The AI software market in 2026 is full of products that are "AI-powered" the way 2014 products were "cloud-enabled" — a label more than a capability. These 8 questions cut through the marketing and tell you whether the tool will actually produce business value or end up as another unused subscription.
1. What specific job does this replace, and how do I measure that? Force the salesperson to articulate a specific workflow change with a measurable before/after. If they can't, the value is theoretical.
2. Show me three of your customers using this in production. Not case studies — actual product demos at customer companies. Real implementations look different from sales demos.
3. What is the actual model behind this? Many tools are thin wrappers on Claude or OpenAI APIs. That is fine — but you should know, because it affects pricing, capability, and whether you should just use the underlying API directly.
4. What happens to my data? Where is it stored? How is it used? Is it training their model? For most B2B tools the answer should be "data isolated to your account, not used for training." Anything else needs scrutiny.
5. What is the realistic time to first value? The honest answer is rarely "minutes" or "no setup required." Most real AI tools need 2-8 weeks of setup before producing value. Tools that claim instant value usually do not produce much value.
6. Who on my team will actually own this? If there's no named internal owner, the tool will get installed and abandoned. This is the single biggest predictor of subscription churn.
7. What is the integration story with my existing stack? A great AI tool that does not integrate with your CRM, comms, or knowledge base will be ignored. Ask specifically how data flows in and out.
8. What does the contract say about exit? Annual commits, auto-renewal, data portability on exit. AI vendors are increasingly aggressive on contract terms. Read carefully.