The 5 Interview Questions Every Leader Should Ask

How do you determine whether a job candidate will flourish within your company?
By: | January 27, 2017 • 5 min read

The best job candidates have qualifications that are more than skills-deep. Discovering these qualities during the interview process is difficult. But moving past impression and into reality is crucial to hiring the right people—that is, the people who have not only the skills, knowledge and experience to do the job, but also the abstract qualities that will allow them to succeed within your organization’s culture.

In an interesting way, the interview process has a lot in common with well-known dating apps such as Tinder. Recruiters swipe left on candidates who are not compatible on a surface level—those who lack the skills, knowledge, or experience we’re looking for. Then there are the ones the recruiters swipe right on—these are the candidates who appear to meet the job requirements and have the potential to be a strong candidate.


After the recruiter swipes right, the candidate is moved into a smaller pool of potential suitors, but there’s still a lot of filtering to do, of course. Obviously, not everyone we swipe right on will be a match. But perhaps within that smaller pool, we’ll find the person who not only meets the position’s general requirements, but also has that certain je ne sais quoi we’re looking for.

Because our culture is a reflection of what we value, we believe if we look for these values in our candidates, and hire those who display these values, then the ones we bring onto the team will be more likely to flourish within our organization. Of course, discovering these things requires filtering through first impressions and candidates putting their best foot forward. Here at Kabbage Inc., one of the largest online lenders to small businesses, we’ve created a series of questions for our final panel interview to do just that. Every candidate who makes it to the final round of our interview process—no matter the role—gets asked these questions.

These five questions help us understand how candidates think about themselves, how they think about others, and the way they generally think through problems.

What are three negative personal qualities that someone close to you would say you possess?

This question tells us a lot about self-awareness and feeds into our core value of transparency. We are looking for candidates who not only understand what their true negatives are, but are willing to admit them. There are a number of unacceptable answers here. We don’t allow answers like, “I’m a perfectionist” or “workaholic” or other positives-disguised-as-negatives. When we get answers like that, we buzz the candidate (with actual buzzers!) and ask them to try again. There have also been occasions when we’ve had them “phone a friend.” If they’re unable to come up with three negatives on their own, their spouse or mother is usually a  helpful source of information!

We ask them to add two fractions. For example, we might ask, “What is 3/4 plus 1/2?”

This question elicits some of the best responses. What we are looking for is insight into how they handle an unexpected question or situation. This isn’t really about math skills; we’re fine with them grabbing their phone to use the calculator or to google the answer. At Kabbage, our days are rarely predictable. We’re looking to see how they handle the curve ball. Do they panic? Blurt out a lot of wrong answers? Do they freeze and get stuck? Do they give up? One of our core values is innovation; we need to know the people we hire are resourceful, capable of thinking outside of the box, and quick on their feet.

On a scale of one to 10, 10 being the absolute best in the world at your role, where would you rate yourself? And what separates you from being a 10?

Like the first question, this also tells us about a candidate’s self-awareness. This also leads to discussions about growth, ambition and whether he or she aspires to be the best. Given that one of our core values is winning, how a candidate answers this question is extremely important to us. While they might not rate themselves as 10s across the board (there’s nothing wrong with humble confidence), we want to know why and what they’re doing to get there.

Finish this sentence for me: Most people I meet are _______.

One of our core values is caring deeply, so it’s important we understand how a potential new team member views others. The only answer that is off-limits is “interesting,” because it really doesn’t tell us anything. And we’ve found that it might also be a code for something negative in disguise. We want to understand how candidates think about and value other people, and an answer like this is just too vague and open for interpretation.


Give me the first name of someone with whom you work very closely?          

This, too, ties into caring deeply. If a candidate answers this question quickly and is able to answer several of the follow-up questions, we can glean that they are good at building relationships at work. It also helps us to understand whether this person will be committed to the Kabbage community. We want to hire people who will take ownership, not only of the products we create and offer, but also the environment and culture in which we work.

The Bottom Line

Interviewing to discover who will succeed in your organization is a crucial component to hiring well. Many candidates will have the skills and qualifications you’re looking for, but only a few will be the right fit. We’re looking for the right person for the job within the context of our organization’s culture. You can discover a good fit in the interview process if you focus on your values, develop specific questions to uncover a potential new hire’s values, and assess the ways in which you align.

Amy Zimmerman is head of global people operations at Atlanta-based Kabbage Inc., a financial technology and data company. Jennifer Richard is Kabbage’s head of learning and development.