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npx skills add liqiongyu/lenny_skills_plus --skill "technical-roadmaps"
Install specific skill from multi-skill repository
# Description
Turn an engineering strategy into a written Technical Roadmap Pack (Rumelt-style strategy: Diagnosis/Guiding Policy/Coherent Actions, roadmap table, initiative briefs, and alignment cadence). Use for technical roadmap, tech roadmap, engineering roadmap, architecture roadmap.
# SKILL.md
name: "technical-roadmaps"
description: "Turn an engineering strategy into a written Technical Roadmap Pack (Rumelt-style strategy: Diagnosis/Guiding Policy/Coherent Actions, roadmap table, initiative briefs, and alignment cadence). Use for technical roadmap, tech roadmap, engineering roadmap, architecture roadmap."
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.”
When NOT to use
- The problem/outcome is unclear (use problem-definition first).
- You need to choose which product bets matter most (use prioritizing-roadmap or ai-product-strategy).
- You only need delivery dates, milestone tracking, and RAG governance (use managing-timelines).
- You need a deep platform strategy / ecosystem design (use platform-strategy).
Inputs
Minimum required
- Audience + decision: who this roadmap is for (Eng leadership, Execs, Product) and what decisions it must enable.
- Time horizon + format: e.g., 6 months / 12 months; Now-Next-Later vs quarterly.
- Current-state diagnosis inputs: top pain points, reliability/latency/cost signals, incident themes, scaling constraints, key architectural bottlenecks.
- Constraints: capacity assumptions, compliance/security requirements, platform constraints, non-negotiables.
- Candidate initiatives: known platform/architecture/tech-debt items (even a rough list).
Missing-info strategy
- Ask up to 5 questions from references/INTAKE.md.
- If answers aren’t available, proceed with explicit assumptions and list them under Open questions.
Outputs (deliverables)
Produce a Technical Roadmap Pack in Markdown (in-chat; or as files if the user requests):
1) Technical Strategy (Rumelt): Diagnosis → Guiding policy → Coherent actions (template: references/TEMPLATES.md)
2) Roadmap table (Now/Next/Later or quarters) with owners, dependencies, milestones, confidence, and metrics
3) Initiative briefs for the top 3–6 roadmap items (1 page each)
4) Dependency + risk register (top cross-team deps, key risks, mitigations)
5) Alignment + governance plan (review cadence, update rules, decision owners, comms template)
6) Risks / Open questions / Next steps (always included)
Expanded guidance: references/WORKFLOW.md
Workflow (7 steps)
1) Intake + audience alignment
- Inputs: User request; references/INTAKE.md.
- Actions: Confirm the audience, horizon, and roadmap “shape” (quarters vs Now/Next/Later). Identify the decision the roadmap must enable (funding, sequencing, headcount, trade-offs).
- Outputs: Intake summary + explicit assumptions + open questions list (if any).
- Checks: You can state: “This roadmap is for
to decide over using .”
2) Write the strategy (Rumelt: Diagnosis → Guiding policy → Coherent actions)
- Inputs: Current-state signals; constraints; product/business context.
- Actions: Draft a written strategy using the Rumelt structure. Keep it concrete: name the constraints and trade-offs.
- Outputs: Technical Strategy section using references/TEMPLATES.md.
- Checks: A reader can answer: “What’s the problem?”, “What’s our approach?”, “What actions are we taking (and not taking)?”
3) Build the initiative inventory (candidate “coherent actions”)
- Inputs: Candidate initiative list; strategy; incidents/metrics; architecture notes.
- Actions: Normalize initiatives into a table (theme, outcome, why now, dependencies, effort, risk). Merge duplicates; split overly broad items.
- Outputs: Initiative inventory (draft roadmap backlog).
- Checks: Each item has an outcome + a “why now” tied back to the Diagnosis/Guiding policy.
4) Prioritize + sequence (make trade-offs explicit)
- Inputs: Inventory; constraints; dependencies; capacity assumptions.
- Actions: Prioritize based on: (a) alignment to strategy, (b) risk reduction, (c) enabling product work, (d) cost/effort, (e) dependency criticality. Sequence via dependencies and “first unlocks.”
- Outputs: Ranked list + sequencing rationale + explicit non-goals/cut list.
- Checks: You can justify the top 3 items in 1–2 sentences each, including what you deprioritized.
5) Convert into a roadmap (quarters or Now/Next/Later) with execution detail
- Inputs: Ranked list; sequencing; calendar constraints.
- Actions: Create the roadmap table with owners, milestones, dependencies, confidence, and success metrics. Add “decision gates” where uncertainty is high.
- Outputs: Roadmap table + milestone highlights.
- Checks: A team could start execution without guessing owners/dependencies; high-uncertainty items have a gate (spike/RFC/prototype).
6) Draft initiative briefs + alignment plan
- Inputs: Roadmap; top items; stakeholder map.
- Actions: Write 1-page briefs for the top 3–6 items and a comms/governance plan (review cadence, update rules, decision owners).
- Outputs: Initiative briefs + alignment/governance section (templates in references/TEMPLATES.md).
- Checks: Stakeholders know when/how the roadmap will change and what inputs trigger a refresh.
7) Quality gate + finalize
- Inputs: Full draft pack.
- Actions: Run references/CHECKLISTS.md and score with references/RUBRIC.md. Ensure Risks / Open questions / Next steps are present with owners and dates where possible.
- Outputs: Final Technical Roadmap Pack.
- Checks: The pack is “debuggable”: written, coherent, measurable, and reviewable.
Quality gate (required)
- Use references/CHECKLISTS.md and references/RUBRIC.md.
- Always include: Risks, Open questions, Next steps.
Examples
Example 1 (platform scaling): “We’re seeing reliability issues and slow delivery. Create a 2-quarter technical roadmap and strategy we can review with leadership.”
Expected: a Rumelt-structured strategy plus a sequenced roadmap with owners, dependencies, milestones, and metrics.
Example 2 (architecture modernization): “We need an architecture roadmap to migrate off a legacy monolith while still shipping product features.”
Expected: explicit trade-offs, dependency-aware sequencing, decision gates, and a governance cadence to keep alignment.
Boundary example: “Write a detailed project plan with dates for every task for the next 6 months.”
Response: use managing-timelines for delivery planning; this skill is for strategy → roadmap (themes/initiatives/milestones), not task-level scheduling.
# Supported AI Coding Agents
This skill is compatible with the SKILL.md standard and works with all major AI coding agents:
Learn more about the SKILL.md standard and how to use these skills with your preferred AI coding agent.