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Discipline 02 · 3 white, 8 brown, 4 black

Cowork Dojo

Hand the desktop agent real work: skills, connectors, scheduled runs. The capstone is a distributable Business OS other people install.

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15 modules · 166 prompts · 109 sourced
White · 3 modulesBrown · 8 modulesBlack · 4 modules
White Belt3 modules50 promptsNot started
Brown Belt8 modules85 promptsNot started
Black Belt4 modules31 promptsNot started
Version 2.0.12·Revised 2026-09-13·Refreshed weekly·42 sources cited
Inventory
Modules15
Prompts166
Prompts sourced109
Sources cited42
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// 01 / The ladder

Fifteen modules

White belt is a desk the agent can work from. Black belt is a Business OS somebody else installs and runs.

White Belt
Fundamentals
Not started
01Up next
What is Cowork (and When to Use It)
Understand the three Claude surfaces: Chat for answers, Cowork for deliverables, Code for software. Build the judgment to route any task to the right one, then run your first real delegation.
~50 min (est)28 prompts 26 beginner · 2 intermediate
02
Setup and Configuration
Configure your Cowork environment properly: a dedicated work folder, global instructions that brief Claude on who you are, and context files that make every session start smart instead of generic.
~45 min (est)13 prompts 11 beginner · 2 intermediate
03
The Delegation Framework
Master the craft of delegating to Cowork: end-state prompting, the three-question framework, dummy files, change logs, checkpoints, and reviewing agent work against the spec.
~45 min (est)9 prompts 6 beginner · 3 intermediate
Capstone · White BeltKnot open
The Delegation Desk
Build the workspace, then prove it earns its keep. You will set up a complete Cowork environment from an empty folder and run three real delegations through it, reviewing the agent's work like a manager instead of hoping like a spectator. The pass bar is not that the setup exists, it is that a real task you used to do by hand got done well inside it.
  • Create a dedicated work folder with a clean structure for inputs, outputs, and references, and connect Cowork to it.
  • Write Global Instructions that capture your role, preferences, and work style in terms an agent can act on.
  • Create CLAUDE.md and at least two context files (for example branding.md and memories.md) with real, useful content, not placeholders.
  • Pick three genuine tasks from your actual week and, for each, decide deliberately whether it belongs in Chat, Cowork, or neither, writing one line of reasoning per call.
  • Delegate the Cowork-suited tasks using end-state prompts built with the three-question framework, one at a time.
  • Review the change log after each delegation and classify every change as expected or unexpected before accepting the output.
  • Take your weakest result, diagnose what the prompt failed to specify, and redelegate with a sharper prompt until the output passes.
DeliverableA fully configured Cowork workspace (folder structure, Global Instructions, CLAUDE.md, context files) plus a delegation log showing three real tasks completed, each with its routing decision, prompt, change log review, and one documented redo that improved the result.
Brown Belt
Advanced
Not started
04
File and Document Management
Use Cowork to sort, rename, and batch process files, and to generate professional documents: Excel, PowerPoint, Word, PDF, invoices, and expense reports.
~45 min (est)9 prompts 1 beginner · 6 intermediate · 2 advanced
05
Skills System Mastery
Understand the skills system: built-in skills, custom SKILL.md files, YAML frontmatter, progressive disclosure, and skill stacking.
~45 min (est)9 prompts 2 beginner · 5 intermediate · 2 advanced
06
Connectors and Integrations
Connect Cowork to the services where your work actually lives: Gmail, Calendar, Slack, Notion, and thousands more via Zapier MCP. Then make those connections earn their keep.
~45 min (est)12 prompts 2 beginner · 4 intermediate · 6 advanced
07
Plugins and Plugin Building
Install, evaluate, customize, and build plugins: bundles of skills, connector configurations, sub-agents, and slash commands packaged for distribution.
~40 min (est)8 prompts 2 beginner · 3 intermediate · 3 advanced
08
Scheduled Tasks
Automate recurring work with scheduled tasks: daily briefings, weekly reports, expense processing, and the discipline that keeps unattended automation trustworthy.
~45 min (est)24 prompts 2 beginner · 4 intermediate · 18 advanced
09
Projects and Memory
Persistent project workspaces that remember your decisions, your people and your conventions across sessions, so you stop re-briefing Cowork every session.
~40 min (est)8 prompts 1 beginner · 6 intermediate · 1 advanced
10
Sub-agents and Parallel Work
Work split across parallel sub-agents instead of one long sequential task, and how to design the split so the merge actually works.
~40 min (est)8 prompts 1 beginner · 5 intermediate · 2 advanced
11
Computer Use
