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Roadmap planning

Skill Dragoon0x/product-skills/skills/pm-strategy-vision/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 and communicate a product roadmap that balances customer needs, business goals, and team capacity. Covers outcome-driven planning, stakeholder communication, and roadmap hygiene. Use when planning quarters, aligning stakeholders on direction, or when the roadmap feels like a feature wishlist.

SKILL.md

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Roadmap Planning (PM Craft)

Build a roadmap that tells a strategic story, not a feature backlog with dates.

How to use

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

Constraints

Outcome-Driven

  • MUST start with outcomes, not features. What business or user result are we driving?
  • Every roadmap item MUST connect to a measurable outcome
  • SHOULD use the "Now / Next / Later" format: committed, planned, exploratory
  • NEVER put dates on items beyond the current quarter unless contractually required
  • MUST include what you're NOT doing and why. The "not now" list is as important as the roadmap.

Input Synthesis

  • MUST incorporate: customer feedback, business strategy, technical needs, competitive signals
  • SHOULD weight inputs by evidence quality, not volume or loudness
  • MUST distinguish between what customers ask for and what they actually need
  • NEVER build a roadmap from a single source — sales requests alone create a lopsided product

Stakeholder Communication

  • For executives: outcomes and strategic alignment. Why this moves the business forward.
  • For engineering: scope, dependencies, and sequencing rationale
  • For sales: what's coming that addresses deal-loss reasons, with honest timing
  • For customers: themes only. NEVER promise specific features or dates externally.
  • MUST communicate trade-offs transparently when priorities change

Roadmap Hygiene

  • MUST review and update the roadmap at least monthly
  • SHOULD have a clear process for adding or removing items mid-cycle
  • MUST track roadmap accuracy: are you shipping what you planned? If not, why not?
  • NEVER let the roadmap become stale — an outdated roadmap is worse than no roadmap

Anti-Patterns

  • The Feature Factory: shipping because it's on the list, not because it serves an outcome
  • The Sales-Driven Roadmap: building whatever the loudest customer asked for
  • The Fantasy Roadmap: 18 months planned in detail when you can barely predict next month
  • The Secret Roadmap: only PM knows the plan. Everyone else guesses.
  • Zero Slack: every hour allocated, no room for discovery, bugs, or learning

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