As far as opinions and feedback you are in a advisory role to your boss. Meaning you can disagree with him but ultimately the decision is his to make because he

As far as opinions and feedback you are in a advisory role to your boss. Meaning you can disagree with him but ultimately the decision is his to make because he is responsible for the outcome. So you are free to disagree, but you are not free to insist and press the issue. Now what happens when you disagree so hard on an issue that you simply can't accept your boss's position? First make sure it's really a make or break situation an not just a useless hill to die on. Then just state the fact as calmly as possible. If telling your boss he's about to do something stupid means you will no longer be working working with him that's a good thing too. Not even close to a trap. If the stupid thing is not compatible with your principles (happened to me while working for a casino) then you should move on to something else. And if the boss is a proud idiot who can't take no criticism (I don't remember meeting one in 25 years) then you don't want to work with him either. So no matter what, speak your mind. Even if you do it in a horrible way (I suspect this is the case with the parent poster), or you yourself are wrong, it is still better that you open your mouth and receive outside feedback than to develop an ugly hidden persona.