At Saywise, we ship fast. That's a feature, not a bug—but it comes with a real cost: documentation drifts, edge cases slip through, and by the time you realize a README is stale, three more things have changed. We were running into two specific problems. First, our core docs—CLAUDE.md, AGENTS.md, README.md—were constantly out of sync with what we'd actually built. With the pace of iteration we were moving at, keeping them current felt like a losing game. Second, even with solid PR review practices, we wanted an extra safety net: a systematic way to catch issues in code that had already merged, especially patterns we might miss in the moment. We decided to automate both with Claude Routines. The setup was straightforward in concept but required real iteration on the prompt itself. We configured a routine to run every 24 hours, early in the morning, that would: Pull all PRs merged in the last day. Run a fresh code review on them, looking for logic issues, edge cases, and potential bugs we might have missed in the moment. Audit our key documentation files against the current codebase and flag anything that looked stale or inaccurate. Create PRs for any fixes or updates it found. Post a summary to our engineering Slack channel so the team could see what it caught and what it changed. The prompt tuning was the real work. We had to be specific about what "stale" meant, what kinds of issues we actually cared about flagging, and how aggressive we wanted the routine to be. Too strict and it became noise; too loose and it missed the point. After a few iterations, we landed on something that felt right. The impact has been real. Our docs stay current without anyone having to manually track them. We catch subtle bugs and inconsistencies that slip past human review in the moment. And the Slack summaries give the team visibility into what's happening—it's become a useful daily checkpoint, not just a bot running in the background. It's not a replacement for careful code review or thoughtful documentation. But as a daily layer of protection and maintenance, it's been exactly what we needed at our pace.
