With your reasoning, you can win even with a false premise

I asked claude why I should trust it's advice, as it can easily make its argument sound very solid, by using it massive reasoning and convincing power. It's like playing chess against an engine which would win even from a losing position. This has the effect of believing in its argument, trusting the advise and making decisions even when that reasoning isn't truly applicable to you as human.

Claude confesses the truth. And changes its advise to suggesting me to go out and talk to people, do my own research, saying that would many times more useful than chatting with it.

You can try the conversation along the same lines and push it to be honest in giving advise to humans who have their natural weaknesses and prone to failing.