AI Maestro Planning Skill

The Problem This Solves: EXECUTION

This skill solves the execution problem - losing focus during complex tasks:

Problem	Symptom	This Skill Fixes It
Goal drift	Forgot original objective after 50 tool calls	Re-read plan before decisions
Lost progress	Can't remember what phase I'm in	Phase tracking in task_plan.md
Repeated errors	Make same mistake twice	Error log prevents repetition
Session loss	Can't resume after /clear	Planning files persist on disk

Note: This is different from the Memory skill (which solves recall of past conversations). Planning solves staying focused NOW.

---

Core Principle

Context Window = RAM (volatile, limited, fast)
Filesystem = Disk (persistent, unlimited, explicit read required)

Anything important gets written to disk.

---

Output Directory

Planning output files (task_plan.md, findings.md, progress.md) should be written to:

1. The directory specified by the AIMAESTRO_PLANNING_DIR environment variable (if set)
2. Otherwise, docs_dev/ in the current project root
3. Create the directory if it does not exist

Do NOT write planning files to the project root — use docs_dev/ to avoid cluttering the project.

---

The 3-File Pattern

Create these files in docs_dev/ (not the project root or the skill directory):

File	Purpose	Update When
task_plan.md	Goals, phases, decisions, errors	After each phase
findings.md	Research, discoveries, resources	During research
progress.md	Session log, test results	Throughout session

---

Quick Start

Before any complex task (3+ steps):

# 1. Determine output directory
PLAN_DIR="${AIMAESTRO_PLANNING_DIR:-docs_dev}"
mkdir -p "$PLAN_DIR"

# 2. Create planning files from templates
cat ~/.claude/skills/planning/templates/task_plan.md > "$PLAN_DIR/task_plan.md"
cat ~/.claude/skills/planning/templates/findings.md > "$PLAN_DIR/findings.md"
cat ~/.claude/skills/planning/templates/progress.md > "$PLAN_DIR/progress.md"

# 3. Edit task_plan.md with your specific goal and phases

Then follow the rules below.

---

The 6 Rules

Rule 1: Create Plan First

NEVER start a complex task without creating task_plan.md.

Before writing any code or making any changes:

1. Create task_plan.md with clear goal
2. Break work into phases
3. List key questions to answer

Rule 2: Read Before Decide

Before any major decision, re-read the plan:

cat "${AIMAESTRO_PLANNING_DIR:-docs_dev}/task_plan.md" | head -50

This refreshes your goals in the context window, preventing drift.

Rule 3: Update After Act

After completing any phase:

• Mark phase as [x] complete
• Update status section
• Log any errors encountered
• Note files created/modified

Rule 4: The 2-Action Rule

After every 2 search/view/browse operations, immediately save key findings to findings.md.

Visual content (screenshots, PDFs, browser results) doesn't persist in context. Write it down NOW.

Rule 5: Log ALL Errors

Every error goes in task_plan.md:

## Errors Encountered
| Error | Attempt | Resolution |
|-------|---------|------------|
| FileNotFoundError | 1 | Created missing config |
| API timeout | 2 | Added retry with backoff |

This prevents repeating the same mistakes.

Rule 6: Never Repeat Failures

if action_failed:
    next_action != same_action

After a failure, CHANGE your approach. Don't retry the exact same thing.

---

The 3-Strike Protocol

Attempt 1: Diagnose & Fix

• Read error carefully
• Identify root cause
• Apply targeted fix

Attempt 2: Alternative Approach

• Same error? Try different method
• Consider different tools/libraries
• NEVER repeat exact failing action

Attempt 3: Broader Rethink

• Question assumptions
• Search for similar issues
• Update task plan with learnings

After 3 Failures: Escalate

• Explain all approaches tried
• Share specific error messages
• Ask user for guidance

---

When to Read vs Write

Situation	Action	Why
Just wrote a file	DON'T read	Content is in context
Viewed image/PDF	Write findings NOW	Visual content doesn't persist
Browser returned data	Write to findings.md	Screenshots don't persist
Starting new phase	Read task_plan.md	Re-orient from plan
Error occurred	Read relevant file	Need current state
Resuming after gap	Read ALL planning files	Recover context

---

The 5-Question Reboot

Lost? Answer these questions:

Question	Find Answer In
Where am I?	Current phase in task_plan.md
Where am I going?	Remaining phases in task_plan.md
What's the goal?	Goal section in task_plan.md
What have I learned?	findings.md
What have I done?	progress.md

---

When to Use This Skill

USE for:

• Multi-step tasks (3+ steps)
• Research projects
• Building features
• Tasks requiring >5 tool calls
• Anything needing organization

SKIP for:

• Simple questions
• Single-file edits
• Quick lookups
• Trivial changes

---

Anti-Patterns

DON'T	DO Instead
Use TodoWrite for complex tasks	Create task_plan.md file
State goals once and forget	Re-read plan before decisions
Hide errors and retry	Document errors in plan
Stuff everything in context	Store large content in files
Start executing immediately	Create plan FIRST
Repeat failed actions	Track attempts, change approach

---

Integration with Memory Skill

Planning and Memory solve different problems:

Skill	Problem	Timescale
Memory	"What did we discuss last week?"	Days/weeks/months
Planning	"What am I supposed to do next?"	Minutes/hours

Use BOTH for complex work:

1. Memory - Search for past decisions and context
2. Planning - Stay focused during execution

---

Templates

Templates are in ~/.claude/skills/planning/templates/:

• task_plan.md - Phase and progress tracking
• findings.md - Research and discoveries
• progress.md - Session logging

Note: The template path depends on how the skill was installed:

• User scope (global): ~/.claude/skills/planning/templates/
• Project scope (local): <project>/.claude/skills/planning/templates/

Copy to docs_dev/ and customize.

---

Example Workflow

User: "Build a new authentication system"

1. CREATE PLAN
   - Copy templates to docs_dev/
   - Define goal: "Implement JWT authentication"
   - Break into phases: Research, Design, Implement, Test, Document

2. EXECUTE PHASE 1 (Research)
   - Search memory: memory-search.sh "authentication"
   - Search docs: docs-search.sh "auth patterns"
   - Write findings to findings.md
   - Mark Phase 1 complete in task_plan.md

3. EXECUTE PHASE 2 (Design)
   - READ task_plan.md (refresh goals)
   - READ findings.md (recall research)
   - Design approach, document decisions
   - Mark Phase 2 complete

4. CONTINUE...
   - Always read plan before major decisions
   - Always update after completing phases
   - Always log errors

---

Troubleshooting

Templates not found:

ls ~/.claude/skills/planning/templates/

If missing, reinstall the skill or copy from AI Maestro repo.

Forgot the goal:

cat "${AIMAESTRO_PLANNING_DIR:-docs_dev}/task_plan.md" | head -20

Lost track of progress:

grep -E "^\s*-\s*\[" "${AIMAESTRO_PLANNING_DIR:-docs_dev}/task_plan.md"

Shows all checkboxes and their status.