Create Roadmap Command

Facilitates strategic roadmap creation for quarters or years by gathering strategic goals, analyzing projects, prioritizing initiatives, mapping dependencies, allocating resources, and generating comprehensive roadmap documentation.

Arguments

$1: Timeframe (required)
- q1, q2, q3, q4 - Quarterly roadmaps
- 2025-q1, 2025-q2 - Specific quarter with year
- annual, 2025, 2026 - Annual roadmaps
- 6-months, 12-months - Custom timeframes
$2: Roadmap name (optional, auto-generated if not provided)
- Custom name for the roadmap
- Default: auto-generated from timeframe

Workflow

When this command is invoked with /project-manager:roadmap-create [timeframe] [name]:

Phase 1: Context Gathering

Invoke coordinating-projects Skill:
- Automatically activates for strategic roadmap planning
- Provides roadmap frameworks and best practices
Determine Roadmap Scope:
- Parse timeframe from $1
- Calculate start and end dates
- Determine planning horizon
Gather Strategic Context:
- Prompt user for:
  - Company/team goals for period
  - OKRs (Objectives and Key Results)
  - Strategic priorities
  - Known constraints

Discover Active Projects:

# List all repositories if multi-project
gh repo list [org] --limit 100 --json name,description,url

# Or analyze current repository
gh repo view --json name,description,topics

# List all open issues and epics
gh issue list --limit 500 --json number,title,labels,milestone

Review Existing Roadmaps (if any):

# Check for previous roadmaps
ls .claude-project/roadmaps/

# Read most recent for context
cat .claude-project/roadmaps/[previous]-roadmap.md

Phase 2: Strategic Analysis

Identify Themes & Initiatives:
- Group work into strategic themes
- Examples:
  - Developer Experience
  - Performance & Scale
  - Security & Compliance
  - Technical Debt
  - New Features
Map Goals to Projects:
- For each strategic goal/OKR:
  - Identify projects that support it
  - Estimate effort and timeline
  - Assess strategic value
Prioritize Initiatives:
- Apply strategic prioritization (delegate to coordinating-projects skill)
- Consider:
  - Strategic alignment (supports OKRs?)
  - Business value (revenue, retention, acquisition)
  - Dependencies (what must come first?)
  - Resource availability
  - Risk vs opportunity

Research Unknowns:

For initiatives with unclear complexity:

Delegate to investigator:
"Research [technology/approach] for [initiative] to estimate complexity and identify risks"

Phase 3: Resource Allocation

Calculate Available Capacity:
- Team size and composition
- Timeframe duration
- Account for:
  - Maintenance/support (15-25%)
  - Technical debt (10-20%)
  - Unplanned work buffer (10-15%)
  - PTO, holidays, training
Allocate Resources to Themes:
- Percentage-based allocation
- Example for Q2:
  - Developer Experience: 40%
  - Performance: 25%
  - Security: 20%
  - Tech Debt: 15%
Balance Portfolio:
- Quick wins vs long-term investments
- Innovation vs optimization
- Customer-facing vs internal
- Risk distribution

Phase 4: Timeline & Milestones

Create Monthly/Quarterly Milestones:
- Break timeframe into periods
- Assign initiatives to periods
- Identify dependencies and sequence
Map Critical Path:
- Identify longest chain of dependencies
- Calculate minimum timeline
- Identify opportunities for parallelization
Define Success Metrics:
- For each initiative:
  - Clear deliverables
  - Success criteria
  - Measurable outcomes

Phase 5: Dependency & Risk Analysis

Map Dependencies:
- Technical dependencies (A needs B's API)
- Resource dependencies (same engineer needed)
- External dependencies (vendor, partner, approval)
Identify Risks:
- Technical risks (unknowns, complexity)
- Resource risks (hiring, retention)
- Dependency risks (external blockers)
- Market risks (competition, timing)
Create Mitigation Plans:
- For each high-impact risk:
  - Mitigation strategy
  - Contingency plan
  - Owner and timeline

Phase 6: Documentation & Artifacts

Generate Roadmap Document:
- Use template from coordinating-projects skill:
```
cp coordinating-projects/templates/[quarterly|annual]-roadmap-template.md .claude-project/roadmaps/$1-roadmap.md
```
- Fill in comprehensive roadmap:
  - Executive summary
  - Strategic goals and OKRs
  - Themes and initiatives
  - Timeline and milestones
  - Resource allocation
  - Dependencies and risks
  - Success metrics

