Choose the paid job
Start with a repeated, expensive decision or handoff, not with a generic chatbot. Name the buyer, triggering event, approved inputs, useful output, accountable owner, and the measurable sign that the job is complete. If you cannot test the output, you cannot promise it responsibly.
Expertise is usually tacit: you notice signals, reject weak evidence, ask a better next question, and know when the case is unusual. Uploading a pile of files captures information but not the decision method that makes it useful.
Record a baseline before launch, then compare completed jobs, corrections, safe refusals, time, support load, and cost.