9 profound interview questions CEOs ask job candidates

Some interview questions have become so standard, job candidates offer up equally standard, possibly even scripted responses. As a result, the conversation is both inorganic and also a less effective predictor of a candidate's potential for success in the given role.

Few CEOs field such queries to candidates vying for a role near the top. Instead, questions aim to assess a potential leader's soft skills and gauge his or her mentality. All CEOs have different techniques to access this insight during an interview.

Quartz spoke with 10 CEOs and other senior executives about their interview techniques and the one "killer" question they ask job candidates.

1. "Would you rather be feared or respected?" Michael Gregoire, CEO of IT management software company CA Technologies, said this question always catches people off guard and "really reveals what they think about their leadership style," according to the report.  

While there may not be a correct answer in theory, each option shows which way the candidate leans and how this might impact his or her ability to collaborate with others.

2. "Why are you here today?" Gordon Wilson, CEO of Travelport, a U.K.-based software firm, said he is looking for a specific answer when he asks candidates this open-ended question.

"I'm surprised how many times people talk about the benefit of the job from their point of view, versus the benefit that they're going to bring to the company," said Mr. Wilson, according to the report. At the very least, Mr. Wilson looks for an even split between benefits to the company and personal ones, though he strives for 75 percent geared toward the company and 25 percent focused on the self. "If you benefit the enterprise, the personal thing will come."

3. "What's your biggest dream in life?" Zhang Xin, co-founder and CEO of SOHO China, a commercial property developer, asks candidates this question to assess their level of ambition. She said she is most attracted to people whose responses illustrate they are "free spirited," according to the report.

4. "I ask how they were treated." Rick Goings, CEO of Tupperware, doesn't pose this question to job candidates, but instead to the people who would have come in contact with them on the candidate's way to the interview.

"I talk to the driver who brought them in from the airport, my assistant, and the receptionist who welcomed them. I ask how they were treated. There you learn how this person acts," said Mr. Goings, according to the report. He is aiming to assess the "non-cognitive skills" that strong leaders possess to manage and inspire their teams.

5. "What is your favorite property in Monopoly, and why?" Ken Moelis, founder and CEO of investment bank Moelis & Co., throws this unexpected question at recent MBAs interviewing for mid-level positions because he thinks it's a "great way to hear how people think of risks and rewards," according to the report.

6. "Tell me about when you failed." Roger Crandall, CEO of American insurance group MassMutual, said a candidate who can speak honestly and openly about past failures is attractive, but only if they can also explain how they have become "a better person, partner, leader and manager as a result."

Along the same lines, Davide Serra, founder and CEO of London-based hedge fund Algebris, asks candidates, "What's the biggest mistake you've made and what have you learned from it?"

7. "Talk to me about when you were seven or eight. Who did you want to be?" This question is part of Barbara Byrne's "airplane test." Ms. Byrne, vice chairman of investment banking at Barclays, wants to know, "Could I sit on a plane from New York to LA with you and not be bored out of my mind?" Discussing childhood dreams opens a window of insight into who a person really is on the inside, she said.

8. The wine list test. Instead of holding a traditional interview, Charles Phillips, CEO of enterprise software company Infor, takes a candidate out to dinner with a handful of other senior executives to "watch how they handle themselves in an unstructured environment," according to the report.

Mr. Phillips gives the candidate the wine list and watched what they do. A candidate will either convince the group that they know a lot about wine, pretend they do, pick the most expensive bottle or ask for help. How they handle their wine selecting duties and how successful they are in explaining themselves is a big part of the test. The other is how the candidate treats the waiter.

9. Live your hobbies. Atul Kunwar, president and chief technology officer of Tech Mahindra, doesn't have a go-to interview question. Instead, he lets the candidate's passions and interests direct the conversation. When one candidate said he loved to sing, Mr. Kunwar said he asked him to sing for the senior panel of executives in the room.

"He had the gumption to do it, and he sang very well," Mr. Kunwar told Quartz. "To me, it meant he was passionate and able to build skills on his own. And when the crunch time came, he had no hang-ups. We need people with that sort of belief and passion."

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