Workplaces nowadays have changed drastically and with that, so have the strategy and attitude of the CEOs.  Previously, CEOs would remain cooped up in their office and delegate tasks from behind the desks. They mostly remained in their offices and were hardly visible to employees on a normal working day.

The CEOs would delegate tasks to the executive team who passed them down to the managers and so forth down the hierarchy. However, times have changed and so have the operational needs.

A modern-day CEO is more visible and approachable. They prefer an open-door policy as opposed to working behind closed doors. Some employees are now able to have a one on one with them apart from the monthly town halls. CEOs now take a hands-on approach and are more concerned with company culture and management.

Over the past few years, CEOs have realized the value and importance of staying visible and approachable within an organization. Hence, now we see a lot more interaction between CEOs and employees.

As this change unfolds, you may find yourself in a one-on-one session with your CEO. And you would want to make the most out of it. How do you do that? You need to prepare a list of questions to ask a CEO.

Although CEOs have adopted a new approach in their role, they still have a lot on their plate. Notoriously busy, CEOs attend to an array of tasks and face challenges on a daily basis. Their guidance not only steers the company in the right direction but is also valuable in helping you find your success.

Therefore, it is imperative that you go in fully prepared and have questions that are relevant But before that…

Things to Be Mindful Of  When Talking to Your CEO

It’s Not a Q&A Session

If you get a chance to have a one on one with your boss, consider yourself lucky. However, make sure that you don’t fire off questions like you’re going through a checklist. Try to keep the conversation natural and go with the flow.

Pro Tip: Ask questions in a way that naturally leads to one another. This will help avoid awkward, silent moments. Also, the CEO will walk out with a great impression of you.

Display Genuine Interest

Just because you have the chance of questioning the CEO, you don’t ask every question under the sky. Your questions should be relevant and must reflect your interest. This is because you’ll be able to interact and participate more. The conversation will unfold in an interesting way and you will have your CEO’s undivided attention.

Ask One Question at a Time

Yes, you have to go in with a list of questions but you don’t have to throw them all in at once. Ask one question at a time, listen attentively, and then hop on to the second one. If you feel, you have to ask a question that is not there on the list but will add value to the conversation, ask away.

Dress Appropriately

This is an important point. You’re going in to meet the highest person in the hierarchy, you better plan your outfit beforehand. No one’s asking you to dress up for a wedding but it should be business formal. Show up in clean, wrinkle-free clothes. Nude tones are preferable and avoid anything that is too flashy. Also, don’t forget to put on deodorant.

Prepare Your Answers

Naturally, a one-on-one session is more like a conversation between two people. This means that your CEO can also question you on your role in the company, your view on company culture, and so on and so forth. While you would want to be honest, you have to be careful to not bad-mouth the company or any colleagues.

Say No to Gossipy Questions

If you really consider yourself lucky to be sitting in a one-on-one with your CEO, ask productive questions. Questions, that are valuable to you and your future. Avoid asking questions that are too personal or gossipy. For instance, why did you leave your former company, how long do you plan to work here, etc?

If you have a thing for juicy details, consider working for a tabloid maybe?

Questions to Ask a CEO About the Company

Why Did You Start/Join This Company?

This question will determine whether your CEO is an entrepreneur who fulfilled their dream or a savvy business-minded individual who was on the lookout for a successful venture. Either way, this is a good question that will uncover valuable business knowledge.

The answer to this question may also motivate you to think along similar lines if you have an entrepreneurial mindset.

What Goals Do You Have for This Business?

This is a great question to ask if you are looking to align your goals and actions with that of the company. The CEO’s vision for the company will determine the area you should focus on. It will help you decide which path to take and what new skills to acquire.

Moreover, asking this question will also express your interest and will set a good impression.

Tell Us About the Biggest Strength of the Company?

Every person has a different approach to conducting a SWOT analysis of the company. Your CEO’s answer will determine the aspects that they prioritize the most. For instance, if your CEO finds that the biggest strength of the company is the culture because it fosters employee appreciation, you know what’s your next step. If you are a manager or someone who leads a team, you can incorporate this factor into your daily routine.

What Is the Best Form of Communication for a Company?

The answer to this question will tell a lot about the CEO. Communication is an important tool for an organization to succeed. Moreover, CEOs need to be communicative with their employees and should make an effort to engage with them.

If your CEO discourages a hierarchical system, it means that they believe in open dialogue, effective communication, and an overall decentralized system. It may also mean that the upper management supports inclusivity, collaboration, and discussion.

