ooligo
claude-skill

First-pass NDA/MSA redlining with Claude

Difficulty
intermediate
Setup time
45min
For
legal-ops · in-house-counsel · contract-manager
Legal Ops

Stack

A Claude Skill that takes a counterparty’s NDA or MSA in .docx form, classifies every clause against your firm’s red/yellow/green playbook, proposes redlines drawn from a pre-drafted fallback library, and flags anything outside the playbook for a human attorney. The skill produces a tracked-changes Word document plus a 1-page deviation summary the in-house team can paste into the deal channel. Drop the playbook in once; run it on every inbound contract from then on.

When to use

Use this skill when an inbound NDA, MSA, DPA, order form, or vendor agreement lands and you want the first-pass redline grounded in policy before a lawyer opens the file. The economics work when contract volume is high enough that the per-deal time saving compounds — typically a legal-ops team handling 30+ inbound contracts per month at the Tier 2-3 level of a contract review SOP. Below that volume, the playbook-maintenance overhead exceeds the saving.

The skill assumes you already have a documented playbook (see the NDA playbook and MSA redlining rubric for the structure it expects). If the playbook does not exist yet, build it first — the skill amplifies the policy, it does not invent it.

When NOT to use

  • Final approval or sending the redline back to the counterparty. The skill proposes; a named human attorney reviews every change before it leaves. The output is a head start, not a sign-off.
  • Edits to your own contract-as-source-of-truth template. Template changes are a playbook update — edit references/1-playbook-template.md directly so every future run picks up the new position. Do not run the skill on your own template “to refresh it.”
  • Highly bespoke instruments. M&A definitive agreements, complex IP assignments, regulated-industry side letters — the playbook cannot encode these. The skill will flag every clause as out-of-policy and burn tokens doing it.
  • Final-round negotiation drafts. By turn 3, the redlines are deal-specific concessions the playbook cannot anticipate. The skill is for the opening position only.
  • Privileged work product routed through a non-Tier-A AI vendor. If your firm’s AI policy excludes the model the skill would call, escalate to a human attorney instead of relaxing the policy. Privilege is not worth the speed.

Setup

  1. Drop the bundle. Place the contents of apps/web/public/artifacts/contract-redline-claude-skill/ into your Claude Code skills directory (~/.claude/skills/contract-redline/) or upload the folder to a Claude.ai project. The skill exposes one entry point that classifies and redlines a passed contract.
  2. Replace the templates. The bundle ships with three template files in references/. Replace each with your firm’s actual content before the first run:
    • references/1-playbook-template.md — your red/yellow/green positions per clause type.
    • references/2-fallback-positions.md — counsel-approved drop-in paragraphs the skill substitutes verbatim (no paraphrasing).
    • references/3-escalation-criteria.md — the rules that decide when a clause routes to a human instead of getting a proposed redline. Critically, this is also where you list the AI vendors you authorize for legal work product — the skill refuses to run otherwise.
  3. Test on a known contract. Run against a contract you have already redlined manually and diff the outputs. Tune the playbook where the skill’s positions feel off; tune the fallback-position paragraphs where the wording feels stilted. Two or three iterations gets to a good baseline.
  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 roughly 60 seconds. The reviewer opens the .docx in Word, walks the tracked changes (each one carries a Word comment citing the matched playbook section ID), and sends back to the counterparty only after their own review.

What the skill actually does

The skill runs four sub-tasks in order; they are not parallelized because each step depends on context from the previous one. The full method, with engineering rationale, lives in apps/web/public/artifacts/contract-redline-claude-skill/SKILL.md. Briefly:

  1. Classify the contract type. NDA (mutual / one-way), MSA, DPA, order form, vendor agreement, or “other.” If “other,” stop and emit a single escalation block. The skill does not attempt redlines on contract types the playbook does not address — that is the most common silent-drift failure mode.
  2. Clause-by-clause classification. Split the contract by heading (fall back to numbered-section parsing). For each clause, match to a playbook entry by clause-type heuristic and classify as green (acceptable), yellow (fallback substitution), red (must-have rewrite), or out-of-playbook (escalate). Every classification cites the matched playbook section ID in the output so the reviewer can audit decisions in seconds.
  3. Redline proposal. For every yellow clause, paste the corresponding fallback paragraph from references/2-fallback-positions.md verbatim. For every red clause, paste the must-have paragraph. Why pre-drafted paragraphs instead of free-form rewrites: counsel has already reviewed this language. Free-form rewrites would introduce novel wording every run and force the reviewer to re-read each fallback from scratch — defeating the time saving.
  4. Escalation flagging. Every out-of-playbook clause and every clause matching a rule in references/3-escalation-criteria.md gets an escalation block instead of a redline. The skill does not guess.

