Set up
Try a plugin
The Engineering plugin ships with /tech-debt and /standup already structured to read a closed cycle and a channel window and split the output into discussion themes versus operational watch-fors. 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
Keep your retro template, the running action-items list, and last sprint's retro in one folder. Cowork reads the format from there and writes both docs back so the retro and the handoff live next to their predecessors. Create a Cowork project(opens in new tab) from the folder so your team's definition of "shipped" and the discussion-prompt style carry over every cycle.
The prompt
Copy this into Claude Cowork
Read the just-closed Linear cycle and two weeks of #team-platform and #oncall-platform. Write the sprint retro (shipped, slipped with reasons, themes worth discussing) and a separate on-call handoff (open alerts, toil, what the next rotation should watch). Pull quotes where they help. Keep each section to what's discussable in a 30-minute meeting.
Why this works
Ask for the reason behind each item. The retro is about why, not the list. Asking forces the synthesis.
Split outputs that serve different purposes. One is a conversation, one is operational. Mixing them buries both.
Set a length limit. A length budget kills the exhaustive list and surfaces what's worth talking about.
Combine complementary sources. Tickets say what moved; Slack says why. The pair is the whole story.
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 /tech-debt skill with my feedback.
Make it repeatable
Run it when the cycle closes
Retro prep shouldn't be the TPM's Friday afternoon. Type /schedule in the prompt, or open Scheduled in the Cowork sidebar, and the customized skill drafts both docs the moment the cycle ends.
/schedule Every Friday at 3pm, run /tech-debt on the cycle that just closed and /standup on the last two weeks, write both to Platform/retros/<sprint>/, and post the handoff to #oncall-platform.
At cycle close, runs /tech-debt and /standup, writes both to the dated retro folder, and posts the handoff to the on-call channel.
Share with your teammates
Your customized /tech-debt now knows your tracker, your channels, your template, and what counts as a theme versus a status update. Share it so every squad runs the same retro prep and on-call handoffs read the same way org-wide.