technical-roadmap-planning

technical-roadmap-planning is a skill for Claude Code, Codex from tmcfarlane/oh-my-cursor. It costs 31 tokens per session (2,236 once invoked), scanned A, original, MIT.

A guide for planning how a software system should evolve over several quarters or years. It connects architecture, infrastructure, technology choices, and business goals.

In plain words
What is it for?
Use it to plan system modernization, platform scaling, reliability work, legacy migrations, infrastructure upgrades, and technology standardization.
Why use it?
It helps teams schedule large technical changes and decide which technology investments should happen first.

Skill for Claude CodeCodex

Written for no agent in particular: nothing here depends on one.

Install

Getting it into your agent

One page per mod, every tool's command on it. A separate URL per tool would split the same page into five that compete with each other.

agentmods
npx agentmods add skills/tmcfarlane/oh-my-cursor/technical-roadmap-planning
Any agent
npx skills add tmcfarlane/oh-my-cursor --skill technical-roadmap-planning
Clone the repo
git clone --depth 1 https://github.com/tmcfarlane/oh-my-cursor

Made for: Claude Code, Codex.

Wrote this? Show the measurements

A badge with what this costs and how it scanned, read live from this page, so it follows the numbers instead of freezing them. Markdown for a README, HTML for a documentation site or a project page.

agentmods badge for technical-roadmap-planning

README.md
[![agentmods](https://agentmods.dev/badge/skills/tmcfarlane/oh-my-cursor/technical-roadmap-planning.svg)](https://agentmods.dev/skills/tmcfarlane/oh-my-cursor/technical-roadmap-planning)
Your own site
<a href="https://agentmods.dev/skills/tmcfarlane/oh-my-cursor/technical-roadmap-planning"><img src="https://agentmods.dev/badge/skills/tmcfarlane/oh-my-cursor/technical-roadmap-planning.svg" alt="Measured on agentmods" height="20"></a>
Per session 31 Skills are progressive disclosure: only the name and description are preloaded; the body loads when the skill is used.
When invoked 2,236 The whole file, excluding the scripts and references it only reads on demand.
Security scan A 0 findings. Scan, not verified.
Origin original No closer match found in the catalogue.
Token cost

What it costs to keep this loaded

Counted locally with the o200k_base tokenizer, which is exact for GPT models; Claude uses its own tokenizer and its counts differ. Treat this as one consistent yardstick across the catalogue rather than a bill. Prices are per million input tokens.

ModelPer sessionOnce invoked
Fable 5.1 $0.00031 $0.02236
Opus 5 $0.00015 $0.01118
Sonnet 5 $0.00006 $0.00447
Haiku 4.5 $0.00003 $0.00224

Measured 6d ago against content hash b5840a295f66, method: parsed. Prices are Anthropic first-party input rates as of 2026-09-05, from the pricing page.

Security

Grade A, and why

technical-roadmap-planning scanned grade A with 0 findings against 26 rules in 11 categories — prompt injection, anti-refusal, data exfiltration, privilege escalation, supply chain, agent snooping, system-prompt leakage, SSRF and excessive agency — measured 6d ago.

A static scan of the body, not an audit. Every finding is printed with the line that produced it so you can judge whether it matters here. A mod is markdown that instructs an agent; that is exactly why what it instructs is worth reading.

Nothing flagged

None of the 26 patterns this scan looks for appear in this file: no shell pipes, no recursive deletes, no credential paths, no hidden text, no instruction-override or anti-refusal phrasing, no agent-config snooping. That is not a guarantee, it is the absence of the things that are checkable.

skills/technical-roadmap-planning/SKILL.md · 373 lines

How it starts

The opening of the file, as written. The whole thing — 373 lines — stays where its author put it; the contents beside it link to each section on GitHub.

Technical Roadmap Planning

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

Instructions

1. Roadmap Framework

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

Initiatives:
  - Kubernetes Migration Phase 1
    Status: In Progress
    Team: 4 DevOps engineers
    Expected Completion: March 31
    Business Impact: 30% cost reduction
    Risks: Learning curve, resource constraints

  - Database Modernization Planning
    Status: Planning
    Team: Data Engineering
    Expected Completion: February 28
    Business Impact: 10x query performance
    Blockers: Vendor selection

---

## Q2 2025: Execution Phase 1

Theme: Scale & Performance

Initiatives:
  - Kubernetes Migration Phase 2
    Dependency: Q1 completion
    Team: 5 engineers
    Expected Completion: June 30
    Risk Level: Medium

  - Microservices Architecture
    Team: Architecture + Development
    Expected Completion: May 31
    Effort: 3 person-months
    Strategic Impact: High

  - Redis Caching Layer
    Team: 2 engineers
    Expected Completion: April 30
    Estimated Impact: 50% faster API responses

---

## Q3 2025: Execution Phase 2

Theme: Reliability & Observability

Initiatives:
  - Observability Platform (ELK/DataDog)
  - Chaos Engineering & Resilience Testing
  - Multi-region Deployment Capability
  - Database Sharding Strategy Implementation

---

## Q4 2025: Consolidation & Planning

Theme: Stabilization & Innovation

Initiatives:
  - Platform Stabilization & Bug Fixes
  - Developer Experience Improvements
  - 2026 Strategic Planning

---

## 2026-2027 Vision

Long-term Initiatives (Candidate):
  - AI/ML Platform Development
  - Real-time Data Pipeline
  - Graph Database Evaluation
  - Blockchain Integration (Future)

Read the full file on GitHub · 373 lines

Changes

What this file has done since we first saw it

Hashed on every crawl. A supply-chain change to an agent config is a question of when, not whether, so the history is kept rather than the latest state alone.

  1. 6d ago First seen · 373 lines · 31 tokens per session scan A b5840a295f66

Subscribe to this mod's changes

technical-roadmap-planning is a skill published in the GitHub repository tmcfarlane/oh-my-cursor (108 stars, last pushed 2mo ago), licensed MIT. It adds 31 tokens to every session and 2,236 once invoked, about $0.0002 per session on Opus 5. A static security scan graded it A with 0 findings. No closer match exists in the catalogue, so it is treated as the original; first seen 2026-08-30.

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