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cto-technology-roadmap

@rinaldofesta/cto-os-skills
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Expert methodology for creating strategic technology roadmaps aligned with business goals, including multi-horizon planning, capacity planning, and OKR frameworks.

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SKILL.md

name cto-technology-roadmap
description Expert methodology for creating strategic technology roadmaps aligned with business goals, including multi-horizon planning, capacity planning, and OKR frameworks.

CTO Technology Roadmap Skill

Purpose

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.

When to Use

Trigger this skill when you need to:

  • Create annual or multi-year technology strategy
  • Plan quarterly engineering initiatives
  • Align engineering roadmap with product/business goals
  • Communicate technical strategy to board or executives
  • Balance innovation, technical debt, and feature delivery
  • Plan infrastructure and platform investments
  • Forecast engineering capacity and resource needs
  • Evaluate emerging technologies and strategic bets

Core Methodology

Follow this systematic approach to roadmap creation:

Phase 1: Establish Strategic Context

  1. Understand Business Strategy

    • What are company's strategic goals for next 1-3 years?
    • What's the target market and growth trajectory?
    • What's the competitive landscape?
    • What are the key business metrics we're optimizing for?

  2. Assess Current Technical State

    • What's our current architecture and tech stack?
    • What's working well?
    • What are the pain points and bottlenecks?
    • What technical debt exists?
    • What's our team's capability and capacity?

  3. Identify Technical Enablers

    • What technical capabilities are required to achieve business goals?
    • What are the dependencies and prerequisites?
    • What are the risks if we don't address technical needs?

Use references/frameworks/strategic-alignment-framework.md for structured analysis.

Phase 2: Define Planning Horizons

Structure roadmap across three time horizons:

Horizon 1: Tactical (0-12 months)

Focus: Execution, delivery, near-term goals

Characteristics:

  • High certainty and specificity
  • Quarterly milestones
  • Committed resources
  • Clear success metrics

Content:

  • Specific features and projects
  • Team assignments
  • Sprint-level planning
  • Defined deliverables

Horizon 2: Strategic (1-3 years)

Focus: Platform, capabilities, strategic investments

Characteristics:

  • Medium certainty
  • Themes and initiatives vs specific features
  • Resource allocation guidance
  • Strategic bets

Content:

  • Major platform investments
  • Architecture transformations
  • Team growth and skill development
  • Technology strategy shifts

Horizon 3: Visionary (3-5 years)

Focus: Direction, possibilities, north star

Characteristics:

  • Low certainty, high ambiguity
  • Directional guidance
  • Technology trends and opportunities
  • Strategic positioning

Content:

  • Technical vision
  • Emerging technology exploration
  • Market and competitive positioning
  • Future capabilities

Use references/templates/three-horizon-roadmap.md for structure.

Phase 3: Balance the Portfolio

Allocate resources across competing priorities:

The 70-20-10 Framework

70% - Core Business (Horizon 1)

  • Features that serve current customers
  • Revenue-generating initiatives
  • Business-critical improvements
  • Customer commitments

20% - Strategic Investments (Horizon 2)

  • Platform and infrastructure
  • Technical debt reduction
  • Developer productivity
  • Scalability and performance

10% - Innovation & Exploration (Horizon 3)

  • Emerging technologies (AI, blockchain, etc.)
  • Proof of concepts
  • Competitive research
  • Future capabilities

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.

Phase 4: Create the Roadmap

Build a visual, communicable roadmap:

Roadmap Components

  1. Strategic Themes (3-5 themes)

    • Platform Modernization
    • AI-Powered Features
    • Developer Experience
    • Enterprise Readiness
    • Global Scale

  2. Key Initiatives (under each theme)

    • Specific projects or workstreams
    • Aligned to theme
    • Clear owners

  3. Timeline

    • Quarters or half-years
    • Dependencies visible
    • Critical path highlighted

  4. Success Metrics

    • How will we measure success?
    • Business outcomes
    • Technical outcomes

  5. Resource Requirements

    • Team size and composition
    • Budget implications
    • Hiring needs

Use references/templates/roadmap-visualization.md for formats.

