Seven questions to ask anyAI vendor before you sign

Every AI vendor demo follows the same shape. Something impressive happens on screen, a number appears, and forty minutes later you have seen a great deal and learned very little about what you would actually be signing.

These are the seven questions that change that. They are short, they are not technical, and you can ask all of them in a first call. Ask them of us too — if we cannot answer them plainly, that tells you something worth knowing.

01 — Where does our data physically sit, and who else can read it?

Push past "it's encrypted" and "it's secure." Both are true of nearly every system and neither answers the question.

What you want is a specific location, a specific list of parties with access, and a specific mechanism. "Our staff cannot access customer content" is a claim; "our staff cannot access customer content because the system runs inside your network with no outbound route, which you can verify with a packet capture" is a mechanism. Mechanisms can be checked. Claims cannot.

A weak answer sounds like: enterprise-grade, bank-level, fully compliant. A strong answer sounds like: here is the diagram, here is what we can see, here is how you turn our access off.

02 — What happens to our data if we leave, and what happens if you go out of business?

Every vendor has an answer for the first half. Fewer have one for the second.

You are buying from a young company in a fast-moving market. That is not a reason to avoid them — but it is a reason to ask what your position looks like if they disappear in three years. Does your system keep operating? Do you hold the licence? Can you export your own material without their cooperation?

If the honest answer is that everything stops working, you are not buying infrastructure. You are renting access, and you should price it accordingly.

03 — What does this cost when we use it twice as much?

This question separates the two pricing models more clearly than any spec sheet.

Metered pricing means your bill scales with adoption. That sounds fair until you realise it means the tool working well is the thing that makes it expensive — and that your team learns to ration it. Fixed-cost systems have the opposite property: heavy use makes each use cheaper.

Neither is automatically correct. Light usage genuinely favours renting. But you should know which curve you are on before you sign, not eighteen months later when finance asks why the line item tripled.

04 — Who runs this after it is installed, and what do they need to know?

A system nobody in your organisation can operate is a system you will stop using.

Find out honestly whether your existing IT person can run it, or whether you would need to hire a specialist. Ask what routine maintenance actually involves and who does it. Ask what happens at 6pm on a Friday when it stops responding, and ask for the number that gets answered.

Then ask for the runbook. A vendor who hands you documentation that would let you operate without them is confident in the product. A vendor who cannot is selling dependency.

05 — Can you show me it failing?

The most useful question on this list, and the one almost nobody asks.

Every demo shows the happy path. Ask to see what happens when the model does not know an answer, when a document is malformed, when two people ask at once, when the machine is under load. Ask what the error looks like to a member of staff who is not technical.

You are not trying to catch anyone out. You are trying to find out whether the people building it have thought about the ninety percent of operating life that is not the demo.

06 — What are we not a good fit for?

A vendor who says their product suits everyone has either not thought hard about it or is not telling you.

Real answers exist. Some workloads genuinely belong on public frontier models. Some organisations are too small for owned hardware to make sense. Some problems are process problems that AI will not touch.

The willingness to name those cases is the single best proxy for whether you will get straight answers later, when something is going wrong and you need the truth quickly rather than a comfortable one.

07 — What would you need from us to give an honest quote?

The answer reveals the whole engagement model.

If they can quote immediately, they are selling something standard — which may be fine, but know that you are getting a package rather than a fit. If they need to understand your workflows, your data, your headcount, and your existing hardware first, that is a longer process and usually a better outcome.

What you are listening for is whether the diligence happens before the contract or after it. Work discovered after signing becomes a change order.

The vendors worth working with are the ones who will talk you out of the wrong purchase.

Using these

Send them ahead of the call. The quality of the written response, and how quickly it comes back, will tell you most of what you need before anyone joins a meeting.

Then ask them again live, and watch which ones produce a pause. The pause is the useful part.