The Ultimate Guide to Executive Interview Questions


Alongside your retained executive search firm, you’ve narrowed down the candidates to a select few. Now it’s time to let your executive interview questions shine. But it’s just as easy for hiring executives to make mistakes as it is for the candidates they interview. That’s why closing candidates in today’s competitive hiring market is never guaranteed. There are many opportunities for the most experienced and coveted executives.

It’s not simply a matter of finding that person you’d like to have in the seat next to you when you’re stuck on the tarmac for four hours, and it’s not all about salary and benefits, either. If you want to hire the right person, the interview process matters — it says a lot about your company and its leadership team. 

Not surprisingly, a Glassdoor study finds that in professional and technical industries, tough interviews have a higher acceptance rate. Maybe that’s because a difficult hiring process subconsciously signals better quality control and a greater value placed on the skills in which the candidate is vested. Of course, the goal is not to make your future executive hire squirm. It’s to understand who they are, what they can do and the value they will contribute to your business. 

The ultimate C-level interview requires the best questions. This guide will tell you how to put together questions that give you the results you need. 

Purpose of the Executive Interview Questions

Before a C-level candidate gets in front of your hiring team, the Y Scouts executive interview process is intended to understand the individual beyond what is presented on the résumé. This includes their purpose and values, as well as the successes and achievements they have experienced during their career. 

But even before that, we help you to gain clarity on the type of person you need. It’s never about finding the exact right set of qualifications. There are tons of capable people for almost every position. 

It’s about finding the person who will be able to contribute to your organization in unique and surprising ways. 

The interview questions should be tough. It’s what executive-level candidates have come to expect. But the questions should also be intentional. This means that they allow the interviewer to discover important aspects of the interviewee’s experiences and beliefs that the résumé doesn’t cover and that the interviewee may not expect to discuss. You want to assess the quality of their work, but you also want to hear how they talk about their accomplishments. They shouldn’t be too satisfied; rather, they should be eager to grow with a new experience.

There are three principles that are universal among great leaders. These principles form the foundation of the Y Scouts leadership model. They are the following:

  • Learn relentlessly: Be brave enough to fail.
  • Drive results: Measure the gain and the gap.
  • Develop others: Be clear, collaborate and commit.

We are looking for those leaders who pursue knowledge, even when it means admitting that they don’t know everything. These leaders are resilient in the face of challenges, always with an eye on accomplishing what they set out to do. They lift others, mentoring and coaching them to develop the next generation of leaders. To top it off, they do it all with gratitude and grace, finding the gems in every situation, including the most difficult lessons and challenges. 

Once we’ve rounded up the best of the best, the ball is in your court to ask the right questions and determine who among these leaders is the right fit for your company. 

Types of Questions

There are a number of types of questions you can ask. The most effective ones include, for example, the following:

Behavioral: This popular style uses questions that address how the executive has behaved in the past and the situations in which they have experienced challenges, successes and even failures. 

Leadership: These questions reveal the leader’s approach to developing others and attitudes about their personal impact. 

  • Example: As you think about your career, who is a team member you had a huge impact on and what are they doing today as a result of your leadership?

Problem solving: Executives must be able to recognize and solve problems. This requires analytical thinking and the ability to make prudent decisions. As long as you press for specifics (i.e., “How did you do it?”), these types of questions allow candidates to demonstrate the thought process they use to tackle thorny issues.  

  • Example: Describe a time when you identified a problem, considered your options and picked an effective solution.

Communication: These questions gauge how a candidate might handle a difficult communication challenge, as well as the ability to use empathy and think from another perspective. 

Introspection: The best executives think deeply about their actions and what they might have done differently in challenging situations. These questions provide the opportunity to assess whether a candidate learns from past situations. 

  • Example: What’s the one mistake you’ve made in your career that you wish you could go back and fix?

Hypothetical: These questions are framed in the context of what could be an actual job situation, assessing the candidate’s ability to perform. 

Company research: These questions assess how much the candidate knows about the company and whether or not they’ve done the level of research that indicates genuine passion and interest in your future viability.

  • Example: How do you see the company changing in two years, and how do you see yourself creating that change?

Culture fit: These questions can provide a glimpse into aspects of the interviewee’s character and values and whether or not they are likely to align with your company. 

  • Example: Tell me about your five closest and strongest professional relationships to date. Describe to me what a good interaction looks like with [one of the people on the list]?

Outside-the-box: These offbeat questions seek insights into the executive’s thought processes and creativity. They should be used with caution and not to excess.

  • Example: What animal are you most like?

Avoid These Interview Questions

Every executive knows that there are questions they should avoid. Interview questions are supposed to relate to success on the job. However, it is alarmingly easy for bad questions to slip out, both when you feel comfortable with the interviewee and when you do not. You simply cannot ask questions like, “Where did you grow up?” or “When did you graduate?” If you want to leave your interviewee with a positive view of your company, avoid the following tactics:

Leading questions: Avoid giving away the answer to the test and insulting a potential hire with questions that suggest an answer. 

