technical-roadmap-planning — Claude Code skill: plan tech evolution
Builds a technical roadmap across quarters and years: architecture, infrastructure, stack investments. Useful before a big modernization push.
npx skills add aj-geddes/useful-ai-prompts --skill technical-roadmap-planning -a claude-codeWhat technical-roadmap-planning does
The skill walks the agent through the shape of a technical roadmap. Inside is a template with fields for organization, planning period, owner and vision, plus a strategic goals block and a quarter-by-quarter breakdown with a theme for each. The sample fills in a 2025–2027 period and an owner at CTO or VP Engineering level, but that is an example rather than a hard rule.
The references/ directory holds three guides: dependency-mapping.md, technology-evaluation.md and execution-planning.md. They cover dependency mapping, technology evaluation and execution planning — the parts the short template only sketches.
A separate practices section lists what to avoid: planning at 100% utilization with no buffer, chasing every new technology, making major changes during peak usage, locking the roadmap without flexibility. The skill does not crunch budgets or pull data from your systems, so goal numbers like a 40% cost reduction are yours to set. Without someone on the team who owns the roadmap, the document turns into a wish list fast.
What it helps with
- tie technical goals to business objectives over several years
- lay out a legacy system migration quarter by quarter
- build contingency into the critical path
- justify a technology choice to leadership
- schedule an infrastructure upgrade without peak-hour downtime
Example prompts for the agent
- Draft a technical roadmap for 2025–2027 for our platform, owner is the VP Engineering
- Break the architecture modernization into quarters with themes and goals
- Review our roadmap draft against the skill's checklist and flag where there's no buffer
How to install technical-roadmap-planning
1Skills CLI (Vercel)
npx skills add aj-geddes/useful-ai-prompts --skill technical-roadmap-planning -a claude-code2Manually: put the files in place
~/.claude/skills/technical-roadmap-planning/SKILL.mdCopy the whole skill folder; for one project use .claude/skills/technical-roadmap-planning/
1Skills CLI (Vercel)
npx skills add aj-geddes/useful-ai-prompts --skill technical-roadmap-planning -a codex2Manually: put the files in place
.agents/skills/technical-roadmap-planning/SKILL.mdFor all projects use ~/.agents/skills/
1Skills CLI (Vercel)
npx skills add aj-geddes/useful-ai-prompts --skill technical-roadmap-planning -a cursor2Manually: put the files in place
.cursor/skills/technical-roadmap-planning/SKILL.mdCursor also reads .agents/skills/ and .claude/skills/
1GitHub CLI
gh skill install aj-geddes/useful-ai-prompts technical-roadmap-planning2Manually: put the files in place
.github/skills/technical-roadmap-planning/SKILL.md1Skills CLI (Vercel)
npx skills add aj-geddes/useful-ai-prompts --skill technical-roadmap-planning -a gemini-cli2Platform CLI
gemini skills install https://github.com/aj-geddes/useful-ai-prompts --path skills/technical-roadmap-planningManually: put the files in place
.devin/skills/technical-roadmap-planning/SKILL.mdThe legacy .windsurf/skills/ path still works
Skills CLI (Vercel)
npx skills add aj-geddes/useful-ai-prompts --skill technical-roadmap-planning -a opencodeClaude.ai
Zip the folder and upload it in Settings → Capabilities → Skills
Step by step, with commands for each platform: How to install skills in Claude Code: five ways
Questions about technical-roadmap-planning
How do I install technical-roadmap-planning in Claude?
Run npx skills add aj-geddes/useful-ai-prompts --skill technical-roadmap-planning -a claude-code. The skill file then lands at ~/.claude/skills/technical-roadmap-planning/SKILL.md.
What does technical-roadmap-planning do?
It gives the agent a structure for a technical roadmap: vision, strategic goals, a quarter-by-quarter breakdown. It also ships guides on dependencies, technology evaluation and execution planning.
Which platforms can run this skill?
Beyond Claude there are install paths for Codex, Cursor, GitHub Copilot, Gemini CLI and OpenCode. Each platform has its own command and its own skill file location.
Source text
SKILL.md · MIT
--- name: technical-roadmap-planning description: > Create comprehensive technical roadmaps aligned with business goals. Plan technology investments, architecture evolution, and infrastructure improvements over quarters and years. --- # Technical Roadmap Planning ## Table of Contents - [Overview](#overview) - [When to Use](#when-to-use) - [Quick Start](#quick-start) - [Reference Guides](#reference-guides) - [Best Practices](#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: ```yaml 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](references/dependency-mapping.md) | Dependency Mapping | | [Technology Evaluation](references/technology-evaluation.md) | Technology Evaluation | | [Execution Planning](references/execution-planning.md) | 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
© aj-geddes · MIT · aj-geddes/useful-ai-prompts
