Inside My Cowork Setup: How I Built an AI Chief of Staff
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Did you just open Claude Cowork and chat? That's like hiring a chief of staff and only asking them the weather. This webinar shows you - screen by screen - exactly how I structured Cowork to run my business, remember context, and work autonomously.
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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.
What We'll Cover
Inside My Cowork Setup
45 minutesLive walkthrough of my folder structure, CLAUDE.md files, connectors, skills, plugins, and scheduled tasks — screen by screen, with explanations of why each layer matters and how they work together
AI in the News
5 minutesQuick hits from the week in AI
Q&A
10 minutesYour questions about setting up Cowork for your role
Total Duration: Approximately 30-45 minutes
About Your Host
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.