Cowork Prompt Library

Twenty prompts, seven capability clusters. Each one is a real prompt you can paste straight into Cowork's prompt bar. Under each prompt: what should happen, what a successful output looks like, and which Cowork capability it exercises.

This is not a checklist. It's a buffet. Skim the clusters, find three prompts that map to what you actually do this week, fire them, watch what works, and adapt the ones that hit. Two prompts that become weekly habits are worth more than twenty prompts that you read once and forget.

Most of these assume you've finished First 60 Minutes with Cowork — you've approved at least one working folder, installed a plugin or two, and authenticated a connector or two. If you haven't, start there.

Three prompts that exercise Cowork's folder access directly. The folder you approved during onboarding becomes the workspace; these prompts treat it as a real desk.

Organize my Downloads folder by file type — group everything into subfolders by extension (PDFs, images, archives, code, etc.).

Cowork reads the folder, proposes a grouping, and asks before moving anything. A good output: a clean preview of the proposed structure, a clear list of edge-case files (unknown extensions, dotfiles), and a one-click confirm. Capability: folder access (read + write).

Find every PDF in this folder that looks like a duplicate of another (same file size, modified within 24 hours of each other). List the candidates.

Cowork scans the approved folder, compares file sizes and timestamps, and returns candidate pairs. A good output: a table of pairs with both paths, sizes, and timestamps — no deletes performed, just the list, so you decide. Capability: folder access (read).

Rename every screenshot in this folder so the filename starts with YYYY-MM-DD based on the file's date.

Cowork enumerates files matching screenshot patterns, reads each file's date, and proposes the rename. A good output: a dry-run preview with old → new, flagged conflicts, and a confirm step before any rename happens. Capability: folder access (read + write).

Three prompts that exercise the doc-coauthoring skill (or its equivalents in your plugin) along with your working folder. Bring your own topic.

Draft a one-pager on [topic]. Audience: [audience]. Use the doc-coauthoring skill and save it as a Word doc in my working folder.

Cowork picks the doc-coauthoring skill via description match, drafts the one-pager, and writes the file. A good output: a structured doc (lede, three sections, close), saved with a clear filename in the folder you approved, with a link to open it. Capability: skills directory + folder access (write).

Take these rough call notes and turn them into structured action items, with owners and due dates: [paste notes].

Cowork extracts action items from the prose and structures them with explicit owners and dates — flagging ambiguous ones rather than inventing detail. A good output: a clean list of items, plus a short section of unclear — needs your call items at the bottom. Capability: skills directory (productivity / task-management).

Summarize this PDF in five bullets and three questions I'd want to ask the author. [attach file]

Cowork reads the attached PDF, returns the five-bullet summary, and proposes three substantive questions tied to the content. A good output: the bullets capture the argument (not the table of contents), and the questions are ones you couldn't have written without reading the doc. Capability: file attachment + skills directory (research-summarizer or equivalent).

Three prompts that exercise the Google Calendar and Gmail connectors. Read-only scopes are enough for all three; granting send scope is a separate decision for prompt 3.

What meetings do I have this week? Group by day and flag any with people I haven't met before.

Cowork queries Calendar for the week, groups results by day, and cross-checks attendees against your past meeting history. A good output: a day-by-day list with new-attendee flags called out clearly, and a short here's why this person is on your calendar note where one is available. Capability: Calendar connector (read).

Find every email from the last 7 days where I'm the only recipient and I haven't replied. List sender + subject.

Cowork queries Gmail with the right filters, walks the result set, and returns the list. A good output: a short, scannable table with sender, subject, and date — no draft replies, no auto-actions, just the inventory. Capability: Gmail connector (read).

Draft a polite decline to [person]'s meeting request, and propose two 30-min slots next week when I'm actually free.

Cowork cross-references your Calendar for free slots, drafts the reply, and shows it for your review before sending. A good output: a draft that sounds like you, two slots that are genuinely free (not just unbooked), and an explicit send button rather than auto-send. Capability: Gmail + Calendar connectors (read; send scope optional and explicit).

Three prompts that exercise web search (Cowork's built-in research surface) and, where helpful, attached files. Best run after you've installed a research-oriented plugin or skill.

Research [company]. Give me a one-page brief: what they do, recent news, leadership, and three angles for first contact.

Cowork pulls from public web sources, structures the brief, and cites where each fact came from. A good output: a brief that holds together on one screen, with citations you can click through, and the three contact angles tied to something specific (not generic). Capability: web search + skills directory (research / sales).

Compare [Tool A] and [Tool B] on pricing, features, and support model. Flag what's not obvious from their marketing pages.

Cowork visits both vendor sites, reads the marketing pages, and surfaces the differences — including the gotchas that don't appear in headline comparisons. A good output: a tight three-column table, citations to source pages, and a worth knowing section that captures the non-obvious. Capability: web search.

