5 Bizarre Interview Questions You Should Consider


It’s no secret that the key to building a successful startup is Team. When faced with the task of building a company from the ground up, it’s impossible to avoid the 18-hour days, the midnight meetings, and the constant fluctuation of fear and joy. The startup, and the success of that startup, becomes an enormous part of your life. Wouldn’t you rather spend those 18 hour days with a team you love to work with?

So how do you build the perfect team? Well, it all starts with interviewing – and believe it or not, there is no perfect way to conduct an interview. Every company has a very unique culture, so you’ll need to get creative with the questions you ask to make sure the candidate fits.

Now, if you’re wondering about every standard question you should be asking, then you came to the wrong place! Instead, I want to share five of the most bizarre interview questions or tactics used by companies who have “made it”. Some might say they add more depth to the interview, while others might call these questions cruel. Regardless, you’ll learn much more about the person you are interviewing by using at least one of these questions in your next interview.

1. A Question You’ll Remember From Elementary School

Think back to your younger years, when the world was perfect and anything was possible! At this age, the imagination runs wild and we all have very vivid visions of “what we want to be when we grow up.” Well, in every interview, Stewart Butterfield (Cofounder of Slack), asks grown men and women, who are already “grown up,” this exact question.

Good answers are usually about areas in which they want to grow, things they want to learn, things that they feel like they haven’t had a chance to accomplish yet but want to accomplish,” Butterfield said. “A very short answer to that question would be automatically bad.”

Best answer I’ve every received: “I still want to be a firefighter.”


2. An Old School Investment Banking Favorite: The Sealed Window

This interview tactic is undoubtedly cruel and unusual, but pretty funny if you think about it. I first saw this tactic when reading Liar’s Poker by Michael Lewis (if you haven’t read it, I would definitely recommend it). If you want to make the applicant sweat, maybe this unconventional investment banking interview tactic is for you. Here’s an excerpt from the book, enjoy!

“Investment bankers had a technique known as the stress interview. If you were invited to Lehman’s New York offices, your first interview might begin with the interviewer asking you to open the window. You were on the forty-third floor overlooking Water Street. The window was sealed shut. That was, of course, the point. The interviewer just wanted to see whether your inability to comply with his request led you to yank, pull, and sweat until finally you melted into a puddle of foiled ambition. Or, as one sad applicant was rumored to have done, threw a chair through the window.”


3. A Question With No Correct Answer

This interview question is a classic question used primarily in Consulting interviews, but could help you better understand how an applicant problem solves. You’ll notice, there is no correct answer. Instead, ask this question and ask the applicant to think out loud. Then, observe how the applicant thinks through the problem and eventually arrives at a conclusion.

My favorite way to ask this question: “How many tennis balls could you fit in Fenway Park?”


4. The Good Samaritan

So this next interview tactic was one I heard through the grapevine. HubSpot, a fellow marketing startup (not much of a startup anymore), apparently tries to gauge the “moral compass” of its applicants. Here’s how it works:

Begin the interview in a room with a table in between the interviewer and the applicant. Place your notebook and disposable coffee cup on the table then begin the interviewer. At some point, suggest changing rooms and pick up your notebook, but leave your empty coffee cup. If the interviewer either alerts you or disposes of the cup, you’ve found a good one!


5. My Personal Favorite

If there’s anything that sticks out about Jebbit, it’s the fun-loving, fearless attitude of each member of our team. So, my favorite question to ask helps me understand if this individual fits the mold: “Tell me a joke!”

I’ve heard everything from knee-slapping hilarious jokes to cricket-calls. However, the quality of the joke means nothing to me. If the candidate owns the joke, tells it with confidence, and enjoys the challenge then I’ve found a candidate who would fit well at Jebbit.


Bonus: Find out which interview question you should be asking. Just answer a few questions and we’ll let you know! FIND OUT