# 50 Prompts for Summarizing and Extracting From PDFs With AI — free download from DollarWise (dollarwise.xyz)

Paste your document text or upload the PDF, replace the [bracketed] placeholders, and run the prompt in ChatGPT, Claude, Gemini, or any AI tool that accepts documents. Always verify dates, amounts, and obligations against the original.

## Summarize (10)

1. Summarize this PDF in under 300 words: state the main argument or purpose, the 5 most important points, and one sentence on who should care about it. [Paste document text or upload the PDF]
2. Create a section-by-section digest of this document: for each major section give a 2-sentence summary plus the single most important quote or figure. End with 3 open questions the document leaves unanswered. [Paste document text]
3. Give me a TL;DR of this document in 5 bullet points, then a one-paragraph executive summary, then the single most surprising or important finding. [Paste document text]
4. Summarize this document at three depths: a 1-sentence takeaway, a 100-word overview, and a 500-word detailed summary with section headers. [Paste document text]
5. Explain this document to a 12-year-old: no jargon, one everyday analogy per major concept, and a 3-sentence recap at the end. [Paste document text]
6. Summarize this report as if briefing a busy executive: decision needed, 3 key facts supporting it, 2 risks, and your recommended next step — all in under 200 words. [Paste document text]
7. Extract the 10 most actionable takeaways from this document, each as a one-line action starting with a verb, ordered by impact. [Paste document text]
8. Compare the claims in this document's executive summary against its detailed sections: list any claim in the summary that the body does not support or that the body contradicts, with page references. [Paste document text]
9. Summarize this document's argument as a debate: the 3 strongest points for its position and the 3 strongest counterarguments a skeptic would raise, all grounded in the text. [Paste document text]
10. Create study notes from this document: key terms with definitions, 5 likely exam questions with answers, and a one-page cheat sheet of the core concepts. [Paste document text]

## Extract tables and data (8)

11. Extract every table from this PDF and rebuild each one as a clean markdown table with the original headers, all rows, and the page number each table came from. Flag any cells that look like OCR errors. [Paste document text]
12. Pull all numerical claims from this document into a table with columns: Figure, Context, Page, and Unit. Then list the 3 figures most critical to the document's argument. [Paste document text]
13. Convert the data in this PDF's charts (described in text) into a structured list: chart title, what it measures, the key values, and the trend it shows. [Paste document text]
14. Extract every date mentioned in this document into a chronological timeline with the event and the page reference for each. [Paste document text]
15. Build a CSV-ready extraction of [specific data, e.g. all product prices]: columns for item, value, and page, with one row per item and no extra commentary. [Paste document text]
16. List every person, organization, and location named in this document, with a one-line description of their role in the text and the page where each first appears. [Paste document text]
17. Extract all definitions from this document into a glossary: term, definition as stated, and page number. Sort alphabetically. [Paste document text]
18. Find every footnote and endnote reference in this document and summarize what each one adds: extra evidence, caveat, or source citation. [Paste document text]

## Q and A over the document (8)

19. I will ask questions about this document. Answer each one using only information stated in the text, quote the supporting passage, and give the page or section it came from. If the answer is not in the document, say so explicitly. [Paste document text]
20. Quiz me on this document: ask me 10 questions one at a time, increasing in difficulty, confirm or correct each answer using the text, and give me a final score. [Paste document text]
21. What are the 7 most important questions this document answers? List each question with its answer quoted or closely paraphrased from the text and a page reference. [Paste document text]
22. Play devil's advocate with this document: raise 5 tough questions a critic would ask, then answer each one using only evidence from the text. Note where the text has no good answer. [Paste document text]
23. If I only have 5 minutes with this document, what 5 questions should I ask to grasp it fully? Ask and answer them from the text. [Paste document text]
24. Explain the cause-and-effect chain in this document: what causes what, in order, with the evidence quoted for each link. Flag any link the document asserts without evidence. [Paste document text]
25. Who is the intended audience of this document, what does it assume they already know, and what 5 background concepts would a beginner need explained first? [Paste document text]
26. Summarize what this document says about [specific topic]: every relevant passage quoted briefly with page numbers, then a 3-sentence synthesis. Say explicitly if the topic is barely covered. [Paste document text]

