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Claude Cowork: An Onboarding Guide

21 June 2026

claude coworkai-nativeworkflowsetup

Most people open an AI tool and start typing — then wonder why the output sounds generic and the work doesn’t stick. Cowork is different: it works with your local files, runs longer tasks, and behaves closer to an agent than a chat box. Set up a small structure once, and it pays back every session. Here’s the whole thing, in about 30 minutes.

5 steps3 context files7 rules● living guide
01Create the folder structure

Cowork reads local files — everything stays on your computer, nothing goes to a server.

Claude-Work/
├── Context/
│   ├── about-me.md
│   ├── work-preferences.md
│   └── current-focus.md
├── Projects/
├── Outputs/
├── Templates/
└── CLAUDE.md
  • Context/ — who you are and how you work. Claude’s memory of you; without it every session starts from zero.
  • Projects/ — input materials: transcripts, notes, PDFs, data.
  • Outputs/ — where finished work is saved.
  • Templates/ — examples of good output, so Claude sees what “quality” means to you.
02Write CLAUDE.md — the behaviour rules

This file loads before every task. It defines what Claude can do, can’t do, and how to work with you.

  • Behaviour: plan before starting · ask if unsure · never delete without permission.
  • Output: save in Outputs/ · Markdown for documents · session-notes.md at the end.
  • Boundaries: no internet unless asked · no changes outside the agreed folder · if unsure, stop and ask.

Keep it under ~2000 words — every word costs tokens on every task. Short and precise beats long.

03Create the 3 context files

This is what separates generic AI output from text that sounds like you.

The easy way: open Cowork, connect your folder, and write — “Interview me one question at a time and create about-me.md, work-preferences.md and current-focus.md.”

  • about-me.md — your role (not a biography), how you define good work, your thinking style.
  • work-preferences.md — preferred format, where/how to save files, when to ask vs. act.
  • current-focus.md — active projects, this period’s priorities, what you’re not doing.
04Set Global Instructions & choose your model

Settings → Cowork → Edit next to Global Instructions. Configure once; applies everywhere. Set language & tone, “read about-me.md first”, structured format, and “always ask before deleting/sending.”

  • Sonnet — daily driver. Fast; great for writing, organising, analysis; saves your limit. ~80% of tasks.
  • Opus — complex tasks: deepest reasoning, strategy, bigger documents. Slower, uses more limit.
05Add the plugins for your work

Each plugin brings ready-made skills for a domain. Install once, use every session: Sales (CRM, proposals) · Legal (contracts, compliance) · Analytics (data, reports) · Communication (email, Slack, meetings) · File Manager (organise, batch rename) · Research (search, synthesis).

Chat vs. Cowork

Claude Chat — plan & write

Planning before action · quick questions & brainstorming · writing/copywriting that needs no files · preparing a clear prompt to hand to Cowork.

Claude Cowork — execute & files

Working with local files · long, complex tasks · creating real Excel/Word/PPT · automated tasks via /schedule while you do other things.

The 7 behaviour rules

  1. Start with the outcome, not the task. Not “make a report” but “a one-page PDF competitor analysis to pitch an investor Wednesday.”
  2. Use Projects for multi-session work. More memory; pick up where you left off.
  3. Ask for a plan before execution. Easier to fix a plan than a finished 20-page document.
  4. Write session-notes at the end. Next time start with “Read session-notes.md.” Zero lost context.
  5. Add only relevant files. Every file loaded costs tokens.
  6. Don’t bring chat habits into Cowork. Chat is for questions; Cowork is for execution.
  7. Plan in Chat, build in Cowork. Exploring inside Cowork is expensive.

● Living guide — updates

  • 2026-06-21 — First published.

This guide is updated as Claude Cowork evolves.