ADVANCED GUIDE — LEVEL 2

Claude Cowork
Power User Guide

You've got the basics. Now learn to build skills, create plugins, automate with Chrome, orchestrate agents, and turn Cowork into your operating system.


← Back to Level 1: Getting Started

What's Inside

If you followed the Level 1 guide, you've already been using skills without knowing it. When you say "new project" and Claude creates folders, memory files, and output directories — that's a skill in action. The "new project" workflow, the file naming conventions, the per-project memory — all of these are patterns that could be (and are) encoded as skills. Now you'll learn to build your own.

A skill is a markdown file called SKILL.md that teaches Claude a specific capability. Every time you find yourself giving Claude the same instructions — "format reports this way," "research companies using this framework," "always check these 5 things" — that's a skill waiting to be built.

When to Build a Skill

You should build a skill when:

You give the same instructions 3+ times. You have a specific workflow or framework. You want consistent output quality across sessions. You want to share a process with colleagues.

You don't need a skill when:

It's a one-time task. The instructions are simple enough to type each time. The process changes frequently and isn't standardized yet.

Skill File Structure

my-skill/ SKILL.md ← Required: instructions + metadata template.md ← Optional: reference files examples/ ← Optional: example inputs/outputs

SKILL.md Anatomy

Every skill has two parts: YAML frontmatter (metadata) and markdown body (instructions).

--- name: company-research description: Deep competitive intelligence research on any company, delivered as a professional Word document. Use when the user says 'research [company]', 'competitive profile', 'company deep dive'. --- ## Instructions When the user asks you to research a company: 1. Search the web for the company's website, recent news, funding, and key people 2. Analyze their product, pricing, go-to-market strategy 3. Identify 3-5 direct competitors 4. Deliver as a formatted .docx with sections: - Company Overview - Product & Positioning - Business Model - Competitive Landscape - Key Risks & Opportunities
The Description is Everything Claude decides whether to auto-invoke a skill based entirely on the description field. Be specific about trigger phrases. Vague descriptions = skills that never fire. Include examples of what users might say: "research [company]", "tell me about [company]", "competitive profile".

Where Skills Live

LocationScopePriority
~/.claude/skills/All your projects (personal)High
.claude/skills/ in projectThat project onlyMedium
Inside a pluginAnyone who installs the pluginStandard
Enterprise managedEntire organizationHighest

The Easy Way: Use /skill-creator

If you have the CoWork OS plugin installed, type /skill-creator in any session. Claude will interview you about what you want the skill to do, write the SKILL.md for you, test it, and optimize the description for reliable triggering. You don't need to write YAML by hand.

Advanced: Dynamic Context Injection Skills can pull live data using shell commands: !`git log --oneline -5` injects your recent commits. !`cat package.json | jq .dependencies` injects your project dependencies. This happens before Claude sees the skill, so the data is always fresh.

A plugin is a folder that bundles skills, commands, and connector configurations into a single installable package. If skills are individual tools, plugins are the toolbox.

Plugin Folder Structure

my-plugin/ .claude-plugin/ plugin.json ← Required: name, version, author skills/ company-research/ SKILL.md person-research/ SKILL.md commands/ research.md ← Slash commands: /research .mcp.json ← Optional: MCP tool connections

plugin.json (The Minimum)

{ "name": "my-research-toolkit", "version": "1.0.0", "description": "Company and person research with Word doc output", "author": "Your Name" }
Critical: Don't Put Skills Inside .claude-plugin/ Only plugin.json goes inside the .claude-plugin/ directory. Skills, commands, and agents go at the plugin root level. This is the most common mistake when building plugins.

Distribution Methods

1. GitHub (Recommended)

Push your plugin folder to a GitHub repo. Anyone installs with: /plugin marketplace add your-username/your-repo. Free, versioned, and easy to update.

2. Direct File Sharing

Zip the plugin folder as a .plugin file and email or share it. Recipients drop it into their Cowork plugins folder.

3. Official Anthropic Marketplace

Submit through Anthropic's review process for broad distribution. Must pass security and quality standards.

