Failure behavior
Ask the vendor to show the system unsure, over budget, and offline. A serious build has a degraded mode that still helps ("I'm limited right now -- leave your info"), never a blank widget. Ask this page's agent what its failure mode is; it will tell you.
Receipts and approvals
"Fully autonomous" is a red flag, not a feature. The trustworthy pattern: the assistant acts, the owner approves anything that touches the calendar or the outside world, and every action is logged. You stay in command of your own business.
A learning loop with a gate
Every assistant gets things wrong. The question is what happens next: mistakes should be logged automatically, reviewed on a schedule, and FIXED only with the owner's sign-off -- improvement with receipts, not an AI quietly rewriting itself.
Owner-side value
The chat bubble is half the product. The owner needs leads, booked meetings, unresolved questions, costs, and a daily brief that stays quiet when there is nothing to say. If the demo never shows the owner's side, there isn't one.
Privacy you can read
How long do conversations live? What gets saved, and with what consent? A vendor who cannot answer in one sentence has not thought about it. (This page's agent: 30 days, consent cards before anything is stored, no exceptions.)
Integration limits
Calendar, CRM, payments, phone, email -- each integration moves the cost and the risk. Make the list visible before anyone quotes a number, and be suspicious of anyone who quotes one without asking what the assistant must touch.