It's pretty difficult to have a useful back and forth with an LLM, because they're really heavily finetuned to be agreeable (and also they're not particularly s

It's pretty difficult to have a useful back and forth with an LLM, because they're really heavily finetuned to be agreeable (and also they're not particularly smart, just knowledgeable, so their 'system 1' is a lot better than their 'system 2', to analogize with 'thinking fast and slow'). Generally speaking if they don't get a useful answer in one shot or with relatively simple, objective feedback, they're just going to flop around and agree with whatever you last suggested.