A few months ago, I found myself drowning in documentation. My team had accumulated hundreds of markdown files—API references, internal guides, architecture decisions—spread across a monorepo. Every time someone asked "How do we deploy to staging?" or "What's the rate limit for that endpoint?", I'd either dig through files or ping the person who wrote it (who usually forgot).
I wanted a bot I could ask questions in natural language and get accurate answers instantly. Here's the journey—including the dead ends, the "aha" moments, and the trade-offs I still live with.
The Problem (My Problem)
Our docs were well-organized, but searching was painful. grep -r found keywords but not context. "What's the max request size?" would return a file with "max_request_size: 10MB" but also a dozen irrelevant hits. I needed semantic understanding.
What I Tried That Didn't Work