  • Example: Are you a good collaborator?

Brain teasers: Popular at one time among consultants and at Google headquarters, brain teasers are so 2010 and an annoying waste of time. Besides, there is a longstanding view that they are as valuable at determining career success as a high school honor cord. 

  • Example: How much does a Boeing 737 weigh?

Illegal questions: You must avoid asking questions about marital status, children, race, disability, citizenship, religion, graduation date, where the interviewee was raised and more. In fact, 25% of women say they have been asked whether they have children. While everyone should know the rules, it’s easy to go off-script. 

  • Example: Were you still at Oregon State when the Ducks won the championship in 20XX?

At Y Scouts, we provide an interview guide to keep everyone on track. This allows every member of the executive team to follow the plan and avoid letting personal bias creep in. 

Interview Questions for C-Suite Executives

On our blog, we have published a number of articles to help you discover some of the best questions to ask:

Best Practices for Executive Interview Questions

Here are four best practices to follow during your interviews:

Prepare in Advance

You can have the best set of questions, but without solid preparation and delegation of responsibilities, you may not cover everything you need to make an informed decision. Adequate planning is one of the essential keys to a successful and equitable interviewing process. Each interviewer should be equipped in advance with an interview guide so that they don’t fall into the trap of asking poor questions and soliciting canned responses. 

To make the best of the interview time, ensure that every interviewer has a role to play. Nothing is more off-putting for an executive candidate than to be asked the same question multiple times. Don’t overlook this important step.

Use the Silence

Those pauses that occur during or after an interview question are good. Use the time productively. Set the expectation with the interviewee that you will be taking notes, referring to your outline and actively processing information. Then use the time to do so. Granted, silence can feel very uncomfortable and most people try to avoid it. The aforementioned interview guide can help interviewers exercise discipline and not feel the need to rush in and fill the void. 

The best part of being silent is what most interviewees do during the gap. Even though you have said that you may frequently pause, you’ll most likely find that the candidate keeps talking. Listen. You’ll obtain much more information from the utterances that break the silence. Of course, you don’t want to allow periods of prolonged silence, because it can significantly raise the candidate’s anxiety level. Interviews are stressful enough. In a classic 1950s research study, interviewers overestimated the period of silence by a factor of 10 to 100. Just imagine how the interviewee feels.

Review Your Techniques

As an interviewer, job one is to guide the discussion into fruitful territory. Ensure that the questions you ask — or the way in which you ask them — don’t lead to obvious answers. You’ll end up speaking to a number of promising candidates without gathering enough information to differentiate them. You are unlikely to get authentic responses from questions like, “What is your biggest weakness?” and “Why should we hire you?” It’s easy to slip into autopilot, particularly when you’re tired or if you’ve already made up your mind. This doesn’t serve the process well and it certainly isn’t fair to the candidate. 

To ensure that you are continually learning from the process, you should observe your technique. You can do this by periodically recording your interviews. A video recording is even better. When you ask questions, does your body language indicate that you are interested and engaged? Or, if you prefer, ask a third party to sit in as an observer. Just make sure you ask someone who follows sound interview techniques and is not afraid to deliver feedback. 

Practice Good Listening

Everyone has biases and stereotypes. You’re not going to overcome yours overnight, nor is it necessary to do so. Some biases are actually good — for example, the bias toward believing all snakes are poisonous. It’s important to be aware of those that will selectively filter the information you are being given in a harmful or negative way.

In an interview, negative biases aren’t helpful. The trouble starts with how we listen. Humans are able to think at roughly seven times the rate of listening, and this can create an unhelpful feedback loop when we use this surplus to make assumptions that are compatible with what we expect to hear based on personal bias. There is a lot that you can do to counteract this tendency.

  • Start with what you know to be true: The person in front of you has promising potential for your organization. 
  • Focus on something you have in common or that you really like about them, whether it’s the color of their tie or their friendly smile. 
  • Listen without interruption with your ears wide open. 
  • Keep listening with the intention of understanding their purpose. 
  • Slow down your thoughts, since they may override what is actually being said. 
  • Ask follow-up questions, not in a challenging way, but in an effort to get more information. 
  • Do the work to truly understand the person’s perspectives. 
  • Stick to your interview guide.

Hiring the Right Addition to Your Executive Team

Of course, before you can interview, you’ll need to find the right candidates to invite into the process. At Y Scouts, we work with you to find your next executive leader. Our radical alignment process matches candidates for purpose and values so that the leaders we introduce to you represent the best of the best. Further, these candidates meet the three principles of our proven Y Scouts leadership model. We leave nothing to chance. The process is as challenging as it is rewarding. It’s your business, and Y Scouts understands that.

If you are looking for your next executive leader, Y Scouts can help.