Once you've built skills or plugins that work well, sharing them is straightforward.

Sharing a Single Skill

Zip the skill folder (the one containing SKILL.md) as a .skill file. Send it to anyone. They drop it into their ~/.claude/skills/ directory. Done.

Sharing a Plugin (via GitHub)

1. Create a public GitHub repo 2. Push your plugin folder (with .claude-plugin/plugin.json at root) 3. Share the install command: /plugin marketplace add your-username/your-repo 4. Recipients run that command in Cowork. Installed instantly.

Community Ecosystem

The Claude skills community is growing fast. Here are places to find and share skills:

anthropics/knowledge-work-plugins

Official Anthropic plugins repo on GitHub. Sales, Finance, Legal, Marketing, Product, Data, Design, Operations plugins with full source code. Great reference for building your own.

travisvn/awesome-claude-skills

Community-curated list of 37+ skills and growing. Covers coding, research, writing, and workflow automation. Fork it, add yours, submit a PR.

Pro Move: Create a Team Plugin If your team repeatedly does the same workflows, build a plugin that encodes your processes. New team members install it on day one and immediately have your best practices available. No training deck needed — the skill IS the training.

Claude in Chrome lets Claude see, click, type, navigate, and interact with anything in your browser. It goes far beyond basic web search.

What You Can Actually Do

Multi-Tab Orchestration

Claude manages multiple tabs simultaneously. Drag tabs into Claude's group, and it can read and act across all of them. "Compare pricing across these 5 competitor websites."

Form Filling & Data Entry

Claude fills forms using context it already has. "Fill out this vendor registration form using our company details." Works with any web form.

Web Scraping & Data Extraction

"Go to LinkedIn and pull the last 20 posts from these 5 people into a spreadsheet." Claude navigates, reads, extracts, and organizes.

GIF Recording

Record browser interactions as GIF animations with click indicators and action labels. Perfect for creating demos, tutorials, and documentation.

Debug & Development

Claude reads console logs, DOM state, and network requests directly. "Check why the login page is throwing a 403" — it reads the actual error.

Scheduled Browser Tasks

Combine Chrome extension with scheduled tasks. "Every morning at 9am, check these 3 dashboards and summarize what changed."

Requirements & Limitations Chrome extension is in beta. Works on Chrome and Edge only (not Brave, Arc, or others). Requires a paid Claude plan. Claude uses your existing login sessions — it can access anything you're logged into, so be mindful of which tabs are in the Claude group.

Chrome extension handles the browser. Connectors handle specific services. But what about everything else — Finder, Notes, Maps, System Settings, Photoshop, Excel (the desktop app), or any native application? That's Computer Use. Claude takes screenshots of your screen, moves the mouse, clicks buttons, and types — just like a remote coworker sitting at your desk.

How Claude Decides What to Use

This is the mental model that makes everything click. When you give Claude a task, it picks the fastest, most reliable tool available:

The 3-Tier Decision Hierarchy

1. CONNECTORS FIRST Slack, Calendar, Gmail, Drive
2. BROWSER SECOND Chrome extension for web apps
3. SCREEN CONTROL LAST Mouse + keyboard for native apps

Connectors are fast and precise (API-backed). Chrome is DOM-aware and reliable. Screen control is the fallback that handles everything else.

How to Enable It

Computer Use is off by default. To turn it on:

Settings → Desktop app → General → Turn on Browser use ✓ → Turn on Computer use ✓

Claude always asks permission before touching a new app. You approve each application explicitly, and you can stop it at any time.

What You Can Do With It

Native App Automation

"Organize my Downloads folder — move PDFs to Documents, images to Photos, delete anything older than 30 days." Claude opens Finder and does it.

Cross-App Workflows

"Pull the metrics from this dashboard in Chrome, drop them into the Excel spreadsheet on my desktop, then email the updated file." Three apps, one prompt.

Fill Desktop Forms

"Fill out this insurance application in Preview using my info from the About Me file." Claude reads your context and types into native form fields.

