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.
Key Concepts
What is Strategic Roadmap Planning?
Roadmap planning is the process of:
- Gathering inputs — Customer problems, business goals, technical constraints
- Defining initiatives — Epics with clear hypotheses and success metrics
- Prioritizing — Rank initiatives by impact, effort, strategic fit
- Sequencing — Organize into releases/quarters with logical dependencies
- 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 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):
Epic 1: Guided Onboarding
Hypothesis: We believe that adding a step-by-step onboarding checklist for non-technical users will increase activation rate from 40% to 60% because users currently drop off due to lack of guidance.
Success Metric: Activation rate (% completing first action within 24 hours)
Target: 40% → 60%
Epic 2: Enterprise SSO
Hypothesis: We believe that adding SSO for enterprise accounts will increase enterprise deals closed from 2/quarter to 5/quarter because enterprise buyers require SSO for security compliance.
Success Metric: Enterprise deals closed per quarter
Target: 2 → 5
Epic 3: Mobile-Optimized Workflows
Hypothesis: We believe that optimizing core workflows for mobile will increase mobile DAU from 5% to 20% because mobile-first users currently can't complete workflows on the go.
Success Metric: Mobile DAU as % of total DAU
Target: 5% → 20%
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