Roadmap Planning Agent Skill

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:

• 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 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):

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