Create Supporting Artifacts:

# Dependency map
cp coordinating-projects/templates/dependency-map-template.md .claude-project/roadmaps/$1-dependencies.md

# Initiative briefs (for each major initiative)
mkdir -p .claude-project/roadmaps/$1-initiatives/

Create GitHub Artifacts (optional):

Delegate to workflow-orchestrator:

"Create milestones for roadmap periods"
"Create project boards for each theme"
"Create epic issues for initiatives"

Phase 7: Validation & Finalization

Quality Check:

Optionally delegate to self-critic:

"Review this roadmap for:
- Strategic alignment
- Realistic scope
- Clear priorities
- Risk coverage
- Completeness"

Generate Summary Report:
- Timeframe and dates
- Number of themes/initiatives
- Resource allocation breakdown
- Key milestones
- Top risks identified
- Links to all artifacts

Examples

Example Usage 1: Quarterly Roadmap

/project-manager:roadmap-create 2025-q2

Expected behavior:

Prompts for Q2 2025 goals and OKRs
Analyzes all projects and issues
Groups into strategic themes
Prioritizes initiatives
Creates monthly milestones
Maps dependencies
Generates comprehensive Q2 roadmap
Creates GitHub milestones

Output:

✅ Q2 2025 Roadmap Created!

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

📅 Timeframe: Q2 2025 (Apr 1 - Jun 30)
🎯 Strategic Objective: Expand enterprise segment

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
📊 THEMES & ALLOCATION
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

1. Enterprise Readiness (40%)
   - Multi-tenancy support
   - SSO integration
   - Audit logging
   - Admin dashboard

2. Developer Experience (35%)
   - CLI tool redesign
   - Documentation platform
   - Onboarding automation

3. Technical Foundation (25%)
   - Microservices migration
   - Observability platform
   - Performance optimization

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
📅 MILESTONES
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

April 2025:
- ✓ Multi-tenancy Phase 1 (50% complete)
- ✓ CLI redesign complete
- ✓ SSO integration complete

May 2025:
- □ Multi-tenancy Phase 2 complete
- □ Documentation platform Beta
- □ Observability platform setup

June 2025:
- □ Audit logging complete
- □ Admin dashboard v1
- □ Performance optimization done

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
📊 METRICS
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Initiatives: 9 total
- Large (>8 weeks): 3
- Medium (4-8 weeks): 4
- Small (<4 weeks): 2

Resource Allocation:
- Engineering: 12 people
- Design: 2 people
- Product: 2 people

Expected Outcomes:
- 10 enterprise customers onboarded
- Developer satisfaction: 4.5+ / 5
- System uptime: 99.9%

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
⚠️  KEY RISKS
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

1. Multi-tenancy migration complexity
   Mitigation: Phase approach, extensive testing

2. Resource constraint (Design team)
   Mitigation: Hire 1 contractor for Q2

3. SSO vendor integration delays
   Mitigation: Start early, have fallback plan

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
🔗 ARTIFACTS
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Roadmap Document: .claude-project/roadmaps/2025-q2-roadmap.md
Dependencies: .claude-project/roadmaps/2025-q2-dependencies.md
Initiative Briefs: .claude-project/roadmaps/2025-q2-initiatives/

GitHub Artifacts:
- Milestones: April, May, June 2025
- Project Boards: 3 theme boards created
- Epic Issues: 9 epics created

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
📝 NEXT STEPS
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

1. Review roadmap with leadership team
2. Socialize with all engineering teams
3. Begin April sprint planning from roadmap
4. Set up tracking dashboards
5. Schedule monthly roadmap check-ins

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Roadmap creation completed!

Example Usage 2: Annual Roadmap

/project-manager:roadmap-create 2025 "2025 Product Vision"

Expected behavior:

Prompts for 2025 annual goals
Creates high-level yearly themes
Breaks into quarterly phases
Maps major initiatives
Generates annual roadmap document

Output:

✅ 2025 Annual Roadmap Created!

