4 Unconventional Interview Questions to Hire Original Thinkers

July 25, 2016

While it’s true that leaders need devoted followers, it’s also true that having too much groupthink and not enough diversity of thought is a perilous position to be in.

In fast-changing times, companies need people who think differently, have the valor to speak up and regularly challenge everything about assumptions, principles and the current business model. This kind of nonconformity leads to adaptability, agility and hence, keeps your team constantly questioning the status quo.

“You want people who choose to follow because they genuinely believe in ideas, not because they’re afraid to be punished if they don’t,” Wharton professor and best-selling author Adam Grant says in an interview with First Round Review. “For startups, there's so much pivoting that’s required that if you have a bunch of sheep, you’re in bad shape.”

For years, Grant sifted through collected data and countless interviews to build profiles of those he calls “originals.” In his new much-lauded book, Originals, Grant identifies four unconventional interview questions (based on three key attributes of originals) that can be used to validate the nonconformists and trailblazers who will end up disrupting any industry they’re in:

Question 1: How would you improve our interview process?

Is the candidate willing to speak up when they see something they don’t like and suggest how it can be better? According to Grant, this question will give you the opportunity to gauge the candidate’s ability and is “a window into their thinking process.”

“It's a chance to learn about their tendency to share opinions that might be unpopular but beneficial,” he explains. “It gives you a little bit of perspective on their ability and inclination to improve their environment.”

Question 2: Tell me about the last time that you encountered a rule in an organization that you thought made no sense. What was the rule? What did you do and what was the result?

Again, the idea here is to figure out whether this is someone who speaks up when they see a problem or merely ignores it because they’re afraid or don’t want to bother with the extra work. At the same time, you don’t want someone who quits over a problem without every trying to figure out the solution.

Here’s an example of what you want the candidate to say: “I saw this rule that I thought didn't make sense. I first did some research to figure out how it was created and why it was this way. I spoke to a couple of people who’d been at the organization longer than I had, asking if they knew what it was initially set out to do. If they didn’t know, I reached out to some people who have influence and sought their advice on ways forward to improve the rule and made a few suggestions on how. I got tasked to lead the committee to change the rule. We made a change and here's the evidence that we had an impact.”

Question 3: Why shouldn’t I hire you?

A crucial indicator of success is the ability to identify potential weaknesses and know how to turn them into opportunities. In his book, Grant mentions how founder Rufus Griscom pitched his company, Babble to investors by listing three reasons why they shouldn’t invest.

Similarly, Sarah Robb O’Hagan, former president of Gatorade and Equinox, once started her job application by listing the qualifications that she didn’t meet, followed by why she should be hired regardless.

“She challenges the job description and shows that she can bring something different than what a company thinks it needs,” says Grant. “Part of why this worked is that, in one fell swoop, she shows extreme awareness: not only of her abilities, but also of the proposed requirements—and why some don’t really matter.”

Question 4. It’s your first few months on the job. What questions would you first ask and to whom?

When people are new to a job, they should be learning as much as they’re doing, explains Grant. Originals stand out from the crowd by asking questions others don’t normally ask, and directing those questions at people who have different perspectives.

During their answer, “listen for examples of open-ended questions—rather than just yes/no or testing-my-own-thinking styles of inquiry—as well as a willingness to draw from and challenge many sources of information,” advises Grant.

Learning what kind of questions a candidate would ask and who their ideal sources would be also gives you a glimpse into their leadership abilities. Richard Branson, who’s definitely considered an original, knows just how important it is for leaders to ask the right questions to come up with new ideas. In his post on LinkedIn, Branson talks about the importance of starting your first days at a new job by getting to know the people around you. He writes:

“Don’t just ask them about practicalities; try to find out a bit about them personally. That way, you’ll start to naturally learn about the people culture of the company.”

Then, write everything down.

“Whether it’s in an old-fashioned notebook like I favour, or on your iPhone, record what you learn and add your own observations too,” continues Branson. “You’ll soon have a priceless resource to build upon. Now, what to do with these copious notes? Start making suggestions for how to improve your workplace.”

*Image by Joe deSousa

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