Let Cowork control the screen when no connector exists: see, click, and type its way through any desktop app or web tool, with you supervising until trust is earned.
~35 min (est)7 prompts 2 beginner · 4 intermediate · 1 advanced
Capstone · Brown BeltKnot open
The Overnight Machine
Build a system that works while you do not. You will combine a custom skill, live connectors, and a scheduled task into a daily briefing pipeline that produces a deliverable before you sit down each morning. The pass bar is brutal and simple: five consecutive days of output with zero manual rescue.
  • Design the daily deliverable first: a briefing, report, or digest with a fixed section format and a one-page cap, specified before any building starts.
  • Build a custom skill (SKILL.md with proper frontmatter) that produces that deliverable from your real data.
  • Connect at least two connectors (for example Gmail plus Calendar) and wire their data into the skill's output sections.
  • Use a sub-agent for at least one component of the run, such as gathering or summarizing one source in parallel.
  • Create a scheduled task that runs the skill at a fixed time every morning.
  • Let it run five consecutive days without manual intervention, keeping a run log: produced or failed, on time or late, output quality out of 10.
  • After day five, fix the single weakest part of the pipeline based on the run log and document what you changed and why.
DeliverableA running daily automation (custom skill + two connectors + scheduled task + one sub-agent step) with a five-day run log proving unattended operation, plus a written post-run improvement note.
Black Belt
Mastery
Not started
12
Dispatch and Remote Control
Tasks fired at your desktop from anywhere rather than from your desk: pair your phone, master fire-and-forget prompts, and come back to finished deliverables.
~35 min (est)7 prompts 4 intermediate · 3 advanced
13
Advanced Skill Engineering
Production-grade skills instead of skills that work on your machine on a good day: built to a spec, tested against edge cases, versioned, and packaged so someone else can run them without asking you a single question.
~40 min (est)8 prompts 3 intermediate · 5 advanced
14
Power User Workflows
Stop using features one at a time. This module chains skills, connectors, sub-agents, and files into complete production workflows: a business OS map, content pipelines, research synthesis, contract review, email triage, and a morning briefing that ties them together.
~40 min (est)8 prompts 2 intermediate · 6 advanced
15
Safety, Limits, and Optimization
Run Cowork like an operator, not a passenger: know exactly where the sandbox boundaries sit, audit what the agent can touch, recover cleanly when something goes wrong, and squeeze maximum output from every token of usage.
~40 min (est)8 prompts 5 intermediate · 3 advanced
Capstone · Black BeltKnot open
Ship the Business OS
Everything you have learned, packaged as one distributable system. You will map your entire automation landscape, build a plugin bundling your core skills with connector integrations and scheduled tasks, run it through a production-grade test gauntlet, and document it so a stranger could install it. This is the difference between someone who uses Cowork and someone who ships systems built on it.
  • Map your Business OS first: inventory every skill, connector, and scheduled task, chart the data flows between them, and pick the gaps this plugin will close.
  • Build a plugin containing at least five skills covering your core workflows, integrating at least three connectors.
  • Include at least two scheduled tasks in the system, one daily and one weekly.
  • Put every skill through the engineering gauntlet: written success criteria, edge-case and failure-condition tests, and a test-results file showing fixes and rerun passes.
  • Run a safety and cost review of the finished system: folder access audit, change log review routine, and a usage check with at least one optimization applied.
  • Create the Business OS dashboard: all automations, data flows, and system health in one view that updates as the system runs.
  • Package for distribution: README with usage examples, documented dependencies, version number, and verification test prompts.
  • Prove it travels: in a fresh session with no memory of the build, install and verify the plugin using only the README and test prompts.
DeliverableA distributable Business OS plugin (five or more tested skills, three connectors, two scheduled tasks) with a live system dashboard, a test-results file, a safety and usage review, and a README package verified by a cold-start install in a fresh session.
Beginner Intermediate Advanced Bar length is the module's prompt count against the longest module here; its segments are that module's own mix. Minutes are the curriculum's per-module estimates, summed over what you have woven.
One cell is one module, at its belt cloth Woven cell: module complete Knot open until the belt's last module is woven. Kept on this device only.
// SOURCES

