I have watched more enterprise AI tool demos than I can count. The format has become predictable enough that I spend most of my attention during demos looking for specific things the vendor does not intend to show me.
These five signals have been more predictive of real-world performance than anything that appears in a prepared demo.
The first red flag is how the tool handles a question where the answer is not in the indexed content.
I always ask this question at some point during a demo, framed as a genuine inquiry rather than a test. Something specific enough that I can be confident it is not covered by whatever content has been indexed for the demo. The tool's behavior here tells you more about its reliability than ten impressive answers on covered topics.
The tools worth considering acknowledge the gap: they say some version of "I don't have reliable information about this in the available documentation." The tools to be skeptical of generate a fluent, confident, plausible-sounding answer anyway. That behavior in a demo is exactly that behavior in production, applied to real employees asking real questions and trusting the outputs.
