Every business owner is now getting pitched AI, usually by someone who has never fixed a printer. Five questions sort the installers from the demos.
Ask: where does my data physically go? If the answer is a name like a hosting brand, press it: which country, which retention window, who can read it, and does the contract actually say that or does a policy page say it today and can say otherwise tomorrow. A vendor who can answer precisely operates transparently. A vendor who waves at their own privacy policy is telling you your prompts are the product.
Ask: what happens when the platform changes? Any hosted model can be repriced, retired, or retrained between your contract renewals. Every workflow you built on a rented frontier is portable only by accident. The honest version of the question is: what does migration cost me, and who owns the prompts, the transcripts, and the knowledge base we built together? It should all be yours.
Ask: what does the phone bill look like in December? Per-use pricing sounds fair in demos and different at volume. Have the vendor model your real call or ticket count, the busy month and the quiet month, and put an alert threshold on it in writing. If they will not, they are buying you for the meter.
Ask: who is accountable when it breaks at 2 a.m.? An AI service is a service, which means a person answers. Find out response windows, escalation contacts, and whether support happens over email with a bot or with a tech who has been in your wiring closet.
Ask: can I see it working on my content? Not the demo reel. Your FAQs, your price list, your hours, your caller patterns, inside a week. A vendor who has built real deployments can spin that up quickly because the training pipeline already exists. A first-timer will suddenly find reasons to show you a slide deck instead.