Making the document estate answer questions, so new hires stop asking people
The situation
A new engineer's first fortnight is mostly reading. Runbooks, architecture notes, SOPs, a SharePoint site with a decade of sediment in it, and a lot of context that exists only in the heads of three senior people who get interrupted constantly. Nobody can point to where the current version of anything lives.
How I'd approach it
Retrieval over the existing corpus rather than a fine-tune — AI Search for the index, Azure OpenAI for generation. Chunking that respects document structure instead of cutting every N characters, because a policy split mid-clause retrieves badly. Two non-negotiables: every answer cites its source document so people can verify it, and retrieval honours the existing permission model so it cannot surface something a new joiner shouldn't see.
What usually bites
The corpus is always worse than anyone admits at kickoff. Three versions of the same policy, no owner on half the documents, PDFs that are scans of printouts. Retrieval quality turns out to be a content-hygiene problem wearing an AI costume, and that lands around week two.
What I'd cut first
A bespoke chat interface. Put it in Teams where people already are and spend the saved time on retrieval quality, which is what decides whether anyone uses it twice.
