Founder Notes
Designed for the Owner, Used by the Saturday Shift

Most compliance software is designed for the owner and used by whoever is working Saturday afternoon.
I keep returning to this gap because it explains most of what I see when readiness fails in practice, and because it is a product problem masquerading as a training problem.
The owner knows where everything lives. They designed the folder structure, they know which supplier is which, and they can find a specific document in about ninety seconds. They are also, statistically, not present at the moment somebody walks in and asks for one.
The person who is there knows the products, the register and the customers. They have never had a reason to open the records system. They do not know it is organised by supplier rather than by the thing being pointed at, or that three documents are still sitting in an email thread.
So the honest test of readiness is not "do you have your records". Everyone has records. The test is whether the person actually on shift can produce the right document, for the specific item being pointed at, in the length of time somebody is willing to stand there.
That reframing changes the design problem substantially. It stops being a storage feature and becomes a retrieval-under-pressure feature, for a user with no context, no training budget, and no stake in the filing system.
Which means most of the usual instincts are wrong. Folder hierarchies assume you know the taxonomy. Search assumes you know the term. Both quietly require the institutional memory of the person who is not there.
The version that works is indexed by the question being asked — the identifier printed on the object in front of you — and is usable by someone who has never seen it before, on their first try, while being watched.
Most products in this space are still solving for the owner. I think that is simply the wrong user, and no amount of polish on the owner's experience closes the gap.