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.

You're absolutely right!

This. I'm right probably 9/10 times, but I prefer it pushes back on that remaining 1/10.