How I AI – Episode Summary

Podcast: How I AI
Host: Claire Vo
Guest: JJ Englert (10X)
Episode: Claude Cowork 101: How to automate your workday without touching code
Date: April 13, 2026

Episode Overview

This episode delivers a hands-on walkthrough of Anthropic’s Claude Cowork feature—a new way for non-coders and technical users alike to orchestrate, automate, and supercharge their workday using AI, without writing any code. Guest JJ Englert, a Cowork superuser from 10X, joins host Claire Vo to demystify the product, demonstrate practical automations, and share actionable strategies for getting started and making the most of AI as your personal work assistant.

Key Discussion Points & Insights

1. What is Claude Cowork?

• Cowork is described as the bridge between simple AI chat and advanced "Claude code" automations.
• Tailored for users who want actionable automations (“AI doing stuff for you”) beyond chat, but who aren’t ready for terminal-based workflows.

Quote:

“Cowork is literally doing it for you. In chat, it's like, cool, you told me what to do, but now I got to go do it.” – JJ Englert (05:11)

2. Projects & Skills: Demystifying the Basics

• Projects: Just folders on your computer where files, context, and instructions for a specific topic are stored. This makes persistent context easy for Claude to leverage across sessions.

• Skills: These are reusable, detailed instructions (prompts) that can be containerized and invoked repeatedly for common tasks.

Quote:

“What's a skill? ...Literally, like a file that describes what you want to do... What's a project? A folder with files in it.” – Claire Vo (09:23)

Timestamps:

• 06:20–09:23: Defining projects, folders, and the concept of “brain” (personal context).
• 10:43–12:31: Using workspace maps for orienting Claude and efficient file navigation.

3. Getting Started: Setting Up a Daily Operating System

• Walkthrough: JJ demonstrates creating a "Daily Operating System" project from scratch.
• He includes preferences (“brain”), workflows (emails, Slack), and sets up the workspace in Cowork.
• Instructions and context are stored in the folder for easy access and persistent AI memory.

Timestamps:

• 12:31–16:43: Step-by-step: making a folder, opening it in Cowork, inputting instructions, and setting project context.

4. The Power of Connectors

• Connectors allow Claude Cowork to access tools like Gmail, Slack, Notion, Google Drive, etc.—both for ingesting data and taking actions (e.g., drafting emails, scanning calendars).
• Permissions are granular and customizable.
• JJ demonstrates using connectors to analyze his sent emails and build a personalized email-writing skill.

Timestamps:

• 18:47–20:59: Adding and managing connectors.
• 20:59–22:28: Creative use case: having AI read past emails to create an “email style guide,” allowing the AI to draft in your authentic voice.

5. Automating & Orchestrating Workflows

• Cowork enables “AI orchestration”—users become “AI orchestrators,” running many agents/tasks at once.
• Project view gives a high-level dashboard of running/active agents and tasks.
• Ability to assign roles, chain workflows, and maintain persistent, task-specific context.

Notable Quote:

"Even though you might not be a developer, you're now an AI orchestrator. You can run many agents at once and have this top-level view..." – JJ Englert (24:27)

6. Building and Using Skills (e.g., Writing, Mentorship, Feedback)

• Skill Examples:

  • Writing emails in your unique tone.
  • “Thinking Partner” skill for prompts like brainstorming, feedback, or decision support.
  • “Sub Advisory” skills that simulate multiple perspectives (e.g., boss, customer, engineer) on drafts using sub-agents for objective feedback.

• Practical Use Cases:

  • Product managers can simulate boss, engineer, and customer feedback before real reviews.
  • Marketers can use sub-agents representing various customer profiles for campaign feedback.

Timestamps:

• 27:28–31:54: Sub-advisory skills, multi-agent feedback, and review workflows.

Quote:

“You can define three individual Personas with a fresh context window, meaning a fresh perspective to go and look at your work in an objective way..." – JJ Englert (30:04)

7. Scheduling Automation: Morning Debriefs & Beyond

• Users can set up scheduled tasks (daily, weekly, etc.) for recurring actions, such as reviewing messages, prepping a daily plan, aggregating critical info from multiple sources, or sending scheduled reminders.
• The context—including connectors and skills—is available for every scheduled run.

