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7 Questions You Should Ask Executive Candidates

May 9, 2024

The right questions are crucial to a successful executive interview process. Standard questions can lead to rehearsed answers, but several guests on The Daily Bolster have shared the strategic questions they ask to get the most out of interviews. 

These questions reveal how candidates handle surprises, think on their feet, and align with your organization's values and goals. 

What would you do with unlimited resources? 

Puja Agrawal emphasizes the importance of attitude over aptitude when interviewing executive leaders. One of her favorite executive interview techniques is to offer a scenario: if the candidate joined the team with free rein and unlimited resources, what would their action plan look like? This is best used after several conversations when potential candidates are familiar with your company and current needs, and it’s a great way to understand how they approach problems, opportunities, and strategies. 

How has curiosity led to growth in your business or career?

Intellectual curiosity is one skill that’s almost impossible to teach. Aimée Lapic asks this question to prompt candidates to talk about how they discovered growth opportunities. What threads did they pull at, or what questions led them to uncover new information? Hire people who are inquisitive and search for answers. 

What is something you’re good at, but don’t enjoy? 

Jenny Lawton likes to ask leaders to share something they’re good at, but dislike doing. If their answer falls within the core responsibilities of the role they’re interviewing for, it’s a sign that the candidate might not be a good fit. Ideally, you want to hire someone who has the skills to excel in a given role—and who enjoys using them. 

Tell me about a project that went wrong.

When Claire Hughes Johnson interviews executives, she’s looking for self-awareness. The way a candidate responds to this question—Do they take responsibility? Did they learn from the experience? Did they solve the problem?—can tell you a lot about who they are as a leader.

How do you question conventional thought patterns?

When interviewing leaders to support their nonprofit, Jon and Jax Bari look for changemakers. These are the people who challenge conventional thought, who don’t default to accepting things the way they appear to be. The real difference makers are those who are constantly looking for a new, better way to do things.

What’s an interesting thing you've learned recently?

Asking executive candidates about what they’ve learned recently is a great way to gauge their curiosity about the world. Claire Hughes Johnson uses this question to get a better idea of a candidate’s growth mindset.

What accomplishment are you most proud of? 

Charles Bonello asks this question to allow candidates to share what is most important to them, what motivates them, and what skills they value the most. This is about more than just their resume—it tells you about the candidate as a leader. 

Want to keep up with The Daily Bolster? We’re on a break between seasons, but you can sign up to get notified when new episodes drop, or find our first three seasons wherever you get your podcasts.

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