What to Ask an AI Vendor Before You Sign Anything

San Diego business owners get pitched AI tools constantly. The demos look great, the ROI claims sound compelling, and the sales rep has an answer for everything. But once you sign, the real product reveals itself — and it’s often not what you expected.

Here’s a short list of questions that separate vendors worth working with from ones that will waste your time and money.

1. Can I see this running on a business like mine?

Not a polished demo environment. Not a generic walkthrough. A live instance — ideally at a company in your industry and size range. If the vendor hesitates or says it’s “not possible for privacy reasons,” that’s a flag. Good vendors have reference customers they’re proud of.

2. What does implementation actually look like?

Every AI tool has a go-live phase. How long does it take? Who does the work — you or them? What happens when it breaks during that phase? If the answer is vague or optimistic, ask them to walk you through a recent customer’s implementation timeline.

3. What data does this touch, and where does it go?

If the tool integrates with your CRM, email, or customer records, you need to know who hosts the data, whether it’s used to train their models, and what happens to it if you cancel. This matters for compliance (HIPAA, CCPA) and for basic security hygiene.

4. What does the contract say about cancellation?

Some AI vendors lock you into annual contracts with auto-renewal clauses buried in the terms. Ask directly: what’s the notice period to cancel, and do I own my data when I leave? If they can’t give you a straight answer, read the contract before you sign.

5. Who supports me after the sale?

The salesperson will not be your point of contact after you sign. Ask to meet the implementation or success team before you commit. Find out what the support SLA looks like — is it email-only? Chat? A dedicated rep? This matters when something breaks on a busy Friday afternoon.

6. What happens when the AI gets it wrong?

Every AI system makes mistakes. The question isn’t whether it will fail — it’s how. Ask for examples of failure cases and how the vendor handled them. A vendor that can’t discuss failure clearly hasn’t thought carefully about their product.

The Underlying Question

All of these questions are really asking one thing: are you selling me a tool, or are you actually trying to help my business? Vendors focused on the second answer will welcome these questions. Vendors focused on the first will get defensive.

If you’re evaluating AI tools and want an independent perspective, reach out — we help San Diego businesses cut through the noise and find what actually fits.