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7 questions to ask your CEO
Illustration by Grey Vaisius

5 min read

7 questions to ask your CEO

One-on-one time with your CEO? Make the most of it with these tips on what to ask, how to act, and what things you should keep in mind.

The attitude of the modern workplace has changed drastically over the years and with that, so have the attitudes of CEOs. No longer are they these behind-closed-doors figureheads who emerge once every quarter to address the masses. Modern CEOs take a more hands-on approach to running an organization, preferring to keep those doors open or even do away with them (and walls) altogether.

This new approachability means that scoring some facetime with your CEO isn’t only likely but perhaps even encouraged. So, what do you do when that moment actually comes to pass, and you find yourself in a one-on-one situation with your CEO? Well, believe it or not, we just happen to have a handy list of questions that you may want to draw from while you have your CEO’s undivided attention. That is, if you’re looking to have a rewarding and enriching conversation that leaves a good impression.

But before we get to that…

Some things to keep in mind

It’s not a Q&A session. You’re having a conversation, a chance to relate to your CEO on a personal level, so don’t just fire off a list of questions like you’re running down a checklist. Keep it natural and flowing. SPOILER: the questions below are listed in a way so they naturally lead into one another. See? We’ve already got your back.

Make sure your interest is genuine. Don’t ask something just because you feel you “have” to. CEOs can be very perceptive, and will see right through that insincere interest pretty quick. Even if you end up asking the most basic questions, so long as it’s coming from a place of genuine interest, you’re good.

Don’t ask more than one question at a time. This may seem obvious, but it’s something that’s easy to slip into, especially if you’re nervous. Do it, and it’ll seem like you’re probing your CEO for info—or worse, digging for dirt. And neither will be seen in a favorable light.

So, how do you prevent morphing from “interested employee” to “pushy reporter”? Simple. Don't do that thing where you ask a question and instead of waiting for an answer, you follow up with a barrage of guesses as to what the answer will be, like you're playing the world's most one-sided game of charades: What motivated you to start your own company? Were you tired of working for someone else? Were you looking for a new challenge? Did you want to be your own boss?

Likewise, avoid strings of “gossipy” leading questions: Why did you decide to leave your former company? Were you forced out? Was it because you didn’t agree with their unethical business practices? You don’t work for TMZ (hopefully), so if juicy details are your thing, scratch that itch with the tabloids and blogs, not your CEO’s time.

Okay, now with that out of the way, let’s get to it!

The questions

We’ll start off with a few questions for your CEO that center around the company itself, where it is and where your CEO sees it going.

1. What do you feel is the biggest strength of our company right now?

Leading off with a question that falls into one of the areas of SWOT analysis (which organizations use to identify their strengths, weaknesses, opportunities, and threats), shows that you’re interested in the bigger picture—that you like to look beyond the bubble of your own department and instead view the company as a whole.

2. What goal do you have for the company?

Seeing what vision your CEO has for the future of your company can get you on track with what they feel is important for the company. It also lets your CEO know that your interest in the company isn't restricted to the here and now.

3. What more can I do in my role to help achieve this (goal)?

Asking this is more about presenting information about yourself to your CEO. It will underline your commitment and investment in the company and convey your desire to contribute to its success.

However, pay attention to your phrasing—"more" is the key word here. Leave it out and it could seem that you aren't aware of what you already do to help towards this goal. Leave it in and it shows that you're willing to go above and beyond what's expected of you for the benefit of the company.

Now we’ll move on to some questions that’ll help you understand your CEO as a person and hopefully give you a chance to learn from, relate to, and be motivated by them.

4. What was the path you took to get to where you are today?

Asking this can help humanize your CEO and make you see them in a new light. Learning about the journeys of successful people can also be very inspiring or motivating.

For example, Richard Branson, founder and CEO of Virgin Group, is a high school dropout who attributes his success to the belief that you can excel at anything you’re passionate about (Virgin Group now controls more than 400 companies worldwide).

5. Why did you start (or want to be CEO of) this company?

The answer to this question will help uncover whether your CEO is a savvy business person with an eye for a successful venture or is a passion-driven entrepreneur who has built their dream company (or both!). Either way, you should be able to gain some valuable business knowledge in return.

6. What have been the biggest challenges you’ve had to overcome?

Learning about the hurdles your CEO had to clear during their career can help you better understand their drive. It can also provide you with insight and inspiration for facing similar challenges in your own life, whether they be personal or professional.

7.What are your outside interests?

CEOs are people too! Show you’re interested in knowing what your CEO likes to do during their downtime, and you may be pleasantly surprised with the results. They could be drawn to something relatively normal (former Yahoo! CEO Marissa Mayer likes to bake cupcakes!), oddly eccentric (Jason Kingsley, CEO of Rebellion Developments, unwinds with medieval-style jousting sessions!), or even the same thing as you! (Although, I don’t think that last point would be the case for me—unless my CEO has a secret obsession with collecting action figures that he’s been hiding from all of us).


Obviously, you may also have some questions of your own that you’d like to bring up to your CEO, and that’s great! This isn’t a set-in-stone list, but rather a guideline. One that can be used to help carry you through your session in a way that makes the most of your time with your CEO, ensures you leave a good impression, and allows you both to walk away with a better understanding of one another.


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Vince Forrington

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