Long Game

Automate the job nobody complains about

28 September 2026

Long Game

Your first AI automation should be the job nobody in your office complains about.

Most owners start with the job that drives them mad. It feels like the obvious place to begin, and that's where people go wrong.

The job that annoys you is usually a person, an exception or a judgement call. AI handles those worst, because every case is a little different and the cost of a wrong answer lands on a client.

The job nobody mentions is the better bet. It happens every week and follows the same steps every time, which is exactly why nobody thinks about it.

Take a small solicitor's office. The job everyone dreads is ringing the client who is disputing their bill. That needs someone who knows the file and knows the client.

The job nobody talks about is drafting the engagement letter and opening the new file. It has run the same way for years.

Before I hand a job like that to AI, I check two things.

First, have the rules stayed the same for a year? If they change every month, you'll spend more time fixing the automation than you ever spent doing the work.

Second, would a mistake show up within a day? A wrong name on an engagement letter gets spotted the moment the client reads it. A wrong figure buried in a file nobody opens for six months can sit there until it costs you money.

You'll tell yourself you'll check everything the AI does. By week two, you won't, so the job has to be one where mistakes find you quickly.

Pick the dull job where a wrong answer gets you a phone call the same day, and start there.