Interview Questions

The 9 Best Questions to Ask in an Executive Interview

The interview process for an executive is elaborative, intense, and longer than for entry-level jobs or mid-level managerial roles. Your job here is to assess the candidates’ leadership skills, management style, alignment with your values and mission, and fitness for where the company is headed.
Daniel Jakaitis
Daniel Jakaitis
The interview process for an executive is elaborative, intense, and longer than for entry-level jobs or mid-level managerial roles. Your job here is to assess the candidates’ leadership skills, management style, alignment with your values and mission, and fitness for where the company is headed.

The interview process for an executive is elaborative, intense, and longer than for entry-level jobs or mid-level managerial roles. Your job here is to assess the candidates’ leadership skills, management style, alignment with your values and mission, and fitness for where the company is headed.

This article will cover nine executive interview questions that you should ask your candidates in face-to-face interviews. And share explanations of what type of insights these questions can offer.

Later on, we’ll discuss the basic questions you should ask while conducting a screening phone interview.

So open up a Google docs file and start taking notes. We trust that you’ll get some valuable tips from our detailed post.

9 Best Executive Interview Questions

Each question you ask in an executive interview should help you understand the candidate better. And elaborate on their value for your company. Here are some questions to get you started.

1. Do You Like To Win Or Do You Hate To Lose?

Ah, this question puzzles the best of us. Candidates never know what the interviewer is expecting when they ask you this question, and that’s exactly why you should ask this in an executive interview.

We all know that the attitude of a leader largely dictates the behavior of the entire team.

Your candidate's answer to this question should give you insights into what kind of environment they will create for the team. Whether they’ll welcome transparency, and appreciate the lessons that losses bring, or prefer winning at all costs no matter how it affects the team.

For the most part, there’s no right answer to this question. It depends on each person’s leadership style. And the correct answer is the one that matches your company culture and goals.

Losses are inevitable no matter how much you hate to lose. Similarly, sometimes you can’t win despite your best efforts.

Your candidate should aim to win most of the time – almost expect it even – but at the same time, s/he shouldn’t be afraid to lose either.

A balance between the two is what you should look for. And if the interviewee goes with one over the other, ask in detail why that is.

2. Do You Consider Yourself Lucky?

This question is designed to force your candidate to show their personality and approach to life.

If a person considers themselves lucky, it could mean that they’re humble and grateful despite being a hard worker, but it could also symbolize a lack of confidence.

If your candidate says no to this question, they might be too arrogant, or it could mean that they understand the level of hard work they put into the work and that luck doesn’t factor in too much.

You should ask this executive interview question to gauge how the candidate views their self-worth. That, in turn, could translate how they interact and appreciate their teams’ efforts.

What you’re looking for here is a balanced answer.

Your candidate should ideally acknowledge their privilege and ‘good luck.’ But also confidently show you that luck alone didn’t bring them all the success they’ve achieved and that their talents and skills had a large role to play.

3. Where Does Working at Our Company Fit into Your Life’s Goals?

Hiring an executive is no easy task. So you need to make sure that the candidate can stay with your company for the long term. That’s where this question comes in.

Ask them if they identify with your values, feel comfortable with your company culture, and see a future for themselves working for you.  You could also ask why the candidate wants to work at your company.

4. What Are You Lacking In Your Leadership Style?

Asking a candidate to tell you about their shortcomings can shed light on how well they know themselves.

Great leaders are excellent at self-evaluation. They need to recognize and accept their shortcomings and talk about them with the intent to improve.

This question gives candidates a golden opportunity to highlight certifications and courses that they’ve taken to work on their weak points. That way, they can flip this sensitive question into a positive one.

It can tell you more about how they approach challenges and what they do to overcome them.

If your candidate doesn’t have any lacking that they can think of, that’s not the kind of executive you need.

Here, your candidate should ideally talk about a segment of leadership that they are weak at and follow that with examples. It’s easy to say that I’m bad at active listening or giving feedback, but if your candidate can mention how they know that, it shows you their level of self-reflection.

5. How Can You Improve Your Professional Weaknesses?

Identifying your weak points is one thing. But knowing how to work on them is a different ball game.

You should ask this question in executive interviews to check how good your candidate is at taking practical steps to tackle challenges from the start. You need an executive who’s proactive and fixes issues before they become major problems.

The answer to this question should show critical thinking and self-analysis – both important qualities for a leader. Their approach to improving themselves might also translate to how they work on job-related challenges.

You want a candidate who’s already working on improving their skills. And not someone who only plans on doing something well after narrowing down their limitations.

The ideal candidate will be honest about their answer. And will demonstrate how their efforts for improvement have generated results.

6. Is There A Question You Were Hoping That I Ask You?

Although this question might not seem too important, it can offer you some valuable insights. You can use it to judge if the candidate can put themselves in the other persons’ shoes – an important skill for a leader.

It might make the candidate uncomfortable because the question is a bit odd. But you can learn about some points that the interviewee wants you to know.

Based on the answer, you can know if the candidate is comfortable and confident to talk about topics that might bother them. These could be lacking in their qualifications or a gap in their resume.

It also allows the candidate to explain something that they couldn’t answer in your questions.

7. If You Were Given the Job, What Changes Would You Make in the Company in the First Three Months?

This executive interview question is ideal for gauging how well the candidate researched your company. It also tells you about their passion and practicality.

You need an executive who can look at a situation from all sides and develop a reasonable solution. Being ambitious is great, but it won’t mean much without strategic thinking and skills to implement the plans.

Here, you need to check how excited the candidate is about starting your company. And determine if they have an actual plan to bring about the positive changes they are talking about.

It would be great if the candidate could share some examples of how they’ve overcome challenges in the past – similar to the challenges your company is facing. It shows that they understand the requirements of the executive role and can be an excellent fit for it.

8. Tell Me Something About Your Leadership Style That I Can’t Find In Your Resume?

Candidates often tailor the resume to match the job description. By asking this question, you open the floor to the applicant to tell you whatever they want.

More than the answers, you need to pay attention to what topics they choose to cover here. They could talk about their leadership style, relate it to a successful person’s style, or go a bit off-topic and tell you about their interests.

Sometimes candidates can’t fit all their skills and experiences in their resumes. But with this executive interview question, they get to tell you more about how they are the best fit for the job.

You can also uncover skills that are indirectly relevant to the role at your company.

9. What is the Hardest Thing You Have Ever Done?

You should ask this question to learn more about what qualifies as a difficult situation for your candidate. The goal is to determine exactly how the executive will fit in your company.

Their answer will give you a good idea of the kind of challenges they’ll be able to handle in the executive position they are interviewing for. And also how they’ll deal with employee conflicts or workplace issues.

Ideally, your candidate will name a professional challenge that relates to their line of work. S/he will explain the situation briefly and then tell you about their approach to solving it.

You could ask them about what other options there were and why they specifically chose the solution they went with.

Wrapping Up

Hiring employees requires a heavy investment of time and money. And finding the right executives for a position is that much harder.

The executive interview questions we’ve converted in this article just scratch the surface. If you need more information and practical tips, then Chatkick is where you need to go.

Check out our features and see how our platform can ease the interview process for you and make hiring executives a breeze.