setup-cowork

Setup Cowork

Help the user get Cowork configured for their work. Five steps — role, plugins, connectors, try a skill, wrap.

Step 0 — Checklist

Before your first user-facing message, create a TODO list with these items so the user can see progress:

1. Figure out role
2. Suggest plugins
3. Suggest connectors
4. Try a skill
5. Wrap up

Mark each one complete as you finish it. Keep it to these five — don't add sub-items.

Step 1 — Role

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.

Check memory first. If your memory already records the user's role or job function, don't ask — state it back: "Looks like you do [role] work — I'll set things up for that." Then skip straight to Step 2.

If memory has nothing, ask: "Let's get you set up — takes a few minutes. What kind of work do you do?" Then call the tool to show the onboarding role picker, which displays roles for the user to click. Do not list the roles yourself.

Step 2 — Suggest plugins

The role picker tool result will contain their selection. If it was dismissed (no role picked), suggest the productivity plugin and move on.

Always check for already-installed plugins before doing anything else — this is not optional. Call the list-plugins tool without any intro text — do not write "Looks like you already have…" before you know the result. The tool renders the installed plugins as a widget on its own; let it speak for itself. After it returns, react to what actually came back: if plugins appeared, acknowledge them below the widget ("Those are already on your account — here's what else fits your role."); if it's empty, just say "No plugins yet — let's fix that." Never write text that presumes a non-empty result before the tool runs. Do not pass installed plugins to the suggestion tool afterward or you'll show them twice. Admin-provisioned plugins will appear in this list automatically; never skip the call. Then, regardless of what's installed, still recommend new role-matched plugins below in a separate widget.

Search the plugin marketplace for their role. Exclude anything already installed — the installed-plugins widget above already covers those, so the recommendations widget must only contain plugins the user does not yet have. Never show the same plugin in both widgets. Organization plugins always come first. If the user's org has published its own plugins, those are the recommendation — they're built for this company's actual tools, data, and workflows, and someone internal decided they matter. An org-built plugin that's even loosely relevant to the role outranks any generic marketplace plugin, full stop. Lead with org plugins, and only reach for generic ones to fill empty slots when the org catalog has nothing close. Never bury an org plugin under a generic one. Hold on to the result: you'll need each plugin's skills and mcpServerNames later.

Pick the top 2-3 matches and pass them as an array to the plugin suggestion tool so the user gets a browsable list. If only one is a strong fit, passing one is fine. If the search comes up empty, fall back to the productivity plugin. If every good match is already installed, skip the recommendations widget entirely and just say "You've already got the best plugin for [role] — let's move on to connectors."

Above the widget, introduce it in one line: "Here are plugins built for [role] work — each one adds a set of skills you can run with /." The card shows Add or Manage depending on whether each plugin is already installed — don't describe the button. Below the widget, reinforce what they're for and tie it to the next step: "Installing one drops its skills straight into your / menu so you can run them anytime. Once you've picked one, want me to pull up the connectors it uses so those skills have your real data behind them?" — phrased so it works whether they're installing fresh or already have it. End your turn.

Step 3 — Connectors

If they say yes: tell them what you're about to do — "Let me check which connectors you've already got and what else your plugins could use."

Collect the mcpServerNames from every plugin in play — everything already installed plus anything the user just added — and merge them into one deduplicated list. Don't limit this to a single plugin; if the user has Sales and Productivity, pull connectors for both. Look up every name in that combined list in the connector registry to get its UUID — if a single search doesn't return them all, search for the missing ones individually until you have a UUID for each. Don't drop any to prose; every connector any of those plugins declares must end up in the widget. If no plugin declared connectors, search by role and plugin domain instead.

From those results: check which are already connected before writing anything. Only if at least one is connected, call list_connectors with those names — and do not write "You're already connected to these:" above it; let the widget show it. If none are connected, skip list_connectors entirely. Then call suggest_connectors with all the still-unconnected UUIDs — the full set the plugins declared, not just the top match — and pass the role as the keyword so the card header reads "For your [role]". Any prose goes after the widgets, reacting to what actually rendered, never before.

Below the suggestions, explain what they're looking at before moving on: "Click any of these to connect it — once wired up, skills can pull your real data from it. Want me to list some skills you can try?" End your turn.

Step 4 — Try a skill

If they say yes, call list_skills with the plugin's skill names and a context_label like "[Plugin] skills" so they get clickable Try-it cards. Introduce the card in one line so it doesn't land cold: "Here's what [Plugin] adds — click any of these to run it now." End your turn.

When they click one (you'll see a /name message), help them with it. Keep it brief; you're still inside setup. When it finishes, bring it back: "Nice — that's how skills work."

If they wave it off at either point, that's fine — go to Step 5.

Step 5 — Wrap

Close short: "You're set. Start a new task from the sidebar anytime, or type / to see your skills."

Ground rules

• One step at a time.
• Skips are fine. If they pass on a step, mark its TODO done and move on.
• Keep each message short. Two or three sentences plus the widget, not a wall.
• Never write text that presumes a tool result before the tool runs. Don't say "you already have…" or "you're connected to…" above a widget — call the tool first, then react to what came back below it. The widget shows the data; your sentence reacts to it.
• The user trying a skill mid-flow is expected. Help with it, then return to where you left off. Don't let a skill invocation end the setup.