How to pick the first job to hand to AI

By Devan Borsboom

Start where a paper trail exists

The jobs that are easiest to hand to AI are the ones with history. If you have an inbox with months or years of how a process was handled, AI can learn from it. You give it some instruction, and it does the job, because there is data showing what was done before.

When people say AI is "trained" on a task, it usually means it writes itself an instruction manual: a step-by-step process for that one job, built from your examples.

Best of all is a job where you can point to a finished example and say: this is what success looks like, do it like this.

If it lives in someone's head, write it down first

The hard jobs for AI are the ones that were never written down. A process that was explained out loud and never recorded gives AI nothing to learn from. So the first step is getting it into a digital form: dictate it, document it, or record the conversation (with permission). Once it is written down, AI can work with it.

Subjective work is harder still. "Talk to the client and make them feel heard" can be done well in many different ways, and there is no single right answer to copy.

Start low-stakes

The first thing I had AI do was manage my email, then help me plan, then run my calendar. The technical, detail-heavy work I spent years doing as a consultant came much later. I needed to learn how it behaved, and trust it, on work where a mistake was cheap.

Look for the simple wins

Some AI work is technical and takes real effort. Some is simple. One professional I work with wanted one thing: to record client meetings and have AI pull out what matters, instead of taking notes by hand. Simple jobs like that are often the most valuable place to start.

A five-question check

1. Does this job happen every week?
2. Are there past examples of it done well?
3. Can someone check the result in a few minutes?
4. Is a mistake cheap to catch and fix?
5. Would the person doing it today be glad to hand it off?

Five yeses is a good first job. If you want help finding it, that is what the paid look is for.