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11 interview questions from high-flying bosses

Curveball questions are usually advised against in job interviews, with their ability to make a confident candidate squirm and having absolutely nothing to do with the role at hand.

11 interview questions from high-flying bosses

However, if a jobseeker has the impressive credentials to land an interview with a superboss, they’ll have to be well-versed in the art of the interview and able to handle an irrelevant to the job question which calls for creativity, logic and skill on the spot.

Collated by Business Insider, the list gathers 11 tactical questions used by some of most successful business people.

1. Are you the smartest person you know?

Larry Ellison, Oracle Executive Chairman and CTO hires only exceptionally talented and intelligent employees and coached his recruiters to find exactly that, writes Business Professor, Sydney Finkelstein in his new book, “Superbosses.” If the candidate answered “yes,” they’d get hired. If they answered “no,” the recruiter would ask, “Who is?” and then try to hire them instead.

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

A little weirdness goes a long way for Zappos, according to CEO Tony Hsieh. He told Business Insider that the number isn’t too important, but it’s more about how people answer the question. However, 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 favourite of Zappos is: “On a scale of one to 10, how lucky are you in life?” Which apparently, if you’re a one, you don’t know why bad things happen to you and probably blame others, whereas if you’re a 10, you don’t understand why good things always seem to happen to you and probably lack confidence.

3. You are standing on the surface of the Earth. You walk one mile south, one mile west, and one mile north. You end up exactly where you started. Where are you?

Tesla and SpaceX CEO, Elon Musk riddles candidates with this one to test their intelligence, despite their being multiple correct answers, according to the biography “Elon Musk: Tesla, SpaceX, and the Quest for a Fantastic Future.”

4. What was the last costume you wore?

Warby Parker, prescription eyeglass company, doesn’t necessarily judge candidates on the costume they wore, but are interested in the reasoning behind it, to see if it matches their core values of injecting “fun and quirkiness into work, life, and everything they do.”

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

5. If you were an animal, which animal would you be?

Stormy Simon, President of Overstock, American internet retailer told the publication: “The animal kingdom is broad, and everyone can identify with a specific animal they think embodies their own personalities and characteristics.

“One time an interviewee said they identified with a red panda because everyone thinks they are so cute and approachable, but it turns out they’re just really lazy. We hired the candidate anyway despite that answer, but we parted ways within three weeks. It just goes to show how important the question is.”

6. 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, Group President of FOCUS Brands said in a New York Times interview that 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 explained. “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.”

She then proceeds to ask: “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?'”

Her explanation being: “People are pretty comfortable talking about that because I’ve pinpointed a person and a point of view.”

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

PayPal Co-Founder Peter Thiel gives candidates this interview question: “Tell me something that’s true, that almost nobody agrees with you on.” In a 2012 interview with Forbes, Thiel explained why: “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.”

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

Ashley Morris CEO, at Capriotti’s Sandwich Shop, believes this question gets to the heart of how a candidate reacts to 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.”

 9. 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, COO of job search engine ZipRecruiter, says this math question often trips up candidates, but if the answer was obvious he wouldn’t be asking it. “Some candidates will instantly blurt out 10 cents, which is obviously wrong,” he explains. “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.”

10. What is your favourite quote? 

This question is favoured by Karen Davis, Senior Vice President of Global Philanthropy and Social Impact at Hasbro, to identify candidates with “a true sense of passion and purpose.”

“You think about the great leaders in this world, and the ones that we remember most are the ones who have really put themselves out there, trying to invoke change,” she says. She wants potential hires to have similar values. “I want to see that somebody has been looking for sources of inspiration.”

11. How would you make money from an ice-cream stand in Central Park?

Yasmin Green, Head of Research and Development at Jigsaw – formerly known as Google Ideas – has one particular quandary she likes to throw at potential hires. During Marie Claire’s Power Trip summit, she revealed that she liked to ask candidates: “How would you make money from an ice-cream stand in Central Park?”

“I’m curious to see how people deal with ambiguity and whether they can have fun while thinking on their feet,” she explains. Green added that her hires should be “innately driven” and “who has that force of spirit that powers them through any obstacle that comes their way.”