planning

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:

1. Clarify: Understand goal, constraints, deadline, resources
2. Choose Approach: Select planning methodology based on project type
3. Decompose: Break down into phases, milestones, and tasks
4. Sequence: Identify dependencies and critical path
5. Estimate: Set realistic timelines with buffers (20-30% for uncertain work)
6. Define Success: Establish milestones and success criteria
7. Identify Risks: Anticipate obstacles and plan mitigation
8. 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:

1. Define end goal (what, when, success criteria)
2. Ask: "What must happen right before this?"
3. Continue backwards to present
4. Reverse sequence for forward plan
5. Add parallel tasks and dependencies
6. 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)

1. Review prioritized backlog
2. Select items based on team capacity
3. Break items into tasks
4. Estimate and commit
5. 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

1. Goal/Objective (what and why)
2. Scope (included/excluded)
3. Timeline (key dates, milestones)
4. Tasks/Phases (work breakdown)
5. Dependencies (critical path)
6. Resources (who, what needed)
7. Risks (identified + responses)
8. 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

1. Start with why - Ensure goal clarity before methodology
2. Right-size approach - Don't over-plan simple projects
3. Involve the team - People doing work should help plan
4. Plan iteratively - Start high-level, refine progressively
5. Include buffers - Be realistic about uncertainty
6. Make it visual - Diagrams > text walls
7. Assign ownership - Every task needs owner
8. Plan for learning - First time takes longer
9. Build in reviews - Regular check-ins catch issues early
10. 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.

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Remember: The best plan is the one that gets executed. Make plans clear, actionable, and realistic. Perfect planning is the enemy of starting.