Live Masterclass: Getting Started with Claude Cowork
Live workshop recap: Learn Claude Cowork from scratch — skills as job descriptions, the What-How-Do-Don't prompting framework, building a Weekly Status Report skill, connectors (MCPs), and security best practices. Hosted by Mark Fershteyn with Cynthia Vazquez.
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Frequently Asked Questions
Is my data safe when I use Claude Cowork?
Anthropic does not train on data from paid plans (Pro, Teams, Enterprise). Your prompts and files are not used to improve Claude's models. That said, always apply the 'Google test' — don't paste anything into Cowork that you wouldn't want appearing in a Google search. Avoid sensitive credentials, private financial data, or confidential client information unless you're on an Enterprise plan with specific data handling agreements.
What's the difference between a skill and an agent?
A skill is the instruction set — a markdown file that describes a task, how to do it, and what to avoid. An agent is the execution engine that runs the skill. Think of it like a recipe (skill) and a chef (agent). The chef follows the recipe, but the recipe is what determines the outcome.
Can I schedule Cowork to run skills automatically?
Yes. Cowork supports scheduling through the /schedule command. You can set skills to run on a recurring schedule — daily morning briefings, weekly status reports, or monthly competitive analyses. The agent runs the skill at the scheduled time and saves the output to your specified folder.
What is Watch Me Once and how does it work?
Watch Me Once is a Cowork feature where you perform a task manually while Cowork observes. It records your workflow — what you clicked, what files you opened, what steps you took — and then creates a skill from that observation. It's the fastest way to automate repetitive tasks because you don't have to write any instructions. Just do the task once and Cowork learns it.
Do I need coding experience to use Claude Cowork?
No. Cowork is designed specifically for non-technical users. Everything in this workshop — from setting up skills to connecting tools — uses plain English. If you can write a clear set of instructions for a human assistant, you can use Cowork.
What are connectors (MCPs) in Claude Cowork?
Connectors are integrations that let Cowork access your existing tools — Google Calendar, Slack, Gmail, Google Drive, and more. MCP stands for Model Context Protocol, but you don't need to understand the technical details. Think of them as bridges between Cowork and the apps you already use.
How is Claude Cowork different from ChatGPT?
ChatGPT is a chat interface — you ask questions and get answers. Cowork is a task executor — it reads your files, follows structured instructions, creates documents, connects to your tools, and runs recurring workflows. It's the difference between talking to an assistant and having one that actually does the work.
What model should I use with Cowork for best results?
Select Opus 4.6 with Extended Thinking enabled. This gives Cowork the strongest reasoning and planning capabilities. For simpler tasks, Sonnet works fine and is faster, but for anything involving multi-step workflows or complex analysis, Opus is worth the wait.
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