Angie Henson - August 29, 2023

The Best Questions to Ask C-Level Executive Candidates

Asking the right questions will help you find the best leaders for your company.

As you carry out your search for C-level executive talent, several candidates may look equally compelling on paper. They each have the right qualifications and a proven track record of experience. But asking the right interview questions will help you identify the best C-level candidates for your company—and filter out those who don’t meet your needs.

In this article, we’ll cover the following points:

  • Why good questions are so important in executive interviews
  • The importance of selecting the right C-level executives
  • The best questions to ask executive-level interviewees
  • Additional considerations for these interviews
  • Common mistakes to avoid
  • FAQs

Let’s look more closely at the benefits of asking great questions. Then, we’ll share some of our favorites.

The Importance of Asking the Right Questions in Executive Interviews

Asking great questions in C-level interviews will help you meet these three key objectives:

  • Ensuring a strong cultural fit. These questions will help you determine whether the candidate will mesh with your culture and contribute positively to it.
  • Identifying qualified candidates. Good questions will help you accurately evaluate a candidate’s experience.
  • Assessing leadership potential. From candidates’ answers, you’ll gain a better understanding of an interviewee’s ability to lead people.

Through these objectives, you’ll ensure an executive contributes long-term value, as we’ll discuss next.

Why C-Suite Positions and Company Culture Matter

The effectiveness of C-level leaders plays a key role in determining a company’s profitability, productivity, and growth. Their decisions, influence, and leadership style guide how the organization performs. Further, they have a pivotal role in shaping company culture through their values, attitude, and communication style. So, organizations should prioritize hiring for cultural alignment and shared values.

The Best Questions to Ask C-Level Executive Candidates

Great questions will help you assess an interviewee’s human skills, strategic thinking, and ability to handle challenges. Here are our top questions for C-level executive interviewees:

  • Tell us about your leadership style and what it looks like in action.
  • What goals would you set for your work with our company, and why?
  • Describe a difficult situation you encountered in the past. How did you navigate it?
  • How do you stay up to date with industry trends?
  • Tell us about a hard decision you had to make, and how you approached it.
  • What are your strategies for success as a leader?
  • How do you work to inspire and motivate your team?
  • Do you feel you’re a good fit for this company’s culture, and if so, why?
  • What steps would you take to further our company’s culture?
  • Describe your biggest failure, and how you handled the situation.
  • Can you tell us about how you’ve mentored an employee—and the outcomes achieved?
  • Have you managed a remote team, and if so, what strategies did you use?
  • How do you handle stress at work?
  • Describe your decision-making process. What steps does it involve?
  • Tell me about one of the leaders who has most inspired you. What qualities do they model?
  • How do you approach giving feedback with your direct reports and peers?
  • How do you approach receiving feedback?
  • Describe how you’ve held people accountable for their commitments.
  • Can you tell us about a time when you took accountability for a mistake?
  • What is the most important way in which you want to grow as a leader this year?
  • How do you remain a lifelong learner?
  • What questions do you have for us? (This one can help you understand their priorities.)

Prepare questions for specific roles as well. For example, ask how a CFO candidate sets budgetary priorities when working with limited resources.

Additional Considerations When Interviewing C-Level Executives

Assess cultural fit through values and attitudes. Don’t just look at what they say—also read between the lines. What attitude do they convey toward people they’ve led, for example?

Determine experience and qualifications through examples and references. Don’t be so swept away by a compelling interview that you forget to confirm their employment history and talk to references.

Understand the candidate’s vision for the company and its culture. Does it align with your current vision or diverge from it too strongly?

Assess communication skills and their impact on leadership. How do you feel when conversing with the candidate? Give people a couple of levels below the candidate the chance to talk with them and share feedback as well.

Common Mistakes to Avoid When Asking Questions

Steer clear of these common errors to get the most valuable insights from your interview process.

  • Focusing on generic or superficial questions. “What’s your biggest weakness?” doesn’t ask them to describe specific behavior, for example. Asking about particular challenges is preferable.
  • Neglecting to explore the candidate’s thoughts on company culture. Ask the candidate about what type of culture they thrive in, as well as challenges with organizational culture they’ve dealt with in the past.
  • Failing to address potential setbacks or challenges. Tackle these hurdles head-on. Don’t worry about scaring candidates away—the right one will be up to the task.

Now, let’s review a few frequently asked questions on this topic.


What are some other common questions to ask during C-level executive interviews?

You may have questions about specific past assignments or roles on the candidate’s resume. For instance, ask about the problem-solving and leadership strategies they used in a prestigious project. Likewise, if the interviewee held roles that differ significantly from the current one, ask how these past roles have prepared them for this opportunity.

How do I prepare for an interview with a C-level executive?

Understand the person’s background as well as possible. Look up the companies they’ve worked for, considering their size, market, key challenges, and other factors. This knowledge may help you ask relevant follow-up questions.

What are some red flags to look for during an interview with a C-level executive?

Seeming highly stressed, having a history of leaving jobs after a fairly short time, and exaggerating qualifications are all red flags. If you notice discrepancies between what’s on paper and what they say during an interview, it might signal that they’re not being entirely honest.

In Conclusion

When it comes to executive talent, finding the best possible match is imperative. Good interview questions combined with a thorough evaluation of a candidate’s background and skills will help you choose the leader who best fits your organization’s needs.


Tags: Business Growth Business Leadership

  1. About the Author:

  2. About the Author:

    As a Principal at Valesco, Angie Henson serves in key roles related to new investment origination, portfolio management, and investor relations. She directs the firm’s strategic acquisition planning and program management as acting head of research and business development operations since 2002. Angie holds a Bachelor of Science from Tarleton State University and a certificate in entrepreneurial studies from Southern Methodist University.

Related Articles

  1. Valesco Invests in Blower Application, LLC – The First Investment out of Valesco Fund III
    Read More
  2. Valesco Industries Successfully Exits Drug Free Sport International, a Valesco Fund II Investment
    Read More
  3. How to Report to a Board of Directors: What to Include
    Read More

Named Founder Friendly Investors 2021 & 2022 by Inc.