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Roadmap planning

Skill Dragoon0x/product-skills/skills/prioritization-roadmapping/roadmap-planning

The product thinking layer for AI agents. 580 skills. 48 commands. 8 domains. - Product strategy, discovery, execution, analytics, growth, experience, conversion, communication and more.

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npx -y skills add Dragoon0x/product-skills --skill roadmap-planning

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Build a product roadmap that balances customer needs, business goals, and technical reality. A roadmap is a strategy communicated through planned work, not a feature list with dates. Use when building quarterly or annual plans, when stakeholders pull in different directions, or when the current roadmap feels reactive.

SKILL.md

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Roadmap Planning

Build a roadmap that communicates strategy, not just a list of features with dates.

How to use

  • /roadmap-planning Apply roadmap constraints to this conversation.
  • /roadmap-planning <goals and context> Build a roadmap for the described situation.

Constraints

Start with Outcomes

  • MUST define 2-3 outcomes before listing features
  • Every initiative MUST connect to at least one outcome
  • If it doesn't connect to an outcome, it shouldn't be on the roadmap
  • Outcomes should be measurable: "Improve Day-30 retention from 25% to 35%"

Input Sources

A roadmap MUST synthesize multiple inputs:

  • Customer feedback: support tickets, sales loss reasons, interviews, usage data
  • Business strategy: revenue targets, market expansion, competitive responses
  • Technical needs: debt, infrastructure scaling, security, compliance
  • Market signals: competitor moves, trends, regulatory changes
  • NEVER build a roadmap from a single input source

Capacity Allocation

MUST allocate across buckets, not just features:

  • Growth stage: 60% features, 20% technical, 10% experiments, 10% buffer
  • Pre-PMF: 80% features, 10% technical, 10% experiments
  • Scaling: 50% features, 30% technical, 10% experiments, 10% buffer
  • Mature: 40% features, 30% technical, 20% optimization, 10% buffer

Time Horizon Structure

  • Now (current sprint/month): high confidence, specific, committed
  • Next (1-3 months): medium confidence, scoped but flexible
  • Later (3-6 months): low confidence, directional only
  • Not Now: explicitly deprioritized. Listing what you're NOT doing is as valuable as what you are.
  • NEVER plan beyond 6 months with false specificity

Sequencing Principles

  • Dependencies: map what needs to exist before something else can work
  • Learning order: front-load experiments and uncertain bets. Information is worth more early.
  • Value delivery cadence: ship incrementally. Don't bunch everything at quarter end.
  • Team energy: alternate hard technical work with visible wins
  • Market timing: competitive responses, seasonal features, partnership deadlines

Communication

  • For the team: full detail — what, why, who, dependencies, success metrics
  • For leadership: outcomes-focused — business goals, resource allocation, milestones
  • For customers: high-level themes only. NEVER promise features or dates externally.
  • For sales: competitive context — what addresses loss reasons, with rough timing

Anti-Patterns

  • The Feature Factory: shipping because it's on the list, not because it serves an outcome
  • The Wishlist Roadmap: everything anyone requested, ordered by who shouted loudest
  • The Date-Driven Roadmap: obsessing over ship dates instead of outcomes
  • The Secret Roadmap: only leadership knows the plan. Teams need context.
  • The Infinite Roadmap: plans extending 12+ months with false specificity
  • No Room for Discovery: every hour allocated, none for research or customer conversations

Keep looking

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