| name | planning |
| description | Structured planning and project breakdown using proven methodologies for goals, projects,
and strategic initiatives. Use when users need to create plans, break down complex projects,
set milestones, estimate timelines, identify dependencies, or develop action plans.
Triggers include 'help me plan,' 'create a roadmap for,' 'break down this project,'
'what are the steps to,' or 'how should I approach.'
|
| allowed-tools | ["*"] |
Planning & Project Breakdown Skill
Guide users through structured, realistic planning for projects, goals, and strategic initiatives using proven project management frameworks.
Quick Start Workflow
When a planning request arrives, follow this systematic approach:
- Clarify: Understand goal, constraints, deadline, resources
- Choose Approach: Select planning methodology based on project type
- Decompose: Break down into phases, milestones, and tasks
- Sequence: Identify dependencies and critical path
- Estimate: Set realistic timelines with buffers (20-30% for uncertain work)
- Define Success: Establish milestones and success criteria
- Identify Risks: Anticipate obstacles and plan mitigation
- Document: Create clear, actionable plan
When to Use This Skill
Activate for requests involving:
- "Help me plan..." / "Create a roadmap for..."
- "Break down this project..." / "What are the steps to..."
- "How should I approach..." / "Build a timeline for..."
- Strategic planning, project kickoff, goal setting
Clarification Phase
Before planning, gather essential information:
Goal & Scope:
- What are you trying to achieve? (clear end state)
- What's in/out of scope?
- What would success look like?
Constraints:
- Deadline? Fixed or flexible?
- Resources available? (people, budget, tools)
- Dependencies? (external factors, approvals)
- Non-negotiables?
Context:
- Stakeholders? Decision makers?
- Past lessons learned?
- Similar projects to reference?
Don't skip this: 5 minutes of clarification saves hours later.
Planning Approach Selector
Choose methodology based on project characteristics:
Work Breakdown Structure (WBS)
Use when: Large, complex projects; scope unclear; need comprehensive task inventory
Process: Top-down decomposition (Project → Phases → Deliverables → Tasks)
Best for: Construction, IT projects, events, product launches
Backward Planning
Use when: Fixed deadline; event planning; goal clear but path uncertain
Process: Start from end goal, work backwards identifying prerequisites
Best for: Event planning, product launches, campaigns, deadline-driven work
Agile/Iterative Planning
Use when: Uncertain requirements; need flexibility; can deliver incrementally
Process: Plan in short iterations (sprints), adapt based on learning
Best for: Software development, research, new product development
Phased/Milestone Planning
Use when: Long project (3+ months); need checkpoints; staged delivery
Process: Divide into phases with gates, plan phase-by-phase
Best for: Research, construction, strategic initiatives, transformation
Hybrid Approach
Combine methods: WBS for decomposition + Agile for execution, etc.
See references/frameworks-detailed.md for detailed guides on each methodology.
Core Frameworks (Concise)
Work Breakdown Structure (WBS)
Hierarchical decomposition of work:
Levels: Project → Phases (3-7) → Deliverables → Tasks (1-3 days each) → Sub-tasks (if needed)
100% Rule: Each level represents 100% of parent's work
Tips:
- Nouns for deliverables, verbs for tasks
- Stop when tasks are 1-3 days
- 3-4 levels usually sufficient
Backward Planning
Process:
- Define end goal (what, when, success criteria)
- Ask: "What must happen right before this?"
- Continue backwards to present
- Reverse sequence for forward plan
- Add parallel tasks and dependencies
- Estimate durations
Key: Be thorough with prerequisites - missing steps are common
Critical Path Method
Identify longest sequence of dependent tasks (determines minimum duration):
Concepts:
- Critical Path: Tasks with zero slack (can't be delayed)
- Float/Slack: Time a task can delay without affecting project
Use: Focus management attention on critical path tasks
Use scripts/critical_path.py for calculation.
Timeline Estimation
Methods:
- Bottom-Up: Estimate each task, sum up (most accurate)
- Top-Down: Estimate overall, allocate to phases (faster)
- Three-Point: (Optimistic + 4×Most Likely + Pessimistic) / 6
- Analogous: Compare to similar past projects
Key Principles:
- Include 20-30% buffers for uncertain work
- Distinguish effort vs duration (40 hours work ≠ 40 hours elapsed)
- Account for capacity (people aren't 100% productive)
- Add contingency for risk mitigation
Avoid: Planning fallacy (underestimating), optimism bias
See references/estimation-techniques.md for detailed methods.
Milestones & Success Criteria
Good Milestones:
- Specific, measurable, meaningful
- Time-bound, visible to stakeholders
- Represent significant progress
Types: Deliverable completion, decision point, event, phase completion
Spacing: Weekly (short projects), bi-weekly/monthly (medium), monthly/quarterly (long)
OKR Framework (Objectives & Key Results)
Structure: 1 Objective + 3-5 Key Results
Objective: Qualitative, aspirational goal (what to achieve)
Key Results: Quantitative measures (how to measure success)
Example:
- Objective: Launch product successfully to market
- Key Results: 1000 active users first month; NPS 50+; $50K MRR by Q4 end
Use for: Strategic planning, not tactical tasks
SMART Goals
Specific - Measurable - Achievable - Relevant - Time-bound
Example: "Increase NPS from 30 to 50 by Q4 end through improved onboarding"
Use for: Individual goals, small initiatives
Dependencies & Sequencing
Dependency Types
Finish-to-Start (most common): B starts when A finishes
Start-to-Start: B starts when A starts
Finish-to-Finish: B finishes when A finishes
Identifying Dependencies
Ask for each task:
- What must complete before this starts?
