Cowork Workflows

Cowork Workflows

**File-based planning workflows for Cowork** — Prevent context loss on complex tasks.

Cowork launched Jan 12, 2026. This is the first community resource for using file-based planning to handle multi-step tasks without hitting context limits.

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The Problem

Cowork (and Claude Code) has a ~200K token context window. When you're working on complex tasks — organizing thousands of files, processing receipts, generating reports — you'll hit this limit mid-task.

**What happens:**

• Context fills up after 50-150 operations
• Cowork loses track of what it was doing
• You have to start over
• Progress is lost

**The solution:** File-based planning. Use markdown files as "working memory on disk."

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How It Works

Instead of keeping everything in context, Cowork writes progress to three persistent files:

1. task_plan.md — What phases exist, what's complete, what's next
2. progress_log.md — Detailed log of every action taken
3. decisions.md — Why choices were made (prevents re-deciding)

When context fills up, you start a fresh Cowork session and tell it:

Read task_plan.md, progress_log.md, and decisions.md

Continue from Phase 3. Do NOT re-do completed work.

Cowork restores context from the files and picks up exactly where it left off.

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What's Inside

Templates

Ready-to-use markdown templates for any task:

• task_plan.md — Phase breakdown, progress tracking, decisions
• progress_log.md — Session logs, file tracking, issues
• decisions.md — Rationale, naming conventions, user preferences

Workflows

Complete workflow examples showing the planning pattern in action:

• 01-organize-downloads.md — Organize 6 months of downloads by type and date
• 02-expense-report.md — Create spreadsheet from receipt images with OCR

Each workflow includes:

• Initial prompt to give Cowork
• Expected phases with context risk warnings
• Planning file examples
• Session handoff instructions
• Expected outco