Check out the paper "Self-Augment with Instruction Back Translation" by Li et al.

It discusses instruction/output pairs and the ability to predict instructions for a set of content. This would be a great initial analysis for users. Kind of like metacognition for your second brain (i.e., know what you don't know

For example, "Welcome to myReach, the content you uploaded can respond best to the following prompts: a, b, c"