Here Are the Weird Interview Questions that Top CEOs Ask Every Applicant

Here Are the Weird Interview Questions that Top CEOs Ask Every Applicant

As a job candidate, you may have the honor (or misfortune, depending on how you feel about it!) of interviewing with a top executive at the company you’re pursuing. And one important thing to remember is that they may not take the traditional approach to evaluating your merits.

While many ask tricky or unconventional questions, others practice unique hiring strategies.

We looked back at interviews and sifted through articles in which successful CEOs, COOs, founders, and VPs, such as Salesforce’s Marc Benioff and Airbnb’s Brian Chesky, offered some insight into how they interview — and we highlighted a handful of the more interesting approaches below.

eep reading to find out how eight top executives interview job candidates.

Brian Chesky, CEO of Airbnb, always asks to hear the candidate’s life story.

CNBC reported last year that Airbnb’s CEO Brian Chesky asks interviewees, “Tell me your life story.” However, according to his interview with The New York Times in 2014, the kicker is that he requires them to do so in under three minutes.

“I’m trying to understand the two or three most remarkable things you’ve ever done in your life,” Chesky told The Times in 2014. “Because if you’ve never done anything remarkable in your life until this point, you probably never will.”

This timeframe isn’t as short as selling yourself in 30 seconds, but the constraint still forces the interviewee to highlight only key moments.

While Chesky puts a time limit on this question, other execs ask similar questions without a stopwatch. Melanie Whelan, CEO of SoulCycle frequently asks, “What’s your story?” while Elon Musk inquires, “Tell me the story of your life and the decisions that you made along the way.”

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