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First, recognize that, for the first time ever, having good docs actually pays dividends. LLMs love reading docs and they're fantastic at keeping them up to date. Just don't go overboard, and don't duplicate anything that can be easily grepped from the codebase. Second, for #3, it's a new hire's job to make sure the docs are useful for new hires. Whenever they hit friction because the docs are missing or wrong, they go find the info, and then update the docs. No one else remembers what it's like to not know the things they know. And new hires don't yet know that "nobody writes anything" at your company. In general, like another poster said, docs must live as close as possible to the code. LLMs are fantastic at keeping docs up to date, but only if they're in a place that they'll look. If you have a monorepo, put the docs in a docs/ folder and mention it in CLAUDE.md. ADRs (architecture decision records) aren't meant to be maintained, are they? They're basically RFCs, a tool for communication of a proposal and a discussion. If someone writes a nontrivial proposal in a slack thread, say "I won't read this until it's in an ADR." IMHO, PRs and commits are a pretty terrible place to bury this stuff. How would you search through them, dump all commit descriptions longer than 10 words into a giant .md and ask an LLM? No, you shouldn't rely on commits to tell you the "why" for anything larger in scope than that particular commit. It's not magic, but I maintain a rude Q&A document that basically has answers to all the big questions. Often the questions were asked by someone else at the company, but sometimes they're to remind myself ("Why Kafka?" is one I keep revisiting because I want to ditch Kafka so badly, but it's not easy to replace for our use case). But I enjoy writing. I'm not sure this process scales. |