12 Questions To Ask a CEO About Leadership

What are some questions that you can ask a CEO about leadership? 

To help you ask better questions about leadership, we asked CEOs and business leaders this question for their insights. From “how do you stay visible,” to “how do you serve the people you work for,” there are several questions you can ask to guide your understanding about leadership.

Here are 12 questions you can ask CEO about leadership:

  • Is this a good idea? Why or why not?
  • What are you currently working towards?
  • What qualities do you think are lacking amongst the leaders of today?
  • What leaders have inspired you?
  • What can I do to improve my leadership skills?
  • How do you respond to problems?
  • What does success mean to you personally?
  • How do you serve the people you work for?
  • Which CEOs do you admire and why?
  •  How do you balance differing goals?
  • How do you lead with empathy?
  • How do you stay visible and available to your employees?

Is this a good idea? Why or why not?

CEOs want execution and solutions, not more problems and questions. The best question to ask a CEO is whether a solution to a problem is a good idea, and if they could receive feedback on why it is or not. For example, if an employee notices that productivity could be higher through a particular innovation, they could ask whether implementing the innovation would be a good idea. This question shows the CEO that an employee identified a problem, came up with a solution and wants to learn more. There's nothing better than that for everyone involved.

Brett Farmiloe, Markitors

What are you currently working towards?

Leaders should strive to continuously improve their skill set and grow. To get insight into a CEO's growth goals, ask them about what they are currently working toward. What is the next step for your company? What do you want it to be in five years? In ten years? Questions like these will give you a big picture of the CEO's strategic thinking and how you can help them achieve their goal.

Henry Babichenko, European Denture Center and Stomadent Dental Lab

What qualities do you think are lacking amongst the leaders of today?

To gain better insights about leadership from a CEO, a good question to ask them is, “What qualities do you think are lacking amongst the leaders of today?” This way you can see from their perspective the shifts and changes that have occurred. This can also help you strategically think about how you want to lead or how you would attempt to fill in these gaps if you were to fill a leadership position. Knowing what's missing will also make you stand out amongst the sea of other people looking to become leaders as well. It might take some creative thinking on how to fill those holes, but knowing that there are holes is half the battle.

Ryan Nouis, TruPath

What leaders have inspired you?

Many successful CEOs have been inspired by a leader or had the opportunity to be mentored. When asking a CEO about leadership, ask them about leaders who have inspired them in the past and what kind of impact they had on the trajectory of their career. You will learn more about them and find inspiration for your own leadership development.

Chris Abrams, Marcan Insurance

What can I do to improve my leadership skills?

If you are seeking mentorship opportunities, asking this question is one of the best ways to start the relationship. While it may be difficult to ask at first, it will become easier with practice, and the responses will be well worth the effort. By asking this question upfront, you'll learn about their fundamental leadership ideals and whether they align with your values and personal or professional goals. If mentorship is not an option, perhaps a sponsor relationship would be more fitting as you continue to advance within your career.

Brandon Berglund, Berglund Insurance

How do you respond to problems?

A CEO will often be concerned with the longevity and success of the business, and the style in which they approach issues that every company will undoubtedly face sets the tone for the culture of the company and the expectations of other employees. If a CEO is calm and calculated during the process, the business will adopt the mentality internally. On the other hand, a CEO that reacts immediately without considering the long-term effects of the situation will set a reactionary tone within the business that may not ultimately serve their bottom line. Asking this question will help to reveal the CEO’s mentality.

Than Merrill, FortuneBuilders

What does success mean to you personally?

Ask a CEO about any community efforts that they are committed to personally or have tied into their mission. As a CEO and co-founder of my current and past organizations, many would imagine that holding a high-ranking position such as that or the profit the companies earn would be equal to success. However, I have found that having the means to give back to my community has brought me a great sense of accomplishment. I founded the Giggle Foundation to provide basic health, education and empowerment for underprivileged communities in India. This commitment has truly been a meaningful part of how I define success.

Allan Switalski, LendThrive

How do you serve the people you work for?

A great question to ask a CEO is, “how do you serve the people you work for?” Ultimately, a good leader will know how to serve the people they are in charge of. Servant leadership involves meeting employees where they are and working with them to grow professionally. Before a person leads, they need to know how to serve.

Craig Carter, Jack Mason

Which CEOs do you admire and why?

Asking this question can provide insights into how a CEO developed their own leadership style, how they defined the company's mission and in which direction they're working to take the business. With this information, an employee can better understand how their role aligns with the goals of the company.

Shaunak Amin, SnackMagic

How do you balance differing goals?

More often than not, leadership comes down to identifying the most needle-shifting priorities and finding ways to make them relate to each other. As such, one question I ask a CEO about leadership is, “how do you balance the need for employee happiness and satisfaction with performance and results?”

Indeed, in any company, it seems as if there is a constant push and pull with employee satisfaction, and the burdensome work it takes to be successful. By asking this question, you can come to understand that there are indeed synergies between both goals that will lead to growth and employee retention.

David Wolfe, Olivers Apparel

How do you lead with empathy?

In the modern environment, leading from a place of understanding and caring with people — both within, and outside of your workplace — is not only the best way to find success but the best way to create a healthy culture. Understanding the best ways to do this and the best ways to be aware is an excellent way to help your company grow.

Boye Fajinmi, TheFutureParty

How do you stay visible and available to your employees?

I have always loved learning about how CEOs and leaders stay visible and available to their employees, especially in the Covid-era.  A good question might be “How do you stay visible and available to your employees?” If you ask this, I'd love to see the answers!

Sylvia Kang, Mira


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