Planning Skills

Agent skills for project planning, sprint management, and strategic decision-making

Planning Skills

Planning skills help agents break down complex projects, estimate timelines, manage dependencies, and facilitate effective planning processes.

Available Planning Skills

Project Planner

Break down complex projects into actionable tasks with timelines and milestones

Sprint Planner

Agile sprint planning with story estimation and capacity management

Strategy Advisor

High-level strategic thinking and business decision frameworks

Decision Helper

Structured decision-making frameworks and analysis

---

Project Planner

Overview

Triggers: Planning projects, creating task breakdowns, defining milestones, estimating timelines, managing dependencies, project planning, roadmap, work breakdown, task estimation

When to Use

• Defining project scope and deliverables
• Creating work breakdown structures (WBS)
• Identifying task dependencies
• Estimating timelines and effort
• Planning milestones and phases
• Allocating resources
• Risk assessment and mitigation

Planning Process

1. Define Success

   • What is the end goal?
   • What are the success criteria?
   • What defines “done”?
   • What are the constraints (time, budget, resources)?
2. Identify Deliverables

   • What are the major outputs?
   • What milestones mark progress?
   • What dependencies exist?
   • What can be parallelized?
3. Break Down Tasks

   • Each task: 2-8 hours of work
   • Clear “done” criteria
   • Assignable to single owner
   • Testable/verifiable completion
4. Map Dependencies

   • What must be done first?
   • What can happen in parallel?
   • What are the critical path items?
   • Where are the bottlenecks?
5. Estimate and Buffer

   • Best case, likely case, worst case
   • Add 20-30% buffer for unknowns
   • Account for review/testing time
   • Include contingency for risks
6. Assign and Track

   • Who owns each task?
   • What skills are required?
   • How will progress be tracked?
   • When are check-ins scheduled?

Task Sizing Guidelines

Too Large (>2 days)

Problems:

• Hard to estimate accurately
• Difficult to track progress
• Blocks other work too long

Solution: Break into smaller subtasks

Well-Sized (2-8 hours)

Characteristics:

• Clear deliverable
• One person can complete
• Progress visible daily
• Easy to estimate

This is ideal!

Too Small (<1 hour)

Problems:

• May be over-planning
• Too much overhead
• Tracking becomes burden

Solution: Combine related micro-tasks

Output Format

## Project: [Name]

**Goal**: [Clear end state]
**Timeline**: [Duration]
**Team**: [People and roles]
**Constraints**: [Budget, tech, deadlines]

---

## Milestones

| # | Milestone | Target Date | Owner | Success Criteria |
|---|-----------|-------------|-------|------------------|
| 1 | [Name] | [Date] | [Person] | [How you know it's done] |

---

## Phase 1: [Phase Name] (Timeline)

| Task | Effort | Owner | Depends On | Done Criteria |
|------|--------|-------|------------|---------------|
| [Task] | [Hours] | [Person] | [Deps] | [Definition of done] |

---

## Dependencies Map

[Task A] ──> [Task B] ──> [Task D] ├──> [Task C] ──┘

---

## Risks & Mitigation

| Risk | Impact | Probability | Mitigation |
|------|--------|-------------|------------|
| [Risk] | High/Med/Low | High/Med/Low | [Prevention] |

Estimation Techniques

Three-Point Estimation

Calculate expected time using three scenarios:

• Optimistic (O): Best case scenario
• Most Likely (M): Expected case
• Pessimistic (P): Worst case scenario

Formula: Expected = (O + 4M + P) / 6

Example:

• Optimistic: 4 hours
• Most Likely: 8 hours
• Pessimistic: 16 hours
• Expected: (4 + 32 + 16) / 6 = 8.7 hours

T-Shirt Sizing

Quick relative sizing for tasks:

• XS: < 2 hours
• S: 2-4 hours
• M: 4-8 hours (1 day)
• L: 2-3 days
• XL: 1 week

Break down anything larger than XL

Planning Poker

Team estimation using Fibonacci sequence:

1, 2, 3, 5, 8, 13, 21 story points

Process:

