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Dear Quota Team,

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I've been in B2B software sales for about two years now, and I'm struggling with something that's eating me up inside. Our product works... sort of. It does what we say it does, but I know from talking to our customer success team that most clients never fully adopt it, struggle with implementation, and honestly would probably be better off with a simpler (cheaper) solution. But everything is going well. I hit my quota every quarter. We have a strong brand in the space. My manager loves me. I'm making great money.

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The problem is, every time I close a deal, I feel like I just convinced someone to buy something that's going to make their life harder, not easier. Last month, I sold our enterprise package to a small marketing agency, and I could tell halfway through the sales process that they really just needed basic project management software, not our complex workflow automation platform. But the commission was too good to walk away from, and they seemed excited about all the "advanced features."

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I keep telling myself that buyers are adults who can make their own decisions, and technically I'm not lying about what our product can do. But I know in my gut that most of my clients are going to be frustrated six months from now. Is this just what sales is? I love the thrill of closing deals and I'm genuinely good at building relationships with prospects, but I'm starting to dread the follow-up calls from new clients when reality sets in. What should I do?

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Feeling Guilty in Location Withheld  

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Dear Feeling,

The guilt you're feeling is a signal that you're in the wrong role or selling the wrong product. Great salespeople genuinely believe their solution improves their clients' lives. Start looking for a company whose product you can authentically champion. Yes, you might take a temporary pay cut, but you'll sleep better and build a more sustainable career. In the meantime, try qualifying prospects more rigorously. Ask harder questions about their actual needs and budget. Sometimes being more selective about who you sell to can reduce that "con artist" feeling while you transition to something better. Trust your gut.