Giving Assistant Best Index or Reference to File Search

I’m uploading about 500 PDFs and 100 JSON files to the File Search in my assistant. Other than providing instructions in the ‘System Instructions’ for the assistant, is there a best practice, like naming conventions or other organizing techniques, to help the Assistant understand the content?

There are basically two dozen knowledge areas I’d like it to learn, for example, navigation, weather conditions, tides, etc. Each is a specific area to master in being a good sailor, and some PDFs pertain to one of these.

1 Like

Anyone any thoughts? Is this documented somewhere?