Set up
Try a plugin
The Operations plugin ships with /vendor-review already structured to diff two contract versions into a redline table and turn usage and comparables into leverage. If your admin manages plugins and it's not available yet, skip this; nothing below requires it.
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 your working folder
Put the current agreement, the renewal proposal, your usage export, and the comparable quotes in one folder. Cowork diffs the two contracts there and writes the redline table and the brief back next to them. Create a Cowork project(opens in new tab) from your procurement folder so your fallback positions and standard contract terms stay attached for every renewal.
The prompt
Copy this into Claude Cowork
Compare the current agreement to the renewal proposal and summarize every material change as a redline table (clause, current, proposed, our position). Then write the negotiation brief: our leverage, their likely pushback, three asks ranked by value, and the walk-away line. Keep it to one page I can take into the call.
Why this works
Name the columns you want. Clause, current, proposed, our position: nothing slips through and Legal can scan it in two minutes.
Ask for a ranked shortlist. Three, by value. You walk in knowing what to trade and what to hold.
Ask for the decision point. The brief isn't done until it says when you'd leave the table.
Ground it in your own spend data. The argument is built from your numbers, not the vendor's slide.
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 /vendor-review skill with my feedback.
Make it repeatable
Run it before every renewal
The brief should exist before the vendor's AE books the call. Type /schedule in the prompt, or open Scheduled in the Cowork sidebar, and the customized skill watches the renewal calendar and drops a brief 60 days out.
/schedule Every Monday at 9am, check the contracts spreadsheet for any vendor renewing in the next 60 days, run /vendor-review against that vendor's folder, and write the brief to Procurement/<vendor>-renewal-<year>/.
Weekly, finds vendors renewing in the next 60 days, runs /vendor-review on each, and writes the redline and brief to the vendor folder.
Share with your teammates
Your customized /vendor-review now carries your standard fallback positions, your redline format, and what your Legal team will and won't accept. Share it so every category owner walks into renewals with the same prep.