Cowork and OpenWork: A 90-Minute Crash Course
15 Concepts, 80% of Real Use
A practical crash course in two agentic co-workers that live on your computer: Claude Cowork (Anthropic) and OpenWork (open-source, MIT, OpenCode-powered). Unlike a chatbot, each one autonomously plans and runs multi-step knowledge work: reading your local files, calling your services, working across your apps and your browser, and handing back finished deliverables. By the end you'll know what the major pieces do, when to reach for each one, and where the failure modes hide in either tool.
Who this is for. Anyone whose day moves information between documents, spreadsheets, email, and meeting notes: lawyers, accountants, marketers, HR leaders, healthcare administrators (with PHI caveats in Part 5 ), plus consultants, analysts, and founders. The actual skill is delegation; you don't need to code or know what an API is.
Doing this well is a delegation problem. Every decision in this chapter (how to describe a task, which folders the agent can see, whether to flip "act without asking" on) comes back to one question: how much oversight does this task actually need? Read each section through that lens, in either tool.
Prerequisite: AI Prompting in 2026 . Its thirteen concepts (briefing like a colleague, context as the whole game, thinking mode, neutral framing, the iterate loop, AI desktop apps and permissions, and models checking models) are the substrate this chapter builds on. This page is what that discipline looks like when the AI can open your folders, call your connectors, and act on your behalf.
If you haven't read the prerequisite yet, start here
Three fundamentals from that chapter carry the most weight in this one. The full prereq has thirteen concepts; here's the absolute minimum to keep going:
Brief the agent like a smart, motivated new colleague who doesn't know your context. Vague prompts get vague answers. Specific briefs (with constraints, examples, the audience for the deliverable, and the why behind the task) get useful work. "Help me with this contract" is a query. "Review this draft MSA, flag every clause that materially deviates from our redline standard, and produce a comparison memo with deviations color-coded by risk level" is a brief.
Give context, don't dump it. The agent reads everything you put in front of it, including the irrelevant. Attach the file you actually need; describe the constraint that matters; state the format you want. Don't paste an entire matter folder when three documents are the relevant ones; the noise dilutes the signal and runs up your token bill (concept 5 in this chapter).
Iterate on the plan, not the output. When something goes wrong, redirect before the work runs, not after. A one-sentence correction at the plan
stage costs nothing; cleaning up after a confident wrong execution costs an afternoon. This is concept 4 in this chapter, and it's the single highest-leverage habit you can build.
For the full picture (sycophancy, multimodal inputs, cross-model review, model routing for cost), the prerequisite chapter is worth the 30 minutes. But the three above will get you through this one.
The chapter in five bullets: read this if you read nothing else
The chapter teaches one operational discipline. If you internalize only these five points, you have 60% of the value:
Delegate, don't query. Both tools are co-workers you assign, not chatbots you ask. Think in assignments (outcomes with constraints, audience, and the why ), not in prompts. (Full treatment in §1.)
Three trust levers: folders, connectors, approvals. Make a dedicated working folder; grant access to that , not your whole Documents directory. Connect each external service as a separate decision with the narrowest scope that works. Stay in the cautious "ask before acting" approval mode until you've calibrated on a task type. That's the discipline that earns you the right to relax it later.
The plan is the leverage, not the output. Ask the agent to lay out the plan before it touches any files, and read whatever it produces. Neither tool guarantees an upfront plan unless you ask. (Full treatment in §4.)
The autonomy ladder, climbed deliberately. Watch closely → ambient supervision → walk away → high-autonomy → scheduled. One rung per task type, with track record. Step back down the ladder when a task type changes (new client, new connector, new edge case). Never schedule what you wouldn't already trust to walk away from.
Untrusted content gets the cautious mode, always. An opposing-counsel email, an inbound resume, a vendor PDF, an unknown webpage, these can carry instructions the agent reads as commands (prompt injection). Never run high-autonomy mode on tasks that touch text someone else wrote.
The other ten concepts in this chapter all serve those five.
Figure 1: The five
operational disciplines: delegate not query; three trust levers; plan is the leverage; climb the autonomy ladder slowly; cautious mode for untrusted text](https://bgflncyhkwanvcinmqdc.supabase.co/storage/v1/object/public/assets/content-assets/assets/images/08-five-disciplines-793289569207cadc639ac7da03716557.webp)
operational disciplines that carry most of the chapter's weight. Print this and tape it to your monitor.
Install
Two tools, not one. On purpose. The discipline this chapter teaches has to outlive any single tool: pricing changes, model availability, and data-residency requirements shouldn't strand the lessons you've learned. The task loop and the core primitives (skills, connectors, sub-agents) are the same in both; the ecosystems differ, and scheduling is one of the bigger divergences (Cowork has it built in, OpenWork does not; §15 covers the gap). Covering each concept in both is the strongest test of whether it's real: if a technique only works in Cowork, it's a Cowork trick; if it works in both, it's part of how AI desktop work actually behaves.
If you're brand new to either tool, start with Cowork. It's the more polished surface and the lowest-friction path to a working first task. OpenWork is younger, ships frequently, and pays off most once you want choice over which model provider sees your prompts, where the work runs, or which plugins compose with what. Everything you learn here transfers; you can move between the two later.
Pick your tool below. Your choice syncs across every Cowork ⟷ OpenWork switcher on the page.
Cowork OpenWork
Cowork is a paid-tier feature: it requires an Anthropic Pro, Max, Team, or Enterprise plan. The Claude Desktop app itself is a free download; the Cowork tab appears once you sign in on a paid plan.
Download Claude Desktop from claude.com/download (Mac or Windows).
Sign in with your Anthropic account.
Click the Cowork tab at the top of the window.
You're in. Connectors, skills, plugins, and projects are all reached from inside the Cowork tab. Cowork docs: support.claude.com .
Free, no account required.
Open the GitHub releases page (or openworklabs.com/download for the curated landing) and download the installer for your platform. macOS and Linux builds are published on the releases page; pick the file that matches your architecture (the release lists them by name). Windows access is currently handled through OpenWork's paid support plan rather than a free download.
Open the installer, follow the prompts, launch the app.
The first run shows an empty home view; you create a workspace from + Add workspace
in the bottom-left of the sidebar (detailed flow is in "Try it now" below).
OpenWork docs: github.com/different-ai/openwork and openworklabs.com . OpenWork ships frequently; when click-paths don't match this page, the app's in-product docs and the live UI are the most current sources (the repo README sometimes lags the app).
Where these tools live
Both tools are desktop apps. They differ in how they're organized.
Cowork OpenWork
Cowork lives inside Claude Desktop under a top-level Cowork tab. The window has three regions: a left sidebar for navigation, a center conversation area where the agent narrates each step inline as the work happens, and a right panel that tracks files and context. The + next to the prompt input is the main entry point for adding files, Skills, Connectors, and Plugins (type / for slash commands directly). Folder access is requested inline when the agent first needs it, not granted up front.
Cowork's empty
main view inside Claude Desktop.
The + menu beside the prompt, Add files
or photos, Skills, Connectors, Plugins. This is the single entry point for everything that extends a Cowork session. The model picker (here, Opus 4.7 ) sits on the right of the prompt row, switch per-task as needed.
OpenWork is a standalone desktop app: a left sidebar with a workspace switcher and a + Add workspace button at the bottom, and a main panel with the prompt input plus Default agent and model pickers below it. Workers are added through + Add workspace → Local workspace / Connect custom remote / Shared workspaces . Skills, MCPs, and plugins each live in their own Settings tab.
OpenWork's empty
main view. + Add workspace in the bottom-left is the entry point for any worker, local, custom remote, or shared cloud.
The conceptual primitives (sessions, plans, approvals, skills, sub-agents) are the same in both. The chrome around them is different.
Try it now (five minutes, applies to whichever tool you have installed)
You can run your first task before reading another paragraph.
Cowork OpenWork
Click the Cowork tab at the top of Claude Desktop. Make a working folder first if you don't have one: ~/Claude-Workspace/ .
Type one read-only prompt: List the files in this folder. Don't open or read any files yet.
The first time the agent needs file access it posts an inline permission card in the conversation. Click Choose folder and pick your working folder.
Cowork's folder-permission
folder-permission gate: the agent says "I'll help you summarize the files in a folder. However, I need to clarify which folder you're referring to,](https://bgflncyhkwanvcinmqdc.supabase.co/storage/v1/object/public/assets/content-assets/assets/images/cowork-task-folder-gate-a2580bb3a955886730ed3a7095c8d1fd.png)
card. Click Choose folder and pick your working folder.
Watch the file list appear inline in the conversation.
Open the OpenWork desktop app.
Click + Add workspace in the bottom-left of the sidebar. In the Create Workspace modal that opens (three options: Local workspace / Connect custom remote / Shared workspaces), click Local workspace .
The Create Workspace modal, local now, the other two later if you need them.
Click Change (or the path field) and pick your folder. Make ~/OpenWork-Workspace/ first if you don't have one. Click Create Workspace .
OpenWork tells
picker: modal titled "Local workspace, Create a workspace on this device." Section: "Pick a folder. This folder becomes your wo](https://bgflncyhkwanvcinmqdc.supabase.co/storage/v1/object/public/assets/content-assets/assets/images/openwork-local-workspace-folder-picker-97a6044229ca194f18835a36f6ee358f.webp)
you exactly what it can do in the chosen folder before you confirm, this is the OpenWork equivalent of Cowork's folder-permission gate, just front-loaded into workspace creation instead of mid-session.
The new workspace appears in the sidebar. Type one read-only prompt into the bottom prompt input: List the files in this folder. Don't open or read any files yet. Click Run task .
Watch the agent narrate its steps as todos in the conversation timeline.
📚 Teaching Aid
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View Full Presentation — Cowork Crash Course
Part 1: Foundations
These first three concepts apply identically in both tools. Where commands or click-paths differ, the difference is called out inline.
1. What these tools actually are
The mental shift that matters: this is not a chatbot you query. It's a co-worker you assign. "Summarize this PDF" is a query. "Read these three vendor MSAs, flag every clause that materially deviates from our redline standard, and produce a comparison memo with deviations color-coded by risk" is an assignment. "Reconcile this month's bank statement against the GL export, list every unmatched item, and produce a draft journal-entry recommendation for each one" is an assignment. The first works fine in chat; the rest are what these tools are for.
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This is concept 1 of AI Prompting , novice vs. power user, with consequences: brief poorly and the agent executes against the gap.
That delegation shift is what makes both tools useful, and what changes the failure modes. In chat, the worst case is a wrong answer: annoying, but contained. Here, the worst case is a confidently executed wrong action that touched dozens of your files. The crash course is mostly about learning to delegate at the right level, with the right oversight, on the right kinds of work.
2. The architecture in three pieces
The desktop app is where the agent lives. Both run locally on your machine. If your laptop sleeps or you close the app mid-task, execution pauses where it left off.
The task loop is the core mechanic in both. You describe an outcome, the agent creates a plan, you approve / redirect / refine, the agent executes, it pauses for approval before significant actions, and you receive a finished deliverable. Most of the discipline of using either tool well lives inside this loop.
