Plan a strategic roadmap across prioritization, epic definition, stakeholder alignment, and sequencing. Use when turning strategy into a release plan that teams can execute.

Purpose Guide product managers through strategic roadmap planning by orchestrating prioritization, epic definition, stakeholder alignment, and release sequencing skills into a structured process. Use this to move from disconnected feature requests to a cohesive, outcome driven roadmap that aligns stakeholders, sequences work logically, and communicates strategic intent—avoiding "feature factory" roadmaps that lack strategic narrative or customer centric framing. This is not a Gantt chart—it's a strategic communication tool that shows what you're building, why it matters, and how it ladders up to business outcomes. Input Works best with: The product and planning horizon (next quarter, next year). Also useful: Strategy or OKRs to ladder to, the candidate initiative list, team capacity, and known stakeholder pressures. Anything supplied with the invocation itself — text after the skill name, a pasted context dump, or an appended ARGUMENTS: line — counts as answers already given. Use it and skip whatever it covers; don't re ask. Arriving empty handed? That works too. The workflow starts by establishing strategic context, then moves through prioritization, epic definition, and sequencing. Example invocation: Plan a 2 quarter roadmap for our mobile app: here are our 3 OKRs and a list of 12 candidate initiatives. Key Concepts What is Strategic Roadmap Planning? Roadmap planning is the process of: 1. Gathering inputs — Customer problems, business goals, technical constraints 2. Defining initiatives — Epics with clear hypotheses and success metrics 3. Prioritizing — Rank initiatives by impact, effort, strategic fit 4. Sequencing — Organize into releases/quarters with logical dependencies 5. Communicating — Present roadmap to stakeholders with strategic narrative Types of Roadmaps Now/Next/Later Roadmap: Now: Current quarter (committed) Next: Following quarter (high confidence) Later: Future exploration (low confidence) Best for: Agile teams, uncertainty, continuous discovery Theme Based Roadmap: Organize by strategic themes (e.g., "Retention," "Enterprise Expansion," "Mobile Experience") Best for: Communicating to execs, showing strategic intent Timeline Roadmap (Quarters): Q1: Epics A, B; Q2: Epics C, D; Q3: Epics E, F Best for: Resource planning, stakeholder communication Feature Based Roadmap (Anti Pattern): Lists features without context (e.g., "Dark mode," "SSO," "Advanced reporting") Why it fails: No strategic narrative, no customer problems framed Why This Works Outcome driven: Ties initiatives to business/customer outcomes Stakeholder alignment: Transparent process reduces political friction Strategic clarity: Shows not just "what" but "why" Flexible: Adapts as you learn from discovery/delivery Anti Patterns (What This Is NOT) Not a commitment: Roadmaps are strategic plans, not contracts Not a feature list: Roadmaps frame problems, not just solutions Not waterfall: Roadmaps evolve quarterly based on learning When to Use This Annual or quarterly planning cycles After product strategy session (translate strategy to roadmap) Onboarding new stakeholders (align on direction) Reframing existing roadmap (shift from feature driven to outcome driven) When NOT to Use This For tactical sprint planning (use backlog instead) When strategy is unclear (run product strategy session first) When stakeholders expect date commitments (address expectations first) Facilitation Source of Truth When running this workflow as a guided conversation, use [ workshop facilitation ](../workshop facilitation/SKILL.md) as the interaction protocol. It defines: session heads up + entry mode (Guided, Context dump, Best guess) one question turns with plain language prompts progress labels (for example, Context Qx/8 and Scoring Qx/5) interruption handling and pause/resume behavior numbered recommendations at decision points quick select numbered response options for regular questions (include Other (specify) when useful) This file defines the workflow sequence and domain specific outputs. If there is a conflict, follow this file's workflow logic. Application Use template.md for the full fill in structure. This workflow orchestrates 5 phases over 1 2 weeks , using multiple component and interactive skills. Phase 1: Gather Inputs (Day 1 2) Goal: Collect business goals, customer problems, technical constraints, stakeholder requests. Activities 1. Review Business Goals (OKRs, Strategic Initiatives) Source: Company OKRs, exec strategy memos, board decks Questions: What are the company's top 3 priorities this year? What metrics must we move? (revenue, retention, acquisition, efficiency) Are there strategic bets? (new markets, partnerships, product lines) Output: 3 5 business outcomes to optimize for 2. Review Customer Problems (Discovery Insights) Source: Discovery interviews, support tickets, NPS feedback, churn surveys Use: Insights from skills/discovery process/SKILL.md (if recently completed) Questions: What are the top 3 5 customer pain points? Which problems affect the most customers? Which problems have highest intensity? Output: 3 5 validated customer problems 3. Review Technical Constraints & Opportunities Source: Engineering leadership, tech debt assessments Questions: Are there technical blockers? (scaling, performance, security) Are there enabling investments? (platform upgrades, API rewrites) What's the technical roadmap? (migrations, deprecations) Output: List of technical investments required 4. Review