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.
A paid expert assistant fails when polished language hides weak sources. Define the questions it answers, the evidence it must show, freshness expectations, what it refuses, and when it routes the customer to a person before designing the paywall.
Record a baseline before launch, then compare completed jobs, corrections, safe refusals, time, support load, and cost.