Most AI procurement goes wrong at the evaluation stage, not the implementation stage. These are the questions that separate a real answer from a confident one.
Before signing, establish six things: what the model was validated on and whether that population resembles yours, how performance is monitored after go-live and who watches it, what the system does when it is uncertain, who is accountable when output is wrong, what happens to your data, and how you exit. A vendor who cannot answer these precisely is telling you something useful.
In most healthcare AI failures we see, the deciding mistake was made before implementation started. The organisation could not tell a substantive answer from a fluent one, so it bought on demo quality and reference customers. Both are weak signals. A good demo shows the system working on data the vendor chose.
Under Singapore's AIHGle 2.0, the deployer carries responsibilities that cannot be transferred to the developer, which makes this conversation part of your governance obligation rather than just good practice.
And the one people forget: what happens if we want to leave in three years. Can you extract your data in a usable format, and what stops working the day the contract ends?
The purpose of this list is not to catch vendors out. Good vendors welcome these questions, because answering them well is how they differentiate from competitors selling on demo polish. The ones who get uncomfortable are telling you something you need to know.
The harder problem is that asking the question is not the same as evaluating the answer. Any procurement team can read a checklist aloud. Knowing whether a validation study actually supports the claim, or whether a proposed monitoring approach would realistically catch drift, requires enough fluency to ask the follow-up. That is the capability gap we spend most of our time closing, and it is why we would rather train the people in the room than hand over a longer checklist.
One rule we give clients: never let the vendor be the only party in the room who understands the system. If that is the case, you are not negotiating, you are being briefed.