AI Maestro Planning

SkillFiles & storage

Planning is a skill that lets an AI agent create and manage persistent markdown planning files for structured task execution. It is used when someone asks to create a plan, track progress, or start a research project, or when a task needs more than 5 tool calls and phase tracking to stay focused and avoid goal drift.

Use AI Maestro Planning in Claude, ChatGPT or Ahel Desktop

Free. Sign in, add AI Maestro Planning and connect your AI. About a minute.

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Then ask your AI: use the AI Maestro Planning skill

Details

Instructions available. Your AI can read the instructions. Execution depends on the setup they require.

Have an agent setup that supports loading skills.

AI Maestro PlanningStart free

What your AI can do with it

  • Create persistent markdown planning files for a task
  • Track tasks through structured phases
  • Update plan files as work progresses
  • Keep long, multi-step work organized and focused
  • Avoid goal drift on tasks requiring many tool calls

Getting started

  1. Have an agent setup that supports loading skills.
  2. Add the planning skill to the available skills.
  3. Ask the agent to create a plan, track progress, or start a research project, and it will use the skill to write and maintain a markdown plan file.

What this skill tells your AI

The instructions your AI receives, as published by davila7/claude-code-templates in cli-tool/components/skills/ai-maestro/planning/SKILL.md and read by ahel’s review.

Solve the execution problem -- staying focused during complex, multi-step tasks. Uses persistent markdown files to track goals, findings, and progress so you never lose context. Part of the AI Maestro suite.

When to Use

  • Multi-step tasks (3+ steps)
  • Research projects
  • Building features requiring >5 tool calls
  • Any task where you might lose track of the goal

The 3-File Pattern

Create in docs_dev/ (or $AIMAESTRO_PLANNING_DIR):

FilePurposeUpdate When
task_plan.mdGoals, phases, decisions, errorsAfter each phase
findings.mdResearch, discoveries, resourcesDuring research
progress.mdSession log, test resultsThroughout session

Quick Start

PLAN_DIR="${AIMAESTRO_PLANNING_DIR:-docs_dev}"
mkdir -p "$PLAN_DIR"

Then create task_plan.md with:

# Task: [Goal]

## Phases
- [ ] Phase 1: Research
- [ ] Phase 2: Design
- [ ] Phase 3: Implement
- [ ] Phase 4: Test

## Decisions
| Decision | Rationale | Date |
|----------|-----------|------|

## Errors Encountered
| Error | Attempt | Resolution |
|-------|---------|------------|

The 6 Rules

  1. Create plan first -- Never start complex work without task_plan.md
  2. Read before decide -- Re-read the plan before any major decision
  3. Update after act -- Mark phases complete, log what changed
  4. 2-action rule -- After every 2 search/browse operations, save findings to findings.md
  5. Log all errors -- Every error goes in the plan with attempt number and resolution
  6. Never repeat failures -- If an action failed, change your approach

The 3-Strike Protocol

StrikeAction
1Diagnose root cause, apply targeted fix
2Try a different approach entirely
3Question assumptions, search for similar issues
After 3Escalate to user with all attempts documented

The 5-Question Reboot

Lost? Answer these from your planning files:

  1. Where am I? (current phase in task_plan.md)
  2. Where am I going? (remaining phases)
  3. What's the goal? (goal section)
  4. What have I learned? (findings.md)
  5. What have I done? (progress.md)

Full AI Maestro Experience

This skill works standalone with no dependencies. For the complete experience including memory search, docs search, graph query, agent messaging, and agent management, install the full AI Maestro platform.

Signals

GitHub stars
32k
Forks
4k
Last commit
Oct 2026

Questions

When should the planning skill be used?
When the user asks to create a plan, track progress, or start a research project, or when a task requires more than 5 tool calls and needs structured phase tracking to stay focused and avoid goal drift.
What format do the plans use?
Markdown planning files that persist across the task and are updated as work progresses.
Advanced
Item type
skill
Key
planning-davila7
Source
github.com/davila7/claude-code-templates