Chat with PDF: 5 prompts that actually work

Chat with PDF works best when you treat it as a fast first reader, not as an oracle. The model retrieves passages from the document and writes the answer using only those passages. If your question is specific, you get a precise answer plus the exact page where it lives.

1. Locate the clause

'Where in this contract is the indemnification clause?' returns specific page references. 'Is this contract enforceable?' returns a vague summary because it's interpretation, not retrieval.

2. Extract the specific number

'What's the termination notice period?' returns the number. 'What about the termination clause?' returns a paragraph. Specific numeric questions are the highest-value use.

3. Find the exception

'Are there any exceptions to the limitation of liability?' is a great chat question. Lawyers spend hours skim-reading for these; the chat surfaces them in seconds.

4. Compare against your standard

'What's the IP-assignment language in this contract?' lets you compare what's in this document to your standard playbook. The chat returns the language; you decide whether it's acceptable.

5. Ask for the absence

'Does this contract include a non-compete?' — even when the answer is 'no, I don't see one', that's useful. Confirming absence is harder for humans skimming and easier for retrieval.