I keep second-guessing myself on whether to take a chance on someone who seems like a fast learner but doesn’t check all the boxes. How do you know when a candidate’s potential outweighs their lack of direct experience? Are there any telltale signs you've come across over the years?

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This is the toughest part of the job. For me, potential stands out when a candidate can talk through how they’ve picked up new skills quickly in past roles even if those weren’t directly related. If they’re asking thoughtful questions, showing genuine curiosity, and are able to explain exactly how they’d tackle real problems here, that’s a pretty strong indicator.

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That’s a though one. In the interview I would ask them how they would handle a problem you may encounter on your team and see how they respond. If you can follow the way they prioritize and attack the problem and it’s a good fit. Then I say hire them.

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Is he the best overall applicant? Is there another applicant who has the experience and seems like they’d be a good fit? If so, give it to the second person. But if he’s the best candidate, give it to him and give him a shot.

For me it would depend on how important the missing boxes are. In general, I would rather work with someone who is excited about the job and willing to learn than someone who may have experience but is not excited about the job.

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