📅 Timeframe: 2025 (Jan - Dec)
📋 Name: "2025 Product Vision"

Quarterly Breakdown:

Q1 2025: Foundation
- Core platform stability
- Technical debt reduction
- Team growth

Q2 2025: Enterprise Features
- Multi-tenancy
- Advanced security
- Admin capabilities

Q3 2025: Scale & Performance
- Infrastructure optimization
- Global deployment
- Performance improvements

Q4 2025: Innovation & Growth
- AI/ML features
- Mobile experience
- Partner ecosystem

Full roadmap: .claude-project/roadmaps/2025-roadmap.md

Example Usage 3: Custom Timeframe

/project-manager:roadmap-create 6-months "H1 2025 Roadmap"

Expected behavior:

Creates 6-month roadmap (next 6 months from today)
Uses custom name "H1 2025 Roadmap"
Generates artifacts accordingly

Important Notes

Prerequisites

Clear understanding of strategic goals (will prompt if not available)
Visibility into all active projects
Recommended: Past roadmap for context

Delegation Points

This command delegates to:

coordinating-projects skill: Auto-invokes for roadmap expertise
investigator: (Optional) For researching unknowns
workflow-orchestrator: For creating GitHub artifacts
self-critic: (Optional) For roadmap quality validation

State Changes

Creates roadmap documents in .claude-project/roadmaps/
May create GitHub milestones (via delegation)
May create project boards (via delegation)
May create epic issues (via delegation)

Roadmap Types

Quarterly (Recommended):

Detailed and actionable
Monthly milestones
Specific initiatives with owners
Best for tactical planning

Annual:

High-level strategic themes
Quarterly phases
Major initiatives only
Best for strategic direction

Custom (6-12 months):

Flexible timeframe
Mix of strategic and tactical
Useful for specific initiatives

Collaborative Process

This command is designed to be interactive:

Prompts for strategic input
Asks for prioritization decisions
Requests resource information
Validates assumptions

Interactive Prompts

Strategic Goals

"Roadmap Creation - Strategic Goals

What are the primary strategic goals for [timeframe]?

Examples:
- Expand into enterprise market
- Improve developer experience
- Achieve 99.99% uptime
- Launch mobile app

Enter goals (one per line, blank line to finish):
> [User input]
> [User input]
> [User input]
>
"

OKR Definition (Optional)

"Would you like to define OKRs (Objectives & Key Results)? [y/n]

If yes, for each goal:
Objective: [User input]

Key Results:
1. [User input]
2. [User input]
3. [User input]
"

Resource Allocation

"Resource Allocation for [timeframe]

Total Team Capacity:
- Engineering: [X] people
- Design: [Y] people
- Product: [Z] people

How should capacity be allocated across themes?

Theme 1: [Name] - [%]
Theme 2: [Name] - [%]
Theme 3: [Name] - [%]
Theme 4: [Name] - [%]

(Should total 100%)
"

Milestone Definition

"Milestone Planning

For [Month 1]:
- What should be completed by end of month?
- [User input]

For [Month 2]:
- What should be completed by end of month?
- [User input]

For [Month 3]:
- What should be completed by end of month?
- [User input]
"

Error Handling

Invalid Timeframe

❌ Error: Invalid timeframe "$1"

Valid timeframes:
- Quarterly: q1, q2, q3, q4, 2025-q2
- Annual: 2025, 2026, annual
- Custom: 6-months, 12-months

Usage: /project-manager:roadmap-create [timeframe] [optional-name]
Examples:
- /project-manager:roadmap-create 2025-q3
- /project-manager:roadmap-create 2025 "Annual Vision"

No Strategic Context

⚠️  No Strategic Goals Provided

Creating a roadmap requires clear strategic goals.

Options:
1. Enter goals interactively now
2. Read goals from existing document (provide path)
3. Use template goals (generic, will need customization)

Without goals, roadmap will be tactical only (not strategic).

Proceed? [1/2/3/cancel]

Conflicting Existing Roadmap

⚠️  Existing Roadmap Found

A roadmap for [timeframe] already exists:
.claude-project/roadmaps/[existing]-roadmap.md

Options:
1. Update existing roadmap (merge new input)
2. Create new version (archive old one)
3. Cancel and review existing first

Choice: [1/2/3]

Output Format

✅ Roadmap Created Successfully!

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
📅 ROADMAP OVERVIEW
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Timeframe: [Timeframe]
Name: [Roadmap Name]
Created: [Date]
Planning Horizon: [X] months/weeks

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
🎯 STRATEGIC OBJECTIVES
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

1. [Goal 1]
   Key Results:
   - [KR 1.1]
   - [KR 1.2]

2. [Goal 2]
   Key Results:
   - [KR 2.1]
   - [KR 2.2]

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
🎨 STRATEGIC THEMES
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Theme 1: [Name] ([X]% capacity)
- [Initiative 1.1] ([timeline])
- [Initiative 1.2] ([timeline])

Theme 2: [Name] ([Y]% capacity)
- [Initiative 2.1] ([timeline])

[...]

