Planning with Files Skill

Persistent markdown-based planning system for session continuity. Adapted from planning-with-files.

Three Planning Files

task_plan.md — Active Task Tracker

• •Maintained as a checklist of current work items
• •Read before starting any implementation work
• •Update checkboxes as tasks complete: [ ] → [x]
• •Add new tasks discovered during implementation

findings.md — Research & Discovery Log

• •Record technical research, API exploration, architecture decisions
• •Include sources, alternatives considered, and rationale
• •Reference when making implementation decisions

progress.md — Session Recovery Journal

• •Log completed work at end of each session
• •Include: what was done, key decisions, next steps
• •Read at start of new sessions to recover context
• •Contains the 5-question reboot check:
  1. •What was the last completed milestone?
  2. •What is the current active task?
  3. •Are there any blockers?
  4. •What files were last modified?
  5. •What's the next planned action?

When to Use

• •Session start: Read progress.md to recover context
• •Before major decisions: Read findings.md for prior research
• •Before implementation: Read task_plan.md for current priorities
• •After completing work: Update all three files as appropriate
• •Session end: Update progress.md with session summary

Hook Integration

This skill works with configured hooks in .claude/settings.json:

• •PreToolUse: Reads task_plan.md before Write/Edit operations
• •PostToolUse: Reminds to update progress.md after modifications
• •Stop: Checks for pending tasks in task_plan.md before session end