Set up
Try a plugin
The Commercial Legal plugin ships with /review and other commercial-contracting skills as a starting point, already structured to walk an agreement against your playbook, flag the deviations, and draft the redlines. It's one of twelve practice-area plugins for legal teams; if your admin manages plugins and it's not available yet, skip this, nothing below requires it.
/reviewReview a vendor agreement, NDA, or SaaS subscription against your playbook./escalation-flaggerRoute a contract issue to the right approver per the escalation matrix in your practice profile, and draft the ask./cold-start-interviewRun the cold-start interview to learn your commercial contracts practice and write your team practice profile.Connect your tools
Claude Cowork is more powerful when it works directly with your systems. You control permissions and access. Learn about tool access(opens in new tab).
Navigate to Customize → Connectors in Cowork to set up.
Set the working folder
Put the incoming MSA and your contract playbook in one folder on your machine, then in Cowork click + Add folder and select it. Save it as a Cowork project(opens in new tab) so your playbook, instructions, and memory stay attached and you don't re-upload them for the next contract — Cowork reads from the folder and writes the clause table and redlined draft back to it.
Files you add stay on your machine and aren't used to train Claude — Cowork reads them locally to do the work.
The prompt
Copy this into Claude Cowork
Review this MSA clause by clause against our contract playbook. For each clause, mark it green, yellow, or red against our standard, explain why in one or two sentences, and where it's yellow or red draft the redline and the rationale for opposing counsel.
Why this works
Compare against your own baseline. G/Y/R means deviation from your playbook, not a textbook.
Ask for the fix and the reasoning. Paste-ready language plus rationale that holds up with counsel.
Save the detail for the problems. One line for standard clauses; detail goes where the risk is.
Write results back to the same folder. Review and redline write back next to the original.
Get a better draft
Add an example to match. Drop an example you like into the folder and Cowork matches your structure and voice.
Ask it to flag uncertainty. Add "flag anything you're not confident about" so you know where to look first when you review the draft.
Make Cowork work for you
A plugin skill is a starting point — customize it with your own practices and expertise. A few minutes of conversation and it runs with your standards from then on.
Make what we've done in this task so far into a skill, or edit the /review skill with my feedback.
Make it repeatable
Make it a live artifact
A review memo is stale the moment opposing counsel sends v4. Ask Cowork to publish the clause table as a live artifact and the deal team has one link that stays current — re-run the skill or schedule it to refresh.
Publish that clause table as a live artifact for the deal team. Re-run it against whatever the latest counterparty draft is in this folder, and keep a short "what changed since last turn" note at the top.
Run it on every new contract
Paper arrives, the first-pass review should already be waiting. Type /schedule in the prompt, or open Scheduled in the Cowork sidebar, and set the customized skill to run every weekday morning, checking the intake folder for new contracts.
/schedule Weekdays at 9am, check Contracts/Intake for new files and run /review on each one, writing the clause table and redlined draft to a subfolder named for the counterparty.
Each weekday at 9am, checks Contracts/Intake for new files, runs /review on each one, and writes the clause table and redlined draft to a counterparty subfolder.
Share with your teammates
Your customized /review now carries your playbook, your red-flag list, and your fallback positions. Share it so every reviewer on the team scores paper the same way, and the business sees a consistent first pass no matter who picks it up.