4. Asking Questions About Your Own Documents

Everything so far has been you asking the AI to make something. This lesson is the opposite, and it is the more useful direction: you give it a document you already have and ask it questions.

Contract clauses. A letter from an insurer. A 40-page report where you need one number. Terms you agreed to 3 years ago. The lease. This is the use case where people who were skeptical suddenly get it, because the alternative is reading 12 pages of defensive legal English to answer one question.

How to do it, mechanically

Two ways, both fine:

• Paste the text in. Works everywhere, including the free tiers. Best for a few pages.
• Attach the file. Most AI apps take a PDF or a Word document via a paperclip or plus button. Best for anything long.

Either way, the important part is not the mechanics. It is the instruction you wrap around the document.

The instruction that stops it making things up

This is the whole lesson. Put this above your document, every time:

Answer only from this text. If something is not stated,
say "not stated in this text" rather than guessing.

Without that line, an AI asked a question the document does not answer will often answer it anyway, from general knowledge about how contracts usually work. That answer might even be correct in general and wrong about your contract, which is the worst possible combination because it is confident and it is about you.

With that line, you get told where the gaps are, and the gaps are usually the thing you needed to know.

A real one

Here is an actual termination clause, the kind that turns up in every service agreement, and 4 questions a normal person would have:

Answer only from this text. If something is not stated,
say "not stated in this text" rather than guessing.

<document>
7.1 Either party may terminate this Agreement for
convenience upon thirty (30) days written notice.
7.2 In the event of termination, Client shall pay for
all Services performed through the effective date.
7.3 Provider shall deliver all work product in progress
within ten (10) business days of the effective date.
7.4 Sections 4 (Confidentiality), 8 (Indemnification)
and 9 (Limitation of Liability) shall survive.
</document>

Questions:
1. How much notice do I have to give to cancel?
2. Do I get the unfinished work?
3. Is there a cancellation penalty?
4. Does the confidentiality clause end when the
   contract ends?

We ran it. The answers, condensed:

Question	What came back
Notice to cancel	30 days written notice, section 7.1
Unfinished work	Yes, within 10 business days, section 7.3
Cancellation penalty	Not stated in this text
Confidentiality after the end	No, it survives, section 7.4

Look at row 3. That is the row that makes this trustworthy. It did not invent a penalty and it did not tell you there was none. It told you the document does not say, and then added the useful nuance: the only payment obligation mentioned is for work already done.

Also notice it cited a section number on every answer. We did not ask for that, but it means you can check each one in about 5 seconds. Ask for it explicitly if you do not get it.

The five questions worth asking any document

Paste these under almost anything and you will learn more than reading it cover to cover:

1. Summarize this in 5 bullet points.
2. What in here would cost me money, and when?
3. What are my obligations, as a list with deadlines?
4. What is unusual compared to a standard version
   of this document?
5. What is NOT covered that I might assume is?

Question 4 is the one people never think to ask, and it is often the best. Question 5 catches the thing that ruins your year: the assumption you made that the document quietly does not support.

Other things this works on

A bill or statement you do not understand. "Explain each line item in plain English. Flag anything that looks like a fee rather than a charge for something I used."

A long report where you need one thing. "Find every mention of [topic] in this document and quote each one with its page or section, then summarize what the document concludes about it."

Two versions of the same thing. Paste both. "What changed between version A and version B? List only the substantive changes, ignore formatting and wording." This is genuinely hard to do by eye and it is very good at it.

Something written to confuse you. "Rewrite this in plain English at a level a 15 year old could follow, keeping every factual detail." Dense writing is often dense on purpose. This undoes that.

Four more document jobs, with the prompt

The renewal notice you did not read.

Answer only from this text. What is the new price,
what was the old price, when does the change take
effect, and what is the last date I can cancel
without it applying?

Renewal letters are written so those 4 facts are in 4 different paragraphs. This puts them in one place.

The form you have to fill in.

Go through this form and list every piece of
information I will need to gather before I start,
as a checklist. Flag anything that usually requires
a document I would have to find.

The thread you were added to at message 40.

Here is an email thread I have just been added to.
Tell me: what is being decided, who wants what, what
is still open, and what specifically is being asked
of me. Answer only from the thread.

The thing you wrote that has to be right.

Read this as if you are the person receiving it and
looking for a reason to say no. What would you push
back on, and what is unclear or missing?

Turning it into an adversarial reader is the most useful review you can get in 20 seconds, and it is more honest than asking "is this good", which reliably gets you a yes.

Where this breaks

• Scanned images and photos of documents. Quality varies a lot. If the source is a photo of a page, check any number you extract against the image yourself.
• Very long documents. Everything technically fits these days, but accuracy on "find every mention of X in 200 pages" is not perfect. Ask for quotes with section numbers so you can verify, rather than trusting a count.
• Tables and figures in PDFs. These often arrive scrambled. If your answer depends on a table, ask it to quote the table back to you first and check that it read it correctly.
• Anything the document contradicts elsewhere. It reads what you gave it. If clause 12 undoes clause 7 and you only pasted clause 7, it has no way to know.

One thing to be careful about

You are uploading a document. Before you paste a contract with your home address in it, or a medical letter, know that most consumer AI products let you turn off training on your conversations in the settings, and business tiers generally do not train on your data at all. Find that setting once, and if the document is genuinely sensitive, delete the identifying lines before you paste. It does not need your account number to explain a fee.

Do this one now

Find a document you have been meaning to read properly and have not. Everyone has one. Paste it in with the "answer only from this text" instruction and the 5 questions above.

Most people's first reaction is finding something in their own paperwork they did not know was there. That is not a demo. That is the tool doing the thing it is genuinely best at.

Next

Lesson 5 is about using it to learn something, which sounds obvious and is the use case where it will lie to you most convincingly.