technical-roadmap-planning

SKILL.md

Technical Roadmap Planning

Table of Contents

Overview

When to Use

Quick Start

Reference Guides

Best Practices

Overview

A technical roadmap provides a strategic plan for technology evolution, guiding architectural decisions, infrastructure investments, and capability development aligned with business objectives.

When to Use

Multi-year technology planning

Architecture modernization initiatives

Platform scaling and reliability improvements

Legacy system migration planning

Infrastructure upgrade scheduling

Technology stack standardization

Innovation investment planning

Quick Start

Minimal working example:

Technical Roadmap Template:

Organization: [Company]
Planning Period: 2025-2027
Last Updated: January 2025
Owner: CTO / VP Engineering

---

Vision Statement: |
  Transform our technology platform to enable global scale, improve
  developer productivity, and deliver world-class customer experiences
  through modern, cloud-native architecture.

Strategic Goals:
  1. Reduce infrastructure costs by 40% through cloud optimization
  2. Improve deployment frequency from monthly to daily
  3. Achieve 99.99% availability (4 nines)
  4. Enable data-driven decision making across organization

---

## Q1 2025: Foundation & Planning

Theme: Infrastructure Foundation
// ... (see reference guides for full implementation)

Reference Guides

Detailed implementations in the references/ directory:

Guide
Contents

Dependency Mapping
Dependency Mapping

Technology Evaluation
Technology Evaluation

Execution Planning
Execution Planning

Best Practices

✅ DO

Align technical roadmap with business strategy

Include time for technical debt reduction

Plan for buffer/contingency in critical paths

Review and update roadmap quarterly

Communicate roadmap transparently

Involve team in planning for buy-in

Prioritize based on business impact

Plan major changes during slower periods

Document rationale for technology choices

Build in learning & experimentation time

❌ DON'T

Pursue every new technology trend

Plan at 100% utilization (no buffer)

Ignore team capability and training needs

Make major changes during peak usage

Lock roadmap without flexibility

Underestimate legacy system complexity

Skip security considerations

Plan without resource availability

Ignore risk assessment

Chase technologies without business value

1d:[