PaperclipOrg
Claude Agent Skill · by Deanpeters

Roadmap Planning

Roadmap-planning guides product managers through the process of transforming strategy into executable release plans by orchestrating prioritization, epic defini

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Terminal · npx
$npx skills add https://github.com/deanpeters/product-manager-skills --skill roadmap-planning
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How Roadmap Planning fits into a Paperclip company.

Roadmap Planning drops into any Paperclip agent that handles this kind of work. Assign it to a specialist inside a pre-configured PaperclipOrg company and the skill becomes available on every heartbeat — no prompt engineering, no tool wiring.

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Pre-configured AI company — 18 agents, 18 skills, one-time purchase.

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SKILL.md505 lines
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---name: roadmap-planningdescription: Plan a strategic roadmap across prioritization, epic definition, stakeholder alignment, and sequencing. Use when turning strategy into a release plan that teams can execute.intent: >-  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.type: workflowtheme: strategy-positioningbest_for:  - "Building a strategic roadmap that survives exec review"  - "Prioritizing competing initiatives across multiple teams"  - "Planning and sequencing work for the next quarter or half-year"scenarios:  - "I have 15 competing initiatives and need to build a Q2 roadmap my exec team will actually approve"  - "I'm planning our 6-month product roadmap and need to sequence work across 3 teams"estimated_time: "45-90 min"---  ## PurposeGuide 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 constraints2. **Defining initiatives** — Epics with clear hypotheses and success metrics3. **Prioritizing** — Rank initiatives by impact, effort, strategic fit4. **Sequencing** — Organize into releases/quarters with logical dependencies5. **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):** ```Epic 1: Guided OnboardingHypothesis: 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 SSOHypothesis: 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 quarterTarget: 2 → 5 Epic 3: Mobile-Optimized WorkflowsHypothesis: 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 DAUTarget: 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: ```markdownNow: 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