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8 Successful Bosses Share Their Favorite Curveball Interview Questions

Posted by | May 19, 2015 | Interviewers, Interviews, Tips

Via Huffington Post : When Oprah interviews a potential hire, she knows exactly how to find out if the candidate is a perfect fit, not just for the job but for the company as a whole. Her secret? Asking out-of-the-box questions that reveal the personality behind the resume.

And she’s not the only business leader to employ this tactic. Unconventional interview questions can help managers make better-informed decisions about how a candidate will mesh with a company’s culture. The more compatible a new hire is with his team and management, the more likely he is to stick around.

According to RoundPegg, a company that advises businesses on their corporate culture, 89 percent of new employees who leave soon after being hired do so because they didn’t jibe with the office culture.

With that in mind, here are eight unique interview questions that can reveal a lot about potential employees.

“What is your spiritual practice?” –Oprah Winfrey

Oprah Winfrey arrives at the 87th Academy Awards nominees luncheon at the Beverly Hilton Hotel on Monday, Feb. 2, 2015, in Beverly Hills, Calif. (Photo by Jordan Strauss/Invision/AP)

Oprah Winfrey arrives at the 87th Academy Awards nominees luncheon at the Beverly Hilton Hotel on Monday, Feb. 2, 2015, in Beverly Hills, Calif. (Photo by Jordan Strauss/Invision/AP)

Sitting down with potential candidates to head up the Oprah Winfrey Network, Winfrey asked questions designed to reveal the inner balance candidates had achieved and help her determine whether their personality was a match for the company,according to Business Insider. Her query about spiritual practices also aims to get people talking about what they do for themselves and how they keep themselves centered, she said.

“What was the last costume you wore?” –Warby Parker co-CEO David Gilboa

David Gilboa, co-founder and co-chief executive officer of eyewear retailer Warby Parker Retail Inc., speaks during a Bloomberg Television interview in New York, U.S., on Thursday, Jan. 8, 2015. Gilboa and fellow co-founder and co-chief executive officer Neil Blumenthal discussed competition in the online prescription eyeglass space. Photographer: Victor J. Blue/Bloomberg via Getty Images

David Gilboa, co-founder and co-chief executive officer of eyewear retailer Warby Parker Retail Inc., speaks during a Bloomberg Television interview in New York, U.S., on Thursday, Jan. 8, 2015. Gilboa and fellow co-founder and co-chief executive officer Neil Blumenthal discussed competition in the online prescription eyeglass space. Photographer: Victor J. Blue/Bloomberg via Getty Images

This question is all about ensuring employees live up to the online eyewear retailer’s core value of “inject[ing] fun and quirkiness into work, life and everything we do.”

It’s also about being vulnerable, which co-CEO Neil Blumenthal expanded on in an interview with HuffPost in 2013.

“The more true confidence you have, that allows you to be more vulnerable,” he said. “When people see you being vulnerable and giving away more trust, they’re more likely to trust you.”

“What would you do in the event of a zombie apocalypse?” — Capriotti Sandwich Shop CEO Ashley Morris

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Morris told Business Insider the idea behind this question is to get a sense of what potential employees might do under pressure. As there’s no right answer, it’s also about fun.

“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,” Morris said.

“What would you like your life to be like in 5 years?” –Huffington Post Media Group Editor-in-Chief Arianna Huffington

NEW YORK, NY - FEBRUARY 11: Arianna Huffington, Editor-in-Chief of the Huffington Post, attends an event promoting the London tech industry with the Mayor of London, Boris Johnson, on February 11, 2015 in New York City. The event is part of Johnson's visit to the United States, where he is visiting Boston, New York and Washington D.C. (Photo by Andrew Burton/Getty Images)

NEW YORK, NY – FEBRUARY 11: Arianna Huffington, Editor-in-Chief of the Huffington Post, attends an event promoting the London tech industry with the Mayor of London, Boris Johnson, on February 11, 2015 in New York City. The event is part of Johnson’s visit to the United States, where he is visiting Boston, New York and Washington D.C. (Photo by Andrew Burton/Getty Images)

Huffington, who interviews each potential hire personally, asks this question to find out what makes them tick.

“For me, the most important thing in an interview is how authentic the person is,” she told Business Insider in 2013.

“When have you been most satisfied in your life?” –Cross Partnership founder and CEO Dick Cross

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It’s all about finding employees with the right character, Cross told journalist Jeff Haden in 2014.

“This question opens the door for a different kind of conversation where I push to see the match between life in my company and what this person needs to be their best and better in my company than he or she could be anywhere else,” the consulting firm’s CEO said.

“Tell me something that’s true, that almost nobody agrees with you on.” –PayPal co-founder Peter Thiel

Peter Thiel, co-founder of PayPal Inc., speaks during a Bloomberg Studio 1.0 Interview in San Francisco, California, U.S., on Monday, Aug. 25, 2014. EBay Inc.'s PayPal service will start accepting bitcoins, opening up the worlds second-biggest Internet payment network to virtual currency transactions. Photographer: David Paul Morris/Bloomberg via Getty Images

Peter Thiel, co-founder of PayPal Inc., speaks during a Bloomberg Studio 1.0 Interview in San Francisco, California, U.S., on Monday, Aug. 25, 2014. EBay Inc.’s PayPal service will start accepting bitcoins, opening up the worlds second-biggest Internet payment network to virtual currency transactions. Photographer: David Paul Morris/Bloomberg via Getty Images

Thiel admits that this question presents a challenge for job candidates, but it forces them to demonstrate that they can think on their feet.

“It sort of tests for originality of thinking [and] for your courage in speaking up in a difficult interview context where it’s always socially awkward to tell the interviewer something that the interviewer might not agree with,” Thiel told Forbes in a 2012 interview.

“What’s your superpower … or spirit animal?” — HootSuite CEO Ryan Holmes

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The tech company CEO said this question can provide some surprising insights into the working habits of a potential employee.

“During her interview I asked my current executive assistant what was her favorite animal,” he told Jeff Haden. “She told me it was a duck, because ducks are calm on the surface and hustling like crazy getting things done under the surface.”

“I’d ask them about their current family and their family history.” –Starbucks CEO Howard Schultz

Starbucks chairman and CEO Howard Schultz smiles as he speaks at the annual Starbucks shareholders meeting Wednesday, March 21, 2012, in Seattle. (AP Photo/Elaine Thompson)

Starbucks chairman and CEO Howard Schultz smiles as he speaks at the annual Starbucks shareholders meeting Wednesday, March 21, 2012, in Seattle. (AP Photo/Elaine Thompson)

If Schultz were allowed to ask a candidate only two interview questions, they’d both be about family, he told The New York Times in 2010. His intent with these questions, he said, is to gauge the level of passion the interviewee is capable of.

“If you don’t love what you’re doing with unbridled passion and enthusiasm, you’re not going to succeed when you hit obstacles,” Schultz added. “We are in an emotional business, and I need people around me who understand that we are an emotional business and have a visceral affection for it.”

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