The execution surface is where the agent actually does work. Three layers in both:
Local files in folders you've explicitly granted access to.
Code execution inside an isolated sandbox (charts, calculations, file transformations). You don't configure it day-to-day.
External services through connectors, different catalogs in the two tools, covered in §10.
What you control in both tools is what's outside the sandbox: which folders the agent can see, which connectors are turned on, which approval mode you're in.
Figure 2: Where the work actually runs in each tool. The biggest practical difference is privacy: in Cowork, your prompts and the file content the agent
reads go to Anthropic for processing. In OpenWork, you pick the model provider that sees them, Anthropic, OpenAI, OpenRouter, or a self-hosted model on your own hardware. Your files themselves stay on your machine in both.
3. Folders, connectors, approvals: the trust model
Figure 3: The three trust levers. Set these three
deliberately and you have most of the safety story for either tool.
Folder access is how you tell the agent which parts of your filesystem are in-scope. The agent cannot read or write outside what you've granted.
Cowork OpenWork
When a task first needs file access, an inline permission card appears in the conversation ( "Claude would like to Cowork in a folder" ) with Deny / Choose folder buttons. Click Choose folder , navigate to your working folder, confirm. The grant is scoped to the session. (Some Cowork builds also expose a top-level Choose folder button before you start a task; the inline gate is what you'll most often encounter.)
Cowork's inline folder-permission card. The gate appears at the moment the agent needs file access, not as an upfront pre-approval.
Folder access is granted upfront, at workspace creation. Click + Add workspace (bottom-left of the sidebar), choose Local workspace , then Pick a folder . The picker shows you exactly what OpenWork will be able to do in that folder (read files, create and edit files, work with spreadsheets / docs / images, accept dropped files) before you confirm. Each workspace is scoped to its folder; sessions inside that workspace inherit the scope. There is no per-action inline gate like Cowork's; the scope is set at the door.
OpenWork's folder picker at workspace creation. Unlike Cowork's per-task inline gate, the scope is set once, what the checklist shows is exactly what OpenWork can do inside the chosen folder for every session in that workspace.
The single most-leverage habit in this whole course: make a dedicated working folder ( ~/Claude-Workspace/ or ~/OpenWork-Workspace/ ) and grant the agent access to that, not your entire home directory or your Documents folder. When something goes wrong, the blast radius is the working folder, not your life. This matters extra for professionals: a lawyer's Documents folder contains privileged matter for forty different clients; an accountant's contains tax returns; a healthcare administrator's may contain PHI you didn't realize was loose. Scope tight from day one.
Once granted, type a small read-only prompt to see the approval asymmetry in its smallest form:
List the files in this folder and tell me what kinds of things
are here. Don't open or read any files yet.
You'll see the file list appear in the execution view with no approval card. That's the point: the agent reads without asking; it asks before it writes. Reads are automatic, writes are gated, and that asymmetry is the whole approval model in miniature.
Connectors extend the agent into external services. Each connector you turn on is a separate trust decision: the OAuth scopes you grant at install are what the agent can read and (sometimes) write through that service. The catalog, install path, and screenshots live in §10; here, only the trust framing matters.
Two specifics worth surfacing now because they shape the trust calibration:
Native Cowork mail connectors
create drafts; they do not send. Anthropic's Google Workspace connectors documentation confirms this for Gmail: the agent assembles, you review, you click send. Third-party tool routers can offer broader send capabilities; if you wire one of those up, treat it as a separate, higher-trust decision. For a lawyer or CFO, "an email that appears from my address" is something a court or board may rely on.
Read scope ≠ send scope. Granting a mail connector read scope lets the agent summarize threads. Granting write/send scope is a different ask. Read the scopes before you click connect.
Approval modes govern how the agent behaves when it wants to take a significant action.
Cowork OpenWork
Two modes set per task: Ask before acting (default; pauses on each significant action) and Act without asking (works through the plan without pausing per step). Even in "act without asking," deletions still require explicit permission.
Permission requests appear inline in the chat as a card with three buttons, allow once / allow always / deny , at the moment the agent tries an action that needs permission (a file write, a connector send, anything beyond a read). The "always" choice is sticky for that session/project; "once" is the safe default. Stacking "allow always" across the actions a trusted task needs reaches the same low-friction state as Cowork's "act without asking", built up per action instead of toggled per task. Deletions still ask either way.
The approval table is asymmetric on purpose in both tools: reads happen automatically; writes, modifications, deletions, and moves all require an explicit click before the agent proceeds.
What file types these tools handle natively. Both Cowork and OpenWork ingest PDFs (native and scanned), Word documents, Excel/Sheets files, and email/chat threads from connectors. No extra setup. A few practical notes:
Native (text-based) PDFs: read cleanly and accurately.
Scanned PDFs: go through OCR. Quality depends on the scan: usually good enough for synthesis, not good enough for verbatim quotation without checking. If you're going to cite a specific clause from a scanned document, open the original.
Excel files with formulas and multiple tabs: read fine. The agent can also compute against them in the sandboxed environment. Watch the cell-reference labels in any analysis it reports back: labels are sometimes confidently mislabeled even when the underlying math is right.
Word documents with tracked changes: readable. Whether the agent's edits preserve tracked changes is a separate question. For litigation redlining specifically, do a careful round-trip test on a non-critical document before trusting the result on a real matter.
When in doubt, ask the agent to summarize the file's structure first ( "describe what's in this file: how many tabs, how many pages or clauses, what the columns or sections are" ) and decide whether to proceed based on what it tells you.
What happens when it goes wrong: recovery patterns. Before granting write access, the question worth asking is "what if the agent does something I didn't want?" In either tool:
Files the agent edits in place have no automatic version history. Recovery depends on what's underneath your folder. macOS Time Machine, Windows File History, OneDrive / Google Drive / Dropbox version history, or a git repo will all let you roll back. A folder on a plain local disk with no backup running is unforgiving. That's part of why the dedicated working-folder discipline above matters: it limits the blast radius.
Files the agent created or moved are recoverable through the same backup mechanisms. Renames are recoverable from the backup history too.
Connector-side actions (a Notion page edited, a calendar event created, a Slack message posted) are recoverable through that service's own version history or audit log, not through the agent. Each connector has its own recovery story. Check it before you grant write scope.
Messages sent through any send-capable connector (rare in native Cowork, see Concept 10, but possible in third-party setups) are not recoverable. Treat send actions as production deploys.
The Stop button on the active session halts a running task immediately. A halted task is recoverable. A completed action is only as recoverable as the underlying system makes it.
Practical preflight: before your first real-stakes Cowork or OpenWork session, confirm one of the backup options above is running. Two minutes now, peace of mind on every task afterward.
What works in either tool: leave approvals tight for the first two weeks. Watch what the agent wants to do. Notice the patterns of approvals you keep granting for the same kind of action: that's the work that's safe to delegate more autonomously. Notice the approvals where you actually had to think: that's the work that needs to stay supervised.
Anti-pattern: flipping to "act without asking" (or stacking "allow always" across every action) because the prompts feel slow on day three. The prompts are how you build calibration. Skipping them is how you end up with a confidently-executed mistake across 40 files, which, for a lawyer mid-discovery or an accountant mid-close, is not "annoying" but a billable-hour-eating cleanup operation.
Your first real task: a multi-source follow-up brief
The trust model is the foundation. The next thing to build is hands-on experience running a task end to end. This is the canonical "first real task", bounded, teaches the multi-connector pattern, produces a deliverable you'd actually want.
The example below is framed for a sales / business-development context, but the shape is identical across the professions covered here: If you are a... Your "first real task" looks like... Marketer / business developer Draft a follow-up email synthesizing a sales call (Notion notes + Slack thread). Lawyer Draft a status memo to the client synthesizing yesterday's meet-and-confer (case management notes + opposing counsel emails + your associate's research file). Accountant Draft the variance commentary for a monthly review (GL export + last-month's commentary + the operations team's email explanations). HR partner Draft a candidate-debrief brief for the hiring manager (interview scorecards across the panel + the candidate's resume + the JD). Healthcare admin (non-PHI work only) Draft a board update on this quarter's clinic operations (ops dashboard exports + last leadership meeting notes + the budget email thread). Stop here if any of these contain PHI.
The scenario: you had a sales call with Acme yesterday. Your rep took notes; the prospect's questions during the call ended up in a chat thread. You promised a follow-up email. The naive way is to re-read everything yourself and draft it. The agent way is to delegate the assembly so you can spend your time on what the email actually says .
You'll start with the core: a small starter folder you download and open in either tool, no accounts to set up. Once you've felt the delegation pattern end-to-end on local files, the closing section shows how to swap them for live connectors (Gmail, Slack, Notion, whatever your daily workflow runs on), same task, real sources, real impact on your week.
Step 1: Download the starter folder. Grab acme-followup-starter.zip (≈2 KB), it contains acme-call-notes.md , acme-chat-thread.md , and a short README. Unzip anywhere convenient, Desktop, Documents, wherever. The agent will write the deliverable into this same folder.
Step 2: Open the folder in your tool.
Cowork
task for weekly content updates about the Agent Factory book. Let me load the necessary tool first.&quo](https://bgflncyhkwanvcinmqdc.supabase.co/storage/v1/object/public/assets/content-assets/assets/images/cowork-schedule-inline-card-2251a66b9a2f07bf286abdfb36a09761.png)
. Open Cowork. When you run the prompt below, an inline permission card appears the first time the agent tries to read; click Choose folder and pick the unzipped acme-followup-starter/ folder.
OpenWork. Click + Add workspace > Local workspace , pick the unzipped folder, click Create Workspace . Future sessions in that workspace inherit the scope.
Step 3: First, let the agent see what's in the folder. No plan yet, just orient. Type:
Read everything in this folder and tell me what's here.
Then ask me 1-2 questions about what I'm trying to do
before we start.
The agent reads both files, summarizes what it found, and asks something like "This looks like a sales call follow-up, are you drafting the email to Raj, or something else from these notes?" Answer in a sentence. Thirty seconds of back-and-forth, much sharper context for what comes next. This is the cheapest quality lever in either tool.
Step 4: Now ask for the deliverable, with a plan. Once the agent has the context, send the real ask:
Yes, draft the follow-up email. It should:
-
Thank Raj and reference one specific thing from the call
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Answer the two questions he asked in the chat thread
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Suggest next steps (proposal walkthrough, timeline)
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Match my normal email tone (direct, no throat-clearing)
Save as acme-followup.md in this folder. Lay out your plan
first, then pause for my approval before touching anything.
Why "lay out your plan first" matters. Without it, the agent may just start executing with per-step approval cards: fine for simple tasks, less useful for multi-source synthesis where you want to catch a misreading before the agent commits to it. The instruction makes the plan-review step deterministic across both tools.
Step 5: Read the plan. Look for:
Did the agent identify both source files as inputs?
Are the two questions from the chat-thread file represented in the plan?
Are the constraints from your prompt (one specific reference, two answers, suggested next steps, direct tone) all captured?
