The biggest problem with having an LLM do this, from what I've observed of at least frontier models, is that the way they are trained/forced to behave makes them do one of two things, neither of which is educational or helpful:

1. They ask you a "hard question" but then immediately give you some kind of "hint" which makes it obvious what the "answer" is (or, even worse, they just tell you what it is).

2. They get pedantic (and I mean maximum emphasis on the word), to the point that they will nitpick the exact, precise wording you use, even if the context makes it blatantly obvious what you meant. GPT is currently the biggest offender in this area (it is ridiculously pedantic even though I haven't told it to be so).

And yes, in case anyone is wondering, I do actually read the output of tools like Claude and I have tried, repeatedly, to get them to do something like this, and one of the two aforementioned things always happens for some reason. I'm not sure if this is a problem with how they were trained, an issue with their system instructions, or what.