Run a three-item pilot before you hand over the whole job

Say you have a folder of receipt PDFs to rename and file by month. It's a good job to hand off, and a good job to get wrong at scale: if the first assumption is off, every file inherits it. (This is a hypothetical scene, for illustration.)

A pilot is cheap and tells you a lot. The routine works for any repetitive job, whether a person, a script or an AI assistant does it:

1. Pick three items on purpose: an easy one, a typical one and an awkward one. The awkward one is the file with the missing date, the odd layout or the strange name.
2. Write the brief for the whole job, not for the pilot. The point is to test the brief.
3. Run only those three. Read the results the way you would read the finished job.
4. Check each one against your finish line. Did the awkward one get handled, or quietly skipped?
5. Settle every ambiguity you noticed, in writing: which date to trust, what to do when a field is missing, where uncertain items go.
6. Scale up in steps: a small batch, then a larger one, then the rest. Let how clean the last step was decide how big the next one is.

A pilot also gives you a first read on cost. Compare the estimate for the pilot with what it actually cost before you decide whether the full run is worth it.

Octuo is a personal assistant and one starting point for work across AI, tools and specialist services. Cost is previewed before and reported after every turn, so a pilot's cost is something you can read rather than guess, and it reports back when a job is done. Octuo is available for macOS.