## Contracts and legal review (8)

27. Review this contract and list: all obligations I am agreeing to, all payment terms and amounts, the termination clause in plain English, and 5 clauses that are unusual or unfavorable compared with standard agreements. This is not legal advice. [Paste contract text]
28. Extract every deadline, renewal date, and notice period from this agreement into a chronological list with the exact clause reference for each. Highlight anything requiring action from me within 30 days. [Paste contract text]
29. Translate this contract into plain English section by section: what each clause means in practice, who it protects, and what could go wrong for me under it. This is not legal advice. [Paste contract text]
30. Compare these two contract versions [paste both] and list every substantive change: added clauses, removed clauses, and modified wording, with a one-line note on who each change favors. [Paste contract texts]
31. Identify the liability, indemnification, and limitation-of-liability clauses in this agreement. Explain my maximum financial exposure in plain English with the clause numbers cited. This is not legal advice. [Paste contract text]
32. Check this freelance or employment contract for: payment schedule, late-payment terms, intellectual property ownership, non-compete scope and duration, and termination rights. Flag anything missing that should be there. [Paste contract text]
33. List every fee, penalty, and automatic charge in this agreement with the triggering condition and amount for each, then total my worst-case first-year cost. This is not legal advice. [Paste contract text]
34. Draft 10 questions I should ask the other party or a lawyer before signing this agreement, based on the ambiguities and gaps you find in the text. [Paste contract text]

## Invoices and receipts (8)

35. Extract from this invoice: vendor name, invoice number, date, every line item with quantity and unit price, subtotal, tax amount and rate, total due, payment terms, and due date. Present as a clean table. [Paste invoice text]
36. Compare this invoice against the quoted estimate [paste quote]: list every line where price or quantity differs, compute the total variance, and flag charges with no matching quote line. [Paste invoice text]
37. Categorize every line item on this receipt or invoice into expense categories (e.g. travel, meals, software, office) and give subtotals per category plus the grand total. [Paste receipt text]
38. Check this invoice for errors: verify that line items times quantities equal the subtotal, that tax math is correct, and that the total matches. List any discrepancy with the exact numbers. [Paste invoice text]
39. Extract payment details from this invoice: accepted payment methods, bank or account details shown, payment terms, late-fee policy, and the exact due date. Warn me about anything unusual. [Paste invoice text]
40. Process this batch of receipts [paste all]: one row per receipt with vendor, date, total, and category, then a grand total and the 3 largest expenses highlighted. [Paste receipt texts]
41. Does this invoice meet standard tax-invoice requirements? Check for: vendor tax ID, invoice number, date, itemized lines, tax breakdown, and totals. List anything missing. [Paste invoice text]
42. Summarize my spending from these invoices [paste all] by vendor and by month: total per vendor, total per month, and any duplicate charges across invoices. [Paste invoice texts]

## Academic papers (8)

43. Summarize this academic paper for a non-expert: the research question in one sentence, the method in 3 sentences, the main finding in 2 sentences, and the biggest limitation the authors admit. [Paste paper text]
44. Break down this paper's methodology: study design, sample size and selection, variables measured, analysis method, and 3 threats to validity. [Paste paper text]
45. Extract every result from this paper's results section into a table: finding, statistical value with units, significance level, and which hypothesis it supports. [Paste paper text]
46. What does the literature review in this paper claim about prior work? Summarize the 5 most cited prior findings and note any disagreement among them. [Paste paper text]
47. List this paper's limitations as stated by the authors, then add 3 limitations a critical reviewer would raise that the authors do not mention. [Paste paper text]
48. Explain the key figure or table in this paper: what it shows, how to read it, what the main takeaway is, and what a casual reader might misinterpret. [Paste paper text]
49. Compare this paper's findings with [other paper or known result]: where they agree, where they conflict, and what methodological difference might explain the conflict. [Paste paper text]
50. Draft a 150-word abstract for this paper in standard academic style, plus 5 keywords and a one-sentence lay summary suitable for a press release. [Paste paper text]