Stakeholder Requests Source: Sales, marketing, customer success, execs Questions: What are sales asking for? (enterprise features, integrations) What's marketing requesting? (growth initiatives, positioning) What's customer success flagging? (churn risks, expansion blockers) Output: List of stakeholder requests (not yet committed) Outputs from Phase 1 Business outcomes: 3 5 OKRs or strategic goals Customer problems: 3 5 validated pain points Technical investments: Platform/tech debt items Stakeholder requests: Feature requests from internal teams Phase 2: Define Initiatives (Epics) (Day 3 4) Goal: Turn inputs into epics with hypotheses, success metrics, and effort estimates. Activities 1. Define Epic Hypotheses Use: skills/epic hypothesis/SKILL.md (component) For each initiative: Write hypothesis statement Format: "We believe that [building X] for [persona] will achieve [outcome] because [assumption]." Participants: PM Duration: 60 minutes per epic Output: 10 15 epic hypotheses Example Epics (SaaS Product): 2. Estimate Effort (T Shirt Sizing) Participants: PM + engineering lead Duration: 90 minutes Method: Small (S): 1 2 weeks (1 2 engineers) Medium (M): 3 4 weeks (2 3 engineers) Large (L): 2 3 months (3 5 engineers) Extra Large (XL): 3+ months (5+ engineers) Output: Effort estimate per epic 3. Map to Business Outcomes For each epic: Tag with primary business outcome Example: Epic 1 (Guided Onboarding) → Retention Epic 2 (Enterprise SSO) → Acquisition (enterprise) Epic 3 (Mobile Workflows) → Engagement Outputs from Phase 2 10 15 epics: Each with hypothesis, success metric, effort estimate Business outcome mapping: Which epics drive which OKRs Phase 3: Prioritize Initiatives (Day 5) Goal: Rank epics by impact, effort, and strategic fit. Activities 1. Choose Prioritization Framework Use: skills/prioritization advisor/SKILL.md (interactive) Participants: PM Duration: 30 minutes Output: Recommended framework (RICE, ICE, Value/Effort, etc.) 2. Score Epics Participants: PM, engineering lead, product leadership Duration: 120 minutes Method: Apply framework to all epics Example (RICE scoring): Epic Reach Impact Confidence Effort RICE Score Guided Onboarding 10,000 users 3 (massive) 80% 1 month 24,000 Enterprise SSO 500 users 3 (massive) 90% 2 months 675 Mobile Workflows 5,000 users 2 (high) 60% 3 months 2,000 Advanced Reporting 2,000 users 2 (high) 50% 2 months 1,000 3. Adjust for Strategic Fit Review scores: Do they align with business goals? Strategic overrides: Promote epics that align with strategic bets (even if score is lower) Example: Enterprise SSO scores lower, but it's critical for enterprise expansion strategy → boost priority Outputs from Phase 3 Ranked backlog: Epics sorted by priority (RICE score + strategic adjustments) Top 10 epics: Highest priority initiatives for roadmap Phase 4: Sequence Roadmap (Day 6 7) Goal: Organize epics into quarters/releases with logical dependencies. Activities 1. Map Dependencies Questions: Does Epic B depend on Epic A? (e.g., "Advanced Reporting" requires "Data Pipeline Upgrade") Are there technical blockers? (e.g., "Mobile App" requires "API Redesign") Output: Dependency graph (Epic A → Epic B → Epic C) 2. Sequence by Quarter (or Release) Now (Q1): Top 3 5 epics, no dependencies Next (Q2): Next 3 5 epics, may depend on Q1 completion Later (Q3+): Remaining epics, lower confidence Example Roadmap (Timeline Based): Alternative: Now/Next/Later Roadmap 3. Validate with Engineering Participants: PM + engineering lead Questions: Is sequencing realistic? (capacity, dependencies) Are there hidden technical blockers? Do we need to adjust scope? Output: Validated roadmap sequence Outputs from Phase 4 Sequenced roadmap: Epics organized by Q1, Q2, Q3 Dependency map: What depends on what Capacity check: Engineering agrees sequence is feasible Phase 5: Communicate Roadmap (Week 2) Goal: Present roadmap to stakeholders, gather feedback, build alignment. Activities 1. Create Roadmap Presentation Format: 30 45 min presentation Structure: Slide 1: Strategic context (business goals, customer problems) Slide 2 3: Roadmap overview (Q1, Q2, Q3) Slide 4 6: Deep dive per quarter (epics, hypotheses, success metrics) Slide 7: What's NOT on roadmap (and why) Slide 8: Dependencies and risks Participants: PM, design Duration: 2 3 hours to prepare 2. Present to Stakeholders Audience: Execs, product leadership, engineering, sales, marketing, CS Duration: 45 min presentation + 15 min Q&A Focus: Strategic narrative: "Here's why we're prioritizing X over Y" Outcome focus: "Each epic drives [business outcome]" Flexibility: "This roadmap is a plan, not a commitment; we'll adjust as we learn" 3. Gather Feedback Questions to ask: Do these priorities align with business goals? Are we missing critical customer problems? Are dependencies clear? What concerns do you have? Output: List of feedback, concerns, questions 4. Refine Roadmap Based on feedback: Adjust priorities, add missing epics, clarify dependencies Duration: 1 2 days Output: Final roadmap v1.0 5. Publish Roadmap Internal: Share with team (Confluence, Notion, Productboard, etc.) External (Optional): Public roadmap for customers (use Now/Next/Later format) Format: Visual roadmap + narrative doc Outputs from Phase 5 Roadmap presentation: 30 45 min deck Stakeholder alignment: Feedback incorporated, concerns addressed Published roadmap: Accessible to team (internal) or customers (external) Complete Workflow: End to End Summary Total Time Investment: Fast track: 1 week (existing epics, quick alignment) Typical: 1.5 2 weeks (define epics, stakeholder review) Examples See examp

roadmap-planning