In this solo episode, I walk through the exact process of setting up Claude Cowork from scratch — the right way — using the free Cowork Onboarding plugin I built and made open source. I go step by step through the full onboarding flow, from picking your workspace folder and connecting tools, to building three core context files (About Me, Brand Voice, and Working Style), generating global instructions that tie everything together, setting up scheduled tasks like a daily morning briefing and quarterly context review, and running an optional security review to lock in sensible rules.

Timestamps

00:00 – Why Cowork is useless out of the box

02:22 – Starting the onboarding flow from scratch

03:30 – Choosing workspace folder and onboarding path

04:37 – Workspace structure and file access permissions

05:45 – Connecting Google Workspace tools (Gmail, Drive, Calendar)

06:56 – Building context files: About Me, Brand Voice, Working Style

10:58 – Linking existing brand materials from Google Drive

12:44 – Generating global instructions from your context files

15:00 – Skills and plugin recommendations from the marketplace

17:24 – Setting up scheduled tasks: morning briefing and quarterly review

19:46 – Running the optional security review

23:23 – Wrapping up: what we built and the two manual steps left

Key Points

• Most people skip the onboarding and then wonder why Cowork feels generic. The entire point of setting it up properly — building context files and global instructions — is so Claude never has to ask who you are again. Every session loads with that context automatically.
• The three context files (About Me, Brand Voice, Working Style) are the foundation of the whole setup. Without them, Cowork is writing responses for a stranger. With them, it knows your business, how you communicate, and how you like your deliverables structured.
• Global instructions are the piece most people miss. Once you paste your generated global instructions into Cowork's settings, every single session loads that context from the start — no repeating yourself, no re-explaining your preferences.

Links Mentioned

Free Cowork Onboarding plugin — download it to run the full guided setup described in this episode: https://return-my-time.kit.com/f00d78554c

Build with AI community — get the full onboarding plugin including the self-assessment, workflow audit, and custom skill blueprints tailored to your business: https://www.skool.com/buildwithai/about

WisprFlow — the talk-to-text tool used during the onboarding to answer Claude's questions faster: https://wisprflow.ai

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