How to pick the first process to automate (and why most companies pick wrong)

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Companies usually nominate their most painful process first. That’s almost always wrong: the most painful process is painful because it’s complex, political, and full of exceptions — the worst possible first project.

What a good first project looks like

High frequency, clear rules, measurable cost, one owner. Think invoice matching, lead routing, or report assembly — processes where the before/after numbers are undeniable within weeks.

Why momentum matters more than size

A small win in six weeks buys you organizational trust for the bigger builds. A stalled “transformation” buys you a frozen budget.

The 30-minute shortcut

List your five most repetitive workflows, estimate hours per week on each, and score them for rule-clarity. The winner is usually obvious — and it’s rarely the one everyone complains about loudest.