17 Top Executives Share Their Favorite Interview Question

richard branson
richard branson

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Richard Branson likes to ask: “What didn’t you get a chance to include on your résumé?”

Interview questions like, “What’s your biggest strength?” and, “What’s you biggest weakness?” aren’t as telling as they seem.

That’s probably why most savvy CEOs and executives steer clear of these cliché queries and instead ask more meaningful ones.

In fact, many top execs have their one favorite go-to question that reveals everything they need to know about a job candidate.

Some prefer to ask more serious questions, while others believe that silly queries about costumes and the zombie apocalypse, for instance, best uncover an applicant’s creativity. 

This is an updated article originally written by Alison Griswold and Vivian Giang.

On a scale of one to 10, how weird are you?

One of Zappos’ core values is to “create fun and a little weirdness,” Tony Hsieh, CEO of the company, tells Business Insider.

To make sure he hires candidates with the right fit, Hsieh typically asks the question: “On a scale of one to 10, how weird are you?” He says the number isn’t too important, but it’s more about how people answer the question. Nonetheless, if “you’re a one, you probably are a little bit too straight-laced for the Zappos culture,” he says. “If you’re a 10, you might be too psychotic for us.”

Another question Zappos usually asks candidates is: “On a scale of one to 10, how lucky are you in life?” Again, the number doesn’t matter too much, but if you’re a one, you don’t know why bad things happen to you (and probably blame others a lot). And if you’re a 10, you don’t understand why good things always seem to happen to you (and probably lack confidence).

What didn’t you get a chance to include on your résumé?

Virgin Group founder Richard Branson explains in his new book “The Virgin Way: Everything I Know About Leadership,” that he isn’t a fan of the traditional job interview, reports Business Insider’s Richard Feloni.

“Obviously a good CV is important, but if you were going to hire by what they say about themselves on paper, you wouldn’t need to waste time on an interview,” Branson writes. That’s why he likes to ask: What didn’t you get a chance to include on your résumé?

How would you describe yourself in one word?

The best candidates are the ones who know exactly who they are. That’s why Dara Richardson-Heron, CEO of women’s organization YWCA, always asks her candidates this question.

Richardson-Heron says she doesn’t judge people on the word they choose, but it does give her insight into how people package themselves. She tells Adam Bryant at The New York Times that she likes when people take time to ponder the question and answer thoughtfully.

Give me an example of a time when you solved an analytically difficult problem.

Laszlo Bock, Google’s HR boss, says the company ditched its famous brainteaser interview questions in recent years for behavioral ones.

“The interesting thing about the behavioral interview is that when you ask somebody to speak to their own experience, and you drill into that, you get two kinds of information,” Bock tells The New York Times. “One is you get to see how they actually interacted in a real-world situation, and the valuable ‘meta’ information you get about the candidate is a sense of what they consider to be difficult.”

What’s your superpower… or spirit animal?

Earlier this year writer Jeff Haden asked a bunch of smart people from a variety of fields for their favorite interview question. HootSuite CEO Ryan Holmes says his is: “What’s your superpower…or spirit animal?”

“During her interview, I asked my current executive assistant what was her favorite animal. She told me it was a duck, because ducks are calm on the surface and hustling like crazy getting things done under the surface,” he tells Haden. “I think this was an amazing response and a perfect description for the role of an EA. For the record, she’s been working with us for over a year now and is amazing at her job.”

How old were you when you had your first paying job?

Hannah Paramore, president of Paramore, a Nashville-based interactive advertising agency, told the New York Times’ Adam Bryant that this is one of her favorite questions. 

“I’m looking for how deeply instilled their work ethic and independence are versus entitlement,” she tells Business Insider. “If they worked part time in high school and college because they needed to, especially in jobs that were just hard work, that shows a huge level of personal responsibility. I love people who have to patch success together from a number of different angles.”

Can you tell me the story of you prior successes, challenges, and major responsibilities?

Lonne Jaffe, chief executive of software company Syncsort, says in a New York Times interview with Adam Bryant that he always wants to see how well a job candidate can tell a story. 

He tells Business Insider that as long as we’ve had language, storytelling has been a powerful communication tool. “In business, creating a compelling narrative is invaluable for motivating a team, explaining strategic priorities in a way that’s easy for others to understand, or communicating complex ideas to customers and prospects. Successful senior-level leaders are good storytellers, and it’s also a very useful skill early on in your career.”

Jaffe says he recognized the importance of storytelling early in his career while working at IBM. “Storytelling is especially important in the tech industry because technology can be “very complex, and sometimes people find technical details to be somewhat boring,” he says.

What would you do in the event of a zombie apocalypse?

This seems like a ridiculous question to ask, but it’s posed to every prospective employee at Capriotti’s Sandwich Shop, a national restaurant franchise. Ashley Morris, the company’s CEO, says it’s the best way to learn how candidates react under pressure.

“There really is no right answer, so it’s interesting to get someone’s opinion and understand how they think on their feet,” Morris explains. “The hope is that for us, we’re going to find out who this person is on the inside and what’s really important to him, what his morals really are, and if he’ll fit on the cultural level.”

Tell me about your failures.

A good answer to this question is important because it means that the candidate isn’t afraid of taking risks and will admit when things don’t work out, says Jenny Ming, president and CEO of clothing store Charlotte Russe and former chief executive of Old Navy.

“It doesn’t even have to be business; it could be life lessons. I think it’s pretty telling. What did they do afterward?” she says. “How did they overcome that? I always look for somebody who’s very comfortable admitting when something didn’t work out.”

