This is the list we walk through on a first call. If three or more are unanswered, you do not have a model problem — you have a scoping problem, and it is enormously cheaper to find that out now than in month four.
01
The data is not ready
It lives in six systems, two of them have no usable API, and the one that actually matters is a shared drive of scanned PDFs with a naming convention from 2014. Every AI timeline that skipped this step is now a data-engineering timeline wearing a disguise.
02
Nobody defined correct
Without an evaluation set, “it seems better” is your only quality signal. You cannot tune, defend, or safely change a system you can only judge by feel, and every prompt edit becomes a coin flip nobody is allowed to lose.
03
Ninety-two percent is not a product
A model that is right nine times in ten makes a spectacular demo and an expensive support queue. Essentially all of the product work lives in the tenth case: detecting it, containing it, and routing it to a human before it reaches a customer.
04
Permissions are the actual project
The moment retrieval can read everything, the assistant can say anything to anyone. An index without an authorization model is a data breach with a friendly interface, and retrofitting per-user access into a working prototype is usually a rewrite.
05
The bill scales with usage, not seats
Tokens, times real volume, times retries, times all the context you quietly re-send on every call. Almost no pilot runs that arithmetic, so the number arrives fully formed in month three and the conversation stops being about capability.
06
The workflow never changed
Bolting a model onto a broken process automates the broken process, faster and at higher cost. A large share of the value in any credible AI project is a process redesign wearing an AI costume, and that part is organisational work, not engineering.
07
It works for the person who built it
Adoption is not a launch email and a wiki page. If the new way is not visibly faster than the old way on the first attempt, on a normal day, under normal pressure, your team is quietly back in the spreadsheet by Tuesday.