15 Questions to Ask Your CEO

Questions to ask your CEO

There is a stereotype that CEOs are constantly busy and have no time for chitchat. However, this is an outdated image and many modern CEOs make sure they are approachable and more hands-on when it comes to running their companies.

Some companies even organize office hours or roundtable discussions with upper management and the CEO to both boost employee morale and realign teams with their larger goals. This presents employees with the opportunity to interact with them and get to know them more personally. A lot can be learned from such successful people, especially if you dream of one day becoming a CEO yourself. In this article you will find 15 questions to ask your CEO.

Why ask questions?

Asking your CEO good questions can give you insight both into the company’s goals and future, which can help you build your own long-term goals for your career within the company. CEOs are also a great resource for practical business advice and guidance. Additionally, asking the right questions can make a good impression on your CEO, which can help you build a positive relationship with them. If your workplace is giving you an opportunity to talk with upper management, it’s a great idea to prepare your questions to ask CEO in advance. 

1. What is our next big goal? How do you see us reaching it?

It’s always beneficial to be aware of the bigger picture and what the CEO’s vision is for the future of the company. After all, since you work there, these plans will directly influence you. You also demonstrate that you are interested and invested in the company’s future success. Knowing about future goals and what the plan is to get there can help you figure out how you can contribute.

2. My career goals are __. How can I better help the company reach its goals while progressing in my career goals at the same time?

This question is similar to the one above but focusing specifically on your goals.  It demonstrates that you want to work with the company to achieve them which will make a good impression on your CEO. It is best to ask how you can better help instead of just what you can do because this implies that you are already helping and want to know how to improve. The answer to this question can guide you in making plans for the near and distant future for yourself in the company.  

3. What do you think are the biggest challenges our company is currently facing and how do you see us overcoming them?

With this question, you are focusing specifically on challenges. By asking about the current issues, you will be more aware of what the company is tackling at the moment. You can just ask about the challenges and think of a different follow-up question based on the answer if you prefer. However, adding the part about overcoming challenges will give you insight into your CEO’s problem solving skills and what they plan to do in the near future. 

4. What is one trait you look for in employees when putting together a leadership team?

Understanding what your CEO values and looks for when promoting to upper management will let you know what you need to succeed in the company. If there are specific traits or skills that are expected, you can work on them so that you are more likely to advance up the career ladder sooner rather than later. This question also shows how driven you are and that you are willing to improve yourself to better fit in with the company’s needs.

5. What strategy helps you perform at your best?

Every CEO has strategies they have honed over the years. You may have seen the countless self-improvement books available for sale which claim to list life hacks and tips from successful CEOs. Why not learn about these strategies more directly? Whether it’s a brainstorming technique or just a routine that gets them focused, you can learn what it is and try it out yourself. 

6. What inspired you to choose this path in business?

This is a more general question you can ask to learn more about the CEO’s own journey in their career. The answer may also reveal some aspects of the values and bigger vision that the CEO has for the company. Discussing inspiration and life choices is also a very engaging topic and can be the beginning of a great conversation. You may even find yourself inspired after the talk and get a boost of motivation.

7. What is the achievement that the company has reached that you are most proud of?

This is another uplifting question that can lead to a productive conversation. The answer will demonstrate what the CEO values in the company and what kind of accomplishments they focus on the most. You can use this information to guide you in your own work and to remind you in the future what you are working for.

8. What would your staff say is your management style?

Since it’s most likely that you don’t work directly under the CEO, this is a great way to learn more about how they manage the company. After all, the way the CEO manages staff affects everyone else. Often the CEO’s management style is one of the biggest factors that influences the work culture of a company. This makes this question a great choice if you are still relatively new to the company and still figuring out the culture and attitudes within the office.

9. In your opinion, what makes a team successful?

  Knowing what your CEO looks for in teams is very important and can guide your own success within the company. You can also learn how you are expected to work with your fellow employees. If you’re a manager, this can also help you in putting together teams for projects and supervising them efficiently. 

10. What do you think of our company values? Which ones are we adhering to the best or worst?

Every CEO has values that they instill into their company and use to guide their work. You probably already know what they are, but it’s different to hear the CEO talk about them in their own words. Often the company values may seem like abstract concepts and you may not see how they connect to your day-to-day work until you hear it explained in more practical terms.  You can also learn about what your CEO thinks the company is doing well at and what needs to be improved, and use this information in your own work.

11. What is your opinion on monitoring employees’ activity?

This question has especially become relevant in recent years since so many companies were forced to make the switch to online work. Executives everywhere had to decide what was the best way to ensure employees are actually working from home. Depending on the current policy in your company, you can adapt this question. You can also ask about the ethics of employee monitoring software. For example, Traqq purposely blurs the screencaps it takes to protect the user’s data. You can research the software your company uses in advance and ask a specific question about how work is measured.

12. What are your thoughts on rewarding success?

Knowing your CEO’s principles on assessing and rewarding employees is key to finding your own success. Every CEO has a different approach so it is important not to assume that things are done a certain way and instead to find out from them directly. Be careful when wording this question, as you don’t want it to seem like you are simply asking when you will be rewarded. Instead make it more about their general attitudes towards rewards and how they work to balance them to keep everyone motivated. 

13. When was the last time you changed your mind about something important?

A CEO’s job is filled with difficult decisions and of course that includes having a change of heart occasionally and having to make new plans. This is a very interesting question that truly reveals a person’s thought process and guiding principles. Ask it to learn more about what motivates your CEO to make decisions and what factors they take into account. You could keep this in mind for the next time you are faced with a decision and are weighing your options. 

14. Do you have a hobby you do in your free time that helps you be a better leader?

This is a great way to show interest into a person’s life while also keeping it professional. Their answer will give you some insight into who your CEO is as a person and also how they improve themselves. You may even find out that you have something in common with your CEO and have an opportunity to make a connection with them.

15. What are your personal goals?

This is a more personal question that is more suited for a more informal setting. However, it is also suitable if all the company related questions have already been asked and you want to learn more about the CEO themselves. It will give you valuable insight into what your CEO values most, which affects the company’s goals as well. 

Bonus tips for asking your CEO questions:

Be genuine

When asking your questions or just talking to your CEO in general, make sure you are showing sincere interest and not just trying to impress them with a smart question. Most CEOs have great social intelligence and can detect fakeness easily. 

You can show interest by asking questions that you actually want to know the answers to, researching your CEO in advance to make your questions more specific and by keeping the conversation engaging by asking follow up questions. 

Don’t bombard with questions

If you’re excited it may be hard not to ask all your questions one after another but remember that you aren’t an interviewer. In the context of a larger meeting you may also be taking time from your fellow employees who also want to ask questions. Be mindful and ask one question at a time. If you may end up only being able to ask one question, start with the one most important to you. 

However, if you have a chance to ask more than one question, make them different types of questions so you don’t seem repetitive. 

Be specific

The suggestions in this article are more generic and can be improved with specific details about your own company. For example, instead of asking about the goals of the company, you can ask about a specific department or current project the company is focused on. You can also do this when asking questions that pertain to the CEO themselves by doing some quick research and finding out more about their own achievements. 


The fact that you are doing research on questions to ask your CEO shows that you’re on the right track and will be going in prepared. Of course, you may have your own questions that you want to ask but we hope our advice and suggestions gave you some ideas on how best to word them. Remember to ask good questions that will both help you in your career and also show that you are a dedicated employee. This will ensure that you make a good impression on your CEO as well which is a great bonus. Good luck!

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