40 Favorite Interview Questions from Some of the Sharpest Folks We Know

Given the high-stakes nature of every hire, interviewing chops are always in need of sharpening. And that means our hunt for a crazy-good interview question is never over. We’re endlessly fascinated by the go-to inquiry in everyone’s back pocket, the kind that makes you want to steal it for your own hiring toolkit. To that end, we’ve spent the past few months reaching out to some of the smartest and most thoughtful operators in our network to pose a simple question: What’s your favorite interview question and why?

The responses we got back were first class. What follows is an exclusive list of 40 interview questions, sent to us by the sharpest folks we’ve met or just outright admire. Some of the questions are (deceptively) short and sweet, some are probing and unexpected, others hinge on targeted follow-ups. Broken down by topic, they tackle everything from how candidates understand the role and process feedback to their first summer job, worst boss, and the last time they changed their mind. Most importantly, these incredible founders and company builders break down why they lean on these questions — and what to look for in the answers you hear.

We hope this collection serves as a rich jumping off point that you can leverage as you design your own process, whether you’re building it from scratch or looking to give it a refresh as you double-down on hiring.

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