Five questions that decide which AI vendor you should pick

Every demo you're shown will go well. That isn't cheating, it's what a demo is: someone showing the part that works, with data they chose, answering a question they prepared for.

The differences live in what nobody demonstrates voluntarily. Five questions dig them out, they take twenty minutes, and all five can be answered on a first call by anyone who knows their product.

We sell one of these ourselves, so read it with that in mind. The questions are still the right ones, and we would rather compete somewhere they get asked.

1. When the customer says yes to Thursday at seven, is the booking in our system by the time the call ends?

This question decides more than all the others combined, and it's almost never answered with a clean yes.

Common answers that sound like yes and aren't: "we email you the booking request", "it fills in your form", "you get a notification in our app", "we put it in a list for you to approve". Those are messenger services. Somebody at your end still has to transfer the booking by hand, and until they do, the slot isn't taken as far as anyone else is concerned.

The follow-up matters just as much: which system? Your real booking system, the one staff already look at? Or a new one at the vendor's end that you now have to keep in sync with the old one?

Two systems describing the same evening isn't an integration. It's double work plus the risk that they disagree.

2. What does a bad month cost?

Ask for a figure for a real month, not a starting price.

Per-minute pricing sounds cheap until you do the arithmetic. It also means your largest invoice arrives in the month you were busiest, or the month something broke and everyone called. The cost tracks activity, not value.

Ask outright: what's the total at three hundred calls? At six hundred? What's included, what sits outside it, and what do the text messages cost? What happens if we want to stop?

If you can't get a number you could put in a budget, that's an answer in itself. We publish our list prices and charge a flat fee for exactly this reason.

3. What does it say when our booking system doesn't answer?

This is the failure nobody demonstrates, and it's the one that does the most damage.

Booking systems go down. A token expires, an API hangs, an update goes wrong. The question is what the AI says during those hours.

The dangerous answer is "fully booked". A system that's merely unreachable looks identical to a full one, and the difference is that the first has the agent turning away every single customer for days while everything looks calm in the dashboard. You get no alerts, because from the system's point of view nothing happened.

What you want to hear is that it says it can't check right now and hands over to a person. Ask how you find out that it happened.

4. What happens when it doesn't know?

There are three possible behaviours and only one of them is acceptable.

It can guess. It can find something that sounds adjacent and answer from that. Or it can say it doesn't know and hand over.

Ask them to show you. Not describe it, show it: ask something the business doesn't have written down anywhere, and listen to what happens. It's the only way to tell a product built never to be wrong from one built always to have an answer.

Ask where the unanswered questions end up, too. If nobody collects them, you learn nothing from them.

5. Can we call it before we sign?

Not watch a recording. Not watch the salesperson call it. Call it yourselves, with a real question, ideally an awkward one.

Voice quality, waiting, and how it handles being interrupted can't be judged from a video. And a vendor who won't hand over the phone usually has a reason.

The same goes for chat: ask for a link and type in it for ten minutes, with typos and half sentences, the way your customers actually write.

And one question for yourselves

What should it do that you don't already do?

That sounds obvious and rarely is. An AI that answers questions faster than you already answer them well is a cost. The value sits in the conversations that currently don't happen at all: after closing, during the lunch rush, the fourth simultaneous ring, Saturday morning.

Work those out first. Then the five questions above are easy to prioritise, because you know what you're buying.

If you'd like to put the questions to us, book a demo — or call the number on the site and put them straight to Kim, which is the answer to question five.