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5 Unexpected Interview Questions to Ask Executive Candidates

August 31, 2023

Interviewing is a mix of art and science. If you’re interviewing a candidate, you’re participating in data collection, gathering information ultimately meant to help your hiring team make the right decision.

Interviewing potential executive talent is its own challenge, since these candidates could have a drastic impact on the direction of your organization. It’s important for the interview team to be intentional and prepared.

Each member of the interview team should know what they’re responsible for focusing on, whether it’s particular skills, key personality traits, or core job competencies. Without this focus, interviewers are in danger of asking similar questions—"tell me about yourself"—and defeating the purpose of multiple interviewers.

So, how should you approach the interview process? It’s helpful to have an interview team kickoff meeting, so everyone knows what to cover in their interview. From there, it's key to gain an understanding of where the candidate has been and what they’ve accomplished. Find out if they can point to areas of growth in each of their recent roles, and see if there’s potential for growth in your open role.

We’ve gathered five interview questions that can help you get to the heart of a candidate’s potential.

Can you tell me about a time when you had to shift out of your normal role to accomplish something important?

Startups often need all hands on deck. You want a leader who is prepared to step in where they’re needed, even if that means doing work that doesn’t always fall under their job title.

A candidate’s answer to this question can help you understand whether they have a wide or narrow view of their role. Those who are willing to adjust their scope are more likely to be successful.

How have you successfully pivoted your role, team, or focus due to changing business needs?

Similarly, a candidate’s response to this question can tell you a lot about their perspective. The ability to articulate how and why they made a change in a previous role demonstrates flexibility, a team-player mindset, and a depth of understanding of organizational needs.

Tell me about a time you made a mistake. What did you do to improve the next time?

This question is a good way to assess someone's growth mindset. Admitting to mistakes takes humility, and learning from them is a valuable skill.

Tell me about a time when you were asked to do something you weren't skilled in. How did you accomplish it?

As your startup scales, members of your team may need to pick up tasks outside their proficiencies. A candidate’s ability to stretch their comfort zone and work through challenges is a great indicator of how they will fit into your organization.

This question is a good way to gauge how willing your candidates are to grow in their role, and how they use resources, along with both internal and external support, to move forward.

What are you great at? What do you absolutely love doing, what gets you out of bed in the morning? And what’s the intersection of those two things?

This one is borrowed from Matt Blumberg, Bolster’s CEO. He uses it to get someone talking about themselves authentically, something that can help determine their fit for both the organization and the role.

Looking for more support in your interview process?

Bolster can help you assess your team, understand your exact needs, and get aligned as you begin your executive search.

We take time to understand the gaps you need to fill and guide you through the process of meaningfully assessing the specific skills and experiences required of your next executive. We’ll also create goals for your search and help you get buy-in from your team. Identifying these needs and expectations ahead of time is key to a smooth and successful search.

Want to supercharge your next executive search? Bolster matches CEOs and their teams with transformational executives, mentors, and board members—without the hassle of traditional talent sourcing. Built by entrepreneurs for entrepreneurs, our no-nonsense, no-frills approach makes it easier than ever for teams like yours to find the right leaders.

Start your search at