How to evaluate any AI tool pitch in 10 minutes
Aug 2026
Every vendor call this year has an AI angle. Most of the pitches sound similar, so I've settled on a short checklist that separates the useful ones from the noise quickly.
Ask what happens when it's wrong
If a vendor can't clearly describe their failure mode, and who's accountable when the model gets something wrong, that's the answer. Confident demos hide this by design.
Ask where your data goes
Not as a compliance exercise, as a product question. If they can't explain data flow in one sentence, the product wasn't built with that question in mind.
Ask for the boring use case, not the demo one
Demos are optimized for the moment. Ask instead: "walk me through the least exciting task your customers use this for every day." That's where you learn if it's actually load-bearing.
The takeaway
None of this requires deep technical knowledge, it requires being willing to ask a plain question and sit with an uncomfortable non-answer.
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