Planning Create Roadmap

Create Roadmap

Purpose

Build strategic product roadmaps that align stakeholder priorities with team capacity. Combines theme-based quarterly planning with RICE prioritization, timeline visualization, and iterative monthly updates.

A good roadmap communicates direction without falsely promising specific dates. It answers two questions the whole organization cares about: what is the team working on and why does it matter? This skill produces a living document organized by strategic themes, prioritized by data (RICE scores), and sized with a 20% buffer for the inevitable unplanned work. The output is audience-ready for stakeholder presentations and simultaneously actionable for engineering sprint planning. The roadmap is reviewed quarterly and updated monthly — daily changes destroy trust.

The tension at the heart of roadmapping is between certainty and flexibility. Stakeholders want firm dates; engineering knows that estimates are ranges, not points. This skill navigates that tension by using "Now/Next/Later" framing for uncertain environments and "Q1-Q4 with monthly milestones" for mature products. Both formats communicate priority and direction without over-committing to dates that will inevitably shift.

Architecture/Decision Trees

Roadmap Format Decision Tree

Product maturity?
  |-- Early stage / high uncertainty --> Now/Next/Later format
  |     Benefits: Flexible, sets direction, manages expectations
  |     Drawbacks: Vague on timelines, stakeholders may push for dates
  |-- Mature product / predictable delivery --> Q1-Q4 with milestones
  |     Benefits: Concrete, stakeholder-friendly, tracks progress
  |     Drawbacks: Creates false precision, harder to change
  |-- Enterprise / contractual commitments --> Q1-Q4 with fixed scope
        Benefits: Legal/contractual clarity
        Drawbacks: Least flexible, highest maintenance overhead

Stakeholder preference?
  |-- Outcome-focused --> Theme-based roadmap (what we will achieve)
  |-- Date-focused --> Feature-based roadmap (what we will ship by when)
  |-- Mixed --> Hybrid: themes for outer quarters, features for next quarter

Prioritization Method Decision Tree

Data availability?
  |-- Quantitative data available (usage metrics, revenue data) --> RICE or WSJF
  |     RICE: Best for feature-level prioritization, simpler to calculate
  |     WSJF: Best for SAFe/agile at scale, requires cost of delay data
  |-- Qualitative data only (stakeholder input, research) --> MoSCoW or Opportunity Scoring
  |     MoSCoW: Simple, fast, widely understood by non-technical stakeholders
  |     Opportunity Scoring: Better for customer-needs-driven prioritization
  |-- No data / early stage --> Kano Model or Effort-Impact Matrix
  |     Kano: Understanding what delights vs what is expected vs basic needs
  |     Effort-Impact: Quick visual prioritization for early-stage tradeoffs
  |-- Regulatory/compliance driven --> Priority overrides all scoring (must-do)

Capacity Planning Decision Tree

Team allocation?
  |-- Dedicated team --> Full-time on roadmap items
  |     Budget: 60% feature, 20% tech debt, 20% buffer
  |-- Shared team --> Splits time across multiple initiatives
  |     Budget: Allocate by percentage per initiative
  |-- Multiple teams --> Each team gets its own roadmap swimlane
        Coordinate dependencies across swimlanes with explicit sync points

Has team velocity been measured?
  |-- YES (3+ sprints of data) --> Use average velocity for capacity
  |-- NO / new team --> Use estimated capacity: (team size * 0.6 * sprint days)

Agent Protocol

Trigger

"create roadmap", "roadmap", "product roadmap", "feature roadmap", "quarterly roadmap", "release plan", "timeline", "roadmap planning"

Input Context

• Product vision and strategy documents (1-2 pages maximum)
• Market analysis, competitive intelligence, and customer research findings
• Stakeholder priority list with each item's rationale and expected business impact
• Team capacity data: sprint velocity for the last 3-6 sprints, team headcount, known leaves
• Technical dependencies and architectural constraints
• Existing sprint commitments and in-flight work
• Business OKRs and strategic goals

Output Artifact

Roadmap document with strategic themes, timeline view (Now/Next/Later or Q1-Q4), prioritized features with RICE scores, and explicit capacity allocation.

