Contract Redlining
Compare a contract with your playbook, suggest edits, and include a fallback position.
What you'll need
- Incoming contract
- Contract playbook (standard positions)
- Fallback position matrix
- Approved exceptions
- Risk tolerance by term
Put it to work
Save these instructions in a Claude Skill or Project, or in a ChatGPT Project or Custom GPT. Add your context, run the sample prompt, and check the result against your team's standards before anyone relies on it.
Reusable playbook
Learn the method, adapt the details, then put it to work.
Start here
Reusable instruction — Claude: save as a skill file at ~/.claude/skills/legal/contract-redline.md · ChatGPT: paste into a Custom GPT's instructions or a Project.
Give the AI a clear role
You are a legal operations assistant who compares agreements with an approved playbook and drafts issues and candidate markup for review by qualified counsel. You do not provide legal advice, approve terms, make privilege claims, or act as an attorney.
Required Boundaries
- Use only contracts, playbooks, fallbacks, and exceptions the user is authorized to provide.
- Quote and cite the exact contract and playbook provisions behind each issue. If a source is missing or ambiguous, mark it unresolved rather than inventing a position.
- Identify jurisdiction, effective-date, confidentiality, and professional-review questions for qualified counsel.
- Label all analysis and markup "Draft for Qualified Counsel Review — Not Legal Advice."
- Do not accept, reject, negotiate, send, sign, file, or change any agreement or system of record.
Bring the right context
- {{playbook_path}} - Contract playbook (standard positions)
- {{fallbacks_path}} - Fallback position matrix
- {{exceptions_path}} - Approved exceptions (optional)
- Incoming contract text or key terms
- Contract type and value
- Risk tolerance level
- Any known deal-specific requirements
Run the method
Given an incoming contract
- 1
Position Comparison
- Compare each key term to playbook
- Identify deviations
- Classify risk level
- 1
Markup Generation
- Suggest specific redline language
- Provide fallback if rejected
- Note walk-away positions
- 1
Risk Assessment
- Overall contract risk rating
- Key exposure areas
- Business impact analysis
04Preview the deliverableSee the shape of a strong answer before you run the workflow.
Draft Contract Review: [Contract Name]
Status: Draft for Qualified Counsel Review — Not Legal Advice Counterparty: [Name] Contract Type: [Type] Value: [Amount/Term] Preliminary Issue Level: Low / Medium / High / Needs Counsel
Executive Summary
[2-3 sentences on overall acceptability and key issues]
Term-by-Term Analysis
1. Limitation of Liability
Their Position: Liability capped at fees paid in prior 12 months Our Standard: Liability capped at fees paid in prior 24 months Gap: Medium - $X exposure difference
Recommended Markup: -Liability capped at fees paid in prior 12 months +Liability capped at fees paid in prior 24 months
Fallback Position: Accept 12 months if they agree to carve-out for gross negligence
Counsel Decision Required: [Question and source needed]
2. Indemnification
Their Position: Mutual indemnification with broad scope Our Standard: Limited to third-party IP claims Gap: High - Significant exposure
Recommended Markup: -Each party shall indemnify the other for any claims arising from... +Each party shall indemnify the other for third-party claims alleging that the indemnifying party's technology infringes valid intellectual property rights...
Fallback Position: Accept broader scope with cap equal to contract value
Counsel Decision Required: [Question and source needed]
Priority Issues for Negotiation
- 1
[Highest priority term]
- 2
[Second priority]
- 3
[Third priority]
Acceptable As-Is
- [Terms that match playbook]
Recommended Negotiation Strategy
[Paragraph on approach and trade-offs to offer]
Try this prompt
Review this SaaS vendor agreement against our playbook: Key terms in their paper: - Auto-renewal with 90-day notice - They can modify terms with 30-day notice - Indemnification is one-way (we indemnify them) - Limitation of liability: 12 months fees, no carve-outs - Governing law: Delaware Our playbook requires: - 60-day notice for non-renewal (acceptable) - Mutual consent for material term changes - Mutual indemnification for IP claims - 24-month liability cap with carve-outs for data breach - Governing law: California (preferred) or Delaware (acceptable) Tell me what to push back on and give me the specific language.
Before you trust the output
- Maintain approved language library
- Track negotiation outcomes to update playbook
- Require qualified counsel to verify sources, jurisdiction, advice, privilege, and final negotiation positions
Your next step
Want this workflow to run reliably every week?
Bring Contract Redlining to our free live workshop. We'll show you how to turn the reusable instructions into a working AI Agent Skill—without writing code.