Chances are that you may end the meeting feeling positive, motivated, and committed more than ever.

Is There Anything That You Would Like to Change About the Company?

Change is the only constant and one must always be open to it.

Asking this question will determine ways in which your boss wants to improve the operations of the company. Knowing that will give you an opportunity to assist them in meeting their objectives.

For example, if the CEO wants to bring changes in the customer service department, it exhibits that they value client satisfaction. Understanding the areas that need change and development will also allow you to set your best foot forward and showcase flexibility.

Questions to Ask a CEO About Their Success

How did you get to where you are today?

We admire CEOs for what they do for the company and employees. We also envision ourselves becoming like them. But for that, it is important for us to know a little about their hardships and struggles.

It is obvious that no one achieves success without having their fair share of ups and downs.

Asking this question will help you get to know your CEO better. It will allow you to see them in a different light than you would have otherwise and gain encouragement and inspiration.

What Were Some of the Challenges You Faced?

In an answer to this question, your CEO may share professional as well as personal challenges. The good thing about this question is that you will get acquainted with the hurdles your CEO faced in their career. It will give you the encouragement and motivation to overcome them and not feel overwhelmed at any point.

Would You Like to Tell Us About Your Accomplishments Last Year?

While this question doesn’t have to be time-specific, we have included this to encourage your boss to evaluate the work they did. The accomplishments shared will be the recent ones that had a positive impact on the business.

Personal Questions to Ask a CEO

What Do You Like to Do in Your Free Time?

Showing an interest in your CEO’s hobbies adds a personal touch to the conversation. This is a good question to ask a CEO as it may leave you pleasantly surprised. For instance, your CEO may like to read, exercise, or just Netflix in their downtime. There is a probability that you may share similar interests as a result of which you can engage in interesting and thoughtful conversations with your CEO besides work.

Are There Any Other CEOs That You Admire?

This is another personal question to ask a CEO. Getting to know other CEOs that your CEO admires tells you a lot about what they draw their inspiration from. It also gives you a chance to get to find out about other accomplished leaders in the industry.

Questions to Ask a CEO About Employee Engagement

Why Is Employee Engagement Important?

This question will do you substantial favors if you belong to HR. Getting to know your CEO’s thoughts will help you see the matter from a different view. Furthermore, a discussion with the CEO may uncover some crazy employee engagement techniques that you were previously unaware of. Also, you can also share your ideas of employee engagement with the boss and bag some valuable insights and suggestions.

Which Teams in the Company Are Most Engaged and Why?

This is a great way of finding out what impresses your CEO the most. When your CEO sheds light on the most engaged teams, it will certainly give you ideas to engage your team better. You will extract some great knowledge and answers from this question.

Questions to Ask a CEO About Growth

What Is the Key to Success?

This is a question that will explicitly help you in getting to the top. While answering this, your CEO will share tried and tested ways of achieving success. Moreover, they may also share ways that are more specific to your career and situation.

Most importantly, this answer will showcase values that your CEO abides by. For example, the answer might be staying true and honest to work.

What More Can I Do to Achieve This Goal?

If you want to convey your investment and commitment to the company, this is one of the ways of doing so. When you ask such a question, your CEO will consider you as someone who wants to stay with the company and go above and beyond to ensure goal fulfillment.

Questions to Ask a CEO About Culture

What Do You Expect From Employees?

Asking this question can help you in two ways:

  • Determine management’s expectation of you that will help you develop goals in line with them
  • Represent you as the one who cares and want to keep improving

What Is the Most Important Thing to Have as Part of a Culture?

Again, this question holds tremendous significance if you are from HR. Also, keep in mind that a CEO has truckloads of experience. They have worked in different cultures and their answer will be nothing short of truth and wisdom.

Listen attentively.

Questions to Ask a CEO About Diversity and Inclusion

What Do Diversity and Inclusion Mean to You?

This question will demonstrate your CEO’s perspective and how important do they feel this topic is. It will tell you that the company does not believe in discrimination and it will make you feel proud of being associated with such an organization.

How Does Our Company’s Leadership Support D&I Strategies?

Here, the CEO will throw some light on the strategies that the company is or will take to augment Diversity and inclusion. It will give you a chance to participate and make you feel motivated to work for a company that believes in giving equal opportunities to people.


Now, this is not a set-in-stone list of questions. You can add or subtract as per your understanding. This is only a guideline to help you get started. Whatever the questions are, make sure of the following:

  • Make the most of your time with your CEO
  • Leave a good impression
  • Develop a good understanding of one another