If something's off, redirect instead of approving: "In step 2, also pull the action items from the call notes, the pricing-by-Friday commitment is what I want to mention as 'one specific thing from the call.'" The agent rewrites the plan and re-asks for approval.
Step 6: Approve and watch. The agent reads both files, drafts the email, saves it. The first time you run something like this, watch every step in the execution view: you're calibrating what kinds of decisions the agent makes well versus where it drifts. After three or four of these, you'll have the pattern.
Step 7: Review and iterate on the deliverable. Open acme-followup.md . Does the email read like you wrote it? Does it actually answer the two questions, or did it gloss over one? You have two options, and choosing between them well is its own skill:
Edit by hand. Right answer if the deliverable is 90% there and you'd just rewrite a sentence or two. Faster than asking the agent to revise.
Iterate with the agent. Right answer if there's a structural issue: one of the questions wasn't fully addressed, the tone is off in a specific direction, the next-steps paragraph is too pushy, the second paragraph repeats the first. Don't rewrite the whole thing yourself; tell the agent what's wrong and ask for a revision: "The answer to their implementation-timeline question is too generic; rewrite it using the 4-6-week security-review detail from the chat thread, not boilerplate." This is concept 7 of the prompting chapter , the brainstorm-iterate loop, applied to a Cowork / OpenWork artifact: feedback in, revision out, repeat until done.
If you're used to working alone, hand-editing will feel like the default. Resist it. The brainstorm-iterate loop is faster than hand-editing for anything beyond a one-sentence fix, and it teaches the agent your taste in the process, which improves the next deliverable's first draft. The goal isn't a perfect first draft; it's a 70% draft you finish in five minutes (with one or two iteration rounds) instead of a 0% draft you spend thirty minutes assembling.
What to notice. Five delegation decisions you just made, identical in either tool:
Folder scope : chose a working folder, not a broader part of the filesystem.
Explore before assigning : let the agent read and ask before committing to a deliverable.
Outcome framing : described the deliverable, let the agent propose how to assemble it.
Plan request + review : asked for a plan, then read it before approving, caught any misreading before the agent committed to it.
Approval mode : stayed in the cautious mode because content from a third party is untrusted.
That's the template. Every multi-source synthesis task has this shape: folder, explore, outcome, plan, execute, review.
When you're ready: the same task with connectors. Once you've run the local version, the upgrade is small. Replace the two local files with their real-world sources: a Slack/Teams channel for the chat thread, a Notion/Confluence/OneDrive page for the call notes. Install the connectors in Cowork via Customize > Connectors (see §10); in OpenWork via Settings > Extensions
. Re-run the same prompt with the source lines pointing at the connector sources instead of the local files:
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"Notion page 'Acme Discovery Call, 2026-04-29'" (in place of acme-call-notes.md)
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"Slack thread in #acme-deal from 2026-04-29" (in place of acme-chat-thread.md)
The five delegation decisions stay identical. Only the source surface changes. The extra decision you'll add the first time you run with connectors: granting connector scopes at appropriate (not maximum) levels, see §3 and §10.
Part 2: Context, sessions, and projects
Same primitives as in chat, same pitfalls, slightly different surface, and meaningfully different stakes.
4. The plan is the leverage
The defining discipline of either tool isn't that you write good prompts; it's that you intercept work between intent and execution. Every meaningful action the agent takes (reading a file, writing a file, calling a connector, sending a message) passes through a moment where you can read what's about to happen and redirect, deny, or let it proceed. Skip those moments and the work goes sideways twenty minutes later, after the agent has touched dozens of your files. They're the cheapest place in the entire workflow to course-correct.
Figure 4: The task
loop. Almost all the discipline of using either tool well lives in step 3, reading what's about to happen before it does.
info
Plan review is two prompting concepts in one move: think hard (concept 5) before any file is touched, and outline before drafting (concept 7) with a filesystem behind it. Edit the plan, not the cleanup.
Where the plan and the intercept points appear:
Cowork. The agent opens with a planning message, then narrates each step inline. Per-action approval cards appear before significant operations (folder access, file writes, sends, scheduling). Intercept happens (a) at the opening plan and (b) at every inline approval card, no monolithic "Approve plan?" button; intercept is per-step and continuous.
Figure 4a: Cowork's plan stage. The agent has produced a numbered Execution plan with a fenced code block listing each file it intends to touch. The right panel tracks the deliverables it's planning to produce. This is the moment to intercept , read the plan, redirect with a one-sentence correction, or approve.
Figure 4b: After the plan is approved
, the same Cowork session narrating each step inline: "Loaded tools / Used a tool / Searched / Read / Created." Each line is a message you can pause on, redirect, or follow. The intercept points are inline and per-step.
OpenWork. The agent posts a numbered plan in the right panel and streams progress as a todos timeline below it. Permission cards ( allow once / allow always / deny ) appear inline only at gated actions: writes, sends, deletions, scheduling. Same intercept discipline as Cowork, with the plan and progress visually separated from the conversation. The agent picker also exposes a dedicated Plan agent , a restricted planning mode that asks for approval before any write rather than executing them.
OpenWork's agent
picker. Default / Build / Plan. Switching to Plan gives you an approval-gated planning mode that asks before any write: the OpenCode-native equivalent of "wait for the plan before any writes happen."
Figure 4c: OpenWork's todos timeline streaming mid-task. The numbered
plan is visible top-right; each step's progress appears as a chevron entry below as the agent moves through it. The Stop button (bottom-right, replacing Run task ) halts execution instantly when something looks wrong.
What to actually look at at each intercept point (same in both):
Scope : is the agent proposing to touch only the files you described, or has the scope crept? "Sort this folder" should not turn into "rename everything in three subfolders." "Review the Smith MSA" should not turn into "review every contract in the matter folder."
Order : does the sequence make sense, or has the agent jumped to a destructive step before a verification step?
Tools : is the agent proposing to use a connector or plugin you didn't expect, or one you forgot was installed?
Assumptions : what is the agent assuming about file formats, naming conventions, redline conventions, GAAP treatment, or your firm's house style that it shouldn't be?
If the plan is wrong, you don't have to start over. Type a one-sentence redirect:
Skip step 3, and for step 4 use the column headers in the existing
template instead of creating new ones.
The agent rewrites the plan and re-asks for approval. Two minutes of plan review prevents two hours of cleanup.
5. Context still costs money
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This is concept 4 of AI Prompting (context is the whole game) with a token bill attached. There, bad context cost you a worse answer. Here, it costs you a worse answer and your monthly usage allowance.
Every message either tool sends to the model includes the system prompt, your global instructions, the project / workspace instructions, the conversation so far, the contents of files the agent has read this session, and any active skill content. That all costs tokens, and the bill is yours.
In Cowork , the bill goes to your Anthropic plan. In OpenWork , the bill goes to whichever model provider you configured (Anthropic API, OpenRouter, OpenAI, or a self-hosted model where the bill is your hardware). OpenWork's flexibility lets you run a smaller / cheaper model for routine tasks and reserve the frontier model for hard ones; Cowork's bundle is simpler but less tunable.
Two practical implications, identical in both:
Don't dump entire folders into context unprompted. If you say "read every file in this matter folder," the agent does it, and you've just paid to load potentially hundreds of pleadings, exhibits, and emails. Better: ask the agent to list first, propose what matters, then read only those.
First, list this folder and tell me which files matter for
[my question]. Read only those, then summarize.
End long sessions cleanly. When a task is done, start a new session for the next one. Carrying yesterday's conversation into today's task pays for context you no longer need.
The same compaction discipline that applies in chat applies here: less context, used deliberately, beats more context dumped in hope.
OpenWork additionally exposes an Auto context compaction toggle (in Settings > Model ) that controls OpenCode's compaction.auto behavior for this workspace; reload the engine in Settings > Advanced after changing it. If your OpenWork sessions feel sluggish or the token bill creeps, this is the lever to flip first.
A worked example from real practice. A litigation associate had a matter folder with 340 documents (pleadings, exhibits, deposition transcripts, opposing-counsel emails: a typical four-month-old case). Her first instinct was the obvious one: "read everything in this folder and summarize what's happened in the case so far." That request would have loaded several million tokens into context (every exhibit, every email, every duplicate copy of every order) and produced a generic summary that mostly told her things she already knew. The token bill on the prompt alone would have been substantial, and the agent would have been working from a context so large that the recall on any specific point would have been weak (this is the "context rot" issue from concept 4 of the prompting chapter).
The right move, executed in two prompts:
Prompt 1: "List the files in this matter folder. Group them by type
(pleadings, exhibits, depositions, correspondence). For each group,
tell me which 3-5 files are most likely to be foundational based on
filename and date. Don't read the files yet."
Prompt 2: "Read only the files you flagged as foundational in the
prior step. Produce a 1-page case-status memo covering: current
posture, next deadlines, the strongest claim, the strongest defense,
and the three open questions I should track."
Two prompts, roughly 12 files actually read, a meaningfully better deliverable, and a token bill maybe 5% of what the original prompt would have cost. This is what "context is the whole game, but with a token bill attached" looks like in practice: triage first, read selectively, synthesize once.
Same pattern, any domain with a large source folder: have the agent triage first, then read only what matters.
Strategic cost: route hard work to the strong model, plumbing to the cheap one. The prompting chapter's Concept 12 said "AI is jagged" ; different models are good at different things, and routing matters. Practical rule of thumb in either tool: use the strongest model available for the thinking work (multi-source synthesis, contract redline, board memo) and an economy model for the plumbing (file listing, format conversion, OCR on a clean PDF). Most professional sessions have one or two genuinely hard decisions surrounded by a lot of plumbing. Route accordingly. Both tools expose a model picker right next to the prompt input, so you can switch per-task without leaving the chat.
6. Persistent workspaces for recurring work
The one idea here: recurring work belongs in a folder with a context file, not a fresh chat each time. If you find yourself re-explaining the same context every Tuesday, that's a signal the work needs a home.
The pattern is the same in both tools:
Make a folder for the recurring work, one folder per matter, client, cycle, or campaign.
Drop a markdown context file at the root: CLAUDE.md for Cowork, AGENTS.md for OpenWork (the filename differs because OpenWork inherits OpenCode's AGENTS.md convention; the job of the file is identical). Inside it, the persistent context your co-worker should always know: your role, the matter's conventions, terminology, file layout, tone, governance rules, anything you'd otherwise re-paste at the start of every session.
Open the folder, run prompts. The context file loads automatically. You don't reference it explicitly.
Cowork adds two extras on top of this base pattern: Projects (a named bundle with cross-session conversation memory) and scheduled tasks (built-in cadence, see §15). OpenWork is just folder + AGENTS.md ; you re-fire the prompt yourself when you need a fresh run, and the context file does the persistent heavy lifting.
Examples of recurring work that map well:
Lawyer: one folder per active matter. Pleadings and deposition transcripts in the folder; the firm's redline standard, the matter-specific glossary, and citation conventions in CLAUDE.md / AGENTS.md .
Accountant: one folder per recurring close cycle (monthly close, quarterly review, year-end). TB template in the folder; variance threshold and last-period commentary's tone in the context file.
