The long document, worked through
Every Swiss SME has one document people keep asking questions about. Here is how to make it answerable, in an afternoon, without a project.
A standard, a supply contract, an insurance policy, a machine manual, a cantonal regulation. Every company has one long document that people repeatedly need answers from and that nobody wants to read again.
With last week’s larger context windows this has become a genuinely practical task. Here is the whole of it.
Step one: choose the right document
Three criteria. It is long enough that nobody reads it fully. Questions about it come up at least weekly. And getting an answer slightly wrong is inconvenient rather than dangerous.
That last criterion is the 12 September question three, and it is the one that rules out the tempting candidates. Do not start with anything where a wrong answer reaches a customer or a regulator unchecked.
Step two: collect the questions people actually ask
Not hypothetical ones. Go to the two or three colleagues who field these questions and write down the last ten real ones.
This takes twenty minutes and is the step that determines whether the exercise works. Real questions are specific and awkwardly phrased; invented ones are clean, which is why testing with them misleads.
Step three: put the document in and ask the ten
Ask each question exactly as it was asked to you. For each answer, check it against the document yourself — this is the only time you will do this, and it is what tells you whether to trust it afterwards.
Expect roughly eight good answers out of ten and two that are subtly wrong. The two matter more than the eight: look at what they have in common. Usually it is a question that requires combining two distant sections, which is the known weak point.
Step four: write the instruction down and hand it over
One short paragraph: which document, what to ask, and the sentence check the answer against the section it cites before acting on it.
That is the 23 July reusable prompt at its simplest, and it is what makes this survive past the person who set it up — the 17 November problem, avoided in advance.
What this is not
Not a document system. It is one person pasting one file and asking a question, and for a company of thirty people that is frequently the correct amount of engineering.