I understand your point. I've work with people at both extremes: - Negative people ruins ambiance and creates resentment. They think everything is doomed, and

I understand your point. I've work with people at both extremes: - Negative people ruins ambiance and creates resentment. They think everything is doomed, and criticizes everything all the time. Their usual last words : "Anyway it won't work". - Cheerleaders as you are calling them refuse to face the real problems, delaying the inevitable until it's too late. None of these attitudes are productive, and they are not held by people who both care and grasp the situation. Sometimes cheerleaders care, they just don't understand what's happening (eg managers who don't understand anything about technology...). By saying "here's why, and here's how to fix it", you show that you care, so you're definitely on the right path. The problem is that once you've said "That sucks" whoever you are talking to will stop listening. So it doesn't matter whether you say "That sucks, here's why, and here's how to fix it", or just "That sucks". It's pretty much the same. And that's the hard point. How to make people understand that something is wrong without making them go defensive. A common "trick" is honest praise. Honest. It must absolutely be honest otherwise it will fail. Something positive. Just find something great, praise it, and only then you can throw your critic, in a humble way. A critic must never feel like a critic, but more like an encouragement. It might sounds stupid, but it works. It's often easier to have people do a u-turn by pushing them forward. And it will give much more weight to your words when you actually have to throw a "Well, if we continue like that, we're doomed.". If you are known are someone positive, that will make people think...