Mentally Stumped on How to Structure Content

Hello all - Im brand new and have not yet started the training program, although I did read through all of it 1st so that I could conceptually understand what we are building (sorry but that's how my brain works best, 😊).

Anyway, I was trying to think about what I need 1st, and it is a Al Agent Coach for my courses. I think this sytem could work well, but I'm stumped on how I would structure the content of my markdown files to make a useful coach.

For example - would I break my content down by category of information in each micro section of my teachings, or do I try to anticipate all the questions/problems people have and then build the knowledge base around that? Or do both?

Im getting confused because (in my mind), its not the same as what we are learning in the training because its not as structured. For example - theres a specific step to building a video, etc. But a coach has to read the info, then compare it to the student's questions, and then give them tailored responses that align with the concepts in the knowledge base- whether the KB specifically addressed it or not. (This is a spiritual coaching program btw, so many of the answers will be similar in context, but not tge same output). So it's that fluidity Im trying to understand how to best capture.

Thanks for any insights that you may have!

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Mentally Stumped on How to Structure Content