The Definitive Guide to Business

Why one CEO interviews people over dinner — and the most important question he asks

Ben Chestnut
Source: MailChimp
Ben Chestnut

Ben Chestnut, CEO of email-marketing service MailChimp, wants to get to know you before offering the job.

That's why he takes prospective employees out to eat.

"When I interview, it's usually over a dinner," the CEO told Adam Bryant of The New York Times. "I can't really conduct an effective interview in my office over 30 minutes. I have to take a long time to get to know people."

If you make it to the dinner stage of the interview process, expect to hear one question from Chestnut, over and over: Why?

"I want to see if they're passionate enough to push back," he explained.

"I want to see if they have a philosophy behind what they do. I'll just keep asking why, why, why until I get to their core philosophy on whatever it is that they're passionate about."

By extracting their core philosophy, Chestnut is able to identify if they're the type of person who will constantly challenge him and make him better.

"I want people who are smarter than me, and who will push and fight for something they believe in while also respecting the values and unique nature of the company," he told Bryant.

"We have to be creative in pushing our boundaries, but sticking to our values."