6 min read

How to choose your first AI automation (most people pick wrong)

The instinct is to automate the most annoying task. The better test is what slips every week, has a judgeable output, and produces something you can measure.

Last updated 16 August 2026

Almost everyone picks the most irritating task. That is usually the wrong one, because irritating rarely means valuable and often means complicated.

Three tests a good first automation passes

  • It slips every week. Not occasionally — reliably. You already know it matters and you already know it is not happening.
  • You can judge the output in seconds. A social post you can approve at a glance beats a research report you would have to verify for an hour.
  • It produces something countable. Posts published, enquiries answered, quotes sent. If you cannot count it, you cannot tell in thirty days whether it worked.

What to avoid first

  • Anything customer-facing with legal or financial consequence.
  • Work that depends on context living only in someone's head.
  • Processes you are about to change anyway.
  • The task you find annoying but which happens twice a year.
The thirty-day test

Whatever you pick, define now what "it worked" means in numbers, and check on day thirty. Teams that skip this end up arguing about vibes and usually cancel something that was working.

Related: what agentic AI actually means and the real cost of running agents.

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