The Evaluation Problem
Enterprise AI vendor evaluations have become a parody of due diligence. RFPs with 200 questions. Proof-of-concept projects that take 8 weeks. Reference calls with hand-picked customers. At the end of this process, most companies know less about the vendor's actual capabilities than they did after the first demo.
Here is a faster approach. Sixty minutes, five questions, and you will know more than a 200-question RFP will ever tell you.
The Five Questions
Question 1: Show me a failure. (10 minutes)
Ask the vendor to describe a customer deployment that did not go well. How it failed, why it failed, and what they changed. Any vendor that claims they have never had a failure is either lying or has not deployed enough to learn anything. The quality of the failure analysis tells you everything about their operational maturity.
Question 2: Walk me through your architecture, live. (15 minutes)
Not a slide deck. Open a whiteboard and draw the system architecture for a deployment similar to what you need. Ask about data flows, latency, error handling, and monitoring. If the vendor's sales team cannot do this, bring in their engineers. If their engineers cannot do it clearly in 15 minutes, the architecture is either too complex or too poorly understood.
Question 3: What happens when the model is wrong? (10 minutes)
Every AI system produces wrong outputs. Ask the vendor what their system does when this happens. Is there a confidence threshold? A fallback? A human escalation path? How is the error detected? How is the model improved? This question separates vendors who have deployed in production from those running demos.
Question 4: Show me your monitoring dashboard. (15 minutes)
Ask to see the actual monitoring and observability tooling for a production deployment. Not a mock-up. The real thing. You want to see: model performance metrics over time, error rates, latency distributions, usage patterns, and cost tracking. If they do not have this, they do not have production-grade operations.
Question 5: What do you not do well? (10 minutes)
Ask directly where their solution falls short. What use cases should you not use their product for? What scale breaks it? What data types does it handle poorly? A vendor that answers this honestly is a vendor you can trust. One that deflects is one that will surprise you in production.
What This Framework Reveals
These five questions test for the things that actually matter: operational maturity, architectural soundness, production readiness, and intellectual honesty. They cannot be prepared for with a polished sales pitch, which is exactly the point.
The vendor who passes this 60-minute evaluation is worth a deeper engagement. The vendor who fails it would have failed your deployment too, just at much higher cost.