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Edition 05 · Free PDF · Nurture

The AI Vendor Interrogation Kit

The questions to ask before you sign — and the scoring card that tells you when to walk away.

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8 pages 8 min read A4 print-ready Free PDF

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An AI vendor just gave you a demo. It looked impressive. But will it work with your data? Where does your data go? What happens when the contract ends? This 8-page guide gives you 20 questions to ask every AI vendor, a scoring card to rate their answers, and a walk-away threshold — because the best deal is sometimes no deal.

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What's inside

6 sections, 8 pages.

  1. Why demos lieEvery AI demo uses cherry-picked data and a rehearsed script. The guide explains what the demo won't show you — and how to find out anyway.
  2. The 20 questionsTwenty questions, four categories: data, reliability, cost, exit. Print the list. Take it to every demo. The vendor's reaction tells you more than their answers.
  3. The scoring cardRate each answer 1–5. Total below 60? Walk away. Between 60 and 80? Proceed with a short pilot. Above 80? Worth a serious conversation. The card fits on one page.
  4. Red flags that mean walk awayFive red flags that should end the conversation immediately. The most common one: the vendor can't explain where your data lives after the contract ends.
  5. What a good answer sounds likeA good answer is specific, references their infrastructure, and includes a number. A bad answer is vague, references 'the cloud', and deflects to their sales team.
  6. The contract clauses that matterThree clauses that protect you: data export format, spending cap, and a 30-day exit window. If the vendor won't sign them, you know why.
Common questions

Questions this guide answers.

What should I ask an AI vendor before buying?
Twenty questions, grouped into four areas: data handling (where does my data go, who can see it, what happens when the contract ends), reliability (what's the uptime SLA, what happens when the model changes, how do you handle errors), cost (what's included in the price, what triggers overage charges, can I set a spending cap), and exit (can I export my data, what format, how long do you keep it after I leave). The guide lists all 20 with explanations of what a good answer sounds like.
How do I evaluate an AI vendor?
Use a scoring card. Rate each of the 20 questions on a 1–5 scale. A total below 60 means walk away. A total between 60 and 80 means proceed with caution and a short pilot. Above 80 means the vendor is worth a serious conversation. The guide includes the scoring card as a printable worksheet.
What are the red flags when buying AI software?
Five red flags: the vendor can't explain where your data is stored; there's no spending cap on usage-based pricing; the contract auto-renews for 12 months with no pilot period; the vendor won't let you export your data in a standard format; and the demo uses a different model than the one you'll get in production. The guide explains each red flag and what to do if you see one.
How do I compare AI vendors?
Run the same 20 questions past each vendor and compare the scoring cards side by side. Don't compare features — compare answers. A vendor with fewer features but honest, specific answers about data handling and exit terms is usually the safer bet. The guide includes a comparison template.

Other guides in the series

01Where AI Actually Helps 02The 30-Day AI Pilot 03Your Data, Your Rules 04Writing AI Instructions That Actually Work 05The AI Vendor Interrogation Kit (this guide) 06Your First AI Employee 07Set Up Your Own AI Agent 08Is This Worth Doing? 09Build the Thing 10Get Found 11Get the Conversation 12Close the Deal

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