- What can run in parallel?
- What's waiting for this?
- Any external dependencies?
Categories: Mandatory (technical), Discretionary (preference), External (outside control), Internal (team control)
Parallelization
Look for:
- Tasks with no dependencies
- Tasks with same prerequisites
- Tasks that can be split
Benefit: Shorter duration, better resource use
Caution: Don't over-parallelize (coordination overhead)
Risk Management (Brief)
Identification
Common categories: Schedule, Technical, Resource, External, Scope, Quality
Ask: "What could go wrong?" Review past issues. Use pre-mortems.
Assessment
For each risk: Probability (1-5) × Impact (1-5) = Risk Score
Prioritize: High-score risks for mitigation
Response Strategies
- Avoid: Eliminate risk by changing plan
- Mitigate: Reduce probability or impact
- Transfer: Shift to another party (insurance, contracts)
- Accept: Monitor with contingency plan
See references/frameworks-detailed.md for risk register template.
Resource Planning (Brief)
Categories
People: Roles, skills, time commitment, availability
Tools: Software, hardware, procurement time
Budget: Personnel, tools, contingency (10-20%)
Other: Space, materials, information access
RACI Matrix
Responsible (does work) - Accountable (ultimately accountable) - Consulted (provides input) - Informed (kept in loop)
See references/templates.md for RACI template.
Planning Horizons
Strategic (Annual/Quarterly): Goals, themes, major initiatives. Tools: OKRs, roadmaps. Review quarterly.
Tactical (Monthly/Sprint): Deliverables, projects. Tools: WBS, sprint planning. Review weekly.
Operational (Weekly/Daily): Immediate tasks. Tools: Task lists, kanban. Review daily.
Principle: Plan detail should match certainty - detailed near-term, high-level long-term.
Agile/Iterative Planning (Brief)
Sprint Planning (2-week iterations)
- Review prioritized backlog
- Select items based on team capacity
- Break items into tasks
- Estimate and commit
- Define sprint goal
Iteration Reviews
- Demo: Show completed work
- Retrospective: What went well, what to improve
- Adapt: Adjust for next iteration
Tips: Keep iterations short (1-2 weeks). Don't skip retrospectives. Protect from disruptions.
See references/templates.md for sprint planning template.
Contingency Planning
Buffers
Schedule: 20-30% for uncertain work, more for novel/complex
Resource: 10-20% budget contingency, backup personnel
Scope: Prioritize features (must-have vs nice-to-have), have cut list
Plan B
For critical paths, ask:
- What if this takes 2x longer?
- What if resources unavailable?
- What if dependency fails?
Document: Trigger points, alternatives, decision makers
Monitoring & Adaptation
Track: Compare actual vs planned, identify variances early
Re-plan when: Assumptions wrong, scope changes, resource changes, risks occur
Remember: Plans are tools, not contracts. Adapt when reality differs.
Documentation Formats
Essential Plan Elements
- Goal/Objective (what and why)
- Scope (included/excluded)
- Timeline (key dates, milestones)
- Tasks/Phases (work breakdown)
- Dependencies (critical path)
- Resources (who, what needed)
- Risks (identified + responses)
- Success Criteria (measurements)
Output Formats
High-Level Plan:
PROJECT: [Name]
GOAL: [What achieving]
TIMELINE: [Start] - [End]
OWNER: [Person]
PHASES:
1. Phase Name (dates) - Major deliverables
2. Phase Name (dates) - Major deliverables
MILESTONES:
- [Date]: Milestone
- [Date]: Milestone
TOP RISKS:
1. Risk [Mitigation]
2. Risk [Mitigation]
Detailed Task List:
TASK: [Description]
├─ Owner: [Person]
├─ Duration: [Estimate]
├─ Dependencies: [Prerequisites]
├─ Deliverable: [Output]
└─ Status: [Not started/In progress/Complete]
Use scripts/timeline_visualizer.py for visual timelines.
See assets/templates/ for ready-to-use formats.
Common Patterns
Product Launch: Backward plan from launch date, include dry-run, post-launch monitoring
Research Project: WBS + phased approach, exploratory time, iteration based on findings
Event Planning: Backward plan, critical path for venue/speakers, detailed day-of checklist
Software Dev: Agile sprints, testing in each iteration, deployment and monitoring
Process Improvement: Phased rollout, training/change management, measurement cycles
Tips for Effective Facilitation
- Start with why - Ensure goal clarity before methodology
- Right-size approach - Don't over-plan simple projects
- Involve the team - People doing work should help plan
- Plan iteratively - Start high-level, refine progressively
- Include buffers - Be realistic about uncertainty
- Make it visual - Diagrams > text walls
- Assign ownership - Every task needs owner
- Plan for learning - First time takes longer
- Build in reviews - Regular check-ins catch issues early
- Stay flexible - Reality trumps plans
Using Supporting Resources
Additional resources in this skill:
- references/frameworks-detailed.md: Step-by-step methodology guides
- references/estimation-techniques.md: Complete time estimation methods
- references/templates.md: Ready-to-use planning templates
- scripts/critical_path.py: Calculate project critical path
- scripts/timeline_visualizer.py: Generate visual timelines
- assets/templates/: Markdown and CSV templates for immediate use
Reference these for deeper guidance or ready-made formats.
Remember: The best plan is the one that gets executed. Make plans clear, actionable, and realistic. Perfect planning is the enemy of starting.
