Every year, at Harvard Business School, the Dean holds a town-hall meeting. Like many such meetings in academia and the private sector, these get-togethers help the rank-and-file learn what’s on the mind of top leadership. These question-and-answer based conferences are great opportunities for employees and guests to engage with key players in an organization on topics like the state of affairs, current and long-term goals, and company culture.

Whether you have a chance to speak with the CEO in a town hall setting, during an interview, or in a simple one-on-one meeting, you can use it as a chance to build rapport and learn more about your leader. Considering the types of questions you might want to ask ahead of time can help you get the most value out of the conversation—and is an essential business skill everyone should understand.

Here are four suggestions for questions to ask the CEO if you're ever given the opportunity.

1. If you could change one thing about the company, what would it be?


Honest leaders will always have an answer to this question. Knowing what concerns the CEO will give context to initiatives that get focus and projects that get funded. It also can be an indication of alignment; do other leaders from around the organization have similar answers to the same question? If not, why not? Finally, knowing the answer also allows you to do your part to make the change the CEO most wants (or make the case that there is something more important to work on!).

2. When it comes to the company, what are you most proud of?


This is (sort of) the flip side of the first question. The answer, I find, can be very telling. Is the CEO proud of earnings? Proud of the firm’s social responsibility? Proud of the benefits it gives its employees? The response to this question gets to the core of what animates the leadership in a firm and, by definition, animates the firm itself.

I would suggest that the answer should be aligned to some degree with the mission of the firm. If the CEO of a medical device company with a mission to “improve the lives of children with heart anomalies” says he’s most proud of getting price concessions from vendors, then I think a follow up question might be in order. That’s not to say that price concessions can’t be an important part of running a good company, but it would be unusual for leadership to be most proud of something that seems so far outside of the organization’s mission.

3. How do you spend your day?


Often, especially in larger entities, employees have little insight into what the chief leader does on a day-to-day basis. Like the first question, it can help add some color to what the CEO thinks is most important if we assume that how time is allocated is an indication of what’s most important.

It also is a great way to identify other questions to ask. If you hear about the CEO spending time on something you didn’t even know was “a thing,” then probing further can help you and your colleagues learn something about where the company is headed.

4. What do you do when you are not at work?


You were likely asked something like this during the “easy” part of your job interview. Yet rarely do subordinates get to ask their superiors the same question. A venue like a town hall meeting gives a great opportunity to turn the tables. Knowing what the CEO does when not in the office may not help you better understand what you should do in your own job, but it can do a great deal to humanize the man or woman at the top.

If you don’t like your CEO, you may be tempted to avoid this question, worried that humanizing them will go against your perception of who they are. That, I would argue, is all the more reason to ask it. All of us have a personal and professional side. Knowing both sides, even if only at a surface level, can help foster better understanding and move the needle just a little to when it comes to improving teamwork in an organization.

Learn from Your Leaders

When faced with the opportunity to talk with top-level leadership, it’s always a good idea to take advantage of it. You can gather valuable information about the current state of the company, its culture, and its long-term goals. And you just might learn important lessons about leadership from someone with experience.

If you’re interested in broadening your business knowledge, explore our online Credential of Readiness (CORe) program, and discover how you can advance your career by furthering your education.

This post was updated on July 19, 2019. It was originally published on October 5, 2017.

Patrick Mullane

About the Author

Patrick Mullane is the Executive Director of Harvard Business School Online and is responsible for managing HBS Online’s growth and long-term success. A military veteran and alumnus of Harvard Business School, Patrick is passionate about finding ways to use technology to enhance the mission of the School—to educate leaders who make a difference in the world.