10 CEOs Shared Their Toughest Interview Questions. Could YOU Answer Them?

job interview questions

I don’t know about you, but I always spend evenings before interviews going over my resume and reciting some well-rehearsed answers to myself.

“In five years, I plan to be…”

“My greatest weakness? Well, I’m a perfectionist, so sometimes my work takes a little longer — but it always turns out really well for the same reason.”

That’s right, turn the weakness into a strength. I am so good at interviews, you guys.

Hard Interview Questions — Like, Really Hard

Even though I’m the best at interviews, after reading an article at Quartz about some of the hardcore questions CEOs pose during high-level interviews, I’m pretty stoked not to be on the job hunt right now.

And it’s not just because I adore my job.

These questions are hard.

I have no idea how I’d answer them. Having only (barely) survived one panel interview, I’m pretty sure if someone asked me to sing for a bunch of people, I’d literally turn inside out.

Outsourcing provider Tech Mahindra’s President and CTO Atul Kunwar asked one (lucky?) interviewee to sing for the panel of senior execs who’d been questioning him.

To be fair, the candidate had mentioned he was a keen singer early in the interview. Make sure the “Hobbies and Skills” section of your CV isn’t just for show!

Other noteworthy questions include a Machiavellian “Would you rather be respected or feared?” and “What is your favorite Monopoly property, and why?”

Tupperware CEO Rick Goings circumvents the interview entirely by asking other people the questions — like, “How were you treated?” to the candidate’s driver.

Granted, these impossible questions are coming from extremely high-level executives — even company owners — who are interviewing candidates for important leadership positions….

But come on.

Making someone choose a bottle of wine from a fancy restaurant’s list as a high-pressure psych experiment? That’s just sadistic.

Your Turn: What’s the worst interview question you were ever asked? How did you handle it?

Jamie Cattanach (@jamiecattanach) is a junior writer at The Penny Hoarder. She also writes other stuff, like wine reviews and poems. She definitely, definitely has a five-year plan.