Asking about a candidate’s work history may give an interviewer insight into their greatest accomplishments, but learning how an prospective employee thinks on the fly, or what it might be like to work with them, will require digging a little deeper. That can mean asking questions that get at who a person is, or how they handle moments of failure. “I find the most interesting questions are those that open up a larger dialogue,” says Karla Gallardo, the cofounder and CEO of fashion brand Cuyana.
Whether you’re a CEO or job candidate about to be interviewed by a CEO, here are the questions Gallardo and eight other founders like to ask potential hires.
Who or what has shaped who you are?
When Gallardo has been in the hot seat herself, she has often found that questions that allow her to get more personal are the most compelling and informative. (One such example: “What is your superpower, and what superpower would you like to have?”) These questions can launch the sort of conversations that help her determine if a candidate is a good fit. “A core value at Cuyana is hiring ‘good people,’ which we define in part as people with integrity, a sense of gratitude, and confidence in showing their vulnerability without ego,” Gallardo says. “So I love questions that help reveal those qualities, as opposed to those solely focused on job qualifications.”
What are we doing well, and where is there opportunity to grow?
This might seem counter to conventional wisdom. But Gabe Kennedy, cofounder of CBD wellness startup Plant People, always asks potential employees to offer constructive feedback on his business. “I want complete honesty, even if it is uncomfortable,” he says. “What is their perception, who are we as a business? What are we doing well, and where is there opportunity to grow? The more diversity of perspectives, opinions, and inputs we get, the better we become.”
What have you failed at?
When she conducts a job interview, Carly Stein, the founder and CEO of wellness brand Beekeeper’s Naturals, is most concerned with sussing out how a candidate thinks and overcomes new challenges. That’s why she likes to ask candidates about the moments in which they’ve faltered. “Being able to share your shortcomings is critical,” she says. “This question highlights the ability to rebound and learn.” Failure, Stein believes, is short-term. What she’s interested in is resilience—how someone can bounce back from a misstep.
What would your best friend say they like the least about you?
This question often solicits unexpected responses about pet peeves, according to Galyn Bernard, cofounder and co-CEO of children’s apparel startup Primary. “I usually get some pretty honest and insightful answers that help me understand what it might really be like to work with this person day-to-day,” she says. Another things Bernard likes to ask about is a candidate’s favorite day at work. “This helps me get at what really motivates people and how passionate they are about the work they do,” she says.
How many degrees separate the minute and hour hands of a clock at 3:15?
If this seems like a surprising question, well, that’s sort of the point. “I want to understand how somebody thinks about a very new problem in a difficult situation, and how they respond to that under pressure,” says Scott Cutler, the CEO of online marketplace StockX. Questions like this one are often less about the answer and more about how a candidate thinks through the question or problem-solves in an interview setting. (Cutler says that as an interviewee himself, he fielded questions in that vein, such as “How many manhole covers are there in the U.S.?”)
To get a read on a candidate’s emotional intelligence, Cutler also likes to ask about their weaknesses. “It’s a very standard question for most interviewers, but it is still surprising to see how many people talk only about their weaknesses and don’t put them into context to demonstrate how they have learned from them,” he says.
Why are you passionate about what we do?
This may seem like a typical question for most interviewers, but as the CEO of sexual wellness company Unbound, founder Polly Rodriguez says it can be a key question in her sector. “I ask this question both to gauge their passion on the topic and to get a sense of their maturity when it comes to the subject matter,” she says. “Working in the sexual wellness industry requires a high level of emotional intelligence—a candidate must have the ability to show empathy and vulnerability without making the other person uncomfortable.”
More often than not, Rodriguez knows from a candidate’s response to this question whether she wants them to advance to the next round. For example, a male candidate who responded with “Women? Sex? What’s not to like?” did not make it to the next round of interviews.
Can you tell me about a tough day you had at work and how you pushed through?
To Mark Lawrence, the founder and CEO of parking startup SpotHero, questions about a candidate’s achievements or skill set aren’t necessarily all that telling. “I’m always interested in what people have done to improve themselves or how they’ve expressed vulnerability in a way that helped them grow professionally or personally,” he says. Asking someone to talk about a tough day they had—or even a shortcoming they’ve tried to improve upon—can show a range of qualities, he says, from a candidate’s adaptability to their willingness to collaborate and learn from others.
Would you rather be rich or would you rather be king?
When he questions candidates, Harold Hughes—the founder and CEO of blockchain-based analytics company Bandwagon—tries to understand if they’re a team player but also how they might handle autonomy. This particular question gives Hughes insight into how the candidate thinks about power. “There’s no wrong answer between rich and king,” he says. “What’s more important is the reasoning. If the response is to be rich but they use their new wealth in ways to help others, that speaks to their empathy and compassion. If they choose to be king, I’m interested in their views on impacting power structures.”
Could you tell me about a time you got tough feedback?
Evan Maridou, the CEO and founder of pet healthcare startup Milo, always tries to ask behavioral questions about making mistakes or receiving critical feedback. “My belief is that the best people I’ve ever worked with have the right balance of humility and intelligence,” he says. In asking those type of questions, he usually shares an example from his own life—when he was almost fired earlier in his career.
“When it comes to interviewing, you are trying to get to know the ‘real version’ of who you are going to be working with,” he says. “To do that, you need to create trust in a very short amount of time. If they feel anxious, they may start answering questions based on what they think you want to hear.” Sharing his own story, Maridou believes, can make the candidate feel more at ease. “I’ve found the answers from the candidates are much more authentic when I show a little vulnerability,” he says.