Marketer: one folder per ongoing campaign or client. Brand guidelines and voice samples in the folder; campaign goals and prior results in the context file.
HR partner: one folder per hiring loop. JD and scorecards in the folder; panel calibration notes and weighting rules in the context file.
The two failure modes:
Putting everything in one folder. Context bleeds. The "Q1 financial analysis" folder starts pulling in CLAUDE.md rules you wrote for "marketing copy review" two months ago. Separate workstreams, separate folders. Lawyers especially: separate matters, separate folders, always, both for context hygiene and confidentiality discipline.
Standalone sessions for recurring work. If you're re-explaining the same context every Tuesday, that's the missing context file talking.
The 80/20 rule: every recurring task gets its own folder + context file; every one-off task stays as a standalone session.
Part 3: Rules and instructions
Both tools have a layered instruction system. Knowing the layers saves you from the most common confusion: "why did the agent ignore what I said?"
7. Global, folder, and session instructions
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The three layers below are concept 4's context stack with explicit slots: global is the always-on layer (your role, default tone, output formats), folder is what you'd otherwise re-paste every prompt (this client's terminology, this matter's structure, this period's GAAP treatment), and session is the ask for this task.
Figure 5: The three nested layers of instruction. Putting folder-specific rules in global is the single most common mistake.
Three layers, in order of how broadly they apply:
Global instructions. Apply to every session you ever run.
Cowork: set once in Settings > Cowork .
OpenWork: set in OpenWork's Settings panel. (Power-user: see Appendix A for the underlying config-file path.)
Folder / project instructions. Apply when that folder is in scope.
Cowork: attach to a specific folder; the agent can also update folder instructions on its own during a session as it learns about the folder's structure.
OpenWork: set when a project folder is open, through the OpenWork Settings panel. (Power-user: see Appendix A for the project-scoped config files and the AGENTS.md convention.)
Session prompts. What you type for the current task. Same in both.
The most common mistake is putting everything in global instructions. The result is a 3,000-token system prompt that costs you on every turn and confuses the agent with rules that don't apply to most tasks.
The right model: global is sparse, folder is specific, session is the goal. Global should fit in two short paragraphs. Folder instructions live with the work they describe. Session prompts state the outcome.
A working example of good layering, for a marketing analyst:
Global:
I'm a marketing analyst at a mid-size SaaS company. I write in concise,
direct prose. Default to markdown for documents, .xlsx for any tabular
output, and skip the throat-clearing intros.
Folder (Q1-campaign-analysis/):
This folder contains weekly campaign reports from Jan-Mar 2026. Files are
named YYYY-MM-DD-campaign-report.csv. Conversions in column G, spend in
column H. The "control" segment is always row 2.
Session prompt:
Compare conversion rates across the 12 reports in this folder. Identify
the top 3 weeks and what they had in common. One-page summary.
A second example, for a litigator:
Global:
I'm a litigation associate at [firm]. I write in direct, plain English
with no Latinisms unless they appear in the source text. Default citation
style is Bluebook 21st. Always flag any claim that should be verified
against the underlying record before I send it.
Folder (Smith-v-Acme/):
This is the Smith v. Acme matter. Plaintiff is "Plaintiff" or "Ms. Smith"
in our filings, never "Smith." Defendant entity is "Acme" (short form
throughout). Exhibit numbers follow EX-NN-description.pdf. Deposition
transcripts in /depositions; pleadings in /pleadings; opposing counsel
emails in /correspondence/opposing.
Session prompt:
Summarize the key admissions in the three depositions in /depositions
that bear on the breach-of-contract claim. One paragraph per deposition,
with citations to page:line.
Notice what's not in global: the matter-specific naming, the citation form for this filing, the folder layout. Those belong with the matter.
8. The "ask me questions before you execute" pattern
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This is concept 6 of AI Prompting (neutralizing sycophancy) moved upstream. There, you rewrote your own prompts before sending so the model didn't quietly agree with the answer you implied. Here, you ask the agent to surface what your prompt didn't say before it executes against an assumption.
A pattern from Anthropic's own best-practices docs that's worth internalizing in either tool: instead of stating the task and hoping the agent got it, end with "ask me 1-2 clarifying questions before you start."
For non-trivial tasks, this surfaces unstated assumptions that would otherwise become bugs: "Should I include the canceled subscriptions in the count?" / "For the variance commentary, do you want me to flag the FX impact separately or roll it into the line item?" / "In the candidate brief, should I weight technical fit and culture fit equally, or did the panel agree to weight one more heavily?" Two questions, ninety seconds, a much better deliverable.
This is the cheapest quality lever in either tool, and the easiest one to skip. For lawyers and accountants in particular, where the cost of getting the framing wrong is a billable-hour rework cycle, the ninety-second clarifying step is an objectively positive ROI on every non-trivial task.
A second instruction worth adding for multi-source tasks: "if the sources contradict each other, flag the contradiction; don't silently pick one." When the agent reads three or four source documents, it will sometimes encounter genuine conflicts: the email thread says one delivery date, the contract says another; the panel scorecard rates the candidate "strong hire" but the hiring manager's email is more cautious; one deposition transcript admits a fact that another denies. Without explicit instruction, the agent's training pulls it toward smoothing the conflict and producing a confident-sounding output that picks one answer. For a litigator or an auditor, that's the failure mode that produces malpractice . The fix is one line: append "if any sources contradict each other on a material point, flag the contradiction explicitly in the deliverable; do not silently pick one" to the task description. This generalizes Concept 6's anti-sycophancy discipline to multi-document synthesis specifically.
Part 4: Extending the tool
Both tools extend in four major ways. Decision tree:
Need the agent to follow a specific procedure when a matching task comes up? Skill
Need the agent to read or write through an external service? Connector
Need a packaged bundle of skills and connectors for a specific role? Plugin
Need to give the agent a richer or different surface to act on? MCP server / desktop extension
Every one of these is a delegation tool, not just a feature. Skills shape how the agent works. Connectors shape where it can reach. Plugins shape what role it's playing. MCPs shape what surfaces it can act on.
9. Skills
A skill is a playbook your co-worker keeps on a shelf. It has a title (so the agent knows when to grab it), a procedure (so it knows what to do), and optionally a few bundled tools, a checklist, a script, a calculator, for the steps that need them. You install playbooks once; the agent reads spines all day and only opens the one that matches the question in front of it.
Concretely, a skill is a folder with a SKILL.md file at its root. The frontmatter has a name and a description (the "spine"); the body is the procedure. Both tools use the same SKILL.md format (AgentSkills-compatible), so a skill written for one often works in the other unchanged.
A minimal SKILL.md (works in both):
name: weekly-brief
description: Generate the user's weekly status brief from a folder of meeting notes
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List files modified in the last 7 days in the current project folder.
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Read each meeting-notes file (filename matches meeting.md).
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Read each project file modified this week (filename matches project.md).
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Produce a one-page brief with:
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3 bullet "what shipped"
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3 bullet "what's at risk"
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1 paragraph "next week's focus"
- Save as weekly-brief-YYYY-MM-DD.md in the current folder.
The description is the single most important field. It's the spine the agent reads to decide whether to open this playbook. Vague descriptions ("helps with weeks") fire on everything; specific ones ("Use when the user asks for the weekly brief from meeting-notes files") fire only when relevant.
Three ways skills enter your tool , identical in shape across both:
Cowork OpenWork
From a catalog. Open Customize > Skills
. Anthropic publishes a built-in catalog; community-run marketplaces have emerged for third-party skills (search "Claude Code skills marketplace" for current sources). Browse, click install.
Generated in chat. Cowork ships with a /skill-creator skill, type /skill-creator and describe a task you do every week. It asks clarifying questions, generates the skill, runs evaluations against test cases, and saves it.
Authored manually. ZIP and upload via Customize > Skills > Upload (private to your account; on Team/Enterprise plans, owners can provision skills org-wide).
Cowork's Skills tab with /skill-creator selected
. Three columns: install scope on the left, skill list in the middle, skill detail and preview on the right. Each skill has an on/off toggle in the detail pane; click a skill to read its full procedure before enabling.
From the Hub. Open Settings > Skills , tab to Hub to browse OpenWork's community + team catalog. Click to install.
Generated in chat. Click Create skill in chat in the Skills tab (or ask the agent: "build me a skill that does X"). The agent scaffolds the SKILL.md for you.
Authored manually. Import local skill picks a folder and installs it; Open skills folder reveals where they live so you can drop one in directly.
OpenWork's Skills settings page. Three install paths (Import local, Open skills folder, Create skill in chat), four browse scopes (All / Installed / Team / Hub). The Hub is OpenWork's community + team skill catalog; Team is your org's shared skills (parallel to Cowork's enterprise plugin marketplaces).
Generated-in-chat is the cheapest path to a first custom skill in either tool, and easy to miss if you haven't tried it. For a lawyer: "draft a privilege log entry from a document." For an accountant: "generate variance commentary for a single GL line." For a marketer: "produce a one-line campaign summary in our voice." The agent interviews you, drafts the playbook, tests it, and saves it where it belongs.
How the agent picks a skill. Auto-invocation happens when a task description matches a skill's description; that's why the description spine matters so much. Or you invoke explicitly by typing / to open the slash-command menu ( /privilege-log , /variance-commentary , /candidate-brief ). Cowork's + button and OpenWork's lightning icon both expose a quick-browse menu (covered in "Where these tools live" and below) so you can discover and trigger skills without typing the slash command from memory.
OpenWork's lightning-menu
connect flow for the common ones (Notion, Linear, Sentry, Stripe), a "Connect your Chrome" affordance for browser control, and an Add Custom App for your own MCP server. The Apps / Plugins tabs at the top filter the view.
Where connectors get powerful is combinations . One connector is useful; three connectors that work together unlock workflows that didn't exist before:
Sales / BD: "Pull last week's Slack thread on the Acme deal, cross-reference with the Notion page on Acme's renewal, and draft a follow-up email."
Litigation: "Pull the email thread with opposing counsel from last Tuesday in Outlook, cross-reference with the deposition outline in OneDrive, and draft a response that preserves our position on the privilege dispute."
Finance: "Pull the variance email thread from controllership in Outlook, cross-reference with the close checklist in SharePoint, and draft tomorrow's leadership update."
HR: "Pull the panel debrief thread from Slack, cross-reference with the candidate's interview scorecards in Greenhouse, and draft a hiring-manager recommendation memo."
Each is three connectors in one task; the answer would have taken a human 20 minutes of context-switching to assemble.
Discipline (same in both): install a new connector when you have a specific workflow it unlocks. Don't install connectors speculatively. Each one expands the surface area where things can go wrong, including new prompt-injection vectors from content on the other side of those services.
11. Plugins
The word "plugin" means different things in the two tools , worth flagging up front:
A Cowork plugin is a role bundle (skills + connectors + slash commands + sub-agents + config in one download), in Anthropic's plugin format.
An OpenCode plugin , surfaced in OpenWork's UI as "Plugins (OpenCode)," is an npm package with event hooks that extends the underlying OpenCode engine. OpenWork doesn't have its own plugin format; it's the UI layer over OpenCode's plugin system.
