The Unorthodox Interview Questions These 6 Top Executives Love to Ask

August 16, 2016

Building an innovative company requires a lot of creativity and breakthrough ideas. The good news is that getting there is simply a matter of identifying big-thinking people by asking the right questions that can gain you insight into what they’re like, what they deem important, how they process challenges to find solutions and communicate ideas.

As hiring is one of the biggest jobs of every CEO, below are questions top executives ask to identify unconventional, big-thinking people:

1. “What is the last thing you’ve learned on the job?”

Questions like this require candidates to pause and think about the last thing they learned that made an impact on them. After asking this questions, Andrew Filev, CEO at Wrike, a provider of project management software, listens for how challenging it was to gain this new piece of knowledge and why the candidate learned what they did (Was it a requirement of a job or were they curious on their own accord?). Filev tells Adam Grant in the New York Times that he’s looking for three things from candidates with this question:

  • How smart they are: “I don’t just mean I.Q. smart or Ivy League smart, although that does help,” says Filev. “I mean being smart about how to do the job.”
  • Their motivation: Are they curious or striving for excellence? Are they passionate?
  • Their ability to get things done: “Sometimes a person can be very smart academically or they can deliver an incredibly polished PowerPoint because of their previous corporate experience,” explains Filev. “But then you hire them, and you discover that they just can’t move fast enough for a start-up.”

He adds: “For me, velocity is king in start-ups. If you can iterate quickly, that’s much more important than being a genius who can come up with an incredible solution, because it’s impossible to repeat.”

2. “Tell me something that’s true that almost nobody agrees with you on.”

Not so much a question as a request to reveal some deep context—and that’s exactly why venture capitalist Peter Thiel loves bringing it up during interviews.

"It sort of tests for originality of thinking, and to some extent, it tests for your courage in speaking up in a difficult interview context," Thiel says in a 2012 interview with Forbes. "It's always socially awkward to tell the interviewer something that the interviewer might not agree with.”

Ultimately, Thiel is looking for someone who can be upfront, confident about what they think and originality, which he says is actually “really hard” to find, but when you do find it, “it's really valuable.”

3. “Talk to me about when you were seven or eight. Who did you want to be?”

By the time candidates get to the CEO, or top executive, they’ve often already been vetted several times over. As a result, the only thing Barbara Byrne, vice chairman of investment bank Barclays, needs to test for is whether they can pass her “airplane test,” meaning could she sit next to them on a plane from New York to L.A. and “not be bored out of [her] mind”?

The childhood question, Byrne tells Quartz, is a “good conversation-starter for such a long haul” and you often get to “connect to the real person.” In other words, it’s no longer another boring job interview with rehearsed answers.

4. “What didn’t you get a chance to include on your resume?”

Virgin Group’s Richard Branson is known for his unconventional, eccentric leadership style, so it makes sense that he comes up with creative interview questions. In his book, The Virgin Way: Everything I Know About Leadership, Branson says that if you’re going to hire someone solely because of what they say in their resume, then you wouldn’t need to interview them. Instead, dig deeper and really get to know who they are and what makes them passionate.

5. “How would you describe yourself in one word?”

According to Dara Richardson-Heron, CEO of YWCA, the best candidates are “the ones who know exactly who they are.” It’s not about which word they use, either, she says, but about the way they define themselves and the best candidates are the ones who take some time to reflect before answering.

6. “On a scale of 1 to 10, how weird are you?”

Zappos’ CEO Tony Hsieh likes weird and considers one of his company’s core values is to “create fun and a little weirdness.” This question allows Hsieh to access the candidate’s level of weird (everyone’s a little weird). For instance, if it’s a one, then you’re probably “too straight-laced” for Zappos and if you’re a 10, you might be “too psychotic.”

What’s Hsieh trying to figure out? Basically, it’s all about wanting to see how that candidate’s personality would transform the company’s culture. “I think of myself less as a leader, and more of being almost an architect of an environment that enables employees to come up with their own ideas, and where employees can grow the culture and evolve it over time, so it’s not me having a vision of ‘this is our culture,’ he tells the New York Times.

The bottom line: Most executives believe there is a strong connection between creativity and business success. Coming up with smart behavioral questions to identify candidates with big breakthrough potential takes a lot creativity on CEOs part, too.

Just remember that the idea is not to place too much emphasis on the candidate’s answers. Instead, carefully consider their thinking process and how they got to their answer. What does this reveal about the way they work or what they deem as important in life? What you really want is to gain insight into what kind of impact they can make—for themselves and the company—if they are hired.

For more inspiration, download The Guide to Screening Candidates.

* image by Wikipedia Commons

To receive blog posts like this one straight in your inbox, subscribe to the blog newsletter.