Roadmap Builder

The Roadmap Builder skill helps product teams create strategic roadmaps that align tactical execution with business objectives. It emphasizes theme-based planning over feature lists, outcome-focused goals using OKRs, and flexible planning that adapts to market feedback and changing priorities.

This skill excels at translating business strategy into quarterly themes, breaking themes into initiatives and epics, aligning stakeholders around shared goals, and maintaining roadmap clarity while preserving execution flexibility.

Roadmap Builder follows modern product management principles: outcomes over outputs, themes over features, and quarterly planning with monthly reviews.

Core Workflows

Workflow 1: Create Product Roadmap

Steps:

1. Define Strategic Context

   • Review company vision and business goals
   • Analyze market position and competitive landscape
   • Gather customer insights and pain points
   • Identify key metrics to move (North Star, etc.)
   • Understand resource constraints (team, budget, time)

2. Set Quarterly Themes

   • Define 2-4 themes for next quarter
   • Each theme represents a strategic bet or focus area
   • Themes should be outcome-oriented, not feature lists
   • Examples: "Reduce churn", "Enterprise-ready", "10x performance"
   • Align themes with OKRs or company goals

3. Create OKRs for Each Theme

   • Objective: Qualitative, inspiring goal
   • Key Results: 3-5 measurable outcomes
   • Ensure Key Results are ambitious but achievable
   • Define baseline and target metrics
   • Assign ownership to product/engineering leads

4. Identify Initiatives

   • For each theme, brainstorm potential initiatives
   • Initiative = significant effort to move a Key Result
   • Prioritize initiatives by impact vs. effort
   • Select top 2-4 initiatives per theme
   • Estimate rough timeline (weeks or months)

5. Break Down into Epics

   • Decompose initiatives into epics
   • Epic = large user story spanning multiple sprints
   • Write epic descriptions with user value and success criteria
   • Sequence epics based on dependencies and learning goals
   • Assign to teams or squads

6. Create Timeline View

   • Plot themes, initiatives, and epics on timeline
   • Use swim lanes for different teams or product areas
   • Show dependencies and sequencing
   • Highlight milestones and release dates
   • Add confidence levels (high/medium/low)

7. Stakeholder Alignment

   • Present roadmap to leadership and stakeholders
   • Gather feedback and adjust priorities
   • Communicate trade-offs and decisions
   • Set expectations on what's NOT on roadmap
   • Establish review cadence (monthly or quarterly)

Output: Strategic roadmap with themes, OKRs, initiatives, epics, and timeline.

Workflow 2: Quarterly Roadmap Review

Steps:

1. Review previous quarter's OKRs and achievement
2. Analyze what worked, what didn't, and why
3. Gather updated customer and market insights
4. Assess team capacity and velocity trends
5. Set next quarter's themes and OKRs
6. Adjust long-term roadmap based on learnings
7. Communicate changes to all stakeholders

Workflow 3: Monthly Roadmap Health Check

Steps:

1. Review progress on current initiatives
2. Check if Key Results are trending toward targets
3. Identify risks, blockers, or scope issues
4. Adjust timeline or scope if needed
5. Communicate status to stakeholders
6. Reprioritize if market or business conditions change

Workflow 4: Feature Request Evaluation

When new feature requests arrive:

1. Understand the underlying customer problem
2. Evaluate against current themes and OKRs
3. Assess impact (how many users, revenue potential)
4. Estimate effort and opportunity cost
5. Decide: Add to roadmap, defer to backlog, or decline
6. Communicate decision with clear rationale

Quick Reference

Best Practices

• Themes over features: Organize by strategic themes, not lists of features; themes provide context and flexibility
• Outcomes over outputs: Focus on business outcomes (reduce churn, increase revenue) not outputs (ship feature X)
• Use OKRs properly: Objectives inspire, Key Results measure; aim for 70% achievement (not 100%)
• Plan quarterly, review monthly: Quarter is sweet spot for strategic planning; review monthly to adapt
• Communicate the "why": Every roadmap item should clearly connect to business strategy

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