Before signing with any AI vendor, get clear written answers on data handling, model training, integration effort, pricing at scale and exit terms. A vendor that can’t answer these plainly in writing is telling you something important.
The nine questions to ask every vendor
| # | Question | Why it matters |
|---|---|---|
| 1 | Will our data be used to train your models? | Determines whether your proprietary information could influence outputs for other customers. |
| 2 | Where is our data stored, and for how long? | Affects compliance, especially for regulated industries and public agencies. |
| 3 | What happens to our data if we cancel? | You want a written deletion commitment, not a verbal promise. |
| 4 | What does pricing look like at 3x our current usage? | Many tools price attractively at pilot scale and expensively at production scale. |
| 5 | Which integrations are truly out of the box, and which are custom work? | Custom integration is often the real cost of adoption, not the license fee. |
| 6 | How do you handle model errors or made-up output? | Every AI tool makes mistakes. You need to know what review process and recourse exist. |
| 7 | Can we speak with three reference customers our size? | A vendor that only serves much larger or smaller companies may not fit your needs. |
| 8 | What’s the contract term, and how do we exit? | Avoid auto-renewing annual contracts with no clear off-ramp. |
| 9 | Who owns the output the tool generates? | Matters for anything customer-facing or used in decisions. |
Red flags worth walking away from
- Pricing that’s only available on a call, with no ballpark in writing.
- Reluctance to put data-handling answers in writing, even in an email.
- No clear answer on what happens to your data after cancellation.
- Reference customers the vendor can’t actually connect you with.
Why independent matching helps
Most buyers only get through this checklist with one or two vendors before decision fatigue sets in. An independent matching process runs it across several options at once, so you compare real answers side by side instead of trusting each vendor’s pitch. If we have any relationship with a vendor on your shortlist, we disclose it in writing first. See our AI Strategy & Governance practice.
Frequently asked questions
Should I ask for these answers in writing?
Yes. A verbal answer on a sales call isn’t enforceable. Put data-handling and cancellation terms in the contract itself.
Is it reasonable to test multiple vendors at once?
Yes, especially for a first purchase. Most reputable vendors expect a comparison and will support a limited trial.
Founder & Principal, Lost Tree Consulting. Former state insurance regulator and CEO. About Heather →