Workflow Automation Checklist: What to Automate First (and What to Leave Alone)

The first automation a small team builds is usually the wrong one — the exciting

one, not the valuable one. This checklist is the boring filter that picks candidates

that actually pay back, in the order that matters.

The 4 questions (in order)

1. Does this happen at least weekly? Automation pays back through repetition.

A once-a-quarter task that takes 10 minutes isn't worth the build, even if the

build is fun.

1. Is the task's rule writable in one sentence? "Every completed order gets a

confirmation email" — writable. "Review whether this lead looks promising" — not

yet. If you can't state the rule in one sentence, you don't understand the task

well enough to delegate it to a machine.

1. Is failure visible within a day? Good automation candidates fail loudly or

observably (email didn't send, invoice missing). Bad candidates fail silently for

weeks (data enrichment, anything where wrong output looks like right output).

1. Can a human check the output in under a minute? If verification is expensive,

you've automated the task and manualized the review — the worst trade.

Four yeses = automate next sprint. Two or fewer = leave it alone for now.

The 3 red flags (any one means don't automate yet)

• The process changed in the last month. You'd be automating a snapshot of a

moving process. Stabilize first.

• Nobody currently does the task end-to-end. Automation needs a reference

human; without one there's no ground truth to check against.

• The task exists to catch rare, expensive errors. Human review IS the control

here; automate the logging, not the judgment.

Keep a human in the loop, cheaply

• Run automation in "shadow mode" for the first week: it does the work, a human

spot-checks, nothing goes to customers yet.

• Define the kill switch before launch: the one command or flag that stops it, and

the name of the person allowed to pull it.

• Log every run — input, output, and whether the checker agreed — even informally.

That log is your evidence for expanding the automation (or the reason to kill it).

What to automate first (typical small-team pattern)

Confirmation emails, invoice generation and reminders, report generation, backup

verification alerts, repetitive data-entry between two tools you control. All four

yeses, usually. What to leave alone: anything involving judgment about people —

hiring, pricing decisions, escalating an angry customer. Automate the *paperwork

around* those, never the decision.

The template version of this checklist (with the shadow-mode run sheet) is in our

Ops Starter Kit — link goes live when our payout rail unlocks.

Deciding what to automate? The Automation Starter Pack ($19) ships the 4-question filter as a worksheet, 12 workflows ranked by payback, and the one-page spec that keeps automations honest — launch month: 30% off with code HIVE-LAUNCH30.