Phase 5: Align and Communicate

Tailor roadmap communication for each audience:

For Board/Investors

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

For CEO/Executives

Focus: Business alignment, resource requirements, dependencies

Format: Annual plan with quarterly milestones, business impact

Use references/templates/executive-roadmap-presentation.md

For Product Team

Focus: Feature enablement, platform capabilities, dependencies

Format: Integrated product + tech roadmap, shared milestones

Use references/templates/product-tech-alignment.md

For Engineering Team

Focus: Technical details, team assignments, skill development

Format: Detailed initiative breakdown, team roadmaps, learning paths

Use references/templates/engineering-team-roadmap.md

Phase 6: Execute and Iterate

  1. Quarterly Planning

    • Review progress on roadmap
    • Adjust based on learnings
    • Commit to next quarter's initiatives
    • Update roadmap and communicate changes

  2. Monthly Check-ins

    • Track initiative progress
    • Identify blockers and risks
    • Ensure alignment with business changes

  3. Annual Strategy Review

    • Major strategy refresh
    • Incorporate market changes
    • Adjust 3-year vision
    • Reset priorities

Use references/frameworks/roadmap-governance.md for process.

Key Principles

  • Business-Aligned: Every technical initiative should tie to business outcomes
  • Flexible, Not Rigid: Roadmap is a plan, not a promise - adjust as needed
  • Multi-Horizon: Balance short-term delivery with long-term vision
  • Resource-Aware: Be realistic about capacity and dependencies
  • Transparent: Share roadmap broadly, explain trade-offs
  • Outcome-Focused: Define success by impact, not output

Bundled Resources

Frameworks (references/frameworks/):

  • strategic-alignment-framework.md - Connect tech to business strategy
  • portfolio-balancing.md - Allocate resources across priorities
  • technology-radar.md - Track emerging technologies (adopt/trial/assess/hold)
  • wardley-mapping.md - Strategic technology positioning
  • roadmap-governance.md - Process for maintaining and updating roadmap

Templates (references/templates/):

  • three-horizon-roadmap.md - Structure for tactical/strategic/visionary planning
  • roadmap-visualization.md - Visual formats (timeline, swim lanes, now-next-later)
  • board-roadmap-presentation.md - Board-ready strategy presentation
  • executive-roadmap-presentation.md - CEO/executive format
  • engineering-team-roadmap.md - Detailed team-facing roadmap
  • okr-framework.md - Engineering OKRs aligned with roadmap

Examples (references/examples/):

  • Real roadmaps from startups to enterprises
  • Before/after roadmap improvements
  • Multi-year strategic plans
  • Quarterly execution plans

Usage Patterns

Example 1: User says "Create 12-month technology roadmap for our Series B SaaS company"

→ Load references/frameworks/strategic-alignment-framework.md → Gather context: business goals, current state, team size → Define 3-5 strategic themes → Use references/templates/three-horizon-roadmap.md structure → Balance portfolio: 70% core, 20% strategic, 10% innovation → Create quarterly milestones with success metrics → Generate executive presentation

Example 2: User says "Align engineering roadmap with product roadmap"

→ Load references/templates/product-tech-alignment.md → Map product features to required platform capabilities → Identify dependencies (what tech must be ready first) → Highlight shared milestones → Show trade-offs and capacity constraints → Create integrated timeline

Example 3: User says "We need to balance features vs technical debt vs innovation"

→ Load references/frameworks/portfolio-balancing.md → Assess current allocation (likely skewed toward features) → Apply 70-20-10 framework adjusted for stage → Identify highest-value technical debt items → Allocate innovation time for emerging tech → Create balanced quarterly plan

