aiskillstore/roadmap-planning-expert
skills/andresnaza/roadmap-planning-expert/SKILL.md
When the user asks about roadmap planning, sprint planning, milestone estimation, or capacity planning
$ install --global
skillsauthnpx skillsauth add aiskillstore/marketplace roadmap-planning-expertInstall this skill globally with one command. Works with Claude Code, Cursor, and Windsurf.
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Last scanned: Mar 28, 2026, 6:24 PM36.6s2 files scanned
SKILL.md
- 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 configurationquarters/- Quarterly roadmapsepics/- Epic files with milestonessprints/- Sprint planstemplates/- 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
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