Automate what is boring, frequent, and error-prone: deploy scripts, test runs, lint, dependency updates with CI gates, backup verification, certificate expiry checks.
Do not automate ambiguous product decisions or one-off migrations without human review.
The ROI test: hours saved per month vs hours to build and maintain automation.
Start with toil that wakes people at night — restore scripts, smoke tests post-deploy, rollback buttons.
Automation should fail loudly and visibly, not silently replace thinking.
