Interviewing

6 Entrepreneurs Share Their Favorite Interview Question to Ask People

Don't waste your time asking job candidates to name their greatest weakness.
6 Entrepreneurs Share Their Favorite Interview Question to Ask People
Image credit: Benedetto Cristofani
Magazine Contributor
4 min read

This story appears in the January 2018 issue of Entrepreneur. Subscribe »

Forget about asking job candidates typical interview questions like 'What's your greatest weakness?' or 'Tell us about a challenge you overcame.' Instead, try these tips from six entrepreneurs who offer up their best interview strategies. 

1. Get to the good and bad.

“‘Tell me about your best and worst days at work.’ The answers are very revealing. ‘Best day’ answers demonstrate what makes that person tick, what motivates them. ‘Worst day’ answers tell whether a person is a team player -- if their response focuses on what went wrong without taking any ownership, there is a good chance they won’t thrive in a collaborative environment.” -- Chris O’Neill, CEO, Evernote 

Related: 15 Tips for Improving Your Skills Interviewing Job Candidates

2. Find their passion.

“‘What do you do when you’re not at work?’ It susses out what someone loves. Recently, I was interviewing someone for a social media job, and when I asked this question she told me she contributed to the Center for Artistic Activism. She expressed a vision for life that involved community, one that reminded me of a different project we were hiring for: our podcast Biden’s Briefing. When I asked her how she felt about Joe Biden, she about fell out of her chair. We hired her as a producer, and she’s thriving.” -- Mike Macadaan, CEO, Ground Control 

Related: 8 Costly Mistakes to Avoid When Interviewing a Job Candidate

3. Be creative.

“‘You have two teleportation devices. Where do you place them, and why?’ Questions that are open-ended test for critical thinking instead of zpure knowledge. One candidate told us they’d place one device in their home and one on the moon, because they want to explore space and make new discoveries. That may translate into someone who displays expansive thinking, is curious, and is hungry to learn.” -- David Lortscher, founder and CEO, Curology

4. Put them to the test.

“We like to have a little fun with our sales candidates while testing their ability to connect with people. We act like the interview is done, then call them back in and have them go over everyone they met, including their names and what they talked about. We end by asking directly, ‘Did you get the job?’ It’s a great way to gauge their self-confidence and see if they can hold their own from start to finish in an unpredictable situation.” -- Gil Addo, co-founder and CEO, RubiconMD

5. Scare ’em. 

"The question that is typically the most revealing is ‘If I called your current boss, what would they say about you?’ Interviewees tend to be very honest in their response because they anticipate that there’s an actual possibility I’ll make that call.” -- Chris M. Williams, founder and CEO, pocket.watch

Related: 4 Communication Mistakes Companies Make When Interviewing

6. Ditch the office.

“One great interview strategy I’ve found is to take people out of the office environment, to see how they interact in normal day-to-day settings. I like to conduct interviews over a walk, a meal, or coffee. You can learn a lot about someone from the way they engage with others. It’s a great way to get a sense of their personality and observe behaviors you might not otherwise pick up sitting in a conference room.” -- Lauren Letta, COO, charity: water

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