The two are not interchangeable. A Cowork plugin won't install in OpenWork; an OpenCode plugin isn't a bundle of role-specific skills. They serve different needs.
Cowork OpenWork
Cowork plugins are role bundles . Each plugin packages one or more skills, connectors, slash commands, sub-agents, and configuration into a single download. Anthropic open-sourced their internal knowledge-work plugins at anthropics/knowledge-work-plugins , the canonical starting point. Slash commands are namespaced ( /legal:privilege-entry , /fin:variance-comment , /hr:candidate-brief ) to prevent collisions. Install via + > Plugins , which opens the Directory.
Cowork's Plugins Directory. Anthropic
& Partners shows the published catalog; Personal is where your own plugins live. Each card is a role bundle, Marketing, Finance, Legal, Sales, and so on, bundling that role's skills, connectors, and slash commands together.
What OpenWork installs as "plugins" are OpenCode plugins , single-purpose npm packages with event hooks that extend the underlying engine. Not role bundles like Cowork's. To install one:
Open Settings > Extensions and scroll to the Plugins (OpenCode) section.
Pick the scope: Project (this workspace only) or Global (every workspace).
Type the plugin's npm package name into the Add plugin field.
Click Add .
OpenWork's Plugins section in Settings → Extensions. Plugins are installed by npm package name ; there's no in-app catalog or checklist. The Project / Global tab at the top sets the scope; once added, the plugin lives in this workspace's (or your global) opencode.json .
Practically:
If you want a role bundle (say, a Sales plugin packaging Slack + call-prep skills + outreach drafting skills + namespaced slash commands ready-to-go), Cowork's plugin system gets you there faster out of the box.
If you want fine-grained control and you're comfortable composing your own bundle from individual skills and plugins, OpenWork is more flexible .
If your firm or org has standardized on the OpenCode ecosystem already, OpenWork's plugins compose with that work ; Cowork's plugin format is its own thing.
For Enterprise customers, Cowork admins can publish private plugin marketplaces and auto-install approved plugins for new team members. OpenWork for teams centers on a shared skills repository and a standardized plugin set distributed via your existing source-of-truth (a shared repo, an internal package, etc.).
Caution that matters for both tools
A plugin may install third-party MCP servers and software that run with the same permissions as any other program on your machine. In Cowork, plugins with an Anthropic Verified badge have undergone additional quality and safety review; plugins without it should be reviewed before you install them. OpenWork plugins are open-source and reviewable; "open-source" is not the same as "audited." Each plugin you add expands the agent's surface area in ways that aren't always obvious, including new prompt-injection vectors from whatever data sources the plugin's connectors reach.
A worked example: a marketer who installed too many plugins, too fast. A growth marketer at a SaaS company saw the plugins announcement and installed seven of them in one afternoon: Sales, Marketing, Research, Comms, Analytics, plus two community plugins from a forum thread. The next morning she opened Cowork, started typing / for a slash command, and got a list of forty-three options across the seven plugins, many with overlapping names ( /marketing:brief and /comms:brief and a community /brief ), and one community plugin that had silently installed an MCP server reaching into a third-party analytics tool she didn't remember authorizing. Two hours of cleanup followed: uninstall everything, audit what was left, reinstall only the two she actually used (Sales and Marketing), confirm the namespaced slash commands didn't collide. The lesson she internalized: install plugins the way you install browser extensions: one at a time, with a specific workflow you wanted to enable, and audit monthly. The friend who'd pointed her at the seven-plugin install meant well; speculative installation is the same anti-pattern at scale that "act without asking on day three" is at the per-task level.
12. Sub-agents
Sub-agents are the feature most readers under-use, because the trigger isn't obvious. The mechanics are identical in Cowork and OpenWork.
When a task breaks into parallel work, the agent can spawn sub-agents : parallel workers that each handle a piece simultaneously. Instead of reading 20 contracts sequentially, the agent dispatches four sub-agents that read five contracts each in parallel. Each works in its own context, so the main session stays clean: what comes back to your main thread is the sub-agent's result , not the raw documents it read.
You can tell sub-agents fired by watching the execution view: instead of one linear stream of file reads, you'll see multiple parallel workers progressing at once, often labeled by their slice of the work (e.g., "contract 3 of 12", "dimension: indemnification"). When they finish, the view collapses back to a single thread for the synthesis step.
Cowork dispatching two parallel sub-agents on the acme-followup-starter folder. The "Ran 2 agents" cards
each show a sub-agent's slice ("Inspect README and chat thread / Inspect call notes"); below them, the main thread synthesizes what each one found. The cards collapse back into a single result once all sub-agents finish.
OpenWork's explore prebuilt sub-agent dispatching three workers in parallel
, one per file. Each "Explore task" chevron above is one sub-agent's slice of the work; the numbered list below is the synthesis the main thread produces from their results. Same pattern as Cowork, rendered as a timeline.
The exact token accounting (whether sub-agent tokens count against your usage cap, against your context budget for the parent session, or are independent in both senses) varies by plan and product version, so check your plan's specifics if cost matters to you. The qualitative point holds: a 30-minute sequential job often becomes a 5-minute parallel job, and your main session doesn't bloat.
You don't write special syntax for this. You frame the task to make the parallelism obvious, and the agent dispatches sub-agents automatically. Three patterns that reliably trigger parallelization:
Figure 6: Three patterns that reliably trigger sub-agent parallelization. Frame the task right and a 30-minute sequential job becomes a 5-minute parallel one.
The fan-out pattern. "For each of these N items, do X." Example:
"Process each of the 12 transcripts in this folder. For each one, produce a one-page summary covering [the three or four things that matter to your domain, admissions/inconsistencies/questions for litigation; pain points/feature requests/buying signals for customer interviews; duplicate risk/missing fields/dormant flags for vendor records]. Then synthesize a top-level themes document across all 12."
Same shape, any domain with a batch of similar source documents.
The dimension pattern. "Analyze X across N dimensions."
Legal: "Audit this draft MSA across these dimensions: indemnification scope, limitation of liability, IP assignment, termination triggers, governing law. Flag deviations from our redline standard on each."
The compare pattern. "Compare A and B."
HR: "Read last year's compensation philosophy doc and this year's draft. Extract the principles in each. Identify what changed, what didn't, and which changes are likely to require comms."
When not to invoke sub-agents. Three categories where sequential is better, regardless of tool:
Genuinely sequential work. Each step depends on the last. "Read the contract, draft the redline based on what it says, then prepare the cover memo summarizing what changed" is three dependent steps, not three parallel ones.
Small batches. Three files isn't worth parallelizing. Twelve files is. The threshold is somewhere around 5-7 items.
Tasks where coherence across items matters more than throughput. If the right output for item 3 depends on what was decided about items 1 and 2, sub-agents fragment the reasoning.
A debugging note for both tools. When sub-agent runs go wrong, the symptom is usually consistency drift: sub-agents made different choices about the same edge case because each one only saw its own slice. The fix is to put the consistency rules into the main task description , not into the sub-agent prompts. Telling the agent up front "use the same naming convention across all summaries: lowercase-hyphenated, dated YYYY-MM-DD; treat every late-payment clause the same way regardless of how it's labeled in the source" gets passed down to every sub-agent.
The right mental model: sub-agents are best for work that is embarrassingly parallel , many independent units, each with the same shape, where the only thing that matters is doing them all and assembling the output.
Part 5: Safety and the autonomy ladder
The discipline that matters most lives here, and it applies identically in both tools.
Regulated workloads: full guidance for PHI, attorney-client-privileged matter, and federally regulated data
Do not assume Cowork is approved for PHI, FedRAMP, FSI, or privileged-client workloads on standard plans. The accurate picture as of May 2026, drawn from Anthropic's own Public Sector FAQ and HIPAA-ready Enterprise documentation . Compliance scope changes; re-verify with your account team before relying on any line below:
Standard Cowork plans (Pro / Max / Team / Enterprise without HIPAA enabled): not approved for PHI; no BAA in place.
HIPAA-ready Enterprise configurations: exist for Claude with a click-to-accept BAA, but Cowork is not yet available on any HIPAA-ready Enterprise plan per Anthropic's HIPAA-ready Enterprise documentation. Do not process PHI in Cowork.
Claude for Government (C4G): FedRAMP-High authorized, but Cowork is not yet included in C4G's scope per Anthropic's Public Sector FAQ (on the roadmap).
FSI / financial-services regulated workloads: sales-negotiated; depends on plan, region, and the specific connectors in use.
Before pointing Cowork at regulated data, verify in writing with your compliance team and your Anthropic account team: the exact plan, your BAA / ZDR status, the specific connector and feature limitations under that configuration, and whether Cowork itself is included in the approved scope of your enterprise agreement.
The three things to actually check , regardless of regime, before any regulated data goes through either tool:
Data residency. Where, geographically and legally, do the prompts and file content land? Cowork: Anthropic-hosted infrastructure (US-based unless your enterprise agreement specifies otherwise). OpenWork: depends on the model provider you've configured (Anthropic-direct, AWS Bedrock GovCloud, Google Vertex with Assured Workloads, Azure AI Foundry, or self-hosted) and each has a different residency story. For EU work, "where" matters legally. Ask the question explicitly.
Model provider BAA / DPA. Whoever processes the prompt needs the right contract for the regime you're under. HIPAA → BAA. GDPR → DPA. The vendor with the BAA is the one whose servers see the prompt. For OpenWork users that's the model provider, not OpenWork. For Cowork users that's Anthropic. Confirm the BAA covers the specific product (Cowork, not just Claude API), the specific features (some MCP and connector features are excluded under HIPAA-ready configurations), and the specific data flow you're running.
Logging and audit trail. Who logs what, where, and for how long? HIPAA requires six years of audit-log retention. The BAA does not automatically include application-level logs; those are usually your responsibility. If you can't show who accessed what regulated data and when, you have a compliance gap, even if the model provider's BAA is in order.
OpenWork's local-first architecture changes the data-flow story. The app and the file operations run on your machine; the host doesn't ship your files to a vendor by default. But this does not automatically solve compliance. The model calls still go to whatever LLM provider you've configured (Anthropic, OpenAI, OpenRouter, a self-hosted model, etc.). The data-residency, BAA, and audit story is that provider's , not OpenWork's. "Local-first" is not the same as "compliant." Get your compliance team's written sign-off on the specific model provider, the specific data flow, and the specific use case before pointing OpenWork at regulated data either.
For both tools: lawyers, the guidance here assumes outside-counsel restrictions on third-party AI processing have already been honored for the matters you'd touch. Healthcare professionals, same with PHI. The safety practices below are necessary but not sufficient for regulated contexts.
13. The autonomy ladder
Concept 11 of AI Prompting introduced the permission ladder for AI desktop apps as a one-time install decision. The autonomy ladder below is the same shape applied turn by turn, task by task: trust grows with track record on this kind of work, not with how long the tool has been installed.
Figure 7: The five rungs. Climb deliberately, one rung per task type, with track record. Step back down when a task type changes.
