Installation

$ npx skills add smithery/aiskillstore --skill roadmap-planning-expert

Agent compatibility

Declared targets from SKILL.md / docs. Unmarked agents are not listed — the skill may still install via the CLI.

Claude Code Not declared

Cursor Not declared

Codex Not declared

GitHub Copilot Not declared

Windsurf Not declared

Gemini CLI Not declared

Cline Not declared

OpenCode Not declared

Package contents

Files included with this skill beyond the listing page.

skill md SKILL.md 3,167 B

docs SUMMARY.md 133 B

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:

plan-quarter: Ask about goals, define epics together, rough-size
plan-epic: Ask about milestone breakdown, estimate together
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

roadmap-planning-expert