Managers: Please Stop Asking Riddles in Interviews

Jake Wilder
4 min readAug 2, 2021

You’re Wasting Your Time and Your Credibility

“I need some good questions to throw off this candidate,” a friend recently told me. “I think I’m going to ask how many golf balls would fit in the room.” Try as I might to dissuade her, she was set on asking it. Even more unfortunate, she’s far from the only manager still asking these ridiculous interview questions.

Hiring the right people is one of the most important aspects of a manager’s job. Each hire has the opportunity to strengthen your team or weaken it. Each new employee will either reinforce the culture you’re looking to create or detract from it.

You can’t develop a high-performing team with substandard hires. It simply doesn’t happen. So it would make sense that managers would put real effort into reliably hiring the best candidate. And yet, the opposite occurs. Managers run interviews through a combination of small talk, irrelevant questions, and individual preferences. Instead of focusing on the specific role or simulating real job activities, they fall into the unreliable practice of winging it.

It’s an interesting paradox that as managers allow gut instinct to drive their interviewing practices, they see themselves as skilled interviewers. In actuality, it’s for this very reason that they’re not. The Dunning-Kruger effect continues to find more victims.

Hiring top candidates is already a challenge given the context of the interview. It’s an artificial setting. There’s limited time. It’s difficult enough to gain an appreciation for someone’s qualifications without further removing context with trivial questions.

Brainteasers and riddles may measure how quickly a candidate can solve abstract problems, but this rarely connects to the job. Very few companies spend their days solving riddles and brainteasers. Instead of understanding how a candidate will handle the potential job responsibilities, managers find out riddle skills and little else.

If anything, riddles and brainteasers promote thinking quickly over thinking well.

Asking these questions is a sign of privilege. It emphasizes the power dynamic between interviewer and candidate, making people jump through hoops simply so managers can pass…



Jake Wilder

I don’t know where I’m going. But at least I know how to get there.