride in having 0 voluntary turnover. If the turnover at a company is high, or even worse, if a CEO tells you they don’t know how many people are leaving (or deflects the question), that’s a sign of a serious issue at their company.

How are problems solved at your company? Can you give me an example?

How problems are addressed is a key part of a company’s culture. There are a few ways problem-solving can become its own problem: 

  1. When everything goes through the CEO, they can quickly experience burnout or start to become influenced by politics.
  2. When issues are ignored, problem solving becomes reactionary and fire-fighting is part of everyone’s daily lives.
  3. If a company is inconsistent when it comes to problem-solving, you’ll never know what to expect.

While CEOs typically won’t admit they have issues with solving problems, if they can’t answer your question convincingly enough, that could point to one of the three situations described above. Try to find signs they listen to their team for input and ideas, and that the best solution wins, not the highest paid opinion. 

Do you and your managers have regular 1 on 1s with your staff?

1 on 1s are an essential tool to fix issues, coach your team, improve relationships, and address the things that no one gets around to otherwise. It’s why many leaders like Ben Horowitz, Andy Grove, Michael Wolfe, and Tomas Tunguz swear by them.

If a company doesn’t believe in a culture of 1:1s, imagine what it’s going to be like expressing your needs, ambitions and frustrations there. You are unlikely to have a time to talk about them, let alone actually make progress on these things.

Do you promote from within?

Companies that promote from within are also those that motivate their employees the best.

It turns out, that investment makes a big difference. A workplace study by Wharton management Professor Matthew Bidwell found that “external hires” have a tendency to be the worst of all worlds for companies that go that route:

  • External hires tend to get, “significantly lower performance evaluations for their first two years on the job than do internal workers who are promoted into similar jobs.”

Yet, it’s not only that external hires are less likely to work out. It also affects the morale of the existing team, because they miss out on something they want too: growth.

One of the top reasons people who are otherwise happy leave their job is a lack of opportunities for growth. This has been confirmed by both Mary Meeker’s Internet Trends report and a study from PwC.

If you’re in the process of interviewing, keep in mind you’ll be much more likely to stay and be happy if you know the company invests in your growth. 

Not every role is going to be a promotion from within; sometimes a company needs to hire in outside experience, but if you know they do consider internal candidates often, you’ll have a good shot in the future, too. 

questions to ask a ceo when interviewing

The right question can reveal a lot before you accept a job

No company is perfect. Even the best employer with an awesome culture will still struggle with some of these areas. 

If we look at them separately, none of them are really deal breakers for accepting a new role. However, if you notice several of these red flags at one company, you should seriously consider turning down the offer.

This is why it’s so critical to know what to ask a CEO during the interview process – if you ever get a chance to talk to them early on.

Want more in-depth instructions on how to uncover the true state of a company’s culture? You can check out this post: 

And here are some things you can ask in an interview to ensure you work for a skilled leader, whether a CEO or a mid-level manager:

Additionally, you can check out our other resources on the foundations of healthy companies:

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. 

What you can do instead is get your CEO talking by asking What and How questions. We previously wrote about the power of “what” and “how” from the book, Never Split the Difference,

Despite the book’s focus on negotiation, the point of asking What and How questions can just as easily be applied to town hall discussions. Their biggest advantage 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 otherwise. 

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 and demanding an explanation rather than participating in 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. As a result, any hope of your CEO opening up or an engaging conversation developing 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 that in mind, here are a few examples of What and How questions you can ask in town hall meetings:

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

in less formal meetings, you can focus on non-business related questions to ask your ceo

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:

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

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.

Want help being a better communicator and asking better questions of your team, too?

It all starts with high-quality 1:1s, which Lighthouse software helps you prepare and structure to get the most out of every conversation quickly and easily. Whether you’re talking to someone you report to, or your team, we’ll prepare you by giving you suggestions on what to ask in different situations.

Try it with your team and find out why hundreds of managers use Lighthouse every day to have more meaningful discussions and better working relationships with their teams. Start a 21-day free trial now here.

questions to ask your ceo

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