Print this. Put it next to the contract.
☐ Can you describe exactly where your data goes during inference? Not "the vendor has enterprise terms." Where does it go, which servers, which subprocessors.
☐ What is the price at renewal if you have 2x the users you have today? Get the number in writing before you sign, not as a line item for "future discussion."
☐ If this vendor shuts down in 18 months, what happens to your data? What happens to the workflows you built? Can you export everything in a usable format?
☐ Who in your organization is accountable for this tool being useful in month 14, not just month 3? Is that accountability in their job description or just implied?
☐ Has your legal team seen the DPA, not just the MSA? Has anyone read the subprocessor list?
☐ If you removed this tool tomorrow, which workflows would break? Are you comfortable with that level of dependency?
☐ What does the vendor's support look like after the onboarding period ends? Call an existing customer who is 18 months in and ask them directly.
☐ Have you tested what happens when the AI gives a confident wrong answer to an employee in a high-stakes situation? What does wrong look like, and how would you know?
☐ Is the productivity projection in the business case based on your data or the vendor's published benchmarks? Those are not the same number.
☐ Three months from now, what metric will tell you this was worth it? Define it now, not after you have already committed.
If you cannot answer six or more of these, slow down. The urgency you are feeling is mostly manufactured by the sales cycle, not by any actual business risk of waiting four more weeks.
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