1. Discuss task
2. Everyone estimates privately
3. Reveal estimates simultaneously
4. Discuss differences
5. Re-estimate until consensus

Example: Website Redesign Project

Project: Company Website Redesign

Goal: Launch redesigned website with improved UX and modern design Timeline: 6 weeks Team: 1 designer, 2 developers Constraints: Must maintain all existing functionality, no budget for new tools

---

Milestones

#	Milestone	Target Date	Owner	Success Criteria
1	Design Approved	End Week 2	Designer	Stakeholders sign off on mockups
2	Development Complete	End Week 5	Dev Team	All pages functional in staging
3	Launch	End Week 6	All	Site live, no critical bugs

---

Phase 1: Discovery & Design (Weeks 1-2)

Task	Effort	Owner	Depends On	Done Criteria
Audit current site	4h	Designer	-	List of pages, features, pain points
Stakeholder interviews	4h	Designer	-	Requirements doc with priorities
Create sitemap	2h	Designer	Audit	Updated sitemap approved
Design wireframes	8h	Designer	Sitemap	Lo-fi wireframes for all pages
Design mockups	20h	Designer	Wireframes	Hi-fi mockups with branding
Design review	8h	Designer	Mockups	Stakeholder approval

Total Effort: 46 hours (~6 days)

---

Sprint Planner

Overview

Triggers: Planning sprints, estimating stories, defining sprint goals, managing sprint backlogs, sprint planning, agile, scrum, story points, sprint capacity

When to Use

• Planning sprint iterations
• Estimating user stories with story points
• Defining sprint goals
• Managing sprint capacity
• Prioritizing backlog items
• Identifying sprint dependencies and risks

Sprint Planning Framework

Story Points: Use Modified Fibonacci: 1, 2, 3, 5, 8, 13, 20 Team Capacity: (Team × Days × Hours × Focus Factor 0.6-0.8) Velocity: Average points completed in past 3-5 sprints

Sprint Goal

Clear, achievable objective for the sprint that provides focus

Capacity Planning

Calculate realistic capacity based on team availability and focus

Story Estimation

Use relative sizing with story points for predictable planning

Sprint Planning Output

## Sprint [Number]: [Name]

**Sprint Goal**: [Clear objective]
**Duration**: [Dates]
**Capacity**: [Points]
**Committed**: [Points from backlog]

## Sprint Backlog

| Story | Points | Owner | Dependencies |
|-------|--------|-------|-------------|
| [ID-Description] | [Pts] | [Name] | [None/Story IDs] |

## Risks & Mitigation
[List potential issues and how to handle]

## Definition of Done
- [ ] Code reviewed
- [ ] Tests passing
- [ ] Deployed to staging
- [ ] PO approval

Capacity Calculation

1. Calculate Available Hours

   Team members × Sprint days × Hours per day

   Example: 5 people × 10 days × 8 hours = 400 hours

2. Apply Focus Factor

   Available hours × Focus factor (0.6-0.8)

   Example: 400 hours × 0.7 = 280 productive hours

3. Account for Commitments

   Subtract meetings, time off, support duties

   Example: 280 - 40 (meetings) = 240 hours

4. Convert to Story Points

   Use historical velocity or average hours per point

   Example: 240 hours / 3 hours per point = 80 points

Story Point Guidelines

Points	Complexity	Time Estimate	Example
1	Trivial	1-2 hours	Fix typo, update config
2	Simple	2-4 hours	Add button, simple form
3	Moderate	4-8 hours	CRUD endpoint, basic page
5	Complex	1-2 days	Authentication, search feature
8	Very Complex	2-3 days	Payment integration, dashboard
13	Epic	3-5 days	User system, reporting module
20+	Too Large	Break it down!	Needs decomposition

Sprint Ceremonies

Sprint Planning

When: Start of sprint Duration: 2-4 hours (2-week sprint) Participants: Scrum team, Product Owner

Agenda:

1. Review sprint goal
2. Review velocity and capacity
3. Estimate and commit to stories
4. Identify dependencies and risks
5. Define sprint success criteria

Daily Standup

When: Every day Duration: 15 minutes Participants: Scrum team

Format:

• What did I do yesterday?
• What will I do today?
• Any blockers?

