planning-with-files

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File-based planning workflow for complex tasks. Create and maintain task_plan.md, findings.md, and progress.md as persistent working memory.

materialofair By materialofair schedule Updated 4/1/2026

name: planning-with-files description: File-based planning workflow for complex tasks. Create and maintain task_plan.md, findings.md, and progress.md as persistent working memory.

Planning With Files

Use this skill when the task is complex, long-running, or likely to exceed context continuity.

Use When

  • Multi-step tasks (typically 3+ phases)
  • Investigations requiring many reads/searches
  • Work that spans planning, implementation, and verification

Core Pattern

Context window is volatile; files are durable. Write key decisions and discoveries to disk early.

Standard Files

  • task_plan.md: goals, phases, decisions, errors
  • findings.md: research notes, references, technical findings
  • progress.md: chronological execution and test log

Workflow

  1. Initialize files in project root:
    • bash skills/planning-with-files/scripts/init-session.sh
  2. Before major decisions, re-read task_plan.md.
  3. After every 2 search/view operations, update findings.md.
  4. After each phase, update status and progress.md.
  5. Before handoff, validate completeness:
    • bash skills/planning-with-files/scripts/check-complete.sh

Rules

  • Do not start complex implementation without task_plan.md.
  • Record all meaningful errors and attempted fixes.
  • Do not repeat identical failed actions.
  • Keep plans minimal and reversible.

Templates

  • skills/planning-with-files/templates/task_plan.md
  • skills/planning-with-files/templates/findings.md
  • skills/planning-with-files/templates/progress.md
Install via CLI
npx skills add https://github.com/materialofair/claudecode-omc --skill planning-with-files
Repository Details
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