roadmap-planning-expert

name	roadmap-planning-expert
description	When the user asks about roadmap planning, sprint planning, milestone estimation, or capacity planning

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