Automate the boring path
Automation should remove the steps no human should have to remember — not replace the judgment only a human can bring.
Key takeaways
- The best automations encode a decision you've already made — a reflex you'd apply by hand every time — and the test is simple: would a human do the exact same thing here every time without thinking? If the answer depends on judgment, it isn't boring, it's work, and you should keep it.
- The boring path is the dangerous path, because nobody forgets the interesting parts of their job but they do forget the small mechanical steps that are beneath attention, so automating them is a reliability move, not just a convenience.
- Make automations legible: every automated action should leave a trace saying what fired and why, because an automation you can't see is a haunting, and legibility is also what makes a stale rule safe to delete.
- Draw a bright line on destructive operations — bulk-archiving, mass-closing — by flowing them through a propose-then-approve gate with what's allowed to run unattended coming from a single registry: automate the boring path aggressively, gate the dangerous path deliberately.
Automate decisions you have already made
The best automations encode a rule you would apply by hand every single time if you had the patience and never forgot. When a bug is marked urgent, notify the on-call. When an issue lands in the design team's intake, add the design-review checklist. When a pull request merges, move the linked issue to 'In review'. These are not decisions; they are reflexes you are tired of performing manually.
The test for whether something should be automated is simple: would a human do the exact same thing here, every time, without thinking? If yes, the rule is safe to hand to the machine. If the answer depends on context, judgment, or how you are feeling that day, it is not boring — it is work, and you should keep it.
The boring path is the dangerous path
Counterintuitively, the routine steps are where the worst failures hide. Nobody forgets the interesting parts of their job. They forget to add the label, to notify the right channel, to update the status, to attach the runbook — the small mechanical steps that are beneath attention precisely because they are routine. And the one time the step is skipped is the time it mattered.
Automating the boring path is therefore not just a convenience; it is a reliability move. The machine never gets bored, never has a bad morning, never forgets the third step because it got interrupted by Slack. Consistency on the mundane frees human attention for the parts that actually need a brain.
Make automations legible
An automation you cannot see is a haunting. Things move on their own, statuses change, notifications fire, and nobody remembers why. The cure is legibility: every automated action should leave a trace that says what fired and why — a visible rule, an audit entry, an annotation on the record. If you cannot explain in one sentence why an issue just changed state, the automation is a liability, not a tool.
Legibility is also what makes automation safe to delete. Rules accumulate; teams change; a rule that made sense a year ago is now firing nonsense. If every automation is named, visible, and traceable, pruning it is a five-minute cleanup. If it is buried magic, it survives forever out of fear that something depends on it.
Guardrails on the destructive stuff
There is a bright line between automating a notification and automating a deletion. Bulk-archiving, bulk-updating, mass-closing — the irreversible operations — deserve a different posture. Automation can propose them; a human should approve them. The cost of a wrong notification is mild annoyance; the cost of a wrong bulk delete is a very bad afternoon and possibly a very bad quarter.
Design the system so destructive actions flow through a propose-then-approve gate, and so that what is allowed to run unattended comes from a single registry rather than scattered config nobody audits. Automate the boring path aggressively; gate the dangerous path deliberately. The two rules are not in tension — they are the same instinct, applied where each belongs.