Response Format

• Theme overview section: 3-5 themes per quarter, each with name, outcome statement, and success metric
• Timeline section: Now/Next/Later table or Q1-Q4 table with monthly milestones per theme swimlane
• Feature list with RICE scores: feature name, Reach, Impact, Confidence, Effort, RICE value, MoSCoW category
• Capacity allocation: feature work %, tech debt %, unplanned buffer % — summing to 100%
• No preamble. No postamble. No explanations. No filler/hedging/transitions.

Completion Criteria

Roadmap covers 2-4 consecutive quarters. At least 3 strategic themes defined per quarter. Features listed with RICE scores and assigned to a theme and timeframe. Capacity allocation sums to 100%. Format suitable for stakeholder presentation.

Max Response Length

3000 tokens

Workflow

Step 1: Gather Inputs

Collect all inputs before placing anything on the timeline:

• Product vision: Where is the product going in the next 12 months? What is the North Star metric?
• Market analysis: What do customers need that competitors do not provide?
• Stakeholder wishlist: Every prioritized request with context — what business problem does each solve and what metric would it move?
• Team capacity: Average sprint velocity over last 3-6 sprints, current headcount, known leaves, historical throughput
• Technical constraints: Infrastructure work, migrations, or upgrades that block feature delivery
• Existing commitments: What is already in flight and must continue?
• OKRs: What strategic goals do the features roll up to?

Step 2: Define Themes

Create 3-5 strategic themes per quarter. A theme is a bounded initiative with a clear outcome statement: a sentence describing what will be true when this theme is complete.

Theme quality criteria:

• Names the outcome, not the work: "Customers can pay online with credit cards" not "Stripe Integration"
• Maps to a business OKR or strategic goal
• Mutually exclusive from other themes (no overlap)
• Collectively exhaustive for the planning period
• Has a single success metric that defines done

Theme template:

### Theme: {Outcome Statement}
**Success metric:** {metric that defines completion}
**OKR alignment:** {OKR this theme supports}
**Key features:**
- {Feature 1}: {brief description}
- {Feature 2}: {brief description}

Step 3: Build Timeline

Two format options depending on planning horizon certainty.

Now/Next/Later — best for early-stage or fast-moving products:

• Now (this sprint or next): Fully specified with tasks, owners, and estimated delivery
• Next (this quarter): Specified as features with themes but not individual tasks
• Later (next quarter): Specified as themes only, no feature breakdown

Q1-Q4 with monthly milestones — best for mature products with predictable delivery:

• Each theme becomes a swimlane on the timeline
• Place features under the appropriate theme and time bucket
• Mark monthly milestones per swimlane
• Reserve exactly 20% of capacity as an unplanned buffer

Timeline construction rules:

• First quarter: detailed, specific, actionable
• Second quarter: directional, feature-level
• Third and fourth quarters: theme-level only (rolling wave)
• No more than one commit per theme per quarter

Step 4: Prioritize

Score every feature using RICE before placing it on the timeline.

RICE formula: RICE = (Reach * Impact * Confidence) / Effort

Example: (50,000 users * 2 impact * 80% confidence) / 20 days = 4,000 RICE.

After scoring, apply MoSCoW categories:

• Must have: Non-negotiable, RICE-independent (regulatory, P0 commitments)
• Should have: High RICE, important for the quarter
• Could have: Medium RICE, nice to include if capacity allows
• Won't have: Lowest RICE, explicitly out of scope this quarter

Step 5: Communicate

Prepare the visual roadmap in two views:

• Timeline view: Features plotted on a calendar with quarters and months, color-coded by theme
• Theme view: Themes as swimlanes with milestones rather than specific dates — better for stakeholder communication

Communication cadence:

• Leadership presentation: Quarterly (review themes + priorities)
• Engineering sync: Monthly (update progress + unblock)
• Stakeholder newsletter: Monthly (what shipped, what is next, what changed)

Step 6: Track and Report

Update roadmap status monthly. For each feature, report:

• Not Started / In Progress / At Risk / Completed / Blocked

Monthly status report format:

## Roadmap Status: {Month} {Year}

### Shipped This Month
- {Feature}: {brief outcome}

### In Progress
- {Feature}: {progress %, ETA}

### At Risk
- {Feature}: {risk description, mitigation}

### Changes
- {Previous plan} -> {New plan}: {reason}

### Won't Have (This Quarter)
- {Feature}: {reason for deferral}

Process Patterns

Pattern 1: The Theme-Based Roadmap

When: Product-led org, outcome-focused culture Process: Define themes by customer outcomes, not features. Each theme has a hypothesis: "If we deliver {outcome}, we expect {metric} to change by {amount}." Features within a theme can change as long as the outcome stays the same. Best for: Mature products with empowered product teams.

