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Dear Quota Team,
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I’m an Account Executive at a tech company (shocker). We have a pretty close-knit sales team, and my company is one of my city’s (Boston) most-sought after companies to work for based on its reputation as a solid employer and its ambitious sales culture. 
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I think one of my coworkers has a serious gambling problem. He is a first-year BDR (Business Development Rep). Before this, he was a BDR at another company that let him go. The circumstances of him getting let go weren’t clear to us, but I now suspect it has something to do with his “problem.” Whenever we’re in person, he is constantly texting or checking games. On video calls and meetings, he looks like he’d been up all night with dark bags under his eyes. He is jumpy, nervous, and doesn’t seem like he’s in a good place. 
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When we all went out for a drink one night a month ago, he brought up gambling to me and had this sly grin on his face, but when he realized I had no interest, he basically got bored and stopped the conversation. 
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His performance isn’t great, and it isn’t terrible. But there’s obviously something very wrong with him right now. I heard a rumor that he asked someone in the office to borrow money, but I don’t know if that’s actually true or not. Should I offer to help, or mind my own business? I don’t want to see this kid ruin his life before he has a chance to really get it started. 
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Concerned in Boston
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Dear Concerned,
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It’s admirable that you’re willing to help a younger coworker who might be down on their luck (quite literally in this case), but since he hasn’t asked for your help and hasn’t even confirmed that there’s any problem at all, you need to tread carefully.
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The best thing you could do is approach it from a mentor/mentee perspective. Offer (directly or indirectly) to help him in his career, and guide him toward becoming an AE. Along the way, he might ask for help or advice, or he might not. 
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At the end of the day, you’re there to work, and so is he. And there’s no proof that he has a gambling problem at all. Maybe he stays up all night playing video games or is working on a novel. You can never tell for sure, so your best bet might be to focus on your job and to avoid looking for trouble. Either way, be mindful of the fact that nobody has (yet) asked for help.