System Management

"Check my disk space, clear the trash, and tell me what's taking up the most storage." Claude navigates System Settings and Finder to investigate.

Steering Claude Mid-Task

Computer Use is live — you can redirect Claude while it works. These steering prompts are your remote control:

Steering PromptWhat It Does
"Stop. Don't click that yet."Pauses before a risky action
"Use Chrome, not Safari."Redirects to a different app
"Take a screenshot and show me before you send it."Review checkpoint before proceeding
"Skip Slack. Open the browser instead."Overrides the default tool choice
"Actually, start over. New approach."Full reset mid-task

The "Come Back to Review" Pattern

Combine Computer Use with Dispatch for fire-and-forget workflows:

1. Send a task from your phone (Dispatch) 2. Add: "Text me when it's done." 3. Claude works on your desktop while you're away. 4. You review the result on your Mac when you're back.

This works for any Computer Use task. Export a deck to PDF, attach it to a calendar invite, organize files — all while you're at lunch.

Limitations & Safety Mac only (Windows coming soon). Claude asks permission per app before interacting. Browsers are read-only via Computer Use (use the Chrome extension instead for clicking and typing in web apps). Terminals and IDEs allow clicking but not typing (use the built-in Bash tool instead). Claude won't enter passwords, execute trades, or move money on your behalf.

Cowork can run tasks on a schedule — daily, weekly, or at specific times. Combined with plugins and Chrome, this is where Cowork becomes an autonomous operator.

Cron Syntax (Simplified)

ScheduleCron ExpressionPlain English
Every morning0 9 * * *9:00 AM daily
Weekdays only0 9 * * 1-59:00 AM Mon-Fri
Every Monday30 8 * * 18:30 AM Mondays
First of month0 0 1 * *Midnight, 1st day

Real-World Examples

Morning Briefing

Daily at 9am: summarize unread emails, check calendar, create a priorities list with talking points for today's meetings. Outputs a markdown file you review with coffee.

Weekly Invoice Cleanup

Fridays at 5pm: scan email for invoices received this week, extract amounts and vendors, add to a tracking spreadsheet, flag anything over $5K for review.

Competitor Monitor

Every Monday: check 5 competitor websites for pricing changes, new features, or blog posts. Compile a diff report showing what changed since last week.

Key Limitation Your computer must be awake and the Claude Desktop app must be open for scheduled tasks to run. If your Mac is asleep at 9am, the task runs when you open the lid. Tasks don't run in the cloud.

Claude's memory isn't one thing — it's a hierarchy. With the March 2026 Projects update, there are now four distinct layers. Understanding them lets you put the right information in the right place.

The 4 Layers

Layer 1: Personal Preferences (Global)

Where: Claude Desktop → Settings → Personal Preferences
Scope: Every conversation, every project, every session
What goes here: Your name, role, communication style, personality preferences, behavioral rules. Things that are always true about how you want Claude to work.

Layer 2: Native Project Instructions & Memory (Built-In)

Where: Project → Instructions field + automatic memory.md
Scope: All tasks within that project
What goes here: Project-level tone, formatting rules, and key context in the Instructions field. Auto-memory captures decisions and patterns as you work — Claude decides what's worth saving. First 200 lines (or 25KB) load at the start of each new task.

Layer 3: CLAUDE.md (CoWork OS — Structured Rules)

Where: CLAUDE.md file in your workspace folder (or subfolder)
Scope: That specific folder only
What goes here: Detailed folder protocols, naming conventions, session start behavior, project registry, read-only/write-only rules. More structured and opinionated than native Instructions — this is your operating system.

Layer 4: MEMORY.md (CoWork OS — Explicit Memory)

Where: MEMORY.md in your workspace folder
Scope: Persistent across sessions, user-controlled
What goes here: Decisions, deadlines, status updates — things you specifically want remembered with your exact wording. Say "remember this" to write; "forget that" to delete. Unlike auto-memory, nothing gets saved unless you ask.

