Technical Roadmap Planning

If you're past the startup phase and need to coordinate technical changes across quarters or years, this gives you a structured approach to roadmap planning. It covers the usual suspects: architecture modernization, infrastructure scaling, legacy migrations, and aligning tech investments with business goals. The templates walk through quarterly planning with themes, dependencies, and risk assessment. The best practices section is sensible about building in buffer time and not chasing every shiny framework. Most useful when you're trying to get multiple teams moving in the same direction without constant thrashing, though you'll still need to adapt the templates to whatever chaos your organization prefers.

skills.sh installs: 582
GitHub stars: 379
last updated: Aug 21, 2026

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Install

$ npx -y skills add aj-geddes/useful-ai-prompts --skill technical-roadmap-planning --agent claude-code

Installs into .claude/skills of the current project.

Files

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.

SKILL.md on GitHub