These interview questions can tell you whether someone is the right fit

Hiring well is one of a leader’s most important jobs. Having talented employees is a strong competitive advantage and allows your organization to produce results and create a productive and positive culture.

It’s hard to do well, especially at senior levels where judgment and character become increasingly important, and there’s a high cost of recruiting or replacing someone. Substantive questions help assess a candidate’s skills and readiness for a job, and behavioral questions provide the opportunity to understand how they think and handle themselves. But ultimately, once you’ve established their competency, it’s time to decide whether a candidate’s character is the right fit for your team and company cultural.

I asked several experienced hiring managers from different fields what “secret weapon” questions help them evaluate key intangible qualities that indicate a trustworthy team member’s character. They all have one thing in common. Though each interviewer approaches their inquiry from a different angle, they all ask questions that invite vulnerability and connection.

1.  What’s a time in your life or work when someone helped you?

An executive director of a nonprofit organization that works with inner-city kids swears by this question. His team needs to work together under stressful conditions, so anyone who works there needs to be able to offer and ask for help when necessary.

“I go first—I share my own story of a time when I hit my limit caring for two special needs children as a single parent and finally told my friends that I was at a breaking point and needed help. This opens them up to share their own vulnerable stories, and I learn so much about them. Only once did someone tell me that they had never needed help. I didn’t hire them.”

This person’s team has enviable retention in a field with high turnover. He credits hiring team players, rather than heroes.

2. Tell me about a mistake you made—what happened, how did you react, and what did you do differently after that?

A CFO I spoke to says her team members need to have a high baseline of skills. However, she also knows that no one is perfect. She employs this question to assess a candidate’s willingness to take accountability, apologize (she usually asks this directly if they don’t volunteer it), and change their behavior.

“I appreciate working with people who are smart but also humble, who know the value of saying ‘I’m sorry’ in an authentic way—and who know there’s always room to grow.”

3. When have you changed your mind on a difference of opinion with a colleague?

A CTO I spoke to prides himself on building engineering teams with both a positive culture and a high-quality standard. He likes this question because it gives him insight into “how a candidate handles a conflict and whether they can be flexible and get out of the ‘I’m-right-you’re-wrong’ mindset to collaborate and solve problems.” Having an open mind and being willing to change your view of an issue promotes cooperation and innovation on a team, and is key to building trusting relationships.

Each of these questions gets at the interdependent nature of working on a team and invites the candidate to demonstrate humility versus ego, flexibility versus rigidity, and team orientation versus self-orientation.

Other hiring managers I talked to have used a different approach. One deliberately has pictures of his children, a travel photo, and a guitar displayed behind him, hoping the candidate asks him about himself, his family, or his hobbies. One exec who has interviewed hundreds of candidates scours the often-ignored “Interests” section of the résumé or picks out a project from their portfolio.

“It takes a little preparation, but asking them about their experience as a competitive swimmer or their record collection, or showing interest in a piece of work that they are proud of gives me a chance to see their enthusiasm sparkle,” she says.

The importance of going deeper

Whatever approach you take, remember that the best questions lead to a conversation that goes beyond the surface level. As the interviewer, don’t just accept an answer and move on to the next question.

Instead, dial up your curiosity to ask follow-up questions. You’ll want to probe what they learned from the experience, how it changed their relationships or perspective, and how they balanced trade-offs in a decision.

Questions that ask a candidate to go a layer deeper often reveal more about their values and motives, beyond their specific behavior. Ultimately, this helps you predict how they would respond and fit in your environment.

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