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/roadmap-generator

Generate phased implementation roadmaps with Epic/Story/Task breakdown, effort estimates, and validation checkpoints. Use when cto-architect needs to create actionable technical roadmaps from architecture designs.

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$ npx -y skills add alirezarezvani/claude-cto-team --skill roadmap-generator --agent claude-code

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How this skill gets triggered: by you, by Claude, or both.

  • Fires itselfAuto-invocation. Claude auto-loads it when your prompt matches the work.Auto-invocation is when the right skill fires by itself at the right moment, driven by a FLOW.md router and a hook, instead of you invoking it by name. It is the difference between a skill being installed and a skill actually getting used.Read the full definition →
  • You can call itInvoke it directly when you want it.
  • Slash command/roadmap-generator

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Generate phased implementation roadmaps with Epic/Story/Task breakdown, effort estimates, and validation checkpoints. Use when cto-architect needs to create actionable technical roadmaps from architecture designs.

SKILL.md

roadmap-generator.SKILL.md
name: roadmap-generator
description: Generate phased implementation roadmaps with Epic/Story/Task breakdown, effort estimates, and validation checkpoints. Use when cto-architect needs to create actionable technical roadmaps from architecture designs.

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"

---

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

---

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

---

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

---

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]

---

## 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 |
| Phas
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