First-pass NDA/MSA redlining with Claude

A Claude Skill that takes a counterparty’s NDA or MSA in .docx form, compares it against your playbook, and produces a tracked-changes Word document with redlines plus a 1-page deviation summary. Drop the playbook into the Skill once; run it on every inbound contract from then on.

What you’ll need

• Claude Code or Claude.ai with custom Skills enabled
• Your firm’s playbook documented as one of: an .md file with clause-by-clause acceptable/fallback/walk-away positions, or a .docx of your standard MSA/NDA template
• Microsoft Word installed (for opening the redlined output)
• Optional: Ironclad or another CLM for storing the resulting redlined version

Setup

1. Drop the Skill. Place contract-redline.skill into your Claude Code skills directory (~/.claude/skills/) or upload to Claude.ai project. The Skill exposes two callable functions: redline_against_playbook and summarize_deviations.
2. Add your playbook. The Skill reads playbook/nda_playbook.md and playbook/msa_playbook.md from the Skill directory. See the NDA playbook and MSA redlining rubric for structure.
3. Test on a known contract. Run the Skill against a contract you’ve already redlined manually. Compare outputs. Tune the playbook if the Skill’s positions feel off.
4. Wire to intake. When a new contract arrives via Ironclad intake or email, the assigned reviewer drops the .docx into the Skill and gets the redlined output back in under 60 seconds.

How it works

The Skill takes the contract .docx and runs three sub-tasks in sequence:

1. Classify the contract type. Reads the document, identifies it as NDA, MSA, DPA, vendor agreement, or other.
2. Match each clause against the playbook. Splits the contract into clauses, identifies the corresponding playbook position for each, and computes the deviation level (acceptable / fallback / walk-away).
3. Generate tracked changes. For each fallback or walk-away clause, produces the redline language pulled from the playbook. Writes the redlined version as a Word .docx with native tracked changes plus comments explaining the rationale for each redline.

Output format

• {contract}_redlined.docx — Word document with tracked changes
• {contract}_summary.md — 1-page deviation summary listing every fallback or walk-away clause, the reviewer’s required action, and the relevant playbook position

Where it fits

Use this Skill at the Tier 2-3 level of your contract review SOP. For pure Tier 1 NDAs, LawGeex or BlackBoiler auto-approval is faster; for high-value strategic contracts (Tier 4), an attorney still reads end-to-end. The Claude Skill sweet spot is the high-volume mid-stakes contract where the lawyer wants AI to do the first pass but expects to review every redline.

Watch-outs

• Playbook quality is everything. A vague playbook produces vague redlines. Codify positions explicitly with example fallback language, not abstract principles.
• Not a substitute for legal review. Every redline output is human-reviewed before it goes back to the counterparty. The Skill saves time on the first draft, not on the judgment call.
• Privileged information stays in. Skills run inside your Claude session; document content does not leave your control. But verify your firm’s AI-vendor policy (AI policy for legal teams once published) authorizes Claude for this use case.