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Inside My Cowork Setup: How I Built an AI Chief of Staff

18 March 2026
3:00 PM UTC
1 hour
Structure your local folder so Cowork understands your business — not just your question Write CLAUDE.md files that give Cowork memory, context, and rules for every area of your work Connect Cowork to your real tools — CRM, calendar, email, Slack — so it sees what you see Build skills and plugins that turn repeatable tasks into one-click workflows Set up scheduled tasks so Cowork works while you sleep

Watch the Recording

About This Webinar

You opened Claude Cowork. You had a chat. You thought: "This is just a chatbot with a folder."

That was me six weeks ago. Now Cowork runs my morning briefing, prepares me for meetings, drafts proposals, tracks my commitments across email and Slack, and coaches me on deals — without me asking.

The difference wasn't a software update. It was how I structured the setup.

This Wednesday, I'm opening up my actual laptop and walking you through the exact architecture I built to turn Cowork from a chat window into an AI chief of staff that knows my business, remembers everything, and works autonomously.

What you'll learn

How a simple folder structure on your laptop becomes the foundation Cowork builds on. Why CLAUDE.md files are the secret weapon — and how to write ones that actually work. Connecting Cowork to your existing tools so it has eyes and ears across your business. Building skills that encode your best processes into repeatable, one-click workflows. Setting up scheduled tasks that run autonomously — briefings, scans, reports.

Who should attend

You've got Claude Cowork. You've had a few conversations. You're thinking "I don't quite get it." This webinar is for you. No coding required — everything I show you is something a business leader built, not an engineer.

What you'll leave with

A clear mental model for structuring your own Cowork setup. The exact CLAUDE.md template I use to give Cowork context. A checklist of connectors to set up for your role. Confidence to build your first skill or install a plugin.

About Your Host

Charlie Cowan

Charlie Cowan

Founder & CEO, Kowalah

Charlie hosts our Wednesday Webinars, sharing practical AI strategies and insights to help organizations accelerate their AI adoption journey. With deep expertise in AI leadership and implementation, Charlie provides actionable guidance for executives and teams navigating AI transformation.

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