Native Memory vs. Explicit Memory

This is the most common question: "If Projects auto-remember things, why do I need MEMORY.md?" Because they serve different purposes:

Native Auto-MemoryMEMORY.md (CoWork OS)
TriggerAutomatic — Claude decidesUser-triggered — "remember this"
ContentWhatever Claude thinks is usefulExactly what you told it to save
StructureUnstructured, Claude-formattedYour format, your categories
ControlLow — Claude curatesHigh — you curate
RiskMay save noise or miss critical factsYou might forget to say "remember this"
Best forBackground context, patterns, preferencesKey decisions, deadlines, exact specifications
Use Both Let auto-memory catch the patterns you'd forget to save. Use MEMORY.md for the facts you need to persist with precision. They're complementary, not competing. Auto-memory is your safety net; MEMORY.md is your source of truth.

Multi-Project Isolation

Both native Projects and CoWork OS support project-scoped isolation. Each native Project has its own auto-memory. Each CoWork OS subfolder can have its own CLAUDE.md and MEMORY.md. Your marketing project's Claude has different context than your finance project's Claude.

Keep CLAUDE.md Under 200 Lines Claude reads the entire CLAUDE.md at the start of every session. If it's 500+ lines, you're eating context window for instructions instead of actual work. Move detailed reference material into separate files that Claude can read when needed.

MCP (Model Context Protocol) is how Claude connects to external services. Every connector you use — Google Drive, Slack, Gmail, GitHub — is an MCP server under the hood. You can build your own.

Why Build a Custom MCP Connector?

Connect Internal Tools

Your company's CRM, ticketing system, internal wiki, or custom database. If it has an API, Claude can connect to it.

Automate Proprietary Workflows

"Pull this week's support tickets from Zendesk, categorize them, and create a summary for the team standup." Requires a Zendesk MCP connector.

MCP Architecture (Simplified)

Your Tool / API ↑ MCP Server (your code: translates between Claude and your API) ↑ MCP Protocol (standardized JSON messages) ↑ Claude Desktop (the client that calls your server)

Two Types of MCP Servers

TypeWhere It RunsBest For
DesktopYour local machineLocal databases, file systems, local tools
RemoteCloud server (HTTPS)Web APIs, shared team tools, multi-device access
Start Simple Before building a custom MCP connector, check if one already exists. Cowork's connector directory has 50+ pre-built integrations. Type your tool name in the Customize → Connectors search. If it's there, you're done in 2 clicks.

When Claude encounters a task that can be broken into independent pieces, it automatically spawns sub-agents — parallel workers that execute simultaneously. This is one of the most powerful features most people never discover.

How It Works

Say you ask: "Research these 8 companies and create a competitive matrix." Instead of researching them one by one (slow), Claude spawns 8 parallel agents that each research one company simultaneously. Results come back in minutes instead of an hour.

When to Trigger Parallel Agents

The Magic Phrase: "Use parallel agents wherever possible"

Include this in your request when the task involves multiple independent workstreams. Claude will automatically identify what can run in parallel and split the work. You can also include this in your Personal Preferences or CLAUDE.md so Claude always looks for parallelization opportunities.

Great Tasks for Parallel Agents

Research Multiple Entities

"Research these 5 companies" — each company gets its own agent researching simultaneously.

Multi-File Analysis

"Analyze these 10 spreadsheets and summarize findings" — each file gets its own agent.

Content at Scale

"Write social posts for each of these 8 topics" — parallel content generation.

Code Across Modules

"Update the frontend, backend, and tests for this feature" — three agents working different parts.

Agent Types

TypeWhat It DoesBest For
general-purposeFull capabilities: search, read, write, executeMost tasks
ExploreRead-only: fast search and analysisResearch, codebase exploration
PlanDecision-focused: architecture and strategyPlanning before execution
Token Cost Each sub-agent has its own context window. Running 8 parallel agents uses roughly 8x the tokens of a single agent. This is most effective on Opus or Sonnet where reasoning quality justifies the cost. Don't parallelize trivial tasks.

