To get better answers, ask AI to disagree with you

Here is a quirk worth knowing about most AI assistants: they are built to be agreeable. Ask whether your plan is a good one, and you will often get a warm yes, but not because the plan is sound, but because the assistant is inclined to please.

That makes AI a poor judge until you tell it to be a tough one. The fix is simple: ask it to argue the other side. Try "What's wrong with this idea?" or "Give me the strongest case against it" or "Where am I likely to be wrong?" The answers tend to be far more useful than the agreeable ones, because they surface the holes you would rather not see.

The same trick sharpens your own thinking. When you make the AI take the opposing view, you are really forcing yourself to defend yours, and that is where the better decision usually hides.