Roadmap Generator

Creates structured implementation roadmaps that transform architecture designs into actionable plans with clear phases, milestones, and validation gates.

When to Use

• After architecture design is complete
• When translating strategic goals into execution plans
• Creating project timelines with realistic effort estimates
• Breaking down large initiatives into manageable phases

Roadmap Structure

Three-Phase Framework

Every roadmap follows MVP → Scale → Advanced phases:

Phase 1: MVP (Foundation)
├── Goal: Prove core value proposition
├── Duration: Typically 6-12 weeks
├── Success Criteria: Core functionality working
└── Exit Gate: User validation / metrics threshold

Phase 2: Scale (Growth)
├── Goal: Handle production load, improve reliability
├── Duration: Typically 8-16 weeks
├── Success Criteria: Performance SLAs met
└── Exit Gate: Load testing passed / uptime targets

Phase 3: Advanced (Optimization)
├── Goal: Competitive features, optimization
├── Duration: Ongoing
├── Success Criteria: Feature parity / differentiation
└── Exit Gate: Business metrics achieved

Epic/Story/Task Hierarchy

Epic

High-level capability that delivers business value.

• Duration: 2-6 weeks
• Format: "Enable [user] to [capability]"
• Example: "Enable customers to receive real-time order notifications"

Story

User-facing functionality within an epic.

• Duration: 2-5 days
• Format: "As a [user], I want to [action] so that [benefit]"
• Example: "As a customer, I want push notifications so I know when my order ships"

Task

Technical work to complete a story.

• Duration: 2-8 hours
• Format: "[Verb] [object] [context]"
• Example: "Implement WebSocket connection handler for notification service"

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Effort Estimation Framework

T-Shirt Sizing

Size	Story Points	Typical Duration	Characteristics
XS	1	2-4 hours	Trivial change, no unknowns
S	2	0.5-1 day	Simple, well-understood
M	3	1-2 days	Some complexity, minor unknowns
L	5	3-5 days	Complex, some research needed
XL	8	1-2 weeks	Very complex, significant unknowns
XXL	13+	> 2 weeks	Should be broken down

Estimation Guidelines

1. Include buffer: Add 20-30% for unknowns
2. Account for context switching: Multiply by 1.3 for teams juggling priorities
3. New technology penalty: Add 50% for unfamiliar tech
4. Integration tax: Add 20% for each external system integration

Team Velocity Calculation

Effective Capacity = Team Size × Working Days × Focus Factor × Skill Factor

Focus Factor:
- Dedicated team: 0.8
- 50% allocated: 0.4
- Ad-hoc: 0.2

Skill Factor:
- Expert team: 1.0
- Experienced: 0.8
- Learning curve: 0.5

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Validation Checkpoints

Phase Gate Reviews

Each phase ends with a validation gate:

## Phase 1 Exit Gate

### Go Criteria
- [ ] Core features functional in staging
- [ ] Unit test coverage > 70%
- [ ] Integration tests passing
- [ ] Performance baseline established
- [ ] Security review completed

### No-Go Signals
- Critical bugs unresolved
- Core functionality missing
- Team capacity insufficient for Phase 2
- Business requirements changed significantly

### Decision
[ ] GO - Proceed to Phase 2
[ ] CONDITIONAL GO - Proceed with identified risks
[ ] NO-GO - Address blockers first

Mid-Phase Checkpoints

• Week 2: Architecture validation
• Week 4: Integration milestone
• Week 6: Feature complete checkpoint
• Weekly: Sprint review and course correction

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Dependency Management

Dependency Types

Type	Description	Mitigation
Technical	Service A needs Service B	Start B early, use mocks
Team	Need DevOps for deployment	Reserve capacity early
External	Third-party API integration	Validate early, have fallback
Data	Need production data for testing	Create synthetic data

Critical Path Identification

1. List all dependencies
2. Identify longest chain
3. Mark critical path items
4. Add buffer to critical path (25%)
5. Parallelize non-critical work

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Output Format

Roadmap Document Structure

# Implementation Roadmap: [Project Name]

**Created**: [Date]
**Owner**: [Team/Person]
**Architecture Reference**: [Link to architecture doc]

## Executive Summary
[2-3 sentences on approach and timeline]

## Timeline Overview
[Visual timeline or Gantt representation]

## Phase 1: MVP (Weeks 1-8)

### Phase Goals
- [Goal 1]
- [Goal 2]

### Epics

#### Epic 1.1: [Name]
**Duration**: [X weeks]
**Dependencies**: [List]

| Story | Points | Owner | Dependencies |
|-------|--------|-------|--------------|
| [Story 1] | M | [Team] | None |
| [Story 2] | L | [Team] | Story 1 |

**Tasks for Story 1**:
- [ ] [Task 1] (S)
- [ ] [Task 2] (M)

### Phase 1 Exit Criteria
- [ ] [Criterion 1]
- [ ] [Criterion 2]

### Phase 1 Risks
| Risk | Probability | Impact | Mitigation |
|------|-------------|--------|------------|
| [Risk] | High/Med/Low | High/Med/Low | [Action] |

---

## Phase 2: Scale (Weeks 9-16)
[Same structure as Phase 1]

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## Phase 3: Advanced (Weeks 17+)
[Same structure as Phase 1]

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## Resource Requirements

### Team Composition
| Role | Phase 1 | Phase 2 | Phase 3 |
|------|---------|---------|---------|
| Backend | 2 FTE | 3 FTE | 2 FTE |
| Frontend | 1 FTE | 2 FTE | 1 FTE |
| DevOps | 0.5 FTE | 1 FTE | 0.5 FTE |

### Infrastructure Costs
| Phase | Monthly Cost | Notes |
|-------|-------------|-------|
| Phase 1 | $X | Development environment |
| Phase 2 | $Y | Staging + production |
| Phase 3 | $Z | Full scale |

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## Success Metrics

| Metric | Phase 1 Target | Phase 2 Target | Phase 3 Target |
|--------|---------------|----------------|----------------|
| [Metric 1] | [Value] | [Value] | [Value] |
| [Metric 2] | [Value] | [Value] | [Value] |

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## Appendix

### Assumptions
- [Assumption 1]
- [Assumption 2]

### Open Questions
- [Question 1]
- [Question 2]

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Anti-Patterns to Avoid

The Big Bang

Planning everything in detail upfront without iteration. Fix: Plan Phase 1 in detail, Phase 2 at epic level, Phase 3 at theme level.

The Feature Factory

Listing features without connecting to business outcomes. Fix: Every epic must connect to a measurable business goal.

The Happy Path

No buffer, no risk mitigation, assumes everything goes perfectly. Fix: Add 25-30% buffer, identify top 5 risks with mitigations.

The Kitchen Sink

Including every possible feature in MVP. Fix: Ruthlessly cut to core value proposition only.

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Python Utilities

This skill includes Python utilities for roadmap generation:

• generator.py - Core roadmap generation logic
• templates/ - Output templates (markdown, JSON)

See generator.py for programmatic roadmap generation.

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References

• Roadmap Templates - Standard output formats
• Estimation Guide - Detailed estimation techniques