What Claude Can Create

File TypeWhat You GetExample Prompt
Excel (.xlsx)Formulas, formatting, charts, multiple sheets"Create a financial model with revenue projections"
Word (.docx)Headings, TOC, page numbers, letterhead, tables"Write a 10-page market analysis report"
PowerPoint (.pptx)Slides, layouts, speaker notes"Build a 15-slide investor pitch deck"
PDFFormatted documents, forms, merged files"Merge these 3 PDFs and add page numbers"
HTMLInteractive dashboards, reports, web tools"Create a dashboard from this CSV data"
CSV/DataCleaned data, analysis results, exports"Clean this messy CSV and export with headers"

Power Patterns

CSV → Interactive Dashboard

Upload a CSV and ask: "Create an interactive HTML dashboard with filters, charts, and a summary table." You get a single-file HTML that works in any browser — no server needed. Share it with anyone.

Screenshot → Code

Upload a screenshot of a design mockup and ask: "Convert this to a working React component." Claude's vision analyzes the layout, colors, and spacing and produces functional code.

Multiple Documents → Executive Summary

Drop 5 research documents into your workspace and ask: "Read all of these and create a one-page executive summary highlighting the key insights and contradictions across them."

Interactive Visualizations (NEW — March 2026)

Claude can now create interactive charts, diagrams, and visualizations inline in its responses. Ask "Show me a chart of our monthly revenue" and get a live, clickable chart right in the conversation — not just a static image. These can be exported as standalone HTML files you share with anyone.

Excel & PowerPoint Add-ins (NEW — March 2026)

Claude now lives inside Excel and PowerPoint as native add-ins. Ask questions about your spreadsheet, generate formulas, build pivot tables, or create slides — without leaving the app. Context carries between both add-ins, so Claude understands your data when you switch to building a deck from it. This is a third way to use Claude alongside the desktop app and browser extension.

Each plugin category transforms Claude from a generalist into a domain specialist. Here's what the major categories enable:

Sales

Account research that pulls web data + CRM context into a one-page brief. Call prep that builds agendas with attendee research. Competitive battlecards as interactive HTML with comparison matrices. Pipeline review that flags at-risk deals and creates weekly action plans. Outreach drafting with personalization from research data.

Finance

Journal entries with proper debits/credits and supporting detail. Account reconciliation matching GL to subledger/bank. Variance analysis decomposing budget-vs-actual into drivers. Financial statements with GAAP presentation and period-over-period comparison. SOX compliance testing workpapers and sample selection.

Legal

Contract review against your negotiation playbook with clause-by-clause analysis. NDA triage classifying as GREEN/YELLOW/RED in seconds. Compliance tracking for GDPR, CCPA, and data subject requests. Risk assessment with severity-by-likelihood framework.

Marketing

Campaign planning with objectives, channel strategy, and content calendars. SEO audits covering keyword research, on-page analysis, and competitor comparison. Email sequences for nurture flows and onboarding. Brand voice review checking content against your style guide. Performance reports with KPIs and optimization recommendations.

Product Management

PRDs with problem statements, user stories, and acceptance criteria. Roadmap management using RICE, MoSCoW, or ICE frameworks. User research synthesis turning interview notes into themes and opportunity areas. Stakeholder updates tailored to audience (exec, engineering, customers). Competitive analysis with feature comparison matrices.

Data

SQL queries optimized for your warehouse dialect (Snowflake, BigQuery, Postgres). Data exploration profiling datasets for quality, distributions, and outliers. Visualization with matplotlib, seaborn, or plotly. Interactive dashboards as self-contained HTML with Chart.js filters. Statistical analysis including hypothesis testing and trend detection.

Private Plugin Marketplaces

Create a private GitHub repo as your org's plugin marketplace. Team members install from it directly. Control which plugins are available, which are auto-installed, and which are hidden.

Org-Managed Plugins

Admins can auto-install plugins across all team members. New hires get your org's skills on day one without any setup. Managed plugins take highest priority — they override personal settings.

