Roadmap Planning

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:

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 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 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):

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):

Q1 2026 (Now - Committed):
├─ Guided Onboarding (Retention)
├─ Enterprise SSO (Acquisition)
└─ Mobile-Optimized Workflows (Engagement)

Q2 2026 (Next - High Confidence):
├─ Advanced Reporting (depends on Data Pipeline, Q1)
├─ Slack Integration (Engagement)
└─ Pricing Page Redesign (Acquisition)

Q3 2026 (Later - Lower Confidence):
├─ Mobile App (depends on API Redesign)
├─ AI-Powered Recommendations
└─ Multi-Language Support

Q4 2026 (Exploration):
├─ Marketplace/Plugin Ecosystem
└─ Enterprise Onboarding Concierge

Alternative: Now/Next/Later Roadmap

NOW (Current Quarter):
- Guided Onboarding
- Enterprise SSO
- Mobile-Optimized Workflows

NEXT (Following Quarter):
- Advanced Reporting
- Slack Integration
- Pricing Page Redesign

LATER (Future):
- Mobile App
- AI Recommendations
- Multi-Language Support

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

Week 1:
├─ Day 1-2: Gather Inputs
│  ├─ Review business goals (OKRs)
│  ├─ Review customer problems (discovery insights)
│  ├─ Review technical constraints
│  └─ Review stakeholder requests
│
├─ Day 3-4: Define Initiatives (Epics)
│  ├─ skills/epic-hypothesis/SKILL.md (60 min per epic)
│  ├─ Estimate effort (90 min)
│  └─ Map to business outcomes
│
├─ Day 5: Prioritize Initiatives
│  ├─ skills/prioritization-advisor/SKILL.md (30 min)
│  ├─ Score epics (120 min)
│  └─ Adjust for strategic fit
│
└─ Day 6-7: Sequence Roadmap
   ├─ Map dependencies
   ├─ Sequence by quarter (Q1, Q2, Q3)
   └─ Validate with engineering

Week 2:
└─ Communicate Roadmap
   ├─ Create presentation (2-3 hours)
   ├─ Present to stakeholders (60 min)
   ├─ Gather feedback
   ├─ Refine roadmap (1-2 days)
   └─ Publish roadmap

Total Time Investment:

• Fast track: 1 week (existing epics, quick alignment)
• Typical: 1.5-2 weeks (define epics, stakeholder review)

Examples

See examples/sample.md for full roadmap examples.

Mini example excerpt:

Now: Guided onboarding (activation +20%)
Next: Enterprise SSO (deal velocity)
Later: Mobile workflows (DAU lift)

Common Pitfalls

Pitfall 1: Feature-Driven Roadmap (No Outcomes)

Symptom: Roadmap lists features ("Dark mode," "SSO," "Advanced filters") with no context

Consequence: No strategic clarity, stakeholders don't understand "why"

Fix: Frame epics as hypotheses with success metrics (not just feature names)

Pitfall 2: Prioritizing by HiPPO (Highest Paid Person's Opinion)

Symptom: Execs dictate roadmap, no data-driven prioritization

Consequence: Build wrong things, ignore customer problems

Fix: Use prioritization framework (RICE, ICE) to transparently score epics

Pitfall 3: Roadmap as Commitment (Waterfall Thinking)

Symptom: Roadmap treated as contract, no flexibility to adjust

Consequence: Can't pivot when you learn new information

Fix: Communicate roadmap as "strategic plan, subject to change based on learning"

Pitfall 4: No Dependencies Mapped

Symptom: Sequence epics without checking technical dependencies

Consequence: Q2 epic blocked because Q1 dependency didn't finish

Fix: Map dependencies explicitly in Phase 4, validate with engineering

Pitfall 5: Solo PM Roadmap (No Stakeholder Input)

Symptom: PM creates roadmap alone, presents finished plan

Consequence: No buy-in, stakeholders feel excluded

Fix: Gather inputs (Phase 1) from all stakeholders, present draft (Phase 5) for feedback

References

Related Skills (Orchestrated by This Workflow)

Phase 2:

• skills/epic-hypothesis/SKILL.md (component)

Phase 3:

• skills/prioritization-advisor/SKILL.md (interactive)

Phase 4:

• (Dependencies mapped manually, no specific skill)

Phase 5:

• (Presentation created manually, no specific skill)

Optional/Related:

• skills/product-strategy-session/SKILL.md (workflow) — Run before roadmap planning to establish strategy
• skills/discovery-process/SKILL.md (workflow) — Provides customer problem inputs for Phase 1
• skills/user-story-mapping-workshop/SKILL.md (interactive) — For complex epics requiring release planning

External Frameworks

• Bruce McCarthy, Product Roadmaps Relaunched (2017) — Outcome-driven roadmaps
• C. Todd Lombardo, Product Roadmaps Relaunched (2017) — Now/Next/Later framework
• Intercom, "RICE Prioritization" (2016) — Prioritization framework

Dean's Work

• [If Dean has roadmap planning resources, link here]

Skill type: Workflow Suggested filename: roadmap-planning.md Suggested placement: /skills/workflows/ Dependencies: Orchestrates skills/epic-hypothesis/SKILL.md, skills/prioritization-advisor/SKILL.md, plus manual activities