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.