My system prompt tells it to first challenge my assumptions, and to feel free to be a dick about it where it thinks I'm off on something, or have assumed facts that aren't actually facts. I sometimes wonder how much of my total spend boils down to forcing LLMs to argue with me, but I do feel like it's yielded better outputs than letting it implement things incorrectly because I told it to.

It's a completely dispassionate exchange tho, because you're absolutely right -- there's no winning or losing here, there's only efficiency to be gained or lost, and I'd prefer to lose some up front to gain it back later than the other way around.