We're all bright, friendly, 'cool' people... and yet our decision-making is surprisingly dictatorial.
But if you think about it, this does make sense.
In fields like engineering, medicine, and finance - where there are actual facts that can be brought to bear - it's possible to make an objective challenge.
But advertising is mostly subjective. Our debates are more like one person saying "I like tomatoes" and someone else says "I don't like tomatoes, I prefer avocados."
So someone's got to make the decision, and the person being paid to make the decision is your boss, and that's it.
In a previous agency I once got a dressing-down for being "too challenging."
My ECD flipped out because I was so convinced an idea was great, I came back to him with it three times. (Along with other ones). Incidentally this was quite hypocritical because he would often tell account teams to "go back and try again" when the Client hadn't bought something, but he didn't seem to like the approach when it was applied to him.
Yet if you don't argue with your boss at least a little bit, and don't put your point of view across even if it doesn't match his, you will be viewed as a passive, spineless, yes-person. That is not good.
So my conclusion is that it's actually essential to argue with your boss. But you have to do it carefully.
A good tip is to ask questions. For example, if your boss tells you to fill a wheelbarrow full of shit, you could ask "Do we worry that the smell could be a problem?"
Another option is to fill one wheelbarrow full of shit and a second one with beautiful plants, and present both.
Re-presenting the same idea? Yes, but it's like a murder trial. You can put the case back in front of the judge, by all means, but the second time around, you have to have new evidence. A new spin on it.
Anyway, that's my POV, but I'd be interested to get yours. Is it okay to argue with the boss where you work? Have you ever gotten into trouble for doing it, or do you have a way of arguing that you've found effective and would be willing to share?