An AI assistant on your phone line or website speaks for your business at 11 pm on a Sunday, when nobody is watching. The demo will always look good. These questions are about what happens off the happy path.
1. Where does it get its answers?
It should answer only from a set of facts you’ve approved: hours, service area, services, policies, FAQs. If it doesn’t know, it should say a person will follow up, not fill the gap with something plausible. Ask to see that fact sheet, and ask what happens when a customer asks something that isn’t on it.
2. What does it say about price?
Unless you’ve decided otherwise, it shouldn’t quote. A made-up price is the fastest way to start a dispute. A good assistant repeats only the pricing language you approved (“inspections are free; repairs are priced after the inspection”) and moves to booking.
3. Who writes to the calendar?
The AI should choose from open times; the code should write the booking and refuse a slot that’s taken. Ask what happens if two customers pick the same time at once, and what happens when a customer wants to reschedule. (We learned that one the hard way.)
4. When does it hand off to a person, and how fast?
Emergencies, angry customers, anything it can’t answer from the facts, and anyone who simply asks for a human. Ask who gets alerted, by what channel, and what the customer is told while they wait.
5. Does it say it’s an AI?
It should, on the first message. Customers handle “I’m the company’s virtual assistant” fine. They don’t handle finding out later.
6. Can I read every conversation?
You should have a plain inbox: every chat, text and call, what the customer needed, what got booked, what was handed off. If you can’t review it, you can’t trust it.
7. If it texts customers, is that set up legally?
Business texting in the US has real rules: consent, carrier registration, honoring STOP immediately, sensible hours. Ask how consent is captured and stored. (Our plain-English notes on texting rules.)
8. How will we know it’s working?
Ask for the before-and-after numbers they’ll report: response time, calls answered, appointments booked, measured the same way before and after launch. If the answer is a dashboard of “conversations handled”, that measures activity, not results.
If you want to see how ours behaves off the happy path, ask us for a live walkthrough. We’ll hand you the keyboard and let you try to break it.