Roadmap Planning

Plan what to build and when to build it.

What This Skill Does

Creates strategic product roadmaps that translate positioning and priorities into actionable plans. Defines themes, milestones, timelines, and resource allocation while maintaining flexibility for changing circumstances.

When to Use

Activate this skill when:

• User needs a product roadmap or release plan
• Phrases like "create roadmap", "what's our plan", "upcoming releases"
• Planning quarterly or annual product strategy
• Communicating product direction to stakeholders
• User says "roadmap for next [period]" or "what are we building"

How It Works

The roadmap planning process ensures strategic alignment:

1. Review context - Understand positioning, priorities, constraints
2. Define themes - Group work into strategic themes
3. Set milestones - Identify key delivery points
4. Allocate resources - Match work to capacity
5. Create timeline - Build phased delivery schedule
6. Validate feasibility - Check against constraints and risks

Input Parameters

Parameter	Type	Required	Description
timeframe	string	Yes	Planning horizon (e.g., "Q2 2026", "2026", "next 6 months")
scope	string	No	product (full product), feature (specific area)
granularity	string	No	themes (high-level), milestones (standard), features (detailed)

Output Structure

The skill generates roadmap outputs:

1. Roadmap document (context/roadmap.md) - Visual and detailed roadmap
2. Milestone definitions - Key delivery points with success criteria

Roadmap Document Format

# Product Roadmap: [Timeframe]

## Strategic Themes
| Theme | Description | Business Value | Priority |
|:------|:-------------|:---------------|:---------|
| Theme 1 | [What and why] | [Expected outcome] | P0 |
| Theme 2 | [What and why] | [Expected outcome] | P1 |

## Timeline Overview

Q1 |████████████████████| Theme 1: Foundation Q2 | ████ | Theme 2: Growth Q3 | ████ | Theme 3: Scale Q4 | ████ | Theme 4: Expansion Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec

## Milestones

### Q1 2026 - Foundation
**Goal**: Establish core platform capabilities

| Deliverable | Target | Success Criteria | Risk |
|:------------|:-------|:------------------|:-----|
| Feature A | Feb 15 | [Metric] | [Risk level] |
| Feature B | Mar 30 | [Metric] | [Risk level] |

**Dependencies**: Tech platform v2, API access
**Risks**: Engineering capacity, third-party API limits

### Q2 2026 - Growth
**Goal**: Drive user acquisition and engagement

| Deliverable | Target | Success Criteria | Risk |
|:------------|:-------|:------------------|:-----|
| Feature C | May 15 | [Metric] | [Risk level] |

**Dependencies**: Q1 delivery complete
**Risks**: Market competition, user adoption

## Quarterly Breakdown

### Q1 2026 (Jan-Mar)
**Focus**: Foundation

| Week | Theme | Features | Capacity |
|:-----|:------|:---------|:---------|
| W1-4 | Setup | Infrastructure, auth | 20 pts |
| W5-8 | Core | Feature A, Feature B | 25 pts |
| W9-12 | Launch | Beta release, feedback | 20 pts |

**Total**: 65 story points
**Allocation**: 60% features, 20% tech debt, 20% buffer

### Q2 2026 (Apr-Jun)
**Focus**: Growth

| Week | Theme | Features | Capacity |
|:-----|:------|:---------|:---------|
| W13-16 | Acquisition | Onboarding, invitations | 25 pts |
| W17-20 | Engagement | Feature C, notifications | 30 pts |
| W21-24 | Optimization | Performance, analytics | 25 pts |

**Total**: 80 story points
**Allocation**: 70% features, 15% tech debt, 15% buffer

## Now/Next/Later View

### Now (Current Quarter)
- [ ] Feature A (Week 4)
- [ ] Feature B (Week 8)
- [ ] Beta Launch (Week 12)

### Next (Following Quarter)
- Feature C
- Feature D
- Public Launch

### Later (Future)
- Feature E
- Feature F
- International expansion

## Dependencies & Risks
| Item | Type | Impact | Mitigation |
|:-----|:-----|:-------|:-----------|
| Dependency | External | High | [Plan B] |
| Risk | Technical | Medium | [Mitigation] |

## Resource Allocation
| Team | Q1 | Q2 | Q3 | Q4 |
|:-----|:---|:---|:---|:---|
| Engineering | 2 FTE | 2 FTE | 3 FTE | 3 FTE |
| Design | 0.5 FTE | 0.5 FTE | 1 FTE | 1 FTE |
| PM | 1 FTE | 1 FTE | 1 FTE | 1 FTE |

## Assumptions
1. Engineering headcount increases in Q3
2. No major technical blockers
3. Market conditions remain stable
4. Competitors don't launch major alternatives

Roadmap Views

View	When to Use	Key Elements
Now/Next/Later	Executive communication	3 buckets only
Timeline	Planning sessions	Dates and milestones
Theme-based	Strategic alignment	Grouped by initiatives
Feature-based	Engineering execution	Detailed feature list

Quality Standards

Before delivering, the roadmap should:

• Align with product positioning and strategy
• Be realistic given resource constraints
• Include measurable success criteria
• Identify key dependencies and risks
• Balance new features with tech debt
• Allow flexibility for changes
• Communicate clearly to all audiences

Collaboration Modes

Mode	How It Works
autopilot	Generates roadmap from priorities and constraints
copilot	Drafts roadmap, validates milestones with you
manual	Provides roadmap templates, you complete

Context Integration

Reads:

• context/prioritization.json - Prioritized backlog
• context/positioning.md - Strategic direction

Writes:

• context/roadmap.md - Complete roadmap document
• context/roadmap.json - Machine-readable roadmap data

Read By:

• prd-gen - References roadmap for feature planning
• iteration-planning - Uses roadmap for sprint planning

Example Usage

User: "Create a roadmap for Q2"
→ Generates Q2 roadmap with milestones

User: "What's our product plan for this year?"
→ Creates annual roadmap with themes

User: "Show me now/next/later"
→ Generates simplified 3-bucket view

Best Practices

1. Theme-based, not feature-based - Group into strategic themes
2. Leave room for discovery - Don't fill every slot
3. Communicate uncertainty - Show confidence levels
4. Update regularly - Roadmaps change, keep them current
5. Multiple views - Different detail for different audiences