Planning Strategy Guide

Expert planning assistant that helps you decompose complex tasks, assess complexity, identify dependencies, and create comprehensive implementation plans.

When to Use

This skill auto-activates when:

• Epic breakdown: "Break down this epic into tasks"
• Feature decomposition: "How do I plan this complex feature?"
• Scope estimation: "What's the scope of this work?"
• Complexity assessment: "How complex is this task?"
• Dependency analysis: "What are the dependencies?"
• Risk identification: "What risks should I consider?"
• Planning strategy: "Help me structure this project"
• Effort estimation: "I need to estimate effort for this"

Planning Phases

This skill guides you through 6 planning phases for comprehensive task decomposition:

Phase 1: Complexity Assessment

Purpose: Evaluate task complexity to determine planning approach

Complexity Rubric:

• Simple (1-2 files, clear scope)

  • Single component modification
  • Well-defined requirements
  • No external dependencies
  • Estimated: 1-4 hours

• Medium (3-8 files, some unknowns)

  • Multiple component changes
  • Some research needed
  • Few external dependencies
  • Estimated: 1-3 days

• Complex (9+ files, research needed, multiple systems)

  • Cross-system changes
  • Significant research required
  • Many dependencies and integrations
  • Estimated: 4+ days

Questions to ask:

1. How many files will be modified?
2. Are requirements fully understood?
3. Are there external system integrations?
4. How much research is needed?

Phase 2: Scope Definition

Purpose: Clearly define boundaries and deliverables

Key elements:

• In scope: What will be implemented
• Out of scope: What will NOT be implemented
• Acceptance criteria: How to verify completion
• Success metrics: How to measure success

Questions to ask:

1. What is the minimal viable implementation?
2. What features can be deferred?
3. What defines "done"?
4. What are the acceptance criteria?

Phase 3: Dependency Analysis

Purpose: Identify dependencies and proper execution order

Dependency types:

• Hard dependencies: Must complete A before B
• Soft dependencies: Prefer A before B, but not required
• Parallel work: Can execute simultaneously
• Blocking dependencies: External dependencies not in your control

Questions to ask:

1. What must be completed first?
2. What can run in parallel?
3. Are there external blockers?
4. What's the critical path?

Phase 4: Risk Identification

Purpose: Identify potential challenges and mitigation strategies

Common risk categories:

• Technical risks: Unknown technologies, complex algorithms
• Integration risks: Third-party APIs, external systems
• Performance risks: Scalability, response time
• Security risks: Authentication, data protection
• Timeline risks: Underestimated effort, scope creep

For each risk:

• Likelihood: Low/Medium/High
• Impact: Low/Medium/High
• Mitigation: How to reduce or eliminate
• Contingency: Plan B if it occurs

Phase 5: Task Breakdown

Purpose: Decompose feature into actionable subtasks

Breakdown principles:

• Atomic: Each task is a single, focused unit
• Testable: Each task has clear verification
• Estimable: Can reasonably estimate effort
• Independent: Minimal coupling between tasks
• Ordered: Logical execution sequence

Example breakdown:

Epic: User Authentication
├── Feature: Login Flow
│   ├── Task: Create login API endpoint
│   ├── Task: Add JWT token generation
│   ├── Task: Implement password validation
│   └── Task: Add login UI form
├── Feature: Session Management
│   ├── Task: Add token refresh logic
│   └── Task: Handle session expiration
└── Feature: Security
    ├── Task: Add rate limiting
    └── Task: Implement 2FA support

Phase 6: Effort Estimation

Purpose: Estimate time and resources needed

Estimation approaches:

1. T-shirt sizing: XS/S/M/L/XL (relative sizing)
2. Story points: Fibonacci sequence (1, 2, 3, 5, 8, 13)
3. Time-based: Hours or days (absolute sizing)

Factors to consider:

• Complexity: How technically challenging
• Uncertainty: How much is unknown
• Dependencies: How many blockers
• Experience: Team familiarity with domain

Buffer rule: Add 20-30% buffer for unknowns

Integration with CCPM

Commands that Activate This Skill

This skill enhances the following CCPM commands:

1. /ccpm:plan - Smart planning with phase detection

   • Detects complexity automatically
   • Suggests appropriate planning depth
   • Provides interactive guidance

2. /ccpm:plan - Extended planning with research

   • Activates all 6 planning phases
   • Integrates with docs-seeker for research
   • Creates comprehensive Linear issue

3. /ccpm:plan - Plan modifications

   • Analyzes impact of changes

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