Sprint Review

When: End of sprint Duration: 1-2 hours Participants: Scrum team, stakeholders

Agenda:

1. Demo completed work
2. Review sprint goal achievement
3. Gather feedback
4. Update product backlog

Sprint Retrospective

When: After sprint review Duration: 1 hour Participants: Scrum team

Agenda:

1. What went well?
2. What could be improved?
3. Action items for next sprint

---

Strategy Advisor

Overview

Triggers: Strategic planning, business decisions, competitive analysis, market strategy, business strategy, strategic thinking, high-level planning

When to Use

• Developing business strategy
• Analyzing competitive landscape
• Making strategic decisions
• Evaluating market opportunities
• Planning product roadmaps
• Assessing strategic risks
• Defining vision and goals

Strategic Frameworks

SWOT Analysis

Strengths - Internal advantages Weaknesses - Internal disadvantages Opportunities - External favorable factors Threats - External unfavorable factors

Use to assess current position and identify strategic priorities.

Porter's Five Forces

1. Competitive rivalry
2. Threat of new entrants
3. Threat of substitutes
4. Bargaining power of suppliers
5. Bargaining power of buyers

Use to analyze industry competitiveness and profitability.

OKRs (Objectives & Key Results)

Objectives - Qualitative, aspirational goals Key Results - Quantitative, measurable outcomes

Example:

• Objective: Become market leader in X
• KR1: Achieve 40% market share
• KR2: Net Promoter Score > 70
• KR3: $10M ARR

Blue Ocean Strategy

Create uncontested market space instead of competing in existing markets.

Eliminate - What factors to remove? Reduce - What to reduce below standard? Raise - What to raise above standard? Create - What new factors to create?

Strategic Decision Process

1. Define the Question: What decision needs to be made?
2. Gather Information: Market data, competitive intel, internal capabilities
3. Generate Options: Brainstorm multiple strategic paths
4. Evaluate Options: Use frameworks, analyze risks/benefits
5. Make Decision: Choose direction and commit resources
6. Plan Execution: Define initiatives and milestones
7. Monitor & Adapt: Track progress and adjust strategy

---

Decision Helper

Overview

Triggers: Making decisions, evaluating options, decision framework, pros and cons, decision analysis, choosing between options

When to Use

• Evaluating multiple options
• Making important decisions
• Analyzing trade-offs
• Structuring complex decisions
• Reducing decision bias
• Building consensus

Decision Frameworks

Pros and Cons

Simple list of advantages and disadvantages

Best for: Quick decisions, clear trade-offs

Pros	Cons
[Advantage 1]	[Disadvantage 1]
[Advantage 2]	[Disadvantage 2]

Decision Matrix

Weight criteria and score options

Best for: Multiple criteria and options

Criteria	Weight	Option A	Option B
Cost	30%	8	6
Speed	25%	6	9
Quality	45%	9	7
Total		7.95	7.25

Impact/Effort Matrix

Prioritize based on impact and effort

High Impact,  High Impact,
Low Effort    High Effort
[Quick Wins]  [Major Projects]

Low Impact,   Low Impact,
Low Effort    High Effort
[Fill-ins]    [Avoid]

Pre-mortem Analysis

Imagine the decision failed - why?

Process:

1. Assume decision led to failure
2. Brainstorm reasons it failed
3. Identify risks to mitigate
4. Adjust decision or plan

Decision Checklist

• Have I clearly defined the decision?
• Have I gathered relevant information?
• Have I considered multiple options?
• Have I evaluated consequences?
• Am I aware of my biases?
• Have I consulted relevant stakeholders?
• Is this reversible or irreversible?
• What’s the cost of delay?

---

Installation

Add all planning skills:

npx skills add shubhamsaboo/awesome-agent-skills

Or install individual skills manually.

Next Steps

Coding Skills

Explore software development skills

Research Skills

Discover research and analysis skills

Writing Skills

Find writing and documentation skills

Create Custom Skills

Build your own agent skills