> In a lot of cases, "caring too much" is itself seen as a problem because the boss explicitly just wants you to implement the thing that benefits him. He doesn't really want to hear that its not going to work well and there are better alternatives.

I've been the manager on the other side of a lot of situations that could be described like this. In many cases, it was hard to explain to the person that there were dozens and dozens of inputs that go into my decision making, including a lot of invisible factors and relationships that I was juggling.

It's hard to communicate to someone who sees a very thin slice of the company and wants to disagree and do something different to appeal to their perspective. A lot of the time I knew very clearly that we weren't picking the "best" alternative, but after hearing everyone out and weighing the tradeoffs a decision was made.

> Remember, he ultimately doesn't care if the product works. He cares if he can claim success. You're not helping him claim success, so you're a problem.

HN comments are wildly cynical. People who consume a lot of this cynicism think they're getting a leg up on the workplace by seeing the world for how it really is, but in my experience becoming the uber-cynic who believes all bosses are intentionally destroying the product with bad decisions to claim success (how does that even work?) is the kind of thinking that leads people into self-sabotaging hatred of all bosses. You need to watch out for yourself, but adopting this level of cynicism doesn't lead to good outcomes. Treat it case by case and be open to the idea that you might not have all the information.

>I've been the manager on the other side of a lot of situations that could be described like this. In many cases, it was hard to explain to the person that there were dozens and dozens of inputs that go into my decision making, including a lot of invisible factors and relationships that I was juggling.

I think this is also a really important counterpoint -- sometimes the person who "cares too much" is simply wrong, and is causing problems that should be avoidable. In other words, without more details it's hard to know if it's the manager or the direct report who is really the problem here.

> It's hard to communicate to someone who sees a very thin slice of the company and wants to disagree and do something different to appeal to their perspective. A lot of the time I knew very clearly that we weren't picking the "best" alternative, but after hearing everyone out and weighing the tradeoffs a decision was made.

You're saying it's hard to communicate that, but you've just done it really well. If you were to tell me a bit about those trade offs so I can also consider them the next time, I'd be a perfectly happy camper even if my idea isn't being picked up.