planning-with-files

Implements file-based planning with task_plan.md, findings.md, and progress.md for complex multi-step tasks.

Updated Jan 10, 2026
One-click install
npx skills add https://github.com/Rabbit-Ivan/Ivan-skills --skill planning-with-files-rabbit-ivan
Or copy as Structured Prompt for Agent▼
Please help me install this Agent Skill.
Skill: planning-with-files
Source: https://github.com/Rabbit-Ivan/Ivan-skills/tree/main/skills/planning-with-files
Command: npx skills add https://github.com/Rabbit-Ivan/Ivan-skills --skill planning-with-files-rabbit-ivan

SYSTEM DOCUMENTATION & REQUIREMENTS

💡 This Skill includes scripts (resource) components.

What problem does it solve? Long-running AI agent tasks lose track of goals after many tool calls because context windows are volatile and limited. This Skill persists plans, findings, and progress to markdown files on disk so work survives context resets and session interruptions. ## Core Features & Use Cases - Persistent Planning Files: Creates and maintains task_plan.md, findings.md, and progress.md in your project directory as external working memory. - Session Recovery: A session-catchup script detects unsynced context from previous sessions after /clear, and hooks report phase completion status. - Structured Error Protocols: Enforces a 3-strike error protocol, error logging tables, and read-before-decide rules to prevent repeated failures. - Use Case: When starting a research project or multi-phase feature build requiring more than five tool calls, the agent creates a phased plan file first, logs discoveries after every two search operations, and resumes cleanly after interruptions. ## Quick Start Ask the agent to start a complex task using planning-with-files so it creates task_plan.md, findings.md, and progress.md in your project before executing.

Frequently Asked Questions about planning-with-files

High-intent search queries and answers about installing and using this skill.

FAQPage Schema
How do I prevent an AI agent from losing track of goals in long tasks?▼

Write the plan to a persistent file like task_plan.md and re-read it before major decisions. This keeps goals in the model's recent attention window even after dozens of tool calls, avoiding the lost-in-the-middle effect.

What is file-based planning for AI agents?▼

File-based planning treats the filesystem as external memory: task_plan.md tracks phases, findings.md stores discoveries, and progress.md logs session actions. The agent updates these files after each phase instead of relying on volatile context.

How does session recovery work after clearing context?▼

The session-catchup.py script parses the previous session transcript, finds the last planning file update, and reports unsynced messages. You then run git diff --stat, read the planning files, and update them before continuing.

When should I not use file-based planning?▼

Skip it for simple questions, single-file edits, and quick lookups. The overhead of creating and maintaining three planning files only pays off for multi-step tasks, research, or work spanning many tool calls.

Where are the planning files created?▼

Planning files go in your project directory, not the skill installation folder. Only templates and scripts live in the skill directory; task_plan.md, findings.md, and progress.md are written to your project root.