Compare Two Contract Drafts and Draft Your Response
When opposing counsel sends back a redline, surface what changed with the text quoted, assess the risk, and draft your response in one sitting.
When to use this
A counterparty returns a marked-up agreement and calls the edits minor. The real work is separating the consequential changes (a quietly narrowed indemnity, a flipped 'shall' to 'may') from the cosmetic ones, then responding from a position of clarity. This workflow does the triage, quoting both versions of every change, and drafts the first response.
A returned redline is where deals quietly shift. A version compare shows you where words moved, but not which moves matter: that a softened indemnity just put real risk on your client, or that a definition tweak changed an obligation. Catching the consequential edits is the core of the job.
Claude can help with that triage. Paste both versions, tell it whose side you're on, and it walks the changes clause by clause (material, clarifying, or cosmetic), quoting the old and new text, with a risk note on anything that alters rights, then drafts your response. You stay the decision-maker; Claude builds the map and the first draft.
Run the steps in one conversation so the response is grounded in the same change analysis. Verify every flagged change against the actual documents before you send anything.
The Workflow
Get a prioritized change log
Give Claude both versions in separate <document> tags, then your client's role. Ask it to identify every change, quote the text from both versions, and rate its significance.
Prompt<document id="A" description="our last draft" date="[DATE]"> [PASTE FULL TEXT, INCLUDING EXHIBITS] </document> <document id="B" description="opposing counsel's returned redline" date="[DATE]"> [PASTE FULL TEXT, INCLUDING EXHIBITS] </document> I represent the [BUYER / SELLER / TENANT / CUSTOMER / etc.] in [BRIEF DEAL DESCRIPTION]. Document A is our last draft; Document B is the version opposing counsel just returned. My goal is to know which changes matter and to respond. Compare them clause by clause. For each change, give: - the section number - the exact text in A and the exact text in B, quoted - significance: MATERIAL, CLARIFYING, or COSMETIC - for material changes, the practical risk to my client Include changes to defined terms and exhibits, and note where a definition change alters other sections that use the term. If a section was moved or renumbered, say so. If you are unsure whether something changed (for example, formatting differences), list it under UNCERTAIN rather than guessing.
What you get: A change log with both versions quoted for every change, separating the edits that move risk from the noise, plus an UNCERTAIN list to check by hand.
Confirm the priorities
Have Claude surface the short list worth negotiating and what's safe to accept.
PromptSummarize: which 3–5 changes should I push back on hardest and why, and which changes look acceptable as-is from my client's side? Flag any change that looks cosmetic but carries legal weight (for example, "shall" becoming "may"). For each item, repeat the section number and quoted text so I can find it quickly. Note any judgment call that depends on business context you don't have.
What you get: A negotiation-ready priority list, with quoted text, that you can sanity-check against your strategy.
Draft the response
Ask Claude to draft your reply to opposing counsel, accepting some changes and countering others with reasons.
PromptDraft a professional email to opposing counsel responding to the redline: accept the changes I've marked as acceptable [LIST OR "per your list above, with these edits: ..."], and counter the material ones with a brief, businesslike rationale and a proposed compromise where useful. Refer to each change by section number and quote the language we're proposing. Firm but constructive in tone. Don't state legal conclusions about enforceability or cite law; if a point would benefit from authority, insert [ATTORNEY TO ADD] instead.
What you get: A first-draft response, keyed to section numbers with proposed language quoted, that you can refine to your voice.
Verify against the documents
Check each flagged change and the UNCERTAIN list against the actual text, confirm the risk calls fit the deal, and finalize. Claude can miss a subtle change or misjudge context; the review is yours.
Example Output
Illustrative example — names, facts, and figures are fictional.
CHANGE LOG (excerpt, fictional agreement). Client: Customer Section 7.2: Limitation of Liability [MATERIAL] A: "...shall not exceed two times (2x) the fees paid in the twelve (12) months preceding the claim." B: "...shall not exceed the fees paid in the three (3) months preceding the claim." Risk: sharply lowers what we could recover on a serious breach. Push back toward 12 months. Section 3.1: Definitions [CLARIFYING] B adds: "'Business Day' excludes federal holidays." Acceptable. Section 9.1: Indemnity [MATERIAL, looks cosmetic] A: "Vendor shall indemnify..." B: "Vendor may indemnify..." Risk: turns a duty into an option. Treat as MATERIAL. UNCERTAIN: Exhibit C table formatting differs; content appears unchanged. Check by hand.
Tips
- •Always state which side you represent. The same change is favorable or harmful depending on your client.
- •Paste the full documents, including exhibits, so a buried change isn't missed.
- •Ask Claude to look specifically for changes that look cosmetic but shift meaning. That's where redlines hide their teeth.
- •If the deal is one you triage often, run the incoming draft through your standard-positions playbook too (see the contract triage workflow).
A note on confidentiality
Both drafts contain confidential deal terms (pricing, caps, indemnity positions) and your negotiating posture, and the counterparty's draft may be covered by an NDA or a letter of intent that limits sharing it. Check those terms before uploading, and remove pricing schedules and personal data the comparison doesn't need. Run client work on a commercial plan (Team or Enterprise) whose terms exclude your content from model training. On Pro or Max, disable model training in Privacy settings; a commercial plan's contract terms are the stronger answer for client work. Your duties under ABA Model Rule 1.6 and Formal Opinion 512 apply. Every output is a draft for attorney review: verify each quoted change against both documents before you accept, counter, or send.
Frequently Asked Questions
Does this replace reading the contract myself?
No. It's a first-pass triage that tells you where to focus and drafts a starting response. Claude can miss a subtle edit or misjudge context, so confirm every material change against the actual text before you accept, counter, or send.
Why give Claude both full versions instead of a redline?
Claude can compare complete versions and quote the before-and-after text for each change, which makes your verification faster. Pasting both full drafts (with exhibits) also catches changes a redline view can bury, such as a moved section or a changed definition.
Can it draft the actual response to opposing counsel?
Yes. Once it has the change analysis, it can draft an email accepting some edits and countering others with rationale. Review it for tone, accuracy, and strategy before sending; it's a draft, not a final position.
Prompts used in this workflow
Get New Workflows Like This Every Week
Join the free Claude for Lawyers newsletter — practical workflows, prompts, and guides for everyday practice.