/roadmap-planning

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)

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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.

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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