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
📅 TIMELINE & MILESTONES
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

[Period 1]:
✓ [Milestone 1.1]
✓ [Milestone 1.2]

[Period 2]:
□ [Milestone 2.1]
□ [Milestone 2.2]

[Period 3]:
□ [Milestone 3.1]
□ [Milestone 3.2]

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
📊 RESOURCE ALLOCATION
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Total Capacity: [X] person-months

By Theme:
- [Theme 1]: [X]% ([Y] person-months)
- [Theme 2]: [X]% ([Y] person-months)
- [...]

By Type:
- Strategic Projects: [X]%
- Maintenance: [Y]%
- Tech Debt: [Z]%
- Buffer: [W]%

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
🔗 DEPENDENCIES
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Critical Path: [Initiative A] → [Initiative B] → [Initiative C]
Timeline: [X] months

Dependency Highlights:
- [Initiative X] blocks [Initiative Y]
- [Initiative Z] requires external vendor

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
⚠️  RISKS & MITIGATION
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

High Priority Risks:
1. [Risk description]
   Impact: [description]
   Mitigation: [strategy]
   Owner: [person/team]

2. [Risk description]
   Impact: [description]
   Mitigation: [strategy]
   Owner: [person/team]

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
📊 SUCCESS METRICS
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Completion Targets:
- [X]% of initiatives delivered on time
- [Y]% of OKR key results achieved
- [Z] customer/user impact metrics hit

Quality Metrics:
- System uptime: [target]
- Developer satisfaction: [target]
- Performance: [target]

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
🔗 ARTIFACTS & LINKS
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Documents:
- 📄 Roadmap: .claude-project/roadmaps/[name]-roadmap.md
- 📄 Dependencies: .claude-project/roadmaps/[name]-dependencies.md
- 📁 Initiatives: .claude-project/roadmaps/[name]-initiatives/

GitHub:
- 📌 Milestones: [X] created
- 📊 Project Boards: [Y] created
- 📋 Epic Issues: [Z] created

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
📝 NEXT STEPS
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

Immediate:
1. Review roadmap with stakeholders
2. Validate resource allocations
3. Confirm milestones and dates

Next Week:
1. Socialize with all teams
2. Begin breaking down initiatives
3. Start first sprint planning

Ongoing:
1. Monthly roadmap reviews
2. Quarterly roadmap updates
3. Track progress against metrics

━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

🎉 Roadmap creation completed successfully!

Use /project-manager:project-status to track progress.
Use /project-manager:plan-sprint to execute initiatives.

Advanced Features

Roadmap Comparison

Compare to previous roadmaps
Identify scope changes
Track strategic shifts

Impact Analysis

Estimate customer/user impact for each initiative
Prioritize based on impact
Track actual vs projected impact

Capacity Modeling

What-if scenarios for resource changes
Adjust roadmap based on hiring plans
Model team growth impact

Integration with Sprint Planning

Link roadmap initiatives to sprints
Track sprint contributions to roadmap
Ensure tactical work aligns with strategy

Version Control

Roadmaps are versioned documents
Track changes over time
Understand evolution of strategy

/roadmap-create

Create Roadmap Command

Arguments

Workflow

Phase 1: Context Gathering

Phase 2: Strategic Analysis

Phase 3: Resource Allocation

Phase 4: Timeline & Milestones

Phase 5: Dependency & Risk Analysis

Phase 6: Documentation & Artifacts

Phase 7: Validation & Finalization

Examples

Example Usage 1: Quarterly Roadmap

Example Usage 2: Annual Roadmap

Example Usage 3: Custom Timeframe

Important Notes

Prerequisites

Delegation Points

State Changes

Roadmap Types

Collaborative Process

Interactive Prompts

Strategic Goals

OKR Definition (Optional)

Resource Allocation

Milestone Definition

Error Handling

Invalid Timeframe

No Strategic Context

Conflicting Existing Roadmap

Output Format

Advanced Features

Roadmap Comparison

Impact Analysis

Capacity Modeling

Integration with Sprint Planning

Version Control