7 smart questions to ask your CEO to stand out

By Vince Forrington

8 min read

7 smart questions to ask your CEO to stand out
Illustration by Grey Vaisius

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! 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.

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Questions to ask your CEO about work

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 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. By asking a broad question that pertains to the company's overall strengths, weaknesses, opportunities, and threats, you are demonstrating a deep understanding of the organization's operations and strategy.

You are also showing that you are capable of considering the wider ramifications of decisions, and that you are willing and able to collaborate and communicate with colleagues from across different departments. This kind of strategic thinking is valuable in any organization, and is especially important in fast-paced, complex business environments where agility and adaptability are key.

2. What goal do you have for the company?

It is crucial to establish a shared sense of purpose between employees and superiors in any company. One way to achieve this is by understanding your CEO's vision for the future of the organization. By doing so, you gain insight into what your CEO deems important and can adjust your priorities accordingly. Aligning your goals with those of the company is key to ensuring that you are working towards the same objectives as your superiors.

Furthermore, showing an interest in the future of the company is a signal to your CEO that you are committed to its long-term success. This commitment goes beyond just achieving immediate results. It demonstrates that you are invested in the company and its future, and that you are willing to work towards its long-term goals. By being proactive and taking an interest in the CEO's vision for the future, you can establish yourself as a valuable member of the team and contribute to the overall success of the organization.

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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.

Questions to ask your CEO about themselves

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

Understanding your CEO as a person can help you to build a better relationship with them and ultimately contribute to the success of your organization. In particular, asking about their personal experiences and journey to success can provide valuable insights and inspiration. One notable example of this is Richard Branson, the founder and CEO of Virgin Group. Despite dropping out of high school, Branson believed in his ability to excel at anything he was passionate about, a belief that has led to Virgin Group now controlling over 400 companies worldwide. Branson's story of success highlights the importance of determination, hard work, and following your passions. Learning about the personal experiences of successful people can make you see them in a new light. It can also provide a source of motivation and inspiration for your own personal and professional goals.

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

The answer to this question will be crucial in determining the nature of your CEO's leadership style and business acumen.

By understanding their motivations, you can gain insight into how they approach decision making and problem solving. If your CEO is a savvy business person, they may prioritize revenue growth and profitability. On the other hand, if they are a passion-driven entrepreneur, they may prioritize innovation and creativity. It is also possible that your CEO embodies both of these qualities, in which case they may be focused on building a successful venture that aligns with their personal values and goals.

This questions provides valuable insight into their motivations and helps you understand what motivates their business decisions.

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.

For example, your CEO may have had to overcome financial difficulties when starting their own business. This may have included securing funding, managing cash flow, and making difficult financial decisions. Understanding how they navigated these challenges can provide valuable lessons for your own financial management skills.

Another challenge your CEO may have faced is managing a team. This can include hiring the right people, delegating tasks effectively, and providing feedback and support when needed. By learning how your CEO tackled these challenges, you can better prepare yourself for managing your own team in the future.

7. What are your CEO's outside interests?

It's important to remember that CEOs are not solely defined by their professional lives. It's worth exploring what your CEO enjoys doing in their free time as well. This can give you a better understanding of their personality and provide insight into their leadership style. For instance, former Yahoo! CEO Marissa Mayer is known to enjoy baking cupcakes as a hobby, which reflects her creative side. Another CEO, Jason Kingsley of Rebellion Developments, has a unique way of unwinding with medieval-style jousting sessions, which could indicate a passion for history and a love of physical activity.

So, what are your CEO's outside interests? Do they enjoy hiking, playing sports, or reading books? Or perhaps they have a hidden talent or quirky hobby that you never would have guessed. Don't be afraid to ask and get to know your CEO on a more personal level. Who knows, you might even discover a shared interest or two!

Getting to know your CEO

In order to maximize the time you spend with your CEO and make a lasting impression, it's important to come prepared with a variety of questions. While the list we've provided here is a helpful starting point, feel free to add your own questions that are tailored to your specific situation. This will demonstrate to your CEO that you have put thought and effort into your meeting, and that you are committed to making the most of your time together.

In addition to asking questions, consider sharing your own perspective and ideas on the topics being discussed. This will show your CEO that you are engaged and invested in the company's success, and can lead to a more productive and collaborative conversation.

Remember that the goal of your meeting is not just to get answers, but to build a relationship with your CEO. By being thoughtful and proactive in your approach, you can leave a lasting impression and set the stage for future success.


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Vince Forrington

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