Here's What Richard Branson, Tony Hsieh, and 21 Other Successful Executives Ask in Every Job Interview

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APWarby Parker founders David Gilboa, left, and Neil Blumenthal.
By Jacquelyn Smith

Savvy CEOs and executives know that interview questions like, "What's your biggest strength?" and, "What's your biggest weakness?" aren't as telling as they seem.

That's why they steer clear of these cliché queries and instead ask more meaningful ones.

Many top execs have their one favorite go-to question that reveals everything they need to know about a job candidate. Here are 23 of them.

This is an updated article originally written by Alison Griswold and Vivian Giang.
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Here's What Richard Branson, Tony Hsieh, and 21 Other Successful Executives Ask in Every Job Interview

Billionaire Virgin Group founder Richard Branson explains in his 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?

One of Zappos' core values is to "create fun and a little weirdness," Tony Hsieh, CEO of the company, told Business Insider in 2010.

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 said. "If you're a 10, you might be too psychotic for us."

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 has said 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.

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 told 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."

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 told 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."

Last 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 told 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."

Karen Davis, senior vice president of Global Philanthropy and Social Impact at Hasbro, the toy and game giant, told Business Insider that because her work is focused on giving back — a big part of her job is deciding which organizations and projects Hasbro will help fund —  she looks for candidates with "a true sense of passion and purpose." And the quote question, she told Business Insider's Rachel Sugar, helps her figure out who applicants really are and what they truly care about.

While there's no "right answer," Davis said she wants candidates who have an answer. "I want to see that somebody has been looking for sources of inspiration."

Lonne Jaffe, chief executive of software company Syncsort, said 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 told 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 said 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."

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, said Jenny Ming, president and CEO of clothing store Charlotte Russe and former chief executive of Old Navy, in a New York Times interview.

"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 told Adam Bryant of the Times. "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.

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 explained. "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."

Randy Garutti, the CEO of Shake Shack, told 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 continued: "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."

LearnVest CEO Alexa von Tobel told Adam Bryant at The New York Times that the way a candidate responds to this question reveals their thought process, which "tells you a lot about someone."

She said she also likes to ask about weaknesses, but if the candidate doesn't give a real, honest answer, she'll rephrase the question: "What are you genuinely bad at? What does your spouse or partner or the person you're dating tell you you're bad at? Because if they haven't told you, then you shouldn't be sitting here because I can't work with you if you don't know what you're bad at."

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 told 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 said if you "pursue something that you're passionate about with people who motivate you, then work is really fun, even during the difficult times."

Jeff Zwelling, CEO and cofounder of Convertro, a provider of marketing and advertising measurement services, told Business Insider that 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 said. "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 said 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."

Kat Cole, president of Cinnabon, told 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 said. "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 told the Times. 

ThoughtSpot CEO Ajeet Singh told Business Insider that this question gives him a lot of information about job candidates — "and he may be the only tech exec in Silicon Valley who's asking it," writes Rachel Sugar. 

Singh said it's an incredibly useful question, and not nearly as odd as it sounds.

"This question gets at the essence of what drives a person and what they like to do, what inspires them, what motivates them" he explained."I want to see if I can get some unconventional insight into what people are like when the job search constraints are removed."

Michelle Peluso, CEO of Gilt Groupe, told 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 said 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.

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."

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 told 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."

Jess Levin, the founder and chief executive of Carats & Cake, an online wedding resource that features curated content and information about vendors, told Business Insider she asks this because she looks for people "who get what it means to do big things without a lot of hands."

"There is no one-size-fits-all answer," she added — but she always looks for an example that "communicates independent drive, proactive problem solving, and humility."  

Wayne Jackson, chief executive of the software security firm Sonatype, told 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 told Bryant. And it's important that his employees do the same. 

Retired General Stanley McChrystal, who currently oversees the management consulting firm he founded, the McChrystal Group, recently told "The 4-Hour Workweek" author Tim Ferriss on his podcast that this unusual interview question "puts a person in the position of having to try to articulate what they think the perception of them by others is."

The question essentially forces candidates to consider their least attractive qualities "and also muster enough courage to share them with someone who holds power over their careers," reports Business Insider's Richard Feloni.

Lori Senecal, CEO of the MDC Partner Network and global CEO of advertising agency CP+B, told Adam Bryant of the New York Times that there are three things she looks for in every job candidate, and she asks a certain set of questions to find out if they possess those traits.

First, she says, she looks for the "inventor mind-set." "I'll say, 'What have you invented?'" Senecal told Bryant. "That doesn't mean you have to have created a robot that can get a beer from a fridge. It could be anything. It's to see whether they have the mindset of creating something. That shows a desire to find fresh solutions."

Next she wants to know whether they have the ability or desire to collaborate. To figure out if they've got it, she says: "Talk to me about one of your greatest achievements." 

And lastly, she wants to detect passion and commitment. For that, she says: "Tell me about a time when you really had to stick your neck out for the greater good of the mission."

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