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

Define Success

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

Identify Deliverables

What are the major outputs?
What milestones mark progress?
What dependencies exist?
What can be parallelized?

Break Down Tasks

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

Map Dependencies

What must be done first?
What can happen in parallel?
What are the critical path items?
Where are the bottlenecks?

Estimate and Buffer

Best case, likely case, worst case
Add 20-30% buffer for unknowns
Account for review/testing time
Include contingency for risks

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)
Well-Sized (2-8 hours)
Too Small (<1 hour)

Problems:

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

Solution: Break into smaller subtasks

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) / 6Example:

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 pointsProcess:

Discuss task
Everyone estimates privately
Reveal estimates simultaneously
Discuss differences
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

Calculate Available Hours

Team members × Sprint days × Hours per dayExample: 5 people × 10 days × 8 hours = 400 hours

Apply Focus Factor

Available hours × Focus factor (0.6-0.8)Example: 400 hours × 0.7 = 280 productive hours

Account for Commitments

Subtract meetings, time off, support dutiesExample: 280 - 40 (meetings) = 240 hours

Convert to Story Points

Use historical velocity or average hours per pointExample: 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
Daily Standup
Sprint Review
Sprint Retrospective

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

Review sprint goal
Review velocity and capacity
Estimate and commit to stories
Identify dependencies and risks
Define sprint success criteria

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 factorsUse to assess current position and identify strategic priorities.

Porter's Five Forces

Competitive rivalry
Threat of new entrants
Threat of substitutes
Bargaining power of suppliers
Bargaining power of buyers

Use to analyze industry competitiveness and profitability.

OKRs (Objectives & Key Results)

Objectives - Qualitative, aspirational goals Key Results - Quantitative, measurable outcomesExample:

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

Define the Question: What decision needs to be made?
Gather Information: Market data, competitive intel, internal capabilities
Generate Options: Brainstorm multiple strategic paths
Evaluate Options: Use frameworks, analyze risks/benefits
Make Decision: Choose direction and commit resources
Plan Execution: Define initiatives and milestones
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
Decision Matrix
Impact/Effort Matrix
Pre-mortem Analysis

Simple list of advantages and disadvantagesBest for: Quick decisions, clear trade-offs

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

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

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]

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.

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Advanced Concepts

Agent Skills

Framework Guides

​Planning Skills

​Available Planning Skills

Project Planner

Sprint Planner

Strategy Advisor

Decision Helper

​Project Planner

​Overview

​When to Use

​Planning Process

​Task Sizing Guidelines

​Output Format

​Estimation Techniques

​Example: Website Redesign Project

​Project: Company Website Redesign

​Milestones

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

​Sprint Planner

​Overview

​When to Use

​Sprint Planning Framework

Sprint Goal

Capacity Planning

Story Estimation

​Sprint Planning Output

​Capacity Calculation

​Story Point Guidelines

​Sprint Ceremonies

​Strategy Advisor

​Overview

​When to Use

​Strategic Frameworks

​Strategic Decision Process

​Decision Helper

​Overview

​When to Use

​Decision Frameworks

​Decision Checklist

​Installation

​Next Steps

Coding Skills

Research Skills

Writing Skills

Create Custom Skills

Build docs developers (and LLMs) love

Planning Skills

Available Planning Skills

Project Planner

Overview

When to Use

Planning Process

Task Sizing Guidelines

Output Format

Estimation Techniques

Example: Website Redesign Project

Project: Company Website Redesign

Milestones

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

Sprint Planner

Overview

When to Use

Sprint Planning Framework

Sprint Planning Output

Capacity Calculation

Story Point Guidelines

Sprint Ceremonies

Strategy Advisor

Overview

When to Use

Strategic Frameworks

Strategic Decision Process

Decision Helper

Overview

When to Use

Decision Frameworks

Decision Checklist

Installation

Next Steps