Cost reality

Token cost per contract depends on length and clause count. Concrete numbers:

  • Typical NDA (3-5 pages, ~2k words). Input ~6k tokens (contract + playbook
    • fallback library + escalation criteria), output ~4k tokens (rationale per clause + summary). At Claude Sonnet 4.5 pricing ($3 / MTok input, $15 / MTok output), that’s roughly $0.08 per contract.
  • Typical MSA (15-25 pages, ~10k words). Input ~14k tokens, output ~10k tokens. Roughly $0.20 per contract.
  • Monthly run rate at 100 contracts (50 NDAs + 50 MSAs). Roughly $14 in token cost — order-of-magnitude smaller than the human-time saving (one paralegal hour at $90/hr fully loaded covers ~640 contracts of skill cost).

The real cost is playbook maintenance: counsel needs to keep references/1-playbook-template.md and references/2-fallback-positions.md current. Budget two hours of senior-counsel time per quarter to refresh both, plus an hour per quarter to triage escalation patterns and fold recurring out-of-playbook clauses back into the playbook.

Success metric

Two metrics, watched together, tell you whether the skill is earning its keep:

  • Cycle-time reduction on first-pass redlines. Baseline: median time from contract intake to “first-pass redline ready for human review.” Target: reduce the median by 60-75%. A team baselined at 90 minutes per first-pass redline should land at 25-35 minutes (the skill produces in 60 seconds; the human review takes the rest).
  • % of clauses flagged for human review. Target band: 15-25% of clauses per contract. Below 10% means the playbook is too permissive (the skill is rubber-stamping yellow-zone language as green) — tighten the rubric. Above 35% means the playbook does not cover enough clause types — extend it.

If the cycle-time metric does not move within 30 days of go-live, the bottleneck is the human review step, not the redlining. Common cause: the reviewer does not trust the rationale strings and re-reads every clause from scratch. Fix by making the rationale strings cite playbook section IDs (which the skill does by default) and training reviewers to scan the IDs.

vs alternatives

The decision is between this skill and a vendor-built specialist:

  • vs LawGeex or BlackBoiler. These are vendor SaaS products with pre-trained models on millions of contracts. They win on Tier 1 NDAs (auto-approval against a standard playbook) and on speed-of-deployment if you do not already have a documented playbook. They lose when your playbook has unusual positions the vendor has not seen, when token-level transparency matters (the skill cites your playbook section IDs; vendors cite their own model’s confidence), and on price (vendor seats run $500-2k/seat/month vs the skill’s ~$0.20/ contract token cost plus paralegal-time amortization).
  • vs Ironclad AI Assist or Spellbook. Embedded in CLM / Word respectively; better UX inside the tool you already use; weaker on enforcing your specific playbook because their grounding is partly the vendor’s general training. Pick these if you want zero deployment effort and do not need citation-to-section-ID auditability.
  • vs manual paralegal-driven redlines. The status quo at most firms. Higher quality on novel clauses (humans pattern-match better on unusual language), much higher cost per contract, slower turnaround. The skill is not a replacement for the paralegal — it shifts the paralegal’s time from typing to judgment.

The Claude Skill sweet spot is the high-volume mid-stakes contract where the in-house team wants AI to do the first pass but expects human review on every output and demands every redline trace to a documented playbook position. If you cannot point at the playbook entry behind a redline, the redline does not ship.

Watch-outs

  • Silent playbook drift. A months-out-of-date playbook produces confident redlines from stale positions. Guard: every output writes the playbook’s last_reviewed date in the summary header. Reviewer rejects any output where that date is older than 90 days, and the playbook is refreshed before re-running.
  • Novel clause missed because of heuristic mismatch. Headings rhyme: “non-solicitation” vs “non-compete,” “Limitation of Liability” vs “Cap on Damages.” Guard: every clause classification cites the matched playbook section ID in the output. Reviewer scans the cited IDs and corrects mismatches before the redline goes out. Without the cite, the reviewer cannot tell the skill mis-matched.
  • Privilege leakage via non-Tier-A vendors. Counterparty drafts contain attorney-client-privileged context, especially in DPAs and side letters. Guard: the skill refuses to run unless the configured model appears in the allowed-vendors list at the top of references/3-escalation-criteria.md. Hard precondition; no CLI flag bypasses it.
  • Playbook quality is everything. A vague playbook produces vague redlines. Codify positions explicitly, with example fallback language in references/2-fallback-positions.md, not abstract principles in references/1-playbook-template.md alone.
  • 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.

Stack

  • Claude — Skill runtime (Claude Code or Claude.ai with custom Skills enabled).
  • Ironclad — CLM for intake and storing the resulting redlined version. Optional but the typical pairing for a legal-ops team running this at volume.
  • Microsoft Word — for opening the redlined .docx. Native tracked changes carry the rationale strings as Word comments.

Files in this artifact

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