Build multi-quarter technical roadmaps aligned with business goals, clearly showing strategic investments, trade-offs, and dependencies. Use when planning longer-term technical direction, communicating with stakeholders, or aligning engineering capacity with business priorities.
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Build multi-quarter technical roadmaps aligned with business goals, clearly showing strategic investments, trade-offs, and dependencies. Use when planning longer-term technical direction, communicating with stakeholders, or aligning engineering capacity with business priorities.
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Read, Grep, Glob, Write, Edit
Technical Roadmap Planning
Develop a 3-12 month technical vision that translates business strategy into engineering work, making trade-offs visible and enabling cross-functional alignment.
Context
You are helping create a technical roadmap that guides engineering work for the next quarter or year. A good roadmap explains not just what you're building, but why it matters to the business and what you're not doing (the trade-offs).
Technical roadmaps fail when they're either too detailed (become outdated) or too vague (don't provide direction). The best roadmaps are strategic narratives, not feature lists.
Domain Context
Camille Fournier's "The Manager's Path": Tech leads must translate between business and engineering language
Will Larson's "An Elegant Puzzle": Roadmaps as three-part narratives: what, why, how we'll get there
Tanya Reilly's "The Staff Engineer's Path": Owning multi-team technical direction
Bidirectional alignment: Roadmaps emerge from both product strategy AND technical vision
Transparency on trade-offs: Always show what's NOT being done and why
Milestone-based, not feature-based: Organize by quarters with clear outcomes
When to Use This Skill
You're starting a new year/quarter and need to plan engineering work
Business priorities are unclear; you need to ground engineering decisions in strategy
Teams are working on misaligned initiatives; you need a north star
Stakeholders ask "Why aren't we doing X?" and you need a clear answer
You're allocating engineers across multiple projects and need to justify priorities
Prerequisites
Before building the roadmap, gather:
Product strategy: What's the business trying to achieve next 12 months?
Team capacity: How many engineers? What's realistic velocity?
Technical debt: What's slowing us down? What requires investment?
Platform constraints: What's blocking teams from shipping fast?
Customer feedback: What's breaking? What do customers ask for?
Market dynamics: Are competitors doing something we need to match?
Instructions
1. Gather Inputs
From Product:
Product roadmap (next 3 quarters)
Customer priorities (what do high-value customers need?)
Customer complaints about slow settlement (T+3, need T+1)
High on-call burden (3+ incidents/week)
To maintain growth and compliance, engineering will focus on: reliability (reduce incidents), compliance (PCI-DSS v4 + KYC), and speed (T+1 settlement).
Quarterly Breakdown
Q1 (Jan-Mar): Reliability & Observability
Deploy distributed tracing (APM)
Implement incident response program
Reduce on-call alert volume 50%
Expected outcome: On-call pages drop from 15/week to 8/week