There you go, again! You take one look at the title about disagreeing with bosses and you say, "I know! You are going to give a one word advice - 'Don't'." Really? You think I am going to fill up a whole blog post with 'Don't' like I were back at school and my teacher had given me imposition? (Huh! Do school-kids these days still have to write things like 'I will not be late to class' hundred times?)
Now, exactly why will 'Don't' not suffice? The problem is that there can be times when your boss' decisions can land the whole lot of you neck-deep in shit. AND, when that happens, your boss is going to scream, "Why did you not tell me before that this is likely to happen?" whenever he takes a break from gagging at the smell. Not to mention that if anyone is going to go under it will be you first.
If you think that it is unlikely to happen since your boss is supposed to be better than you in judging things, you are either too stupid to live OR you have not risen high enough in the organisation. In those rarefied heights, where YOU are the expert on law, say, and your CEO has come through engineering...well, there YOU are the one to advice about the law. AND CEOs, being CEOs, are prone to say things like, "Write to them quoting this clause and break the contract." You cannot just say, "Yes, Boss" when you know that you will get screwed in the arbitration. Not disagreeing is not an option...or, well, it IS, provided you are looking forward to a premature retirement.
So, how do you disagree pleasingly, if indeed THAT is not oxymoronic. Not by saying, "That's a stupid idea" that's for sure. If you do that...forget it. If you were the sort to do that, you'd have been filtered out in your very first job interview.
What about, "That will not work, Sir"? Hmm...you sort of assume that, since law IS your subject, the CEO would accept that you'd know more about the subject than him and will not take it amiss if you display that you know more than him. If such were indeed the case, do you really think that he would be laying down the law TO you rather than asking about the law FROM you?
So, what is your choice, then? Simple. Obviously YOU cannot show him up which would mean that you know more than him. So..."I'll talk to our lawyers and ask them to draft a proper legal notice," would be a good first step. And THEN, "Sir, our lawyers say that, in the event of arbitration, we are likely to lose." See what I mean? Now it is the EXTERNAL expert who knows more than your CEO and, after all, if they did not why would you keep them on retainer?
If you are REALLY good then, "Sir! Our lawyers were very impressed by your logic. Unfortunately, the law is an ass, it is not always logical. So, they say that..." THERE! You have stroked the man also, in addition to refusing him!
WHAT was that? Unnecessary payment of legal consultation fees for something that you knew yourself? Are you sure you belong in the corporate world?