The Claude Cowork Setup That Actually Works

Feb 27, 2026

∙ Paid

I’ve been using Claude Cowork since launch day. It’s now the first thing I open every morning.

Not because I’m an AI enthusiast. Because it keeps finishing work I used to spend hours doing myself.

But here’s what took me weeks to learn: Cowork out of the box is mediocre. Cowork properly configured is a different tool entirely.

The gap between those two is about 30 minutes of setup.

The Problem

Cowork has no memory between sessions. Every conversation starts fresh. It doesn’t know who you are, what you do, or how you like things done.

So it produces generic output. You get frustrated. You assume the tool is overhyped.

The fix isn’t better prompts. It’s better setup.

Five things that actually matter:

Context files — Documents that tell Cowork who you are and how you work
Global instructions — Preferences that load automatically every session
Folder instructions — Project-specific context that loads when you select a folder
Plugins — Specialist packs for your specific role (Marketing, Sales, Finance, Legal, Data)
Connectors — Live integrations with Slack, Drive, Notion, and 50+ tools

Configure these once. Every session after that starts with Cowork already understanding your context.

Let me show you exactly how to set each one up. I’ve put together the Ultimate Setup Guide, including:

Three files that make Cowork actually understand you. Exact templates. What to include. What to skip.

Copy-paste instructions I use. The specific phrasings that produce better behavior.

How to set up project-specific context so each client folder loads its own brief automatically.

The exact prompt structure that triggers useful questions instead of Cowork guessing wrong.

Which plugins to install based on what you do. First prompts for each one.

Which tools to connect first. How to prompt Cowork to actually use them.

Copy-paste prompts for:

The limitations I hit. What fails. Honest workarounds.

Premium subscribers get everything I’ve published, including:

Perplexity Computer Playbook — 19 models, 15 workflows
Every Way to Make Slides with Claude in 2026 - 5 methods. Downloadable PowerPoint files. The prompts that work.
Sonnet 4.6 Complete Guide — Benchmarks and prompts
The Viral Content System — The prompt behind 3M weekly views
2,500 Angel Investors Database — Full list with emails

Everything going forward.

Premium begins below

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