Chief Executive Officer’s, or CEOs, are notoriously busy and handle an array of differing projects, systems, and processes.

They are beholden to nearly everyone in the organization, from the shareholders, to the board of directors, to their employees.

Their vision, guidance, and decisions can help lead an organization to newfound success or failure.

To say that there’s a lot of pressure on their shoulders is definitely an understatement.

This makes finding the best questions to ask your CEO all the more important.

When given one-on-one or a focus group session with your CEO, you will want to ensure that you have a list of questions prepared.

These questions should be in relation to the company and should generally be forward-facing.

Previously, CEOs were more attuned to remain in their offices, delegating tasks and needs to their executive team, whom in turn would delegate to their managers, and so-forth down the line.

However, as the importance of company culture has risen, so too have many CEOs to the call.

No longer do CEOs remain cooped in their offices, delegating from behind executive desks.

More and more CEOs are taking a hands-on approach to management and the way the company is run.

From holding town-hall meetings to meeting with employees one-on-one.

CEOs are now starting to see the value in remaining more and more visible throughout the organization.

As the shift to a more engaged executive team occurs throughout both large and small organizations, you may find yourself in a one-on-one position with your CEO.

We’ve compiled a list of the best questions to ask to ensure you stand out and look your best.

Things to Remember

Before jumping into the conversation, meeting, or one-on-one with your CEO, you’ll want to ensure that your own questions are lined up and that you are adequately prepared for the meeting.

Although this opportunity may be extended to a large group of individuals, you will still want to make and leave a great impression.

The CEO may be impressed by your composure, professionalism, and questions that could potentially benefit your career in the long-term.

If you are meeting with your CEO, you should try and dress your best.

This doesn’t mean you should wear a tuxedo or a dress elegant enough for a wedding, but it should be business formal.

Your clothes should be clean, wrinkle-free, and fitted.

Ideally, you should wear neutral tones and steer away from anything too fancy or attention calling.

Additionally, you should keep in mind that the meeting is not simply a question and answer session.

You will want to show genuine, sincere interest in what the CEO is saying.

If you ask a question and believe there is a follow-up to a point made, then feel free to ask it.

In addition, come prepared with your own answers.

Your CEO may ask you questions about your role, how long you’ve been with the company, and your feelings on the health and culture of the company.

While you do want to be honest, you should never talk badly or poorly about the company, your manager, or any of your colleagues.

Lastly, ask questions in a manner conducive to a conversation.

You don’t want to ask personal questions or lay blame directly at the CEO.

You should also absolutely avoid asking questions regarding personal HR issues, such as your own paid time off, holiday schedule, or work from home opportunities.

Those questions should be left to HR or your manager and generally do not concern the CEO directly.

The Questions

Have you had any voluntary turnover this past year?

What steps do you take to ensure all employees are happy and satisfied to work here?

This question looks to see if the CEO has had any direct reports which left recently.

While some turnover, year-over-year, is expected, it may become problematic if it occurs too often.

This question also looks to see if the CEO is actively working on ensuring happiness and a good corporate culture across the board.

How do you see our company changing in the next year, two-years, or five-years?

CEOs are very forward-facing.

They look towards the future and upcoming trends.

Asking this question shows that you understand that and that you are also looking to see which trends will most likely affect the health of the company.

What keeps you up at night?

Asking pointed, direct questions is a great way to have a conversation with a CEO.

This question is looking to see what worries the CEO has and what vulnerabilities they see within the company as it currently is.

You can also follow-up after this question by asking, “what can be done to ensure those fears are mitigated?”

What one word would describe you best?

While you want to ask questions about the health of the company, it is also good to get a better sense of the CEO as a person.

This question will help you more understand how they perceive themselves.

How do you see yourself helping the company to evolve and transform in the digital age?

This is a two-part question.

You are asking the CEO how they see themselves helping the company grow.

But you are also acknowledging the growing trend of the digital age and the challenges that come with it.

This is a great question as most companies will face new struggles in the digital age, so it forces a question of how the company will handle it.

Which other CEOs do you admire?

Another personal question.

Here, we’re looking to see which CEOs the CEO looks up to and admires.

While a somewhat softball question, it gives credence to the CEOs thought process and may shed some light on why they look up to those other CEOs.

The Best Questions to Ask Your CEO

The Questions (Continued)

What, would you say, are your biggest accomplishments in the last year?

What, would you say, are your biggest accomplishments in the last year?

While this question is typically not specific on timeframe, I included the last year only as it forces the CEO to evaluate the work they did.

This means the answer you receive will be one that is recent and had a positive impact on the company.

What, would you say, are you most proud of in this company?

This question looks to see what the CEO is proud of within the company.

While another softball question, it gets to the heart of the company and what is working well.

What do you enjoy most in your current role?

Another personal question, but the answers may surprise you.

While most people think of the compensation, the prominence, or the power associated with an executive role, the CEO may find that it is more simply about helping their employees succeed.

What do you expect from your employees?

All managers have expectation of their employees and direct reports.

However, looking to see what a CEOs expectation are may provide a deeper sense of how to succeed in the company.

How do you ensure upper management is communicating your directives with the staff?

This question looks to see how the CEO manages their own direct reports.

As they are beholden to the entire organization, they should have certain ways to ensure their directive and needs are being communicated and trickled down across the organization.

What initiative do you wish the company started earlier?

This question, while seemingly innocuous, is looking to see which initiative is most important to the CEO.

This will also let you know where you should concentrate and focus your energy on.

What do you find is the best form of communication with the organization?

CEOs need to be communicative and need to engage with their staff and the organization.

You’re looking to see here what the CEO believes is the best form of communication and why they believe so.

Don’t be surprised if the CEO turns this question around and asks you if you find their forms of communication effective.

What example do you look to set for your own team?

CEOs understand that their styles are often emulated and copied across the company.

By asking the CEO what example they look to set, you are asking them to consciously speak to how they treat their direct reports and how that affects the entire organization.

Do you look to promote and hire from within?

Company culture is important, and a company should look to hire and promote from within where possible.

Asking this question looks to determine if the CEO places importance and emphasis on this fact.


Having a one-on-one or small meeting with the CEO is a great opportunity to make an impression and understand their wishes, fears, and management style.

As you will be meeting with the CEO, you will want to ensure that your questions are lined up beforehand and that you are prepared to ask them.

In addition, you should come to the meeting dressed in business formal attire.

You will want to show your professionalism and preparedness which can help you in your career.

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