planning-with-files

Persist planning state to task_plan.md, findings.md, and progress.md files.

Updated Jan 15, 2026
One-click install
npx skills add https://github.com/KaiserWhoLearns/skillsbench --skill planning-with-files-kaiserwholearns
Or copy as Structured Prompt for Agent
Please help me install this Agent Skill.
Skill: planning-with-files
Source: https://github.com/KaiserWhoLearns/skillsbench/tree/main/tasks/organize-messy-files/environment/skills/planning-with-files
Command: npx skills add https://github.com/KaiserWhoLearns/skillsbench --skill planning-with-files-kaiserwholearns

SYSTEM DOCUMENTATION & REQUIREMENTS

💡 This Skill includes scripts (resource) components.

What problem does it solve?

This Skill helps teams and agents manage long, multi-step tasks by keeping goals and progress outside of volatile memory, using a persistent on-disk planning system with task_plan.md, findings.md, and progress.md.

Core Features & Use Cases

  • External memory for complex workflows: create and update planning files to guide decisions across many tool calls.
  • Phase tracking and decision logs: document requirements, decisions, and outcomes in a structured, replayable format.
  • Collaboration-friendly templates: provides standard templates and scripts to initialize and monitor planning sessions.

Quick Start

Create task_plan.md in your project using templates/task_plan.md as reference to begin planning.

Frequently Asked Questions about planning-with-files

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

FAQPage Schema
How do I manage complex task planning across multiple tool calls without losing progress?

You can persist planning state to disk using task_plan.md, findings.md, and progress.md files. This external memory approach ensures goals and decisions survive memory resets or reboots during long-running, multi-step workflows.

What is on-disk planning for multi-step research tasks?

On-disk planning is a method of organizing complex workflows by writing requirements, decisions, and progress to markdown files. It creates a structured, replayable format that guides decisions across many tool calls.

When should I use markdown templates for task management?

Use markdown planning templates for projects requiring 5 or more tool calls, long-running research, or workflows needing phase tracking. They provide external memory to document requirements and outcomes in a structured format.

How do I initialize a planning session for long-running projects?

To begin planning, create a task_plan.md file in your project directory using the provided sample template as a reference. You can use the included scripts to initialize and monitor your planning session.

Does this on-disk planning approach work for workflows requiring automation hooks?

Yes, the system satisfies requirements for phase tracking, planning templates, and automation hooks. It includes sample templates and scripts designed to initialize and monitor automated planning sessions.

Can I use this task planning system to track decisions and outcomes collaboratively?

Yes, the system provides collaboration-friendly templates that document decisions and outcomes in a structured format. Teams and agents can use these standard files to maintain a replayable decision log.