7 Tough interview questions for executives and why they work

John Tilbrook

When recruiting for an executive role, you need to ask the tough questions to find the best candidate for the position.

At Newman Stewart, we fully vet our candidates and create a shortlist to ensure you only see the best people for your executive roles. But once they’re sent over to you, it’s your job to find out who is the best fit. That’s where the interview process comes in.

When recruiting for an executive position like CEO or Managing Director, you aren’t just looking for any old candidate. This is an appointment that you have to get right and it requires you to ask tough questions of the candidates you meet.

Below are seven of the best tough interview questions you should ask executive candidates and why they work.

1. “What Skills Are You Lacking?”

While this question might not seem that tough and is most likely one that the candidate has prepared for and answered in the past, providing a good answer is harder than you’d think. This will challenge candidates to honestly review their skills, no matter how experienced they are and is important for you so you can learn any weaknesses as early as possible.

The best candidates will be honest and upfront about any weaknesses and demonstrate a self-awareness that ensures they don’t take anything for granted. Even better, candidates for senior roles may be caught out by the question as it is often associated with interviews for more junior positions. There’s nothing like throwing in a deceptively simple question to identify the right person for your business.

2. “What’s the One Question You Were Hoping I Wouldn’t Ask?”

There’s no hiding place with this one. This question will get the candidate thinking and force them into a corner. By asking this question in the interview, you challenge the candidate to find a question that makes them uncomfortable.

This challenge should bring the best out of an executive and uncover the points they might rather not talk about. It also demonstrates whether an applicant is comfortable putting themselves in the shoes of other stakeholders – a key skill for any executive.

Depending on their answer, you’ll be able to identify those who avoid addressing difficult subjects and those who don’t.

3. “What’s the First Thing You’d Do If Given the Job?”

If the candidate can answer this question well, it shows they have a deep knowledge of the company and understanding of the position and what they’ll be able to bring – both aspects of a great executive candidate.

This is also a great way to distinguish confident candidates who would have an impact from the get-go. If they can outline exactly what they are planning to accomplish with this role, that might give you a better idea of who would be the best fit for what you are trying to achieve.

4. “What Can You Tell Me About Yourself That Isn’t in Your CV?”

This helps you gain more insight into the candidate’s personality, aside from what they wanted you to know in their CV. It helps to dive deeper into what they are like as a person beyond the standard resume content.

A good candidate will tailor their CV to match the job description, so it’s a good idea to challenge them to think of something that they didn’t think to include. It might even be something that appeals to you and you’ll be glad that you asked

The best candidates, the ones who have a lot to offer, won’t be able to fit all of their qualities in their application and will have plenty more to share with you beyond the four corners of their curriculum vitae.

5. “How Do You Assess the Quality of Your Work?”

When you’re recruiting for a top position in business, there isn’t always someone who can check up on the quality of their work. For that reason, you need to trust that the candidate you choose is capable of casting a critical eye over their own work and practices.

By asking this question, you’ll find out if they are someone who is capable of always questioning how they can do better, or just stuck in their ways and systems. If they can answer this question well, you’ll know you have a leader who you can trust to deliver the performance you expect.

6. “Tell Me About How a Professional Qualification You Have Obtained Has Helped You Personally?”

The best candidates will most likely have taken professional qualifications to enhance their industry skills and knowledge. This question helps to find out what qualifications they have obtained as well as the value it has provided them, not just professionally but as a person.

The reason you want to know how it helped them personally is to find out if they live and breathe their profession. The best candidates will take their work home with them and regularly find the knowledge they gain in a professional capacity seeping into their personal lives and vice versa.

This isn’t about finding a candidate that never leaves the office, it’s about finding one who is genuinely passionate about their industry.

7. “Can You Recall the First Three Questions of this Interview?”

This is a really tricky one. Many candidates will simply hear a question and regurgitate an answer on the spot. While that answer might sound good, it can often be a reactive, rehearsed response and, by asking them to recall the first three interview questions, you test to see if they have been an engaged listener in the interview or if they have simply been reacting.

Interviews are stressful situations, but someone in an executive role will face worse. That’s why it’s essential that you identify who is capable of engaging in the meeting and not just answering off the top of their head.

When we are actively engaged in an interaction, depending on the length, it’s easy to recall the beginning. In an interview, this should be no different. This may be a little different from more conventional interview questions but it can be very effective at finding the most attentive, perceptive executives.


These questions might be tough and executive roles are challenging. That’s why it’s important that you ask questions designed to apply pressure, and why they help you hire effectively.

If they are not right for the executive role, you need to identify that as early as possible and asking tough questions is a great way to tell the best apart from the rest.

If you’re interested in knowing more about how Newman Stewart can help to find your next executive candidate, get in touch.

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