Read these three customer interview transcripts and surface three themes with supporting quotes. [attach files]

Cowork reads the transcripts, identifies recurring themes, and pulls verbatim quotes that support each one. A good output: three themes, each with two or three direct quotes, and a short note on which transcripts the theme appeared in. Capability: file attachment + skills directory (research-summarizer / synthesis).

Three prompts that exercise the /schedule slash command. Each one turns a one-off prompt into something that fires for you on a cadence. Remember the desktop-bound caveat: routines run on the machine where Cowork is installed and awake.

/schedule every weekday at 6am — summarize yesterday's emails grouped by sender, and list the top three things I need to handle today.

Cowork registers the routine, runs it at 6am each weekday, and surfaces the digest in the Scheduled Tasks surface. A good output: a daily digest that's actually short enough to read with coffee, grouped tightly, with the top-three callout pulling from the most senior or time-sensitive senders. Capability: Gmail connector + /schedule routine.

/schedule every Monday at 9am — give me a digest of all my Slack mentions from the previous week, sorted by channel and unanswered count.

Cowork registers the weekly routine and produces the Monday-morning recap. A good output: a per-channel summary, an explicit count of unanswered mentions, and the actual message text for the highest-priority ones so you can decide whether to reply from the digest. Capability: Slack connector + /schedule routine.

In one hour, remind me to leave for [appointment]. Check traffic to the destination before the reminder fires.

Cowork registers a one-shot scheduled task, checks traffic at fire time, and adjusts the leave-by message if conditions changed. A good output: a clear reminder with the current ETA, a flag if you should leave earlier than originally planned, and a link to the route. Capability: /schedule (one-shot) + web/maps lookup.

Three prompts that exercise create_artifact — Cowork's ability to render a live, queryable page that updates from your connected data. Artifacts are the surface that turns Cowork from answers a question into shows you the answer, kept current.

Build a live page showing my pipeline this week — open opportunities by stage, with next action and last-touched date.

Cowork queries your CRM via the relevant connector, renders the artifact, and gives you a URL you can pin. A good output: a single page with stage columns, opportunity cards, and the next-action field surfaced — refreshable, not a snapshot. Capability: CRM connector + create_artifact.

Build a single morning-glance page: today's calendar, unread Slack mentions, unanswered emails — all in one view.

Cowork composes data from Calendar, Slack, and Gmail into one artifact. A good output: three tight columns or stacked sections, no scrolling required on a normal laptop screen, and counts you can act on (not just numbers). Capability: Calendar + Slack + Gmail connectors + create_artifact.

Build a live page tracking my active job applications: company, role, stage, last contact, next step.

Cowork starts the tracker as an artifact you can update — either by editing in place or by telling it new statuses in chat. A good output: a clean table you'd actually keep open in a browser tab, with a row for each application and an add a new one affordance that doesn't require leaving the page. Capability: create_artifact (and optionally Gmail for last-contact extraction).

Two prompts that exercise the Claude in Chrome bridge — Cowork driving (or reading) a browser tab so you can collaborate on something happening in a web app. Higher consent threshold; read these carefully before granting browser scope.

Walk me through configuring a Supabase project. I'll click; you tell me what to click next, and read the page for me when I get stuck.

Cowork pairs with the Chrome tab, watches what you're doing, and offers next-step guidance read off the actual screen. A good output: contextual instructions ("click New project, top-right"), gracefully recovers when you click somewhere unexpected, and never auto-clicks anything without asking. Capability: Claude in Chrome bridge (read + guided assist).

Open the Vercel dashboard, navigate to my [project name] project, and read me the production env vars one at a time so I can paste them into a doc.

Cowork navigates the dashboard, surfaces the env vars page, and reads each one to you in sequence. A good output: pauses between vars so you can paste, names each var clearly before reading the value, and does not paste the values anywhere on your behalf — that stays your job. Capability: Claude in Chrome bridge (read).

Pick three prompts that match what you actually do this week. Fire them. See what works. Adapt the ones that hit — make them yours by changing the bracketed bits, tightening the phrasing, swapping the connector — and the ones that miss, drop. Two prompts that become weekly habits beat twenty prompts you read once and forget.

When a single capability starts pulling its weight — folders, connectors, routines, artifacts — open the Cowork reference page and read the section on that capability. The depth there is the next layer; this page is the on-ramp.

At Vesta Medical. Marcus (CEO) read this library three times before he ran a single prompt, and the only thing it did for him was give him the illusion of progress. The week he picked three prompts and actually fired them — the morning email digest, the weekly Slack mention recap, the live pipeline page — was the week Cowork became part of how he ran the company. The reading is the cheap part. The firing is the part that changes anything.