What to Ask an AI Vendor Before You Sign Anything

The AI vendor market is noisy right now. Every software company has slapped “AI-powered” on their website, and a lot of consultants are selling expensive solutions to problems they don’t fully understand. If you’re evaluating an AI vendor or consultant for your business, these are the questions that separate serious partners from empty pitches.

Can You Show Me a Specific Example From a Similar Business?

Not a demo. Not a case study from a Fortune 500 company. A specific, recent example from a business similar to yours in size and industry. If they can’t point to one, ask why. The answer tells you a lot about whether they’ve actually solved this problem before or whether you’d be paying them to figure it out on your time.

What Does Implementation Actually Look Like?

Press for the mechanics. How long does it take? Who from your team needs to be involved, and how many hours? What systems do they need access to? What happens in the first 30 days? Vague answers here usually mean the vendor hasn’t thought through the operational details.

What Happens When It Doesn’t Work?

Every AI system fails sometimes. A good vendor has a clear answer for what the failure mode looks like and how it gets caught. If they tell you the system “won’t fail” or change the subject, that’s a red flag. You want someone who has thought carefully about the edges — and who has a plan for them.

How Do You Measure Success?

Before you start, agree on the number. Is it hours saved per week? Leads responded to per day? Close rate on inbound inquiries? If the vendor can’t name a specific, measurable outcome, they’re not accountable to anything. The best vendors will help you establish a baseline before they start and show you the delta 60–90 days later.

What Does This Cost to Maintain?

AI tools often have ongoing costs: software subscriptions, token usage fees, periodic tuning. Ask for a realistic estimate of what you’ll be spending 12 months after launch, not just at the start. The initial build cost is rarely the full picture.

Who Owns the Work?

If the consultant leaves, or if you want to move on, do you have the ability to maintain or modify what was built? Some vendors build systems you can only run through them. Others hand you something you actually own. Know which kind you’re getting before you sign.

These questions don’t require technical knowledge to ask — but the answers will quickly tell you whether a vendor is worth your time. If you’re evaluating AI options for your business, we’re happy to talk through what to look for.