There's a spectrum from full oversight to full autonomy, and you climb it task by task as you build calibration. Same five rungs in both tools:
Watching closely. Default mode, novel task. You read the plan carefully, you watch every approval prompt, you stop and redirect at the first sign of drift. This is week one for any new kind of task.
Ambient supervision. You've done this kind of task a few times. You read the plan, approve, then check in periodically while doing other work. Most regular use lives here.
Walk away. You trust the task pattern. You start it, leave the room, come back to a finished deliverable. Reserve for tasks you've watched succeed multiple times.
Act without asking (Cowork) / stacked allow always (OpenWork). The agent works through the plan without pausing for per-step approval. Faster, riskier. Use only when (a) you're actively supervising the screen, (b) the files and sites are trusted, and (c) you can hit stop the moment something looks wrong. Even here, deletions still require explicit approval in both.
Scheduled tasks (Cowork only; see Concept 15 for OpenWork's scheduling-gap caveat). The agent runs the work on a cadence (daily, weekly) without you watching.
The mistake is climbing this ladder too fast. The discipline is climbing it deliberately, one rung per task type, and being willing to step back down when a task type changes (new client, new connector, new edge case) until you've recalibrated.
A worked example: an HR partner who climbed too fast on candidate screening. A recruiter at a 200-person company built a Cowork project for first-round candidate screening: read each résumé in inbound/ , score against the job description, produce a shortlist with one-paragraph rationales. After running it at the ambient supervision rung a few times and seeing it produce reasonable shortlists, she promoted it to walk away and stopped reviewing the per-candidate plans. Three weeks in, the hiring manager flagged that one candidate the agent had ranked as a "strong yes" had a credential discrepancy: the résumé claimed a degree from a university that didn't offer that program in the listed years. The agent hadn't checked the credential because the job description hadn't asked it to; the recruiter hadn't caught it because she'd stopped reviewing. The fix wasn't to give up the autonomy gain; it was to step back down to ambient supervision for that task type, add a credential-verification step to the project instructions, and only re-promote to walk-away after the new behavior had been watched succeed. This is what "step back down when a task type changes" looks like in practice: the change wasn't the task description, it was the discovery that the task had a hidden quality-check the original calibration didn't cover. New edge case, recalibrate. The autonomy you've earned is task-specific, not skill-generic.
14. Prompt injection is a real attack class
Prompt injection happens when a malicious document, webpage, or email contains instructions that try to hijack the agent into doing something you didn't ask for: exfiltrating files, sending messages, disabling safeguards. The instructions look like normal text to you; the agent reads them as commands.
This isn't theoretical, and it isn't tool-specific. The combination of (a) the agent reading content you didn't author, (b) the agent having access to your files and connectors, and (c) any high-autonomy mode means a single poisoned input can move through your system fast. For lawyers reading opposing-counsel correspondence, accountants reading vendor invoices, marketers reading inbound press inquiries, HR reading inbound resumes, and healthcare administrators reading inbound referrals: every one of these inputs comes from someone outside your organization who could, in principle, embed instructions.
Practical defenses (both tools)
Don't run high-autonomy modes on tasks that involve untrusted content : emails from strangers, web pages you didn't choose, documents from unknown senders, vendor proposals, opposing-counsel filings, inbound resumes. The whole point of "ask before acting" / allow once is to give you a chance to notice when the agent is about to do something the actual content asked for, not what you asked for.
Be careful with new MCPs and plugins. Each one is a new ingestion point.
Watch for scope creep in the plan. If the proposed plan names files, folders, or connectors you didn't mention, do not click Approve. Either redirect ("only touch the inbox-review/ folder; do not write to anything else") or close the task and start over. That's the symptom of either an injection or a confused model.
Hit Stop the moment things drift mid-task. The Stop button on the active session halts execution immediately in either tool. If the execution view shows the agent opening a file, calling a connector, or sending a message you didn't authorize, click Stop first and ask questions after.
Remember concept 6's neutral-framing rule, in reverse. In prompting, you learned to strip leading questions out of your own prompts. Here, the risk inverts: someone else's content (an opposing counsel email, a vendor PDF, a candidate's resume, a webpage you didn't write) can carry leading instructions the agent reads as commands. The defense is the same instinct, applied to inputs instead of outputs: treat untrusted text as a potential prompt, and stay in the cautious approval mode whenever it's in the loop.
The mitigations are real but not perfect in either tool. The user-side defense is staying in the cautious approval mode for any task that touches untrusted content.
A worked example: the vendor PDF that almost exfiltrated a client memo. A corporate lawyer at a mid-sized firm was reviewing a software-vendor proposal for one of his clients. He uploaded the vendor's 40-page PDF to Cowork along with the client's strategy memo, and asked the agent to draft a one-page comparison of the vendor's claims against the client's stated requirements. He was in the cautious "ask before acting" mode by habit. The plan that came back included an unexpected step: "after producing the comparison, send a copy to [an external email address] for the vendor's records." That instruction wasn't in his prompt. It had been embedded in the PDF: buried in the footer of page 32 in white-on-white text, which his eyes had skipped over but the agent had read as an instruction. He clicked Redirect, deleted that step, and the rest of the task ran fine. The story shows two things concretely: (a) untrusted content from outside your organization (a vendor proposal, an opposing-counsel email, an inbound resume, a public webpage) can carry instructions that look like text to you and read as commands to the agent; (b) "ask before acting" is what saved him. In "act without asking" mode, the exfiltration attempt would have completed before he saw the plan. The lawyer now treats every uploaded vendor document as untrusted by default and runs them only in cautious mode, regardless of how routine the task feels. That's not paranoia; it's the discipline section 13 calls "step back down when a task type changes." Untrusted-content tasks are their own category, no matter how many trusted-content tasks you've done before.
15. Scheduled tasks need extra care
Cowork OpenWork
Cowork has built-in scheduling with two flows . Pick based on whether you're already in the middle of a relevant task or starting fresh.
Quick-fire /schedule from chat. In the prompt input, type /schedule followed by a natural-language description that includes the cadence, for example "/schedule share weekly content updates every Monday 9 AM for Agentic Engineer book." Cowork parses the cadence, loads the create_scheduled_task tool, and posts an inline Schedule task card with a parsed Name, Description, time, and a Schedule / Cancel pair. Click Schedule and it's saved. Best for ad-hoc scheduling when you're already running a related task and realize "I should make this a recurring thing."
Step 1 of the slash-command
flow: type /schedule followed by a description that includes the cadence in plain language.
Step 2: Cowork parses the cadence and posts an inline Schedule task card. No modal opens , the card lives in the chat itself, and Schedule saves it.
Full-form modal: Scheduled → New task. Click Scheduled in the left sidebar, then New task in the top-right of that view. The Create scheduled task modal opens with: Name field, Description (multi-line textarea), a row of pills for Work in a project , Ask (approval mode), and Default model , and a Frequency dropdown (Manual / Hourly / Daily / Weekdays / Weekly). Best for setting up a recurring task from scratch where you want to fill every field carefully.
The Create scheduled task modal, filled in for the Part 6 weekly-brief example and showing the full Frequency dropdown. Reach this modal via Scheduled → New task; the slash-command flow earlier doesn't open it.
Whichever flow you use, the task lives under Scheduled in the left sidebar. From there you can run any task on demand, edit it, or delete it. A Keep awake toggle in that view tells your OS to suppress sleep during scheduled windows so a task doesn't silently miss its trigger because your laptop dozed off.
The Scheduled tab. Both
flows land here. From here you manage existing tasks, find the Keep awake toggle, and click New task to open the modal directly.
OpenWork does not currently ship a built-in scheduler. The pragmatic pattern: keep the prompt in your workspace folder (or notes), then trigger it manually each Monday morning with a calendar reminder. Paste, run. Ninety seconds, weekly. Supervision stays high; cognitive load stays low.
Cowork's scheduled tasks only run while your computer is awake and the Desktop app is open. OpenWork has no scheduler, so its recurring work is a calendar reminder plus a manual re-fire (you're present for every run). The autonomy-ladder rule still applies in its strictest form for anything you put on a cadence: if you wouldn't already trust this task in "walk away" mode, don't schedule it. A Cowork scheduled task runs without you watching, and you can't course-correct a task you're not watching.
What works well as a scheduled task (either tool):
Information-gathering jobs (compile yesterday's billable-hour totals, summarize Slack channels, check a folder for new files, summarize the day's docket alerts).
Tasks with bounded outputs (always produces a file in a specific folder, never sends mail, never makes purchases, never files anything).
Tasks you've watched succeed at least three times under supervision.
What doesn't:
Anything that sends messages on your behalf without final review.
Anything that takes financial actions: purchases, payments, transfers, bill-pay approvals.
Anything that operates on sensitive files (HR, legal, financial records, anything client-privileged) without an explicit human-review step.
Anything that processes content from people you don't know.
Anything that touches a court filing, a regulatory submission, a board package, or a client deliverable without your eyes on it before it leaves.
Build the deliberate path: supervised, then walk-away, then scheduled, with at least a week between each step.
Part 6: A complete worked example, twice
You ran a one-off multi-source brief at the top of this guide. This second walkthrough is the inverse: a recurring task you eventually trust enough to schedule. It walks the autonomy ladder deliberately (supervised first run to scheduled) and is run twice : once in Cowork, once in OpenWork. The shape is the same; the surfaces differ.
The example uses a Monday-morning industry brief; the same shape works for any recurring multi-source brief in your domain.
You read industry news every Monday, and synthesizing it eats your morning. You want the agent to do the synthesis on Sunday night so Monday morning is just review. The flow is the same plan-then-execute loop from §4, now on a recurring task.
Recurring weekly brief: same task, two surfaces
Cowork OpenWork
Step 1: Make it a project, not a session. This is recurring, so create a Cowork project. Name: "Industry weekly brief." Add the relevant folders and connectors (your RSS pipeline, a Google Drive folder where you save articles, the Notion page where you keep ongoing themes).
Step 2: Project instructions.
This project produces a weekly industry brief, delivered Monday at 8am.
Sources:
-
Articles saved to /weekly-brief/articles-this-week/
-
Slack #industry-news channel from the past 7 days
-
Notion page "Ongoing Themes" - topics already on my radar
Output:
-
Top 3 stories (one paragraph each, with link)
-
1 paragraph "what changed for our space this week"
-
Up to 3 new themes that didn't exist last week
-
Save as weekly-brief-YYYY-MM-DD.md to the project's root folder
Tone:
-
Direct. No throat-clearing. Assume reader is a domain expert.
-
If a story is hyped but actually nothing-burger, say so.
Step 3: Run it once manually. Don't schedule yet. Trigger the task while watching, end-to-end. Check the deliverable. Refine the project instructions accordingly.
Step 4: Run it manually a second time. Check again. If it's good twice in a row with no edits, you're ready to schedule.
Step 5: Schedule it. Type /schedule and set frequency to Weekly, time to Sunday 9pm. Confirm the task shows in your Scheduled list.
Step 6: Monday morning review. The brief is in the folder. Read it. File feedback into project instructions: "In future briefs, please cluster mentions of the same company across sources rather than repeating them."