People always like to tell you about their successes, she explains, but they don’t always want to tell you what didn’t work out so well for them.

What motivates you to get out of bed in the morning?

In a New York Times interview with Adam Bryant, Brad Jefferson, CEO of Animoto, a video slide show service, shared his three favorite interview questions.

He especially loves this one about what motivates people because it helps him understand a candidate’s passions and what makes them tick. “I really try to get in their head about what’s going to keep them going.”

Jefferson tells Business Insider that it’s important to understand what motivates a person at their core because “there will always be ups and downs in any business, and you want to make sure the person will be equally motivated during difficult times, if not more so.”

He says if you “pursue something that you’re passionate about with people who motivate you, then work is really fun, even during the difficult times.”

If we’re sitting here a year from now celebrating what a great 12 months it’s been for you in this role, what did we achieve together?

Randy Garutti, the CEO of Shake Shack, tells writer Jeff Haden that he needs to know candidates have “done their homework, truly understand our company and the role… and really want it.”

Garutti continues: “The candidate should have enough strategic vision to not only talk about how good the year has been but to answer with an eye towards that bigger-picture understanding of the company — and why they want to be here.”

If I were to say to a bunch of people who know you, ‘Give me three adjectives that best describe you,’ what would I hear?

Michelle Peluso, CEO of Gilt Groupe, tells Adam Bryant of the New York Times that this question is far more telling than, “What are you good at?” which is a question she despises.

Here’s what she tells each candidate: “OK, I’ve interviewed an eclectic crowd about you: the guy who delivers your food, the last people you worked with, the person who can’t stand you the most, your best friend from high school, your mother’s neighbor, your kindergarten teacher, your high school math teacher who loved you, and your last boss.” Then she asks: “If I were to say to them, ‘Give me three adjectives that best describe you,’ what would I hear?”

Peluso says if the candidate gives her three glowing adjectives, she’ll remind them that the hypothetical group includes a few people who aren’t particularly fond of them.

A hammer and a nail cost $1.10, and the hammer costs one dollar more than the nail. How much does the nail cost?

Jeff Zwelling, CEO and cofounder of Convertro, a provider of marketing and advertising measurement services, says he often turns to tricky questions during job interviews to get a better sense of who the candidate is.

For example, in the middle of the conversation, he often throws in this curveball math question.

“Some candidates will instantly blurt out 10 cents, which is obviously wrong,” he tells Business Insider. “They don’t have to get the exact right answer, which is a nickel, but I want to see them at least have a thought process behind it.”

Zwelling says he understands that math isn’t everyone’s forte, but he wants them to realize that “10 cents is too easy of an answer, and that if it was that easy, I wouldn’t be asking it.”

What would the closest person in your life say if I asked them, ‘What is the one characteristic that they totally dig about you, and the one that drives them insane?’

Kat Cole, president of Cinnabon, tells Adam Bryant in a New York Times interview that before asking questions, she likes to see how job candidates interact with people in the waiting area.

“I’ll ask people to offer the candidate a drink to see if there’s a general gratefulness there, and they’ll send me notes,” she tells Bryant. “Then, when someone walks into my office, I’ll have a big wad of paper on my floor between the door and the table. I want to see if the person picks it up. I don’t make huge judgments around it, but it does give me a sense of how detail-oriented they are.”

After some conversation, she finally says: “Tell me about the closest person in your life who you’re comfortable talking about. What would they say if I asked them, ‘What is the one characteristic that they totally dig about you?’”

Then she’ll say: “What is the one characteristic that drives them insane, and that they would love for you to do just a little bit less?”

“People are pretty comfortable talking about that because I’ve pinpointed a person and a point of view,” she tells the Times. 

Tell me something that’s true, that almost nobody agrees with you on.

PayPal cofounder, managing partner of the Founders Fund, and president of Clarium Capital Peter Thiel always looks to hire people who aren’t afraid to speak their minds, reports Business Insider’s Aaron Taube.

To do this, he always gives job candidates and the founders of companies seeking an investment this interview prompt: “Tell me something that’s true, that almost nobody agrees with you on.”‘

In a 2012 interview with Forbes, Thiel said the reason he loves this question is: “It sort of tests for originality of thinking, and to some extent, it tests for your courage in speaking up in a difficult interview context.”

What was the last costume you wore?

It doesn’t matter so much what they wore, but why they wore it. If the candidate’s reasoning matches Warby Parker’s core value of injecting “fun and quirkiness into work, life, and everything [they] do,” they might have a real shot at getting a job there.

“We find that people who are able to make the job environment fun build followership more easily,” the company’s cofounder and co-CEO David Gilboa tells Iris Mansour at Quartz. “If we hire the most technically skilled person in the world whose work style doesn’t fit here, they won’t be successful.”

Can you tell me about a time when you almost gave up, how you felt about that, and what you did instead of giving up?

Wayne Jackson, chief executive of the software security firm Sonatype, tells The New York Times’ Adam Bryant that in asking this question, he can learn about what people do outside of work — what drives them, what they think about, what’s important — to determine whether they have “the competitiveness and the drive to get through tough problems and tough times.”

Another reason he loves this question: It helps him figure out if the candidate’s values and mindset are in line with his. “I tend to drift toward things where the stakes are relatively high, the dynamics are really complex, and teamwork matters,” he tells Bryant. And it’s important that his employees do the same. 

Now check out the top résumé mistakes:

15 Things You Should Never Put On Your Résumé

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