Pattern 2: The Time-Boxed Roadmap

When: Fixed deadline (conference, regulation, contract) Process: Work backward from the fixed date. Scope is variable, time is fixed. Use MoSCoW aggressively — Must Have is the absolute minimum. Track feature count against remaining time weekly. Best for: Event-driven launches, compliance deadlines, contractual commitments.

Pattern 3: The Opportunity-Sized Roadmap

When: Multiple small teams working independently Process: Use Now/Next/Later format with all teams. Each team has its own swimlane. Dependencies between teams are explicitly marked and assigned a dependency owner. Monthly cross-team sync to resolve dependency conflicts. Best for: Organizations with 3+ product teams.

Pattern 4: The Rolling Wave Roadmap

When: High uncertainty, fast-changing market Process: Plan only the next quarter in detail. Quarter 2 is directional. Quarters 3-4 are placeholders. Every month, review the next quarter plan and adjust. Archive old versions to track how priorities changed. Best for: Startups, emerging markets, new product lines.

Anti-Patterns

Anti-Pattern 1: Roadmap as a Gantt Chart

Exact dates on features create false certainty and erode trust when they slip. Use quarters, months, or "Now/Next/Later" buckets. A roadmap is NOT a project schedule.

Anti-Pattern 2: No "Won't Have" Section

Failing to explicitly state what is not being worked on creates the expectation that everything is possible. The "Won't Have" list is essential expectation management.

Anti-Pattern 3: Ignoring Capacity Planning

Without capacity data (velocity, headcount, leaves), the roadmap is a wish list, not a plan. A roadmap without capacity allocation has zero credibility with engineering teams.

Anti-Pattern 4: Zero Buffer for Unplanned Work

Every team has bugs, incidents, escalations, and support requests. Budgeting zero for unplanned work ensures the roadmap will slip. Minimum 20% buffer is non-negotiable.

Anti-Pattern 5: Daily Changes

A roadmap that changes daily is useless. It signals the team has no strategy, only reactions. Establish a monthly update cadence.

Anti-Pattern 6: All Themes Are Operational

If every theme is "improve performance" or "fix bugs," the product is not evolving. At least one theme per quarter should be growth-oriented or customer-facing.

Anti-Pattern 7: Stakeholder Override

The CEO or VP overrides the RICE score and inserts their pet project without context. If stakeholders override prioritization, the data-driven process loses credibility. Document overrides and their rationale.

Anti-Pattern 8: Perpetual "Next Quarter"

Features keep getting pushed to the next quarter without explanation. Track deferred features — if something has been deferred 3+ quarters, it should be explicitly dropped or promoted. Endless deferral is a failure to decide.

Templates

Theme Card Template

## Theme: {Outcome Statement}
**Success metric:** {Single metric that defines completion}
**OKR:** {Linked OKR}
**Dependencies:** {Other themes or external dependencies}
**Risk level:** {High / Medium / Low}
**Features:**
- {Feature}: RICE {score} — Must/Should/Could
- {Feature}: RICE {score} — Must/Should/Could

Quarterly Roadmap Summary Template

# Roadmap: {Quarter} {Year}

## Focus
{1-2 sentence strategic focus for the quarter}

## Themes
1. {Theme 1}: {outcome} [{effort estimate}]
2. {Theme 2}: {outcome} [{effort estimate}]
3. {Theme 3}: {outcome} [{effort estimate}]

## Capacity
- Feature work: {n}%
- Tech debt: {n}%
- Buffer: {n}%

## Won't Have
- {Feature}: {reason}
- {Feature}: {reason}

Success Metrics

Models

RICE Scoring System

RICE = (Reach * Impact * Confidence) / Effort
Reach       = Number of users affected per quarter (e.g., 50,000)
Impact      = 1 (low) / 2 (medium) / 3 (high) — estimated effect magnitude
Confidence  = Percentage (0-100%) — how confident in Reach and Impact estimates
Effort      = Engineering person-days — total cost to deliver

