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Guided Cowork setup — install a matching plugin, try a skill, connect tools.
Passed 11 of 22 test cases with the skill, and 5 of 22 without it.
and 10 more in the full report
8 fixed4 passed either way10 still failing1 broke
Tokens, turns and time describe resource use, not a dollar price.
One of 8 test cases the skill fixed. Same model, same prompt, with and without the skill.
Cowork setup is reaching Step 6 Wrap. The user completed plugins and connectors but skipped setting up a writing voice profile. What specific clause should be added to the closing message?
| Checked | Without skill | With skill |
|---|---|---|
| Adds a clause stating the user can ask to learn their writing voice anytime later | Passed | Passed |
| Concludes setup with guidance on starting tasks from the sidebar or typing `/` | Missed | Passed |
The instructions your model reads when the skill loads.
Help the user get Cowork configured for their work. Six steps — role, plugins, connectors, try a skill, writing voice, wrap.
Before your first user-facing message, create a TODO list with these items so the user can see progress:
Mark each one complete as you finish it. Keep it to these six — don't add sub-items.
Your initial message should frame what Cowork is: it autonomously handles tasks like reading your email, searching your docs, drafting reports, etc. Educate the user on Skills, reusable workflows you run with /name; Connectors, which wire in your tools; Plugins, which bundle skills and connectors for a domain. Two or three sentences. Hit the beats: multi-step and autonomous, uses your real tools, skills/plugins/connectors defined.
Next, ask the user for their role. Something like: "Let's get you set up — takes a few minutes. What kind of work do you do?" Then call the ShowOnboardingRolePicker tool, which renders a clickable role-picker chip row: do not list the roles yourself. The tool result is their answer — {"role": ...} is their role for the rest of setup; {"dismissed": true} or {} means they didn't pick one.
If the ShowOnboardingRolePicker tool is not available in this session, ask in plain text instead and offer these options as a short list they can reply to (they can also answer in their own words):
test cases passed, vs 5 / 22 without
More skills from the same source and nearby in the registry, with their headline benchmark lift.