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Expert methodology for creating strategic technology roadmaps aligned with business goals, including multi-horizon planning, capacity planning, and OKR frameworks.
This skill provides a comprehensive approach to creating technology roadmaps that align engineering with business strategy. Use it to build multi-year technical visions, quarterly execution plans, balance competing priorities, and communicate strategy effectively.
Trigger this skill when you need to:
Follow this systematic approach to roadmap creation:
Understand Business Strategy
Assess Current Technical State
Identify Technical Enablers
Use references/frameworks/strategic-alignment-framework.md for structured analysis.
Structure roadmap across three time horizons:
Focus: Execution, delivery, near-term goals
Characteristics:
Content:
Focus: Platform, capabilities, strategic investments
Characteristics:
Content:
Focus: Direction, possibilities, north star
Characteristics:
Content:
Use references/templates/three-horizon-roadmap.md for structure.
Allocate resources across competing priorities:
70% - Core Business (Horizon 1)
20% - Strategic Investments (Horizon 2)
10% - Innovation & Exploration (Horizon 3)
Adjust based on company stage:
| Stage | Core | Strategic | Innovation |
|---|---|---|---|
| Early Startup (PMF) | 85% | 10% | 5% |
| Growth Stage | 70% | 20% | 10% |
| Scale/Enterprise | 60% | 30% | 10% |
| Innovation-Focused | 50% | 30% | 20% |
Use references/frameworks/portfolio-balancing.md for detailed guidance.
Build a visual, communicable roadmap:
Strategic Themes (3-5 themes)
Key Initiatives (under each theme)
Timeline
Success Metrics
Resource Requirements
Use references/templates/roadmap-visualization.md for formats.
Tailor roadmap communication for each audience:
Focus: Strategic positioning, competitive advantage, risk management
Format: 3-5 year vision, key strategic bets, why we'll win
Use references/templates/board-roadmap-presentation.md
Focus: Business alignment, resource requirements, dependencies
Format: Annual plan with quarterly milestones, business impact
Use references/templates/executive-roadmap-presentation.md
Focus: Feature enablement, platform capabilities, dependencies
Format: Integrated product + tech roadmap, shared milestones
Use references/templates/product-tech-alignment.md
Focus: Technical details, team assignments, skill development
Format: Detailed initiative breakdown, team roadmaps, learning paths
Use references/templates/engineering-team-roadmap.md
Quarterly Planning
Monthly Check-ins
Annual Strategy Review
Use references/frameworks/roadmap-governance.md for process.
Frameworks (references/frameworks/):
strategic-alignment-framework.md - Connect tech to business strategyportfolio-balancing.md - Allocate resources across prioritiestechnology-radar.md - Track emerging technologies (adopt/trial/assess/hold)wardley-mapping.md - Strategic technology positioningroadmap-governance.md - Process for maintaining and updating roadmapTemplates (references/templates/):
three-horizon-roadmap.md - Structure for tactical/strategic/visionary planningroadmap-visualization.md - Visual formats (timeline, swim lanes, now-next-later)board-roadmap-presentation.md - Board-ready strategy presentationexecutive-roadmap-presentation.md - CEO/executive formatengineering-team-roadmap.md - Detailed team-facing roadmapokr-framework.md - Engineering OKRs aligned with roadmapExamples (references/examples/):
Example 1: User says "Create 12-month technology roadmap for our Series B SaaS company"
ā Load references/frameworks/strategic-alignment-framework.md
ā Gather context: business goals, current state, team size
ā Define 3-5 strategic themes
ā Use references/templates/three-horizon-roadmap.md structure
ā Balance portfolio: 70% core, 20% strategic, 10% innovation
ā Create quarterly milestones with success metrics
ā Generate executive presentation
Example 2: User says "Align engineering roadmap with product roadmap"
ā Load references/templates/product-tech-alignment.md
ā Map product features to required platform capabilities
ā Identify dependencies (what tech must be ready first)
ā Highlight shared milestones
ā Show trade-offs and capacity constraints
ā Create integrated timeline
Example 3: User says "We need to balance features vs technical debt vs innovation"
ā Load references/frameworks/portfolio-balancing.md
ā Assess current allocation (likely skewed toward features)
ā Apply 70-20-10 framework adjusted for stage
ā Identify highest-value technical debt items
ā Allocate innovation time for emerging tech
ā Create balanced quarterly plan
Example 4: User says "Present technology strategy to board"
ā Load references/templates/board-roadmap-presentation.md
ā Focus on: strategic positioning, competitive advantage, key bets
ā 3-5 year vision with major milestones
ā Explain how tech enables business strategy
ā Address risks and mitigation
ā Keep to 5-7 slides with clear narrative
What it looks like: "Q1: Feature A, B, C; Q2: Feature D, E, F"
Why it's bad: No strategic themes, no platform investment, reactive not proactive
Fix: Group features under strategic themes, include platform work
What it looks like: 100% of capacity allocated to committed work, no buffer
Why it's bad: No room for urgent work, incidents, tech debt, learning
Fix: Plan to 70-80% of capacity, leave buffer for unexpected
What it looks like: Annual roadmap created in January, never updated
Why it's bad: Business changes, roadmap becomes fiction
Fix: Quarterly reviews and adjustments, transparent communication
What it looks like: "Migrate from REST to gRPC, implement event sourcing"
Why it's bad: Business stakeholders don't understand value
Fix: Frame in business outcomes: "Improve API performance by 50%, enable real-time features"
What it looks like: Detailed plan for next 2 quarters, vague beyond that
Why it's bad: No strategic direction, technology doesn't support long-term vision
Fix: Add strategic and visionary horizons, even if less detailed
Track emerging technologies to inform roadmap:
Adopt - Ready for production use
Trial - Worth pursuing in pilots
Assess - Interesting, keep watching
Hold - Proceed with caution or deprioritize
Use references/frameworks/technology-radar.md for detailed methodology.
Realistic roadmap requires understanding capacity:
Team Size: 20 engineers
Weeks per Quarter: 13 weeks
Theoretical Capacity: 20 Ć 13 Ć 40 hours = 10,400 hours
Subtract:
- Holidays and PTO: 10% = -1,040 hours
- Meetings and coordination: 15% = -1,560 hours
- Incidents and support: 10% = -1,040 hours
- Context switching: 5% = -520 hours
Realistic Capacity: 6,240 hours (60% of theoretical)
For new initiatives: 4,680 hours (75% of realistic, 25% buffer)
Small: 200-400 hours (1-2 person-months) Medium: 400-800 hours (2-4 person-months) Large: 800-1,600 hours (4-8 person-months) Extra Large: 1,600+ hours (8+ person-months)
Q1 Capacity: 4,680 hours available
Committed:
Total: 3,100 hours (66% of capacity) ā
Remaining: 1,580 hours for bugs, incidents, unplanned work ā
Why: Current monolith limits team autonomy and deployment speed Initiatives:
Success Metrics:
Why: AI is transforming our market, need to lead not follow Initiatives:
Success Metrics:
Why: Team growing 2x, need to scale productivity Initiatives:
Success Metrics:
All outputs should be:
Version: 1.0.0 Philosophy: Align technology with business strategy, balance short and long-term, communicate transparently
