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40 Favorite Interview Questions from Some of the Sharpest Folks We Know | First Round Review

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Given the high-stakes nature of every hire, interviewing chops are always in need of sharpening. We’ve spent the past few months reaching out to some of the most thoughtful company builders in our network to pose a simple question: What’s your favorite interview question to ask and why? Here are their answers.

Loading the Elevenlabs Text to Speech AudioNative Player... Here at First Round, we’re always searching for advice that gets overlooked or goes unshared, hoping to find the stones that company builders don’t even know to turn over. Whether it’s through in-person events, online discussions on First Round Network (our internal Quora-style platform), or the articles and interviews we share here on the Review, we’re driven by an ambition to create the space founders and startup leaders need to exchange that “ trapped ” knowledge. And in those spaces, we’ve seen time and time again how the conversa

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