Can You Answer These Tough Interview Questions?

Sophie Miura
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Brooke Testoni

Getting asked tough questions has got to be one of our biggest interview fears. You get that sinking feeling in your stomach and fumble around for a response you hope won't jeopardize your chances of landing the job. To make sure that doesn't happen, the team at Quartz spoke to 10 leading CEOs to uncover the hardest questions they've ever asked candidates. Read on for our edit of tough questions to ask yourself in preparation for a job interview. 

"Why Are You Here Today?"

It might seem innocent enough, but there's a right way and a wrong way to approach this 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," says Gordon Wilson, CEO of Travelport. Rather than focus on why you want the job, talk about it as a mutually beneficial fit. Incorporate your skills and expertise into the discussion to show what you'd bring to the role. 

"What's Your Biggest Life Dream?"

When preparing for a job interview, look beyond career questions. Employers often like to probe candidates with questions that reveal their character beyond the workplace. Zhang Xin, co-founder and CEO of SOHO China, asks this tough question to test ambition and values. In your response, discuss your career dream, as well as broader life goals, to give a clearer indication of what you're like as a person. 

"Tell Me About a Time When You Failed."

Yes, it's a doozy, but according Roger Crandall, CEO of MassMutual, this question is very revealing. The purpose is to force the interviewee to self-reflect and show personal growth. Crandall looks for people who are honest, can give a specific example of failure, and, more importantly, explain why they are “a better person, partner, leader, and manager as a result."

"Would You Rather Be Respected or Feared?"

It might seem sadistic, but Michael Gregoire, CEO of CA Technologies, says this is one of his favorite questions. Why? Asking people whether they'd rather be respected or feared catches them off guard and doesn't necessarily have a correct answer. If the role you're interviewing for requires a collaborative approach, it's best to opt for respect and discuss why you excel in a team environment. However, if the job requires you to bring order to the company, fear is a powerful motivator. Consider the role and tailor your response and reasoning to suit. 

"As a Child, Who Did You Want to Be When You Grew Up?"

Barbara Byrne, vice chairman of investment banking at Barclays, says that by the time candidates reach her, it's clear they're capable, so she does the "airplane test." In other words, "Could I sit on a plane from New York to L.A. with you and not be bored out of my mind?” she says. When answering this question, try to build rapport. Show them your personality and give them insight into your background and aspirations. 

"Tell Me a Joke."

Charles Phillips, CEO of Infor, probes candidates with questions that reveal how they react to difficult situations. "Anyone can fake it for 45 minutes," he says. "I like to watch how they handle themselves in an unstructured environment."  One such example is that Phillips asks people to tell a joke. This reveals much more than their sense of humor. It also shows their ability to improvise and deal with uncomfortable situations. 

Looking for other ways to prepare for a job interview? Shop the career how-to below, then visit Quartz for more probing interview questions. 

What's the toughest question you've ever been asked in an interview? Tell us in the comments below. 

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