roadmap-planning

What this skill does

## 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