12 Questions That Separate Serious AI Buyers from the Rest

Short summary

Enterprise AI vendor selection hinges on asking hard questions about data handling, product reliability, and long-term relationship dynamics—not just month-three demos. This guide outlines 12 critical questions across four categories: data flow and compliance, error honesty and retrieval quality, month-18 relationships and renewal pricing, and exit strategy. Vendors evasive about infrastructure details, incident history, or switching costs reveal fundamental differences in how they operate at scale.

• •Ask specific data flow questions (servers, external services, retention) and get vendor subprocessor lists
• •Test vendor honesty by asking about limitations; measure retrieval accuracy on older documents
• •Understand long-term relationship costs: month-18 service quality, renewal pricing at 50% growth, organizational accountability
• •Evaluate exit path: data export formats, handling of M&A scenarios, platform lock-in risk

Generated with AI, which can make mistakes.