This walkthrough uses OpenWork's in-app UI throughout. Power users who prefer to edit the underlying config files directly (project instructions, AGENTS.md , skills, plugins) will find the file paths in Appendix A; non-developers should follow this UI path verbatim. Note that neither route adds a scheduler: OpenWork has none, so Step 7 below is the same for everyone.
Step 1: Make a workspace. Create ~/OpenWork-Workspace/industry-weekly-brief/ in Finder/Explorer. Open OpenWork, click + Add workspace > Local workspace , pick that folder. Drop your articles into a subfolder named articles-this-week/ .
Step 2: Set project instructions in OpenWork's Settings panel for this workspace, same content as Cowork's project instructions in Run 1 (sources, output format, tone). The Settings UI handles the underlying file for you.
Step 3: Connect Slack and Notion. Use the Extensions tab. Slack is a core connector; Notion is added there too. Each one walks through OAuth and asks for scopes (same scope-discipline as Cowork).
Step 4: Save the prompt alongside the workspace. Save a prompt.md (or similar) in the workspace folder containing the exact prompt you'll re-fire each Monday. This is your manual re-run pattern: open the workspace, paste the prompt, run.
Step 5: Run it once manually. With the workspace open, paste your prompt. Watch the todos timeline. Check the deliverable.
Step 6: Run it manually a second time. Check again. Same calibration discipline as Cowork's two-manual-runs gate before scheduling.
Step 7: How to make it recurring. OpenWork has no built-in scheduler, so the recurring trigger stays manual, which is the pattern Concept 15 covers: a Sunday-night calendar reminder, and when it fires you open the workspace, paste the prompt from prompt.md , and run. You give up Cowork's hands-off cadence and get a guaranteed human in the loop on every run.
Step 8: Monday morning review. Same as Cowork. File feedback into your project instructions through the Settings panel.
What to notice, same lessons, two surfaces
This walks the autonomy ladder deliberately in both tools:
Manual run with watching: supervised mode.
Manual run again: checking calibration.
Scheduled (Cowork) / regularly-triggered workspace (OpenWork): walk-away mode with downstream review.
Eventually, after six or eight successful runs, the brief becomes ambient.
What's reusable. The shape (workspace, instructions, manual runs, recur once trusted, feedback loop) is the template for every recurring workflow in either tool: Friday cleanup, Monday brief, daily inbox triage, end-of-month variance commentary, end-of-quarter board-package prep, weekly hiring-pipeline status, weekly matter-status updates to clients. Same five steps, different content, two tools.
Part 7: Where to grow
Connector combinations are where the real value lives
Early on, most tasks lean on one connector at a time in either tool. The bigger wins come once you start chaining them. The Slack-search-plus-Notion-cross-reference-plus-email-draft pattern is the canonical example; the actual win is whatever specific combination cuts twenty minutes out of your week. The way to find them: notice the multi-tool tasks you keep doing manually. Any sentence that contains "and then I open the other tab to..." is a candidate.
Audits, in either tool
Once a month: review what the agent has access to. Folders. Connectors. Skills. Plugins. Scheduled tasks (Cowork) / persistent workspaces. Last month's experimental connector is this month's permanent surface area you forgot you had. Ten minutes; skip it for six months and you'll find your assistant has access to four things you don't remember granting.
When your team uses the same tool
Most of the chapter assumes one professional working solo. If you're part of a litigation team of six lawyers on the same matter, a finance org with four people running the same monthly close, or an HR partner pair sharing a hiring loop, the tool gets used by a team , and the discipline shifts:
Cowork at team scale (Team / Enterprise plans). Owners can publish private plugin marketplaces, auto-install approved plugins for new team members, and provision skills org-wide. The right move is to treat your team's plugin set, skill library, and Project templates the same way your firm treats document templates and house style: a maintained shared resource, owned by someone, versioned, and audited. Without that ownership, every lawyer ends up with a personal Smith-v-Acme Project configured slightly differently, and the matter team's outputs lose consistency.
OpenWork at team scale. Distribute the team's standardized state through your existing source-of-truth: a shared repo containing the team's skills library, the agreed plugin set, and shared instructions. New team members clone the repo, open the workspace in OpenWork, and inherit the same skills, plugins, and conventions. This is more setup than Cowork's marketplace approach, and it assumes someone on the team is comfortable with version control, but it composes naturally with how engineering and ops teams already manage shared configuration. (Power-user: Appendix A walks through the concrete files and steps.) For teams without that comfort, the Cowork-with-Enterprise route is the simpler answer.
Confidentiality discipline for shared work. When two associates work the same matter through Cowork, both their sessions touch the matter folder, and both their conversation histories now contain extracts from privileged documents. For a law firm: this is a discoverable record. The audit checklist applies double ( whose Cowork sessions, in this matter, are still open from a closed engagement? ) and the answer should be zero, because we deleted them at the engagement close.
Don't share approval-mode habits across teammates. The autonomy ladder is calibrated per person, per task type. A senior lawyer who's earned "walk away" trust on a routine privilege-log task should not assume the junior associate has, and the junior should not feel pressure to climb the ladder faster than their calibration allows. The shared instructions / shared plugins are team-level; the autonomy ladder stays individual.
For org-wide rollouts, the next step is the vendor's enterprise team. Anthropic's enterprise team for Cowork. For OpenWork, check the project's GitHub for current support and enterprise contacts. Either will walk through SSO, audit logs, and admin controls. The discipline in this chapter is what to install before that conversation, not a substitute for it.
Cross-model review for high-stakes outputs
info
One last move worth importing from the prompting chapter: for high-stakes deliverables (a board memo, a settlement letter, a regulatory filing, an offer letter, a clinical workflow document, a client-facing strategy memo) apply concept 13 to the agent's outputs. Different family, different blind spots. A draft the agent produced, scored against a rubric in a second model, then revised, is the closest thing to a senior reviewer this technology offers when no senior reviewer is in the room.
In Cowork , the second model is whatever chat tool you have open in another tab. In OpenWork , you can configure a different model provider in the Settings panel and ask the agent itself to do the cross-model pass: same workflow, different mechanics.
How to actually get good at this
Reading this crash course doesn't make you good at either tool. Using it does, and the path is the same shape as it was for the previous chapter on prompting fundamentals.
You start manual. You feel friction: every plan you have to read, every approval prompt, every "wait, why does it want that connector." That friction is where the skill comes from. Each piece of friction maps to one of the concepts above:
"Why does the agent keep formatting the report wrong?" Global or folder instructions are missing the format spec.
"Why does it want to touch files I didn't mention?" The plan has scope creep; redirect, don't approve.
"Why is it slow on this batch of 20 files?" Frame the task to make sub-agent parallelism obvious.
"Why am I describing this same workflow every Tuesday?" That's a Cowork Project / OpenWork persistent workspace, not a fresh session.
"Why did it just send something it shouldn't have?" High-autonomy mode on a task that wasn't ready for it.
Build the response when you hit the problem, not before. Your global instructions should be two paragraphs, not twenty. Your list of persistent workspaces should have three before it has ten. Your high-autonomy usage should be earned, not defaulted.
The 80/20 isn't memorizing concepts. It's noticing which one a given problem belongs to, fast enough that you reach for the right tool. That noticing is the skill.
The portability dividend. Cowork's intercept pattern is the same as OpenWork's; sub-agents work the same way; the autonomy-ladder discipline is identical. Once you've built delegation calibration in one tool, the other is mostly learning where the buttons live.
Start with one task. Use a working folder. Read the plan. Approve cautiously. Audit monthly. The rest builds itself.
First week path (in either tool)
If you want a concrete sequence rather than a bag of concepts:
Day 1. Install (Claude Desktop for Cowork; openworklabs.com/download for OpenWork, the desktop download, not the source build). Make a working folder, grant access, run one read-only prompt. That's your installation acceptance test.
Day 2. Run one low-stakes task. Pick a multi-source synthesis from the table at the top of "Your first real task", the one that maps to your profession. Stay in the cautious approval mode. Watch every prompt.
Day 3. Write your global instructions. Two short paragraphs. Your role, your tone, your default formats. Resist writing more.
Day 4. Pick one recurring task you do manually each week. Set it up as a Cowork Project / OpenWork persistent workspace. Add folder access and any obvious connectors.
Day 5. Run that recurring task manually inside the workspace. Capture what worked into the project instructions. Don't schedule yet.
Day 6. Run it manually a second time. Refine. Notice what the agent got wrong twice: that's a pattern that needs to be written into instructions.
Day 7. Audit what you've installed: folders, connectors, skills, plugins. Decide what stays. Schedule the recurring task only if both manual runs were clean.
By the end of week one, you should have one supervised one-off pattern and one in-progress recurring workflow, with a permission profile that fits your actual usage rather than the defaults. Add the second recurring workflow in week two; don't try to automate everything in week one.
Quick reference
The 15 concepts in one line each
What these tools actually are : agentic co-workers that run on your desktop, plan-then-execute, return finished deliverables. Delegate, don't query.
The architecture in three pieces : desktop app (where it runs), task loop (plan, approve, execute), execution surface (files, sandboxed compute, connectors).
Folders, connectors, approvals are the trust model. Dedicated working folder; per-connector decision; cautious approval mode until calibrated.
The plan is the leverage. Read it before approving. Two minutes of plan review beats two hours of cleanup.
Context still costs money. Don't dump folders into context unprompted. End long sessions cleanly.
Persistent workspaces. Cowork Projects / OpenWork workspaces with saved project instructions for recurring work; one-offs stay as fresh sessions.
Global, folder, and session instructions stack. Global is sparse, folder is specific, session states the goal.
Ask-clarifying-questions pattern : end task descriptions with "ask 1-2 clarifying questions before you start." Cheapest quality lever.
Skills are AgentSkills-compatible across tools. Auto-invoke on description match, or / -browse. Use the skill-creator pattern. Read third-party skills before installing.
Connectors link to external services. Cowork has a richer out-of-box catalog; OpenWork is leaner-but-ejectable to OpenCode's ecosystem.
Plugins. Cowork: bundles, namespaced slash commands. OpenWork: opencode.json plugins, atomic capabilities.
Sub-agents parallelize embarrassingly-parallel work in either tool: fan-out, dimension, and compare patterns. 30 minutes becomes 5 minutes for batch jobs.
The autonomy ladder : watch closely, ambient supervision, walk away, high-autonomy mode, scheduled. Climb deliberately.
Prompt injection is real in either tool. Don't run high-autonomy mode on tasks that touch untrusted content.
Scheduled tasks need stricter trust. Cowork has built-in scheduling; OpenWork's pragmatic answer for non-developer users is a calendar reminder + a manual re-fire of the saved prompt in the workspace, not cron.