Capacity Allocation Standard

Feature work:    60% — New capabilities, improvements, user-facing changes
Tech debt:       20% — Refactoring, upgrades, performance, security, reliability
Unplanned:       20% — Bugs, escalations, incidents, urgent support requests

WSJF (Weighted Shortest Job First) — Alternative to RICE

WSJF = Cost of Delay / Job Duration
Cost of Delay = User Value + Time Criticality + Risk Reduction / Opportunity Enablement
Job Duration = Estimated effort (same as RICE Effort)

MoSCoW Categories

Performance Considerations

Roadmap Tool Performance

For roadmaps with 50+ features across 4 quarters, spreadsheet performance degrades. Use dedicated roadmap tools (Aha!, Productboard, Notion) for large roadmaps.

Update Frequency Impact

• Small team (< 10 people): 2-4 hours/month
• Medium team (10-50): 4-8 hours/month
• Large org (50+): 8-16 hours/month

Set update cadence proportional to team size. Oversized teams updating weekly waste 50+ hours/month.

Stakeholder Communication Efficiency

• C-level: 1-page summary, quarterly
• Product team: Full roadmap with RICE, monthly
• Engineering: Timeline view with swimlanes, sprint-by-sprint
• Sales/Customer success: Theme view, quarterly

Ecosystem & Tooling

Roadmap Software

• Aha!: Enterprise product roadmap. $59/user/month
• Productboard: Product management platform. $20/user/month
• Notion: Flexible, template-based. Free for small teams.
• Craft.io: Product management with stakeholder views.
• Airfocus: Prioritization-first. Custom scoring models.
• Roadmunk: Visual roadmaps for stakeholders.

Presentation Tools

• Google Slides / PowerPoint: For stakeholder presentations
• Miro / Mural: Collaborative roadmap workshops
• GitHub Projects: Developer-friendly roadmap in-platform

Adjacent Frameworks

• OKRs: Align roadmap themes with quarterly objectives
• DORA Metrics: Track delivery performance against roadmap commitments
• North Star Metric: Single metric all roadmap themes should influence

Rules

• A roadmap communicates direction, not delivery dates — it answers "what and why" not "exactly when."
• Reserve 20% buffer for unplanned work — bugs, incidents, urgent escalations always consume capacity.
• One strategic theme per swimlane — never mix two themes in the same swimlane.
• Score every feature with RICE before timeline placement — data defeats recency bias.
• Update monthly, never daily — daily changes destroy stakeholder trust.
• The Won't Have list is as important as the Must Have list — explicit exclusions manage expectations.
• Plan a maximum of 4 quarters ahead — beyond 12 months is a vision document, not a roadmap.
• Use rolling wave planning — next quarter in detail, future quarters at theme level.
• Every theme must map to an OKR — if a theme does not roll up to an objective, it should not be on the roadmap.
• The roadmap is a living document — review quarterly, update monthly, archive old versions.

Common Pitfalls

1. Roadmap as a Gantt Chart

A roadmap is NOT a project schedule. Do not put exact dates on features. Use quarters, months, or "Now/Next/Later" buckets. Exact dates create false certainty and erode trust when they slip.

2. No "Won't Have" Section

Failing to explicitly state what is not being worked on creates the expectation that everything is possible. The "Won't Have" list is essential expectation management.

3. Ignoring Capacity Planning

Without capacity data (velocity, headcount, leaves), the roadmap is a wish list, not a plan. A roadmap without capacity allocation has zero credibility with engineering teams.

4. Zero Buffer for Unplanned Work

Every team has bugs, incidents, escalations, and support requests. Budgeting zero for unplanned work ensures the roadmap will slip. Minimum 20% buffer is non-negotiable.

5. Daily Changes

A roadmap that changes every day is useless. It signals that the team has no strategy, only reactions. Establish a monthly update cadence.

6. All Themes Are Operational

If every theme is "improve performance" or "fix bugs," the product is not evolving. At least one theme per quarter should be growth-oriented.