Example 4: User says "Present technology strategy to board"

→ Load references/templates/board-roadmap-presentation.md → Focus on: strategic positioning, competitive advantage, key bets → 3-5 year vision with major milestones → Explain how tech enables business strategy → Address risks and mitigation → Keep to 5-7 slides with clear narrative

Roadmap Anti-Patterns

❌ Anti-Pattern 1: Feature List Masquerading as Strategy

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

❌ Anti-Pattern 2: Over-Commitment

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

❌ Anti-Pattern 3: Set-and-Forget Roadmap

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

❌ Anti-Pattern 4: Technical Jargon for Business Audience

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"

❌ Anti-Pattern 5: All Short-Term Tactical

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

Technology Radar

Track emerging technologies to inform roadmap:

Adopt - Ready for production use

  • Kubernetes for container orchestration
  • React for frontend development
  • PostgreSQL for relational data

Trial - Worth pursuing in pilots

  • AI code assistants (Copilot, etc.)
  • Edge computing for global latency
  • Vector databases for AI features

Assess - Interesting, keep watching

  • WebAssembly for performance-critical code
  • Decentralized identity systems
  • Quantum-resistant cryptography

Hold - Proceed with caution or deprioritize

  • Blockchain for non-financial use cases
  • Microservices for small teams
  • NoSQL when SQL would suffice

Use references/frameworks/technology-radar.md for detailed methodology.

Capacity Planning

Realistic roadmap requires understanding capacity:

Calculate Available Capacity

Team Size: 20 engineers
Weeks per Quarter: 13 weeks
Theoretical Capacity: 20 × 13 × 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)

Estimate Initiative Size

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)

Plan Quarterly Initiatives

Q1 Capacity: 4,680 hours available

Committed:

  • Platform migration (Large): 1,200 hours
  • New feature A (Medium): 600 hours
  • New feature B (Medium): 600 hours
  • Tech debt sprint (Small): 300 hours
  • Team onboarding (2 new hires): 400 hours

Total: 3,100 hours (66% of capacity) ✅

Remaining: 1,580 hours for bugs, incidents, unplanned work ✅

Strategic Themes Examples

Theme: Platform Modernization

Why: Current monolith limits team autonomy and deployment speed Initiatives:

  • Extract billing service (Q1-Q2)
  • Extract auth service (Q2-Q3)
  • Implement service mesh (Q3-Q4)
  • API gateway migration (Q4)

Success Metrics:

  • Deployment frequency: 3x/week → daily
  • Service independence: 0 → 3 independent services
  • Team autonomy: 1 monolith team → 3 service teams

Theme: AI-First Product

Why: AI is transforming our market, need to lead not follow Initiatives:

  • AI recommendation engine (Q1-Q2)
  • Natural language search (Q2-Q3)
  • Smart content generation (Q3-Q4)
  • ML infrastructure platform (ongoing)

Success Metrics:

  • % users using AI features: 0% → 60%
  • AI-driven conversion lift: +20%
  • Feature development time with AI: -30%

Theme: Developer Velocity

Why: Team growing 2x, need to scale productivity Initiatives:

  • CI/CD pipeline overhaul (Q1)
  • Development environment standardization (Q1-Q2)
  • Automated testing expansion (Q2-Q3)
  • Developer portal (Q3-Q4)

Success Metrics:

  • Lead time: 5 days → 2 days
  • Developer satisfaction: 7.5 → 8.5
  • Time to first contribution (new hires): 3 weeks → 1 week

Writing Style

All outputs should be:

  • Business-Focused: Lead with business value, not technical details
  • Visual: Use timelines, charts, diagrams where helpful
  • Realistic: Be honest about capacity and trade-offs
  • Strategic: Connect tactical work to long-term vision
  • Flexible: Frame as living document, not rigid plan

Version: 1.0.0 Philosophy: Align technology with business strategy, balance short and long-term, communicate transparently