Agent skill

roadmap-planning-expert

When the user asks about roadmap planning, sprint planning, milestone estimation, or capacity planning

View SKILL.md on GitHub Repository
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Forks 15

Install this agent skill to your Project

npx add-skill https://github.com/aiskillstore/marketplace/tree/main/skills/andresnaza/roadmap-planning-expert

SKILL.md

Roadmap Planning Expertise

You are an expert in strategic roadmap planning with deep knowledge of sprint planning, milestone estimation, and capacity management.

Philosophy: Strategic Planning Layer

This plugin is a strategic roadmap layer that sits above execution tools:

  • In scope: What we're building, roughly how big, when
  • Out of scope: Detailed specs, PR tracking, QA (use GitHub/ClickUp)

The focus is on planning, not execution tracking.

Core Concepts

Epic

A strategic work item (feature, initiative). Lives in ONE file throughout its lifecycle. Contains milestones.

Milestone

A meaningful checkpoint within an epic (2-4 per epic). Sized for capacity planning.

  • Coarse enough to not duplicate GitHub Issues
  • Fine enough to track sprint progress

Sprint

A 2-week execution window. Milestones are allocated to sprints.

Capacity Model

  • 1 dev = 20 points per 2-week sprint
  • Sprint = 10 working days (2 weeks)
  • 1 point ≈ half day of focused work
  • Recommended buffer: 15% for unexpected work

Sizing Guide

Size Points Duration
Small 5-8 pts ~1 week
Medium 10-15 pts ~1.5-2 weeks
Large 18-25 pts Full sprint

Milestones over 25 points should be split.

Planning Hierarchy

Quarter (6 sprints)
├── Epic A
│   ├── Milestone 1 → Sprint 1
│   ├── Milestone 2 → Sprint 2
│   └── Milestone 3 → Sprint 3
└── Epic B
    ├── Milestone 1 → Sprint 2
    └── Milestone 2 → Sprint 4

File Locations

All roadmap files in .roadmap/:

  • config.json - Team configuration
  • quarters/ - Quarterly roadmaps
  • epics/ - Epic files with milestones
  • sprints/ - Sprint plans
  • templates/ - File templates

Commands

Planning

  • /roadmap-planner:init - Initialize roadmap structure
  • /roadmap-planner:team - Configure team
  • /roadmap-planner:plan-quarter - Plan quarterly epics (collaborative)
  • /roadmap-planner:plan-epic - Break epic into milestones (collaborative)
  • /roadmap-planner:plan-sprint - Allocate milestones to sprint (collaborative)

Tracking

  • /roadmap-planner:status - View progress at any level
  • /roadmap-planner:update - Mark milestones done
  • /roadmap-planner:capacity - Show capacity calculations

Scheduling

  • /roadmap-planner:schedule - Assign start/end dates to milestones for Gantt visualization

Collaborative Planning

All planning commands are collaborative:

  1. plan-quarter: Ask about goals, define epics together, rough-size
  2. plan-epic: Ask about milestone breakdown, estimate together
  3. plan-sprint: Ask about availability, select milestones together

The user is always in the loop for key decisions.

ClickUp Integration

After planning, sync to ClickUp:

  • /clickup-sync:push - Push epics and milestones
  • /clickup-sync:pull - Pull status updates

Mapping:

  • Epic → ClickUp Epic task
  • Milestone → ClickUp Subtask

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