99% of You Prompt Claude Cowork Wrong

Ryan & Matt Data Science
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💼 Business owner or operator with a team? We build AI automation systems that cut costs and scale ops — done for you: https://ryanandmattdatascience.com/ai-consultant/ 🚀 Want to make money with AI skills? Join our free community — real projects, real client strategies, and the exact stack we use: https://www.skool.com/data-and-ai Most people using Claude Cowork are stuck at level one — and they don't even know it. In this video, I break down the 3 levels of Cowork prompting and show you what it actually looks like to reach level three: chaining multiple skills together, connecting to Gmail and other tools, and building fully automated workflows that run on their own. I'll walk you through building a real blog post workflow inside Cowork, using skills like a YouTube transcript puller, content extractor, and SEO keyword integrator — all chained together. Plus I cover the Trigger → Skill → Output framework that makes everything click. If you've been using Cowork but feel like you're not getting the most out of it, this is the video that changes that. TIMESTAMPS 00:00 - Intro: Why Most Cowork Users Do It Wrong 00:26 - The Biggest Mistake Cowork Users Make 01:17 - The 3 Levels of Cowork Prompting 02:33 - Level 3: Connectors + Gmail Example 03:50 - Using Skills (Content Extractor, Updater, Contacts) 05:08 - YouTube Transcript Skill Demo 06:53 - Turning Workflows Into Reusable Skills 08:11 - The Trigger → Skill → Output Framework 08:37 - Building a Full Blog Post with Cowork 11:11 - Cowork Connectors + Keyword Integration 14:37 - Chaining Skills Together with Hooks 15:03 - Opus 4.6 and Model Selection 15:55 - Multi-Skill Chaining Workflow Demo 18:55 - The Most Common Mistakes to Avoid 19:47 - Outro OTHER SOCIALS: 🌐 Website & Blog: https://ryanandmattdatascience.com/ Ryan’s LinkedIn: https://www.linkedin.com/in/ryan-p-nolan/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-payne-ceo/ Twitter/X: https://x.com/RyanMattDS *This is an affiliate program. We receive a small portion of the final sale at no extra cost to you.

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