If you ask it to never say "you're absolutely right" and always challenge, then it will dutifully obey, and always challenge - even when you are, in fact, right. What you really want is "challenge me when I'm wrong, and tell me I'm right if I am" - which seems to be a lot harder.
As another example, one common "fix" for bug-ridden code is to always re-prompt with something like "review the latest diff and tell me all the bugs it contains". In a similar way, if the code does contain bugs, this will often find them. But if it doesn't contain bugs, it will find some anyway, and break things. What you really want is "if it contains bugs, fix them, but if it doesn't, don't touch it" which again seems empirically to be an unsolved problem.
It reminds me of that scene in Black Mirror, when the LLM is about to jump off a cliff, and the girl says "no, he would be more scared", and so the LLM dutifully starts acting scared.