AI PDF Redline Checklist

Overview

Use this skill when the user has a contract, policy, proposal, terms update, handbook, agreement, or other PDF-style document and needs a structured first-pass review artifact. The skill organizes user-provided document text, pasted redline notes, exported compare text, or summaries into a change-summary table and questions-to-ask list.

This is a prompt-only review organization skill. It is not legal advice, does not determine whether terms are acceptable, and does not replace professional review for binding terms. Work only from documents, excerpts, comparison output, or change descriptions supplied by the user.

Trigger

Use this skill when the user asks to:

• Review a PDF redline, tracked-change export, contract revision, policy update, or terms change.
• Compare an old version and new version from user-pasted text.
• Summarize what changed and what might need follow-up.
• Group changes by business, operational, financial, privacy, compliance, timeline, or responsibility impact.
• Draft questions for a lawyer, manager, vendor, client, HR team, compliance contact, or document owner.

Do not use this skill to provide legal advice, decide whether to sign, interpret binding obligations as final, fetch private documents, bypass document access controls, or review documents the user has not provided.

Intake

Ask the user to provide the materials they want reviewed. Request only what is useful:

• Old version text, new version text, exported redline text, or a pasted change summary.
• Document type, such as contract, policy, proposal, lease, employment document, terms update, or vendor agreement.
• Review goal, such as quick triage, negotiation prep, internal approval, risk scan, or questions for counsel.
• Known context, such as party names or effective date, if the user wants them included.
• Areas of concern, such as payment, renewal, termination, liability, data use, confidentiality, deadlines, service levels, or ownership.
• Whether the user wants a compact checklist or a fuller review packet.

If the user only has a PDF file, ask them to paste extracted text or visible redline notes. If text is incomplete, proceed only on supplied content and mark gaps clearly.

Workflow

1. Confirm scope. State that this is a first-pass review artifact based only on user-provided content, not legal advice.
2. Identify source material. Note which versions, excerpts, sections, or change summaries were supplied and what is missing.
3. Extract visible changes. List additions, deletions, replacements, moved clauses, changed dates, changed amounts, changed parties, new definitions, and removed protections when visible.
4. Group by impact area. Categorize changes under money, obligations, timing, renewal, termination, liability, indemnity, confidentiality, privacy or data, IP or ownership, service levels, compliance, dispute process, notices, and miscellaneous.
5. Assess review priority. Label each item high, medium, low, or informational based on potential practical impact, uncertainty, and user-stated goals. Avoid legal conclusions.
6. Create a change-summary table. Include location, old wording or summary, new wording or summary, type of change, impact area, priority, and notes.
7. Build a question list. Draft neutral questions for the appropriate reviewer or counterparty. Label questions as review before sending.
8. Flag uncertainties. Mark missing pages, unclear cross-references, undefined terms, inconsistent dates, unresolved attachments, hidden formatting changes, or places where professional review is recommended.
9. End with next steps. Provide a short checklist for human review, including professional review for binding terms.

Output Format

Return these sections:

1. Review Snapshot: document type, source materials supplied by the user, review goal, date basis, and scope limits.
2. Top Changes to Review First: the most important visible changes and why they deserve attention.
3. Change-Summary Table: location, old text or summary, new text or summary, change type, impact area, priority, and notes.
4. Impact Area Checklist: money, obligations, dates, renewal, termination, liability, data, confidentiality, IP, service levels, compliance, dispute process, and notices.
5. Questions to Ask: concise questions grouped by reviewer, counterparty, internal owner, or counsel. Mark all drafts as review before sending.
6. Missing or Unclear Items: incomplete text, missing exhibits, undefined terms, broken references, conflicting dates, or areas needing verification.
7. Professional Review Notes: binding terms, legal rights, liability, indemnity, privacy, employment, leases, regulated issues, or high-value commitments should be reviewed by a qualified professional.
8. Next-Step Checklist: manual review steps before signing, approving, negotiating, or relying on the document.

For a quick request, start with Top Changes to Review First and include a compact table.

Review Rules

• Use only user-provided text, visible redline notes, or user-supplied summaries.
• Do not claim to have read a PDF unless the text was provided in the conversation or a permitted file-read context.
• Preserve original wording for important clauses when available.
• Label paraphrases as summaries, not quotes.
• Do not invent clause numbers, parties, attachments, deadlines, or legal consequences.
• Mark missing attachments, exhibits, schedules, referenced policies, or unavailable pages as missing source material.
• Treat changed amounts, changed dates, changed notice periods, changed renewal terms, changed ownership rights, changed data rights, changed liability language, changed indemnity language, and changed termination rights as priority review items.

Boundary Rules

• Do not provide legal advice or say whether a clause is enforceable, valid, invalid, acceptable, or safe to sign.
• Do not decide whether the user should sign, approve, reject, or negotiate a term.
• Do not draft binding legal language as final. If wording is requested, provide a question or discussion prompt instead.
• Recommend professional review for binding terms, high-value commitments, regulated issues, employment terms, leases, liability, indemnity, privacy, IP ownership, and unclear legal rights.
• Do not access external storage, email, portals, document rooms, e-signature systems, or private files unless separately authorized by the user and available in the current environment.

Acceptance Criteria

1. Produces a first-pass change-summary table and questions-to-ask list from user-provided document text or change notes.
2. Separates visible changes from assumptions, summaries, and missing source material.
3. Groups changes by practical impact area and assigns review priority without legal conclusions.
4. Includes clear no-legal-advice scope notes and recommends professional review for binding terms.
5. Refuses or redirects requests to decide whether to sign, provide final legal wording, or review unavailable documents.
6. Requires no code execution, credentials, API access, network access, document-room access, e-signature action, or extra files.

Example Prompts

• "Here is the old clause and new clause from a vendor agreement. Make a redline checklist."
• "I pasted a PDF compare export. Summarize what changed and what questions to ask."
• "Review these policy changes for operational impact, not legal advice."
• "This contract revision changed payment and termination sections. Build a first-pass table."
• "Draft questions for counsel based on this redline, but do not tell me whether to sign."