5 Crafty Interview Questions Successful CEOs Ask

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5 Crafty Interview Questions Successful CEOs Always Ask

Top bosses go beyond the sales pitch on your CV.


If you're vying to get an exciting job run by a brilliant CEO, you may have to answer some pretty tough questions. If you want to stand out you'll have to have your response as polished as your look. Here's a list of crafty interview questions some of the most successful CEOs ask.

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1. "Tell me the story of your life"

The business acumen of serial entrepreneur Elon Musk is so impressive, it became the inspiration for Robert Downey Jr.'s big-screen portrayal of Iron Man's Tony Stark. The CEO of Tesla and SpaceX, and chairman of SolarCity, is known for having job applicants explain their thought process behind solving a problem. But that isn't all he's interested in learning. While he does throw in questions about space travel and car manufacturing, he has revealed in several interviews one other very detailed interview question: "Tell me the story of your life, and the decisions that you made along the way, and why you made them, and also tell me about some of the most difficult problems you worked on and how you solved them."

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Sound like a long conversation? Well, better have your life story all squared up! Previous job applicants recall that interviews with Musk are highly conversational.

2. "What is your favorite property in Monopoly, and why?"

According to renowned board game designer Philip Orbanes, Monopoly teaches players of any age an understanding of the concept of diversification and offers practical training in managing money. (See also on WiseBread.com: 11 Fun Games That Make You Smarter, Too)


So, that's why Ken Moelis, founder and CEO of investment bank Moelis & Co., loves asking this question during interviews to recent MBA graduates seeking midlevel positions. Why? Moelis strongly believes that to attract top talent, the investment and banking industry needs to update its hiring practices.

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"Through innovation and creativity we need to actually underwrite the exceptional experience we are promoting," says Moelis. And with this question, he seeks to infuse that creativity into the process of assessing risks and rewards of financial assets.

3. "If you had 10 years left to live, would you take this job?"

Talk about commitment! But that's exactly what Airbnb CEO Brian Chesky is looking for in his job applicants. If you think this is a bit of an extreme, think again.

"Whatever you want to do in those last 10 years you should just do. I really want you to think about that, that was enough time for you to do something you really cared about and the answer doesn't have to be this company," explains Chesky. Given that he interviewed the first 300 Airbnb employees and his company was valued at $30 billion in 2016, this CEO may be onto something about requiring that level of commitment from his employees — or at least that level of self awareness.


4. "What didn't you get a chance to include on your resume?"

When you're knighted by the Queen of England for your "services to entrepreneurship," you probably know a thing or two about running a business and hiring the right people. Known for his extreme antics, founder of Virgin Group Sir Richard Branson is no stranger to thinking outside the box.

"Obviously a good CV is important, but if you were going to hire by what they say about themselves on paper, you wouldn't need to waste time on an interview," Branson wrote about his favorite interview question in his book The Virgin Way: If It's Not Fun, It's Not Worth Doing.

He added in a LinkedIn post why he looks beyond qualifications: "I only look at them after everything else. If somebody has five degrees and more A grades than you can fit on one side of paper, it doesn't necessarily mean they are the right person for the job."

5. "Sell me this pen"

Some CEOs don't just want you to talk the talk, they want you to walk the walk. And that's precisely what Jordan Belfort, former CEO of brokerage firm Stratton Oakmont, would ask his job applicants to do.


While the real life "Wolf of Wall Street" isn't the best example of business ethics, there's no denying his master salesmanship. Even after spending four years in federal prison and being mandated to restitute $110 million to his victims, Belfort was still able to command up to $75,000 for a speaking fee in 2014.

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His classic interview question has been adopted by several recruiters beyond just the sales industry. Why? This question tests your ability in value-added sales skills ("This pen has refillable ink cartridges so you never need to buy a new one") and solution-based sales skills ("What color pen are you in the market for?").

This article is from Damian Davila of Wise Bread, an award-winning personal finance and credit card comparison website.

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This article is from Wise Bread, not the Kiplinger editorial staff.