roadmap-generator

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

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

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] |

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## 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