Usage Monitoring

Track usage, costs, and tool activity per team via OpenTelemetry integration. See which skills get used most, which teams are heaviest users, and where to invest in more automation.

Custom Branding

Customize the Cowork home screen with your company logo and branded experience.

Important Limitation Cowork activity is NOT captured in enterprise audit logs or compliance APIs. This makes it unsuitable for regulated workloads (financial services compliance, healthcare data, etc.) where full audit trails are required.

Dispatch is a persistent thread between your phone and your desktop Claude. Send a task from anywhere — the airport, a meeting, your kid's soccer game — and Claude executes it on your Mac using your files, connectors, and plugins. It's not cloud-based: your files never leave your computer.

How to Set It Up

4 Steps

1. Open Claude Desktop app on your Mac
2. Click Dispatch in the left sidebar
3. Connect your phone (iOS or Android) via the Claude mobile app
4. Send a task from anywhere. Come back to finished work.

What Makes Dispatch Powerful

Persistent Context

Unlike starting a new Cowork session, Dispatch maintains a single continuous thread. Claude retains context from your previous tasks — no re-explaining.

Full Desktop Access

Since March 2026, Dispatch includes Computer Use. Claude can open apps, move files, fill forms, and navigate your desktop while you're away.

Fire & Forget

"Export the pitch deck as PDF and attach it to my 2pm meeting invite." Send it, pocket your phone. Claude opens the app, exports, attaches. Done.

The 6 AM Pattern

Queue up 5 tasks before breakfast. Review the results over coffee. Entire morning routines — email summaries, calendar prep, report generation — handled before you sit down.

Mobile App Updates (March 2026)

The Claude mobile app now supports fully interactive applications — live charts, sketch diagrams, and shareable visual assets rendered directly in mobile conversations. It also integrates with work tools like Figma, Canva, and Amplitude from your phone. Combined with Dispatch, this means you can review designs, build interactive dashboards, approve assets, and trigger desktop work from anywhere.

Requirements & Limitations Available on Pro and Max plans. Your Mac must be awake and Claude Desktop must be open for Dispatch to work. Single thread only — one task at a time. If your Mac is asleep, the task runs when you open the lid. Desktop must be connected to the internet.

Must-Read Articles

💡

Claude Cowork Guide: 50+ Tested Tips

Karo Zieminski • Substack
The deepest community guide. Covers plugins, memory, sub-agents, and techniques no one else writes about.
📚

Claude Agent Skills: A First Principles Deep Dive

Lee Han Chung • Blog
Technical deep dive into how skills work internally. Best resource for understanding SKILL.md architecture, frontmatter options, and execution model.
📚

Claude Cowork Plugins: What They Are, How to Build One

AIBle With My Mind • Substack
Step-by-step guide to building and distributing your first plugin. Includes manifest.json templates and common pitfalls.
💡

Claude in Chrome: The Browser Extension Guide

AI Maker • Substack
Complete walkthrough of Chrome automation. Multi-tab orchestration, scheduled browser tasks, and real-world automation examples.

GitHub Repositories

RepositoryWhat It Has
anthropics/knowledge-work-pluginsOfficial Anthropic plugins: Sales, Finance, Legal, Marketing, Product, Data, Design, Operations
anthropics/skillsOfficial skills reference and examples
travisvn/awesome-claude-skillsCommunity-curated list of 37+ skills
ykdojo/claude-code-tips45 tips for getting the most out of Claude Code

Official Documentation

TopicLink
Skills Documentationdocs.claude.com/skills
Plugin Developmentdocs.claude.com/plugins
Chrome Extensioncode.claude.com/chrome
Scheduled Taskscode.claude.com/scheduled-tasks
Memory Systemcode.claude.com/memory
Hooks & Automationcode.claude.com/hooks
Agent Teamscode.claude.com/agent-teams
MCP Connectorsmodelcontextprotocol.io

You're a Power User Now

Build your first skill. Share it with a friend. Automate something you do every week. The difference between "using Claude" and "operating with Claude" is everything on this page.

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