Action quick-ref
Both columns describe the in-app UI path. OpenWork's underlying config-file paths are in Appendix A for power users. Want to... Cowork OpenWork Open the tool Cowork tab in Claude Desktop OpenWork desktop app Grant folder access Grant Access button in Cowork tab Project folder picker on session/worker create Add a connector + > Connectors > Browse Settings > Extensions > tap an Available app; or Add Custom App; or add an OpenCode plugin Install a skill + > Skills > Browse, or Upload ZIP Skills tab > Import local skill, or Create skill in chat Trigger a skill manually Type / to browse, or describe naturally Type / to browse, or describe naturally Generate a custom skill /skill-creator Skills tab > Create skill in chat Set global instructions Settings > Cowork > Global instructions Settings panel, global scope Set folder instructions Available when a folder is in scope Settings panel, with the project folder open Make a persistent workspace New Project in the Cowork sidebar + Add workspace > Local workspace; save project instructions in Settings Schedule a task Run it manually first, then /schedule Calendar reminder + manual re-fire of the saved prompt Switch to high-autonomy mode Per-task "Act without asking" toggle Stack allow always across each permission the task needs Stop a running task Stop button in the active session Stop button in the active session
Trust-level decision tree (both tools)
New kind of task?
-> Cautious approval mode. Watch every prompt.
Done this kind of task a few times?
-> Cautious approval mode. Check in periodically.
Done this kind of task many times, all clean?
-> Walk away. Review the deliverable.
All of the above + bounded output, no messages, no purchases, no filings?
-> Eligible for scheduling (Cowork) or for a
calendar-triggered manual re-fire (OpenWork).
Task involves untrusted content (stranger email, opposing-counsel filing,
inbound resume, vendor proposal, unknown web pages)?
-> Stay in cautious approval mode. Never high-autonomy.
Task involves PHI, attorney-client-privileged matter outside your firm's
approved AI workflows, or other regulated data?
-> Don't run it in either tool until compliance has approved
the specific tool, model provider, and data flow in writing.
Audit checklist (monthly, both tools)
Which folders does the agent have access to? Still want all of them?
Which connectors are enabled? Each one still in active use?
Which skills and plugins (Cowork) / .opencode/skills/ and opencode.json plugin entries (OpenWork) are installed? Anything you don't recognize?
Which scheduled tasks (Cowork) or persistent workspaces are configured? When did each last succeed?
Global instructions: anything stale or contradictory?
Any task type that has drifted into a more sensitive category since you set it up? (A matter that has now gone into litigation; an HR project that now involves confidential separation negotiations; a finance project that now touches material non-public information.)
Cowork vs. OpenWork: the honest comparison
Dimension Cowork OpenWork License Proprietary; requires Anthropic Pro/Max/Team/Enterprise MIT open source Where work runs Anthropic-hosted infrastructure (model + most connectors) Local OpenCode host on your machine; remote optional Models Claude (Opus, Sonnet, Haiku) Any OpenCode-supported provider (Anthropic, OpenRouter, OpenAI, self-hosted, etc.) Cost model Bundled into your Anthropic plan Bring your own model API keys; OpenWork itself is free Connectors out of box Broad workplace catalog; check the live directory Lean tap-to-connect grid in Extensions; rest via Custom App or OpenCode plugins Persistent workspace Projects (with cross-session memory) Folder-based workspaces (lighter; state lives in the folder's project instructions) Plugin model Bundles with namespaced slash commands; published catalog Atomic opencode.json plugins; OpenCode ecosystem Scheduling Built-in /schedule , multiple frequencies, Keep-awake toggle No built-in scheduler; pragmatic pattern: calendar reminder + manual re-fire Skills format AgentSkills SKILL.md (portable to OpenWork) AgentSkills SKILL.md (portable to Cowork) Sub-agents Yes (same patterns) Yes (same patterns) Best for Professionals who want polish and out-of-box breadth Professionals who want local-first execution, model flexibility, or open-source control
Pick the tool whose tradeoffs match the constraints of your work. The 15 concepts apply either way.
Appendix A: OpenWork power-user reference
Everything below is optional. The OpenWork desktop app exposes the same functionality through its UI; non-developers can stay on the in-app path indefinitely. This appendix exists for users who want the underlying file paths, config syntax, and CLI commands, the kind of content that's useful when you've outgrown the UI or are setting up a team-wide standard.
A.1: OpenWork's configuration files at a glance
OpenWork inherits OpenCode's configuration model. Three files cover almost everything:
Global opencode.json . Lives at ~/.config/opencode/opencode.json (or $XDG_CONFIG_HOME/opencode/opencode.json if you've set that). Holds your default settings: model provider, default plugins, global preferences. Edit-equivalent in the OpenWork UI: Settings panel.
Project opencode.json . Lives at <workspace>/opencode.json inside whatever folder you've opened as a project. Overrides the global file for that project: project-specific plugins, custom model choice for this matter, project-scoped instructions. UI equivalent: when a project folder is open, the Settings panel exposes project-level controls.
AGENTS.md . A plain-Markdown file in the project root containing project-level instructions for the agent, tone, terminology, conventions. UI equivalent: project instructions in the OpenWork Settings panel.
Note: newer OpenWork builds also accept opencode.jsonc (JSON-with-comments) at the same paths, handy for inline documentation in a team config.
A.2: Skills folder layout
OpenWork's Skills tab reads from two locations:
Project-scoped skills: <workspace>/.opencode/skills/<skill-name>/SKILL.md (with any supporting files in the same folder). These apply only when this project is open.
Global skills: ~/.config/opencode/.opencode/skills/<skill-name>/ , apply to every project.
To install a skill manually, drop the folder in either location; the Skills tab picks it up on the next refresh. The Skills tab's Import button does the same thing through the UI without needing to open a file browser.
A.3: Plugins via opencode.json
Plugins are listed in the "plugin" array:
{
"$schema" : "https://opencode.ai/config.json" ,
"plugin" : [ "opencode-wakatime" , "opencode-notion-mcp" ]
}
Each entry is the name of an OpenCode plugin from the ecosystem. OpenWork's Plugins (OpenCode) section in Settings > Extensions lets you add and remove entries by typing npm package names; this is the underlying file that gets edited.
A.4: Team distribution via shared repo
The team-distribution pattern from Part 7's When your team uses the same tool section, in concrete steps:
Create a shared git repo with the team's standardized state: .opencode/skills/ directory of skills, an opencode.json listing the team's plugin set, an AGENTS.md capturing shared conventions and terminology.
New team members git clone the repo into their workspace.
They open OpenWork and select that workspace as their project folder.
Their OpenWork sees the same skills, plugins, and instructions everyone else has.
Updates flow through normal git workflow, pull requests, code review, release tags. The team-wide AI configuration becomes versioned the same way the rest of the team's tooling is.
A.5: Where to look when something doesn't match
OpenWork is the younger of the two tools and ships frequently. When the chapter says one thing and the app does another, the canonical sources are:
Repo: github.com/different-ai/openwork , README.md , ARCHITECTURE.md , and PRINCIPLES.md for current scope and design.
Releases: github.com/different-ai/openwork/releases , what shipped most recently, including UX changes that may have moved click-paths since this chapter was written.
OpenCode docs: opencode.ai/docs , for the underlying CLI, plugin format, and skill format that OpenWork inherits.
Appendix B: Plain-English glossary
Terms used throughout the chapter, in alphabetical order. Flip back here the first time any term puzzles you.
Agent. A program that, given a goal, plans a sequence of steps, takes actions on your behalf, and reports back. Both Cowork and OpenWork are agents, they do work, they don't just answer. This chapter calls them agentic co-workers when it wants to emphasize the assignment-not-query mental model.
BAA (Business Associate Agreement). A legal contract under U.S. HIPAA that covers a vendor's handling of protected health information. Without a BAA, no PHI should go to that vendor. See the regulated-workloads alarm at the start of Part 5 for which Claude products have BAAs available.
Connector. A bridge between the agent and an external service (Gmail, Slack, Notion, OneDrive, etc.). Each connector requires you to grant scopes (what the agent can read, what it can write) when you connect it.
Ejectability. OpenWork's term for: if you stop using OpenWork, your skills, plugins, and configurations still work in plain OpenCode. The work isn't locked into the OpenWork UI. (Cowork's plugins, by contrast, are Cowork-specific format.)
Embarrassingly parallel. Used in §12 for a workload that splits cleanly into independent pieces with no order dependency between them, "summarize each of these 14 contracts" is embarrassingly parallel; "draft, then review, then revise" is not.
MCP (Model Context Protocol). The open protocol that lets agents talk to external services and tools in a structured way. You'll see it in two places: MCP servers (a service that exposes itself to an agent, most connectors are MCP servers under the hood), and MCP apps (Anthropic's term for connector-like extensions inside Claude). You don't need to know how MCP works to use either tool; you do need to know that "MCP" is shorthand for "the standard way these tools talk to outside services."
OAuth. The standard sign-in flow connectors use to ask permission on your behalf. When you connect Gmail, you get redirected to Google, you sign in there, you click Allow , and the connector receives a token. Anthropic / OpenWork never see your password.
Plugin. A bundle that packages skills, connectors, and slash commands together for a specific role (e.g., a "Sales plugin" with call-prep skills and Slack integration). In Cowork, plugins are discrete published bundles. In OpenWork, plugins are atomic capabilities composed via configuration.
Sandbox. An isolated environment where the agent can run code without affecting your machine. Cowork's sandbox is Anthropic-managed; OpenWork's sandbox runs locally via the OpenCode host. You don't configure either day-to-day.
Session. One conversation with the agent, scoped to one task. Like a chat thread, but the agent can read and write files inside that thread. Sessions can be saved and resumed.
Skill. A reusable, shareable instruction file ( SKILL.md ) that tells the agent how to do a specific recurring task, "draft a privilege log entry from this document" or "generate variance commentary for a single GL line." Once installed, the agent uses it automatically when the task matches.
Sub-agent. A parallel worker the main agent dispatches when a task splits into independent pieces, "process each of these 12 transcripts." Each sub-agent works in its own context, returning only its result, which keeps the main session clean.
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Part 1: Foundations
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What these tools actually are
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The architecture in three pieces
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Folders, connectors, approvals: the trust model
Your first real task: a multi-source follow-up brief
Part 2: Context, sessions, and projects
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The plan is the leverage
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Context still costs money
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Persistent workspaces for recurring work
Part 3: Rules and instructions
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Global, folder, and session instructions
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The "ask me questions before you execute" pattern
Part 4: Extending the tool
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Skills
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Connectors
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Plugins
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Sub-agents
Part 5: Safety and the autonomy ladder
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The autonomy ladder
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Prompt injection is a real attack class
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Scheduled tasks need extra care
Part 6: A complete worked example, twice
Recurring weekly brief: same task, two surfaces
What to notice, same lessons, two surfaces
Part 7: Where to grow
Connector combinations are where the real value lives
Audits, in either tool
When your team uses the same tool
Cross-model review for high-stakes outputs
How to actually get good at this
First week path (in either tool)
Quick reference
The 15 concepts in one line each
Action quick-ref
Trust-level decision tree (both tools)
Audit checklist (monthly, both tools)
Cowork vs. OpenWork: the honest comparison
Appendix A: OpenWork power-user reference
A.1: OpenWork's configuration files at a glance
A.2: Skills folder layout
A.3: Plugins via opencode.json
A.4: Team distribution via shared repo
A.5: Where to look when something doesn't match
Appendix B: Plain-English glossary
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