Want to Interview like a CEO?

by Mike O'Neill

OK, we’ve all done it. At some point in an interview we’ve asked the candidate “what is your greatest weakness?”. And yes, we hear some variant of “well…I’m kind of a perfectionist”.  Blah, Blah, Blah! So, why ask questions that candidates are expecting us to ask? Might we learn from seasoned executives what works for them?

If you would like to interview like a CEO, then hopefully these tips compiled by Entrepreneur magazine will help:



LAUREN LETTA – COO, charity:water

“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.”



CHRIS O’NEILL (no relation) – CEO, Evernote

“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.”


MIKE MACADAAN – CEO, Ground Control

“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.”



“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.


CHRIS M. WILLIAMS – CEO, pocket.watch

“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.”


Want to hire the right people? Bench Builders helps businesses hire, train & keep great employees.



“Whenever you are asked if you can do a job, tell ’em, ‘Certainly I can!’

Then get busy and find out how to do it.” 

– Theodore Roosevelt

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