Timestamps:

• 37:52–41:01: Walkthrough of creating a daily morning debrief and discussion on the value of scheduled, personalized, AI-powered routines.

8. Advanced Tips & Trust Spectrum

• Start slow (“progressive trust”): Let AI draft first, then review before automations are fully hands-off.
• "Skills for everything": JJ has skills not just for work, but for social posts, newsletters, house maintenance, project management, etc.
• Emphasizes how Cowork projects can be used for non-work automations—event planning, home maintenance, recruiting.

Notable Quote:

“People get nervous about this. It's a trade of information for productivity…you give the AI a little bit of information, it can help you be very, very productive.” – Claire Vo (41:01)

Notable Quotes & Memorable Moments

• On feeling alone as a solo founder:

  “I don't know, this is like very sad. All my friends are agents. I'm a solo founder. It is like very hard to just me by myself, ensure that all my ideas are great.”
  – Claire Vo (00:16)

• On lowering the learning curve for automation:

  “Cowork is a really great on ramp to cloud code, teaching you some of the basic skills... without going full terminal mode.”
  – JJ Englert (06:20)

• On the value of multi-perspective feedback:

  “Spin up pre-feedback from AI... allows you to come to those very expensive meetings with much higher-quality, pre-thought-out work.”
  – Claire Vo (31:54)

• On the value of organizing and context in AI:

  “If you're operating within a project, it's very specific context about this specific project and your requirements for it, and it helps you get results faster."
  – JJ Englert (17:43)

Additional Tips & Takeaways

• Progressive Trust: Start with drafting, move towards more autonomy as you gain confidence.
• Skills are Transferable: Once created, your writing/feedback/review skills apply everywhere—emails, docs, newsletters, content, etc.
• "Project" is General Purpose: Can be work-related (event planning, workshops) or personal (house maintenance, hiring, etc.).
• Workspace Map: Let Claude map and navigate your folder/file structure for faster, smarter AI actions.
• Creative Routine Ideas: Use scheduled tasks to send daily news or wellness prompts, not just work plans.

Lightning Round (46:25–49:17)

• Favorite Cowork Use Case: Content creation, document navigation, and planning workshops/events.
• Other Tools JJ Loves:
  • Remotion (programmatic video creation)
  • Pencil.dev (AI for design)
• Prompting Tips: Stay polite, provide good/bad output examples, ask Claude to “ask more questions” if uncertain.

Episode Wrap

Claire and JJ highlight the accessibility, flexibility, and rapid improvement of Claude Cowork, encouraging both technical and non-technical listeners to start small, gradually build trust, and unlock creative new workflows. Projects aren’t just for business—use them for anything that could use a little intelligent automation.

Guide to Top Segments & Timestamps

| Segment | Timestamp | |---------------------------------------------|-------------------| | The Purpose of Cowork | 04:05–05:49 | | Key Concepts: Projects & Skills | 06:20–12:31 | | Workspace Map & Organization Strategy | 10:43–12:31, 11:41| | Creating a Daily Operating System | 12:31–16:43 | | Adding & Using Connectors | 18:47–20:59 | | Building and Using Skills | 27:28–31:54 | | Sub-Agents and Multi-Perspective Feedback | 30:04–33:33 | | Scheduling: Morning Debriefs & Automations | 37:52–41:01 | | Host and Guest’s Favorite Use Cases / Tools | 46:25–49:17 |

Resources

• More workflows and step-by-step guides: [Chat PRD How I AI Blog]
• JJ Englert: YouTube (10X Builder), X (@JJEnglert), LinkedIn
• Claude Cowork: Available via Claude desktop app

Final Note:
Both Claire and JJ emphasize that the real power of Claude Cowork is in its accessibility for anyone—even those without a technical background. By starting with simple automations and progressively building tailored projects and skills, anyone can make AI an indispensable work (and life) partner.