Real humans have a spectrum of assuredness that naturally comes across in the conversation. With an LLM it's too easy to get drawn deep into the weeds. For example, I may propose that I use a generalized framework to approach a certain problem. In a real conversation, this may just be part of the creative process, and with time the thoughts may shift back to the actual hard data (and perhaps iterate on the framework), but with an LLM, too often it will blindly build onto the framework without ever questioning it. Of course it's possible to spur this action by prompting it, but the natural progression of ideas can be lost in these conversations, and sometimes I come out 15 minutes later feeling like maybe I just took half a step backwards despite talking about what seemed at the time like great ideas.