autodoc-agent-kit 1.0.0

package/src/modules/product/skills/roadmap-planning/SKILL.md

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+---
+name: roadmap-planning
+description: 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: workflow
+theme: strategy-positioning
+best_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"
+---
+
+
+## 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`](../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 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:
+
+```markdown
+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

package/src/modules/product/skills/roadmap-planning/examples/sample.md

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+# Roadmap Examples
+
+### Example 1: Good Roadmap Planning (SaaS Product)
+
+**Context:** Annual planning, need to align roadmap with retention and enterprise expansion goals.
+
+**Phase 1 - Gather Inputs:**
+- Business goals: Reduce churn from 15% to 8%, increase enterprise deals from 2/quarter to 5/quarter
+- Customer problems: Onboarding confusion, enterprise SSO gap, mobile access issues
+- Technical: Need to upgrade data pipeline for advanced reporting
+
+**Phase 2 - Define Epics:**
+- Wrote 12 epics with hypotheses (guided onboarding, enterprise SSO, mobile workflows, advanced reporting, etc.)
+- Estimated effort: Onboarding = M (3 weeks), SSO = M (4 weeks), Mobile = L (2 months)
+
+**Phase 3 - Prioritize:**
+- Used RICE framework (recommended by `prioritization-advisor.md`)
+- Scored: Onboarding (24,000), SSO (675), Mobile (2,000), Reporting (1,000)
+- Strategic override: Boosted SSO priority (critical for enterprise expansion)
+
+**Phase 4 - Sequence:**
+- Q1: Guided Onboarding, Enterprise SSO, Mobile Workflows
+- Q2: Advanced Reporting (depends on Data Pipeline in Q1), Slack Integration
+- Q3: Mobile App (depends on API Redesign)
+
+**Phase 5 - Communicate:**
+- Presented to execs: "Q1 focuses on retention (onboarding) and enterprise expansion (SSO)"
+- Feedback: "Can we add pricing page redesign to Q2?" → Adjusted roadmap
+- Published: Internal roadmap (Confluence), external roadmap (Now/Next/Later)
+
+**Outcome:** Clear, aligned roadmap with strategic narrative.
+
+---
+
+### Example 2: Bad Roadmap Planning (Feature List)
+
+**Context:** PM creates roadmap alone, based on stakeholder requests.
+
+**Phase 1 - Gather Inputs:** Skipped (no business goals reviewed)
+
+**Phase 2 - Define Epics:** Listed features requested by sales, marketing, CS
+
+**Phase 3 - Prioritize:** Prioritized by "who shouted loudest"
+
+**Phase 4 - Sequence:** Threw features into Q1, Q2, Q3 with no rationale
+
+**Phase 5 - Communicate:** Presented feature list to execs
+
+**Why this failed:**
+- No strategic narrative ("Why are we building this?")
+- No customer problems framed
+- No hypotheses or success metrics
+- Roadmap felt like random feature list
+
+**Fix with roadmap planning workflow:**
+- **Phase 1:** Review business goals (reduce churn, increase enterprise)
+- **Phase 2:** Turn feature requests into epics with hypotheses
+- **Phase 3:** Prioritize by RICE (impact + effort), not politics
+- **Phase 4:** Sequence logically by dependencies, business goals
+- **Phase 5:** Present with narrative: "Q1 = Retention, Q2 = Enterprise Expansion"
+
+---

package/src/modules/product/skills/roadmap-planning/template.md

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+# Roadmap Template
+
+Use this template to summarize a strategic roadmap with outcomes and sequencing.
+
+## Template
+```markdown
+# Product Roadmap
+
+## Strategy Context
+- [Business goals / OKRs]
+- [Customer problems]
+- [Constraints / dependencies]
+
+## Roadmap (Now / Next / Later)
+
+| Stage | Initiative | Outcome | Metric | Notes |
+|---|---|---|---|---|
+| Now | [Initiative] | [Outcome] | [Metric] | [Notes] |
+| Next | [Initiative] | [Outcome] | [Metric] | [Notes] |
+| Later | [Initiative] | [Outcome] | [Metric] | [Notes] |
+
+## Sequencing (Optional)
+- Q1: [Initiatives]
+- Q2: [Initiatives]
+- Q3: [Initiatives]
+
+## Risks & Dependencies
+- [Risk 1]
+- [Dependency 1]
+```