LESSON 2 OF 5
Work with long documents properly
BY THE END OF THIS LESSON
Get reliable answers out of material far too long to read yourself.
A long context window is not a search engine
Claude can hold a great deal of text at once, and people conclude they can drop in 200 pages and ask anything. You can — but the quality of what comes back depends heavily on how you ask.
A vague question against a long document produces a vague summary. A precise question against the same document produces something genuinely useful.
Ask for location, not just content
Always require it to say where something came from — the section, the page, the clause, the speaker.
This does two things. It makes the answer checkable in seconds instead of minutes. And it makes fabrication much harder, because an invented claim has no location to point at.
Ask what is missing
The highest-value question against a long document is rarely "summarise this". It is:
"What does this document not address that someone in my position would need to know?"
Contracts, reports and specifications are defined as much by their omissions as by their contents, and omissions are exactly what a human skim-read misses.
WORKED EXAMPLE
VAGUE ASK
Summarise this 60-page supplier contract.
PRECISE ASK
Working from this contract only: 1. Every obligation that falls on us, with the clause number. 2. Every deadline or notice period, with the clause number. 3. Anything that automatically renews or escalates. 4. What is NOT covered that a buyer would normally expect — liability caps, exit terms, data handling. Quote the exact wording for anything in 1–3. If something is ambiguous, say so rather than resolving it.
The summary tells you what the contract says. The second tells you what it commits you to, where to look, and what is missing — which is the actual question, and the one a skim-read never answers.
YOUR TURN
Interrogate a long document instead of summarising it.
RUN THIS
I am going to give you a long document. Do not summarise it. Instead: list what it obliges me to do, every date or deadline in it, anything that renews or escalates automatically, and anything a person in my position would expect to find that is absent. Give a location for every point. Where the wording is ambiguous, say so instead of picking an interpretation. Document: [paste or attach]
What a good result looks like
The "absent" list is where the value is. Check two or three locations against the source to confirm it is reading rather than inferring.
KNOWLEDGE CHECK
Answer all 3 correctly to complete this lesson.
1. Why require a location for every claim about a document?
2. What is often the most valuable question to ask of a long document?
3. What should it do with ambiguous wording?
REMEMBER THIS
Demand locations, and ask what the document leaves out.