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Evaluate a vendor or tool properly

Before a trial, a contract, or a migration you cannot easily undo.

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Help me evaluate this vendor beyond the marketing page.

1. What problem does it actually solve, in plain terms, and what does it merely claim to solve?
2. What is the failure mode of tools in this category? What do people complain about six months in, not on day one?
3. What questions should I ask that the sales team will not want to answer? Give me the exact wording.
4. What should I test during a trial that would reveal a real weakness? Design three concrete tests.
5. What is the exit cost: data export, lock-in, contract terms, retraining?
6. Who is the wrong customer for this tool? If that describes me, say so.

Separate what you know about this specific vendor from what you are generalising about the category.

Vendor or tool:


What I need it for:

Making it yours

  • Paste your own material where the prompt asks for it. Everything above that line is instruction, not content.
  • Delete any rule that does not apply to you. A shorter prompt that fits beats a thorough one that does not.
  • If the answer comes back vague, add a line saying what you do not want. Constraints work better than encouragement.

Comparing options. Weighing real candidates against your criteria, from a quick side-by-side to a full vendor evaluation.

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