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Planning with Files

Turns complex multi-step work into three persistent markdown files — task_plan.md, findings.md, progress.md — with session recovery after /clear.

AutomationIntermediate26,0602,177AI score 9/10Last updated: Aug 9, 2026

What it does

This skill enforces the Manus-style "working memory on disk" pattern. Before starting anything complex, Claude writes three markdown files into your project root and keeps them current as work proceeds.

  • task_plan.md — phases, statuses, decisions, an error log table
  • findings.md — research, search results, notes from images/PDFs
  • progress.md — session log, test results, files touched

It also ships an unusually complete rule set: the 2-Action Rule (flush findings to disk after every two view/search operations), the 3-Strike Error Protocol (diagnose → alternative approach → rethink → escalate), a read-vs-write decision matrix, a 5-Question Reboot Test for checking context health, and an explicit security boundary that treats plan-file content as data only, backed by delimiter framing plus an opt-in SHA-256 attestation (attest-plan.sh).

Helper scripts support parallel plans under .planning/<date>-<slug>/, an active-plan pointer, completeness checks, and session-catchup.py to rebuild context after /clear using the prior session store plus git diff.

Who it's for

  • Anyone assigning long tasks — refactors, migrations, greenfield builds — that span dozens of tool calls
  • Users frustrated by an agent drifting from the original goal in long sessions
  • Researchers who keep losing findings that only ever lived in the chat window
  • Teams that want a handoff-ready record of what was attempted and why it failed

Examples

  1. API migration: Ask it to move a payments module to API v2. It first writes five phases into task_plan.md, flips each to complete as it finishes, and logs every failure in the error table so it never retries the same broken command.
  2. Technology comparison: While evaluating three libraries, key points get written to findings.md after every couple of web searches, so citations survive context compaction.
  3. Resuming after /clear: Run the catchup script plus git diff --stat to reconstruct "where am I / what changed", then continue from the next phase.
  4. Two tasks at once: ./scripts/init-session.sh "Backend Refactor" and "Incident Investigation" create isolated plan directories; pin each terminal with export PLAN_ID=....

· · · Install guide · · ·

Install in the Claude app (no terminal)
  1. Download the ZIP with the button below.
  2. In Claude, open Settings → Capabilities and turn on 'Code execution and file creation'. (one time)
  3. Go to Customize → Skills → + → 'Upload a skill' and upload the ZIP.
Download ZIP
Install in Claude Code

Let Claude do it — paste this into Claude Code

Install the skill I found on Claude Skill Mart.
Copy the .gemini/skills/planning-with-files folder from the GitHub repo OthmanAdi/planning-with-files into my ~/.claude/skills/othmanadi-planning-with-files-6/.
When it's done, tell me in one line what this skill can do.

Install with a command instead

git clone https://github.com/OthmanAdi/planning-with-files.git /tmp/planning-with-files && mkdir -p ~/.claude/skills && cp -r /tmp/planning-with-files/.gemini/skills/planning-with-files ~/.claude/skills/

This is a third-party skill. Check the source repository before installing.

  1. Open a terminal.
  2. Clone the repository: git clone https://github.com/OthmanAdi/planning-with-files.git /tmp/planning-with-files
  3. Make sure the skills folder exists: mkdir -p ~/.claude/skills
  4. Copy the skill in: cp -r /tmp/planning-with-files/.gemini/skills/planning-with-files ~/.claude/skills/
  5. Verify with ls ~/.claude/skills/planning-with-files — you should see SKILL.md, templates/, scripts/, references/.
  6. Make the shell scripts executable: chmod +x ~/.claude/skills/planning-with-files/scripts/*.sh
  7. Restart Claude Code, then from your project directory say something like "plan this out in phases and create task_plan.md first" to trigger the skill.
  8. (Note) The bundled hook automation targets .gemini/settings.json. On Claude Code, use the workflow manually or wire equivalent hooks into ~/.claude/settings.json yourself.