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:
code
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"
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
- •Include buffer: Add 20-30% for unknowns
- •Account for context switching: Multiply by 1.3 for teams juggling priorities
- •New technology penalty: Add 50% for unfamiliar tech
- •Integration tax: Add 20% for each external system integration
Team Velocity Calculation
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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
Validation Checkpoints
Phase Gate Reviews
Each phase ends with a validation gate:
markdown
## 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
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
- •List all dependencies
- •Identify longest chain
- •Mark critical path items
- •Add buffer to critical path (25%)
- •Parallelize non-critical work
Output Format
Roadmap Document Structure
markdown
# 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] --- ## Phase 3: Advanced (Weeks 17+) [Same structure as Phase 1] --- ## 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 | --- ## Success Metrics | Metric | Phase 1 Target | Phase 2 Target | Phase 3 Target | |--------|---------------|----------------|----------------| | [Metric 1] | [Value] | [Value] | [Value] | | [Metric 2] | [Value] | [Value] | [Value] | --- ## Appendix ### Assumptions - [Assumption 1] - [Assumption 2] ### Open Questions - [Question 1] - [Question 2]
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.
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.
References
- •Roadmap Templates - Standard output formats
- •Estimation Guide - Detailed estimation techniques