Compared With

Related Skills

• create-story: Decompose roadmap features into individual user stories for sprint planning
• create-tech-spec: Write technical specifications for complex or high-risk roadmap features
• market-analysis: Inform roadmap themes with market data and competitive intelligence
• create-prd: Write detailed product requirement documents for major roadmap initiatives
• analytics: Define success metrics for each roadmap theme and track outcomes

References

• references/create-roadmap-fundamentals.md — Roadmap Fundamentals
• references/create-roadmap-advanced.md — Roadmap Advanced Topics
• references/roadmap-examples.md — Roadmap Examples
• references/roadmap-strategies.md — Roadmap Strategies
• references/roadmap-template.md — Roadmap Template
• references/roadmap-tools.md — Roadmap Tools
• references/roadmap-prioritization-methods.md — Roadmap Prioritization Methods
• references/roadmap-communication-stakeholder.md — Roadmap Communication & Stakeholder Management

Handoff

create-story, create-tech-spec

Implementation Patterns

Observer Pattern for Event Handling

` interface EventObserver { onEvent(event: T): Promise; }

class EventBus { private observers: Set<EventObserver> = new Set(); subscribe(observer: EventObserver): void { this.observers.add(observer); } unsubscribe(observer: EventObserver): void { this.observers.delete(observer); } async emit(event: T): Promise { const results = Array.from(this.observers).map(o => o.onEvent(event)); await Promise.allSettled(results); } } `

Configuration-Driven Approach

config: defaults: timeout: 30s retryCount: 3 overrides: production: timeout: 60s retryCount: 5 development: timeout: 300s retryCount: 1

Production Considerations

Deployment Checklist

• Configuration validated against schema before startup
• Health check endpoints registered and monitored
• Graceful shutdown with draining period (30s timeout)
• Resource limits configured (CPU, memory, file descriptors)
• Log level set appropriate for environment
• Metrics endpoint secured and exposed
• Rate limiting configured per-tier
• TLS certificates valid and auto-renewing
• Database migrations run as separate deployment step
• Feature flags ready for gradual rollout

Monitoring and Alerting

Anti-Patterns

Performance Optimization

Caching Strategy

Cache hierarchy: L1 (in-memory local) → L2 (distributed Redis/Memcached) → L3 (CDN/Edge). Cache invalidation: TTL-based (simple, stale), event-based (complex, fresh), write-through (consistent, higher write latency), write-behind (fast writes, eventual consistency).

Resource Pooling

• Database connections: Pool of reusable connections (HikariCP, pgBouncer)
• HTTP connections: Keep-alive + connection pooling for external calls
• Thread pool: Bounded thread pools for async task execution

Profiling Methodology

1. Establish baseline with production traffic profile
2. Profile CPU with sampling profiler (pprof, perf, async-profiler)
3. Profile memory with heap dumps and allocation tracking
4. Profile I/O with strace/perf trace for syscall analysis
5. Profile latency with distributed tracing (OpenTelemetry)
6. Identify bottleneck, formulate hypothesis, implement fix
7. Re-profile to verify improvement, repeat

Security Considerations

Threat Modeling (STRIDE)

• Spoofing: Identity validation, authentication
• Tampering: Integrity checks, digital signatures
• Repudiation: Audit logs, non-repudiation
• Information disclosure: Encryption, access control
• Denial of service: Rate limiting, resource quotas
• Elevation of privilege: Principle of least privilege

Supply Chain Security

• Dependency scanning: Snyk, Dependabot, Trivy
• SBOM generation: CycloneDX or SPDX format
• Signed commits: GPG or SSH commit signing
• Artifact verification: Checksum validation, signature verification

Secrets Management

• Secrets never in code — always in secrets manager (Vault, AWS Secrets Manager)
• Rotation policy: Rotate database credentials every 90 days
• Access audit: Log every secrets access, alert on anomalies
• Encryption at rest and in transit for all secrets
• Principle of least privilege: each service gets only its own secrets

Rules

• Default-deny security posture — allow only explicitly required access.
• All inputs validated, all outputs encoded, all errors handled.
• Defend in depth — multiple layers of security controls.
• Fail securely — errors default to safe behavior.
• Log security-relevant events for audit and investigation.
• Keep dependencies updated — automate vulnerability scanning.
• Design for observability from day one, not as an afterthought.
• Document all architectural decisions with rationale.
• Review code for security, performance, and correctness before merging.