technical-roadmaps
Technical Roadmaps
Scope
Covers
- Turning “technical work” (architecture, platform, reliability, tech debt) into a written strategy + roadmap that stakeholders can critique and improve.
- Applying Richard Rumelt’s strategy frame (Diagnosis → Guiding policy → Coherent actions) to engineering planning.
- Producing a roadmap that is executable (owners, milestones, dependencies, risks, metrics), not a vague wishlist.
- Aligning a technical roadmap with product/business constraints (quarters, launches, compliance/security, capacity).
When to use
- “Create a technical/engineering/architecture roadmap for the next 2–4 quarters.”
- “We need a written technical strategy and a roadmap we can review with leadership.”
- “We have many tech-debt/platform initiatives; turn them into a prioritized plan with dependencies and milestones.”
- “Our tech roadmap keeps being misunderstood—write it down so we can debug alignment.”
More from oldwinter/skills
personal-productivity
Build a Personal Productivity System Pack (weekly timebox plan, capture+to-do system, daily/weekly review rituals, and a 7-day rollout). Use for timeboxing, calendar blocking, and staying on top of high-volume leadership work. Category: Career.
339github-cli
This skill should be used when users need to interact with GitHub via the gh CLI. It covers repository management (create, delete, clone, fork), CI/CD workflows (GitHub Actions), Issues, Pull Requests, Releases, and other GitHub operations. Triggers on requests mentioning GitHub, repos, PRs, issues, actions, or workflows.
115aws-cli
This skill should be used when users need to interact with AWS services via CLI. It covers all AWS services including EC2, ECS, EKS, Lambda, S3, RDS, DynamoDB, VPC, Route53, CloudFront, Bedrock, Support, Billing, and more. Supports querying, creating, modifying, deleting resources, monitoring, debugging, and cost analysis. Triggers on requests mentioning AWS, cloud resources, or specific AWS service names.
96positioning-and-messaging
Create product positioning and messaging frameworks with validation and iteration guidance.
82kubectl
This skill should be used when users need to interact with Kubernetes clusters via kubectl CLI. It covers pod management, deployment operations, log viewing, debugging, resource monitoring, scaling, ConfigMaps, Secrets, Services, and all standard kubectl operations. Supports multiple clusters (production, staging, local k3s) with predefined aliases. Triggers on requests mentioning Kubernetes, k8s, pods, deployments, containers, or cluster operations.
71setting-okrs-and-goals
Set measurable OKRs and goals with clear alignment, guardrails, and review cadence.
51