Curriculum Record

Every published source this curriculum cites: 42 distinct references, counted from the curriculum brief and from the prompts themselves. Prompts that quote one carry a source line; the rest are marked unsourced author prompts.

  1. 01youtube.comwatch?v=cNf7uVff11Y
  2. 02youtube.comwatch?v=0bRxpRupE5Y
  3. 03findskill.aiclaude-cowork-guide
  4. 04karozieminski.substack.comclaude-cowork-guide-plugins-memory-sub-agents-tips
  5. 05resources.anthropic.comThe-Complete-Guide-to-Building-Skill-for-Claude
  6. 06support.claude.comclaude-cowork
  7. 07o-mega.aiclaude-cowork-the-ultimate-autonomous-desktop-guide-2026
  8. 08support.claude.comget-started-with-claude-cowork
  9. 09anthropic.comclaude-cowork
  10. 10support.claude.comclaude-cowork-architecture-overview
  11. 11medium.comanthropic-ships-17-skills-for-code-and-11-plugins-for-cowork-c752d2ae5a20
  12. 12youtube.comwatch?v=Y0OB8GJh6Pc&vl=en-US
  13. 13rogerwong.meclaude-cowork-guide-56-tips
  14. 14artificialcorner.comcowork-workflows
  15. 15youtube.comwatch?v=skU1-k7_wWE
  16. 16claudecowork.imclaude-cowork-plugins-complete-guide
  17. 17aitoolsclub.comhow-to-automate-your-entire-workflow-with-claude-cowork-5-copy-paste-prompts
  18. 18claudecowork.imworkflows
  19. 19aitomationacademy.comclaude-cowork-automations
  20. 20youtube.comwatch?v=SNo_recKZyY&vl=en-US
  21. 21support.claude.comcreate-and-edit-files-with-claude
  22. 22claudiaplusai.substack.comclaude-cowork-starter-guide-30-examples
  23. 23support.claude.comuse-skills-in-claude
  24. 24support.claude.comhow-to-create-custom-skills
  25. 25buildtolaunch.substack.comclaude-cowork-use-cases-real-workflows
  26. 26support.claude.comuse-google-workspace-connectors
  27. 27aitidbits.aiautomating-workflows-with-claude
  28. 28youmind.comautomate-workflow-claude-cowork-guide
  29. 29support.claude.comuse-plugins-in-claude
  30. 30support.claude.comschedule-recurring-tasks-in-claude-cowork
  31. 31digitalapplied.comanthropic-cowork-recurring-tasks-automate-claude-workflows
  32. 32youtube.comwatch?v=drFGy0hB5ho
  33. 33youtube.comwatch?v=SNo_recKZyY
  34. 34claudecowork.imscheduled-tasks-guide
  35. 35eesel.aiclaude-ai-workflow-automation
  36. 36support.claude.comorganize-your-tasks-with-projects-in-claude-cowork
  37. 37support.claude.comclaude-code-power-user-tips
  38. 38support.claude.comset-up-code-review-for-claude-code
  39. 39support.claude.comlet-claude-use-your-computer-in-cowork
  40. 40support.claude.comassign-tasks-from-anywhere-in-claude-cowork
  41. 41support.claude.comuse-artifacts-in-claude-cowork
  42. 42support.claude.comuse-claude-cowork-safely
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