12 questions to ask before buying a chatbot

The demo always goes well. These are the questions that separate a serious AI agent from an expensive mistake — and what a good answer sounds like for each one.

We have sat in both chairs: selling AI agents, and buying software as a small business. And one thing we know for certain: the demo always goes well. The demo is designed to go well.

What separates a good purchase from an expensive regret is the questions you ask after the demo. These are the twelve we would ask, with the reason behind each one and what a good answer sounds like.

On the honesty of the system

1. What happens when it doesn't know the answer? The most important question on the list. A system that always answers is a system that makes things up. Good sign: "it says it doesn't know and offers to bring in a person". Bad sign: any variation of "it always finds something to say".

2. Can it invent a price, a stock level or a product? Do not accept "the model is very well tuned" as an answer. Language models improvise by design; the question is what deterministic barrier — code, not probability — stops that improvisation from reaching your customer. Good sign: a concrete explanation of that barrier. Bad sign: faith in the model.

3. Does it introduce itself as an AI? Article 50 of the EU AI Act requires that users know they are talking to a machine — and if you sell into the EU, that concerns you regardless of where you sit. Good sign: it discloses itself from the first message, with nothing to configure. Bad sign: "you can switch that on if you like".

On working with your team

4. How does handover to a human work? Ask to see it, not to hear about it. What matters is what your salesperson receives: good sign is the full transcript, the detected intent and the details already gathered; bad sign is a bare notification saying "you have a chat waiting".

5. And if the human doesn't respond? The question almost nobody asks. If your engineer is up a ladder and misses the handover, is the customer left hanging indefinitely? Good sign: the conversation returns to the AI within a few minutes and the customer stays looked after. Bad sign: administrative silence.

6. What happens out of hours? Enquiries arrive when they arrive, not when your team is at its desk — Saturday evening, mostly. Good sign: the system works exactly the same at 10pm on a Saturday as at 10am on a Tuesday, and your team walks in to find the work done. Bad sign: an overnight auto-responder.

On data and compliance

7. Who processes my data, and where? Your sales conversations are your customers' personal data, and under UK GDPR you are the controller. Good sign: a data processing agreement offered without being asked twice, a clear list of sub-processors, and a straight answer on where things are hosted. Bad sign: "legal will get back to you".

8. What happens if I want to switch it off, or switch supplier? The awkward question that tells you the most about a vendor. Good sign: you take your conversations and data away in a usable format, and leaving has no small print. Bad sign: long lock-ins, or silence on export.

On the channels

9. Does it work on WhatsApp AND the website? Your website is where customers find you; WhatsApp is increasingly where they actually want to talk. You need both, with the same brain behind them. Good sign: one agent across both channels, with the web widget installed via a single line of script. Bad sign: two separate products sold separately.

10. Who handles the WhatsApp Business setup? Getting onto the WhatsApp API involves genuine bureaucracy: business verification with Meta, a number, message templates. We wrote up how it works and what it costs. Good sign: the vendor walks you through the whole process. Bad sign: "you sort that out with Meta yourself".

On money and maintenance

11. Does the price depend on volume? Per-conversation pricing has a perverse problem: if the tool works and brings you more customers, your bill punishes you for it. And you cannot budget the year. Good sign: a flat monthly fee you know in advance. The exact structures vary by vendor; ours is published.

12. What maintenance does the content need, and how do I measure whether it works? An agent answers from what it knows, and what it knows goes stale: prices, catalogue, opening hours. Ask who updates that, and what it costs to do so. And ask what you will actually be able to measure: conversations handled, handovers, out-of-hours enquiries. Good sign: updating content is trivial and the metrics come as standard. Bad sign: "email us and we'll change it for you".

The acid test

If a demo dazzles you, save this list and put all twelve questions in writing. A serious vendor answers them without flinching — in fact, they will be pleased you asked, because these are the questions of a buyer who means it.

We built Zatio to be able to answer all twelve properly, and some of the answers — the deterministic hard floors, the automatic rescue, the AI disclosure — are in the product precisely because someone asked us the question first. If you would like to put them to us in person, we are here.

← All articles