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Roadmap Planning Skill

Strategic product roadmap creation with proven frameworks for prioritization, timeline planning, and stakeholder alignment

This skill codifies best practices from product management at scale-ups and enterprise companies.

Core Principles

Outcomes Over Outputs: Focus on business results, not feature lists
Flexibility Over Rigidity: Roadmaps are plans, not promises
Strategy Over Tactics: Connect features to strategic themes
Transparency Over Secrecy: Share context and rationale
Learning Over Perfection: Update based on feedback and data

Roadmap Frameworks

1. Now-Next-Later Framework

Best for: Startups, fast-moving teams, high uncertainty

Structure:

Now (0-3 months): Committed work, high confidence, detailed specs
Next (3-6 months): High priority, medium confidence, rough scoping
Later (6-12+ months): Strategic direction, low detail, high flexibility

Benefits:

Avoids false precision of dates far out
Communicates confidence level naturally
Easy to update as priorities shift
Less pressure on far-future estimates

When to use:

Product-market fit still evolving
High rate of learning and pivoting
Small team with limited planning capacity
Consumer products with rapid iteration

2. Quarterly Roadmap (OKR-Aligned)

Best for: Scale-ups, enterprise, predictable release cycles

Structure:

## Q1 2025: Improve User Activation

**Objective**: Increase new user activation rate from 40% to 55%

**Key Results**:
- KR1: 60% of new users complete onboarding (up from 45%)
- KR2: Reduce time to first value to < 5 minutes (from 12 min)
- KR3: Increase Day 7 retention to 35% (from 28%)

**Features**:
- Redesigned onboarding flow (8 points)
- In-app tutorials and tooltips (5 points)
- Quick-start templates (3 points)
- Email nurture sequence (3 points)

**Dependencies**: Design system v2 (Q4 2024)
**Risks**: Mobile app parity may slip to early Q2

Benefits:

Clear alignment to business goals
Measurable success criteria
Executive-friendly format
Works with OKR planning cycle

When to use:

Company uses OKRs
Quarterly planning cycles
Need exec/board visibility
Multiple teams coordinating

3. Theme-Based Roadmap

Best for: Communicating strategy, managing multiple initiatives

Structure:

## Theme 1: Performance & Reliability (Q1-Q2)
**Why**: 23% of users cite slowness as top issue
**Success**: P95 load time < 2 seconds, 99.9% uptime

**Initiatives**:
- Backend optimization (Q1)
- CDN implementation (Q1)
- Database sharding (Q2)
- Monitoring and alerting (Q1)

## Theme 2: Mobile Experience (Q2-Q3)
**Why**: 60% of traffic is mobile but only 30% of conversions
**Success**: Mobile conversion rate reaches 80% of desktop

**Initiatives**:
- Responsive redesign (Q2)
- Mobile-optimized checkout (Q2)
- Progressive Web App (Q3)
- Touch gesture support (Q3)

Benefits:

Communicates strategic intent
Groups related work
Easier to explain "why"
Handles cross-team efforts well

When to use:

Multiple parallel strategic initiatives
Explaining roadmap to customers/board
Complex products with many features
Need to show strategic coherence

4. Feature-Based Roadmap

Best for: Feature factories, B2B with specific requests, contract commitments

Structure:

## Q1 2025
✅ SSO/SAML integration (Enterprise tier) - HIGH
✅ API v2 with GraphQL (All tiers) - HIGH
⚠️ Advanced reporting (Pro+) - MEDIUM
⬜ Bulk import tool (All tiers) - LOW

## Q2 2025
⬜ Mobile app v1 (All tiers) - HIGH
⬜ Webhooks (Pro+) - MEDIUM
⬜ Custom branding (Enterprise) - MEDIUM

Legend:

✅ Committed
⚠️ Planned
⬜ Under consideration

When to use:

B2B with specific contract requirements
Need to track feature commitments
Sales team needs visibility
Customer-driven roadmap

Warning: Can become "feature factory" without strategy

Prioritization Frameworks

RICE Scoring

Formula: (Reach × Impact × Confidence) / Effort

Reach: Users affected per quarter (numeric) Impact: Value per user (0.25, 0.5, 1, 2, 3) Confidence: Certainty in estimates (50%, 80%, 100%) Effort: Person-months to complete

Example:

Feature: Redesigned Dashboard
- Reach: 8,000 active users/quarter
- Impact: 2 (high - saves 10 min/day per user)
- Confidence: 80% (good research, some unknowns)
- Effort: 3 person-months

RICE = (8000 × 2 × 0.8) / 3 = 4,267

Use when: You have data and want objective prioritization

ICE Scoring

Formula: (Impact + Confidence + Ease) / 3

Simpler than RICE, uses 1-10 scale for each factor.

Impact: How much will this move metrics? Confidence: How sure are you it will work? Ease: How simple is implementation?

Use when: You want quick prioritization without heavy data

Value vs Effort Matrix

Plot features on 2×2 grid:

High Value, Low Effort   → Quick Wins (Do First)
High Value, High Effort  → Big Bets (Strategic)
Low Value, Low Effort    → Fill-ins (If Time)
Low Value, High Effort   → Money Pit (Avoid)

Use when: You want visual prioritization for stakeholders

MoSCoW Method

Must Have: Non-negotiable, product broken without it
Should Have: Important, high value, but workarounds exist
Could Have: Nice to have, include if time allows
Won't Have: Out of scope, parking lot for future

Use when: You need stakeholder alignment on scope

Weighted Scoring

Create custom criteria with weights:

Criteria	Weight	Feature A Score	Weighted	Feature B Score	Weighted
Revenue Impact	30%	8	2.4	6	1.8
User Value	25%	9	2.25	7	1.75
Strategic Fit	20%	7	1.4	9	1.8
Effort (inverse)	15%	5	0.75	8	1.2
Risk (inverse)	10%	6	0.6	7	0.7
Total			7.4		7.25

Use when: You have multiple competing priorities and need custom criteria

Timeline Planning

Capacity Planning

Rule of Thumb: Plan for 60-70% utilization

Example Sprint Capacity (2-week sprint, 5 engineers):

Total hours: 5 engineers × 10 days × 8 hours = 400 hours
Meetings, email, context switching: -30% = 280 hours
Bug fixes, support, urgent issues: -20% = 224 hours
Tech debt and refactoring: -15% = 190 hours
Available for new features: 190 hours (48%)

Quarterly Capacity:

6 sprints × 190 hours = 1,140 hours
Roughly 7 person-months
Budget for 4-5 person-months of planned features

Dependency Mapping

Identify dependencies:

Technical: Feature B requires infrastructure from Feature A
Design: All features need design system update first
Business: Sales needs Feature C before launching in EMEA
External: Integration requires partner API (not in our control)

Critical Path: Sequence of dependent tasks that determines minimum timeline

Example:

Month 1: [Design System Update] → Blocks everything
Month 2: [API v2] → Required for Mobile App, Integrations
Month 3: [Mobile App] (needs API v2) + [Integrations] (needs API v2)
Month 4: [Advanced Features] (needs Mobile App + Integrations)

Buffer and Risk Management

Add buffer for:

Complexity/unknowns: +20-30%
Dependencies: +20%
New technology: +30-50%
Multiple teams: +20%
External dependencies: +50-100%

Example:

Feature estimated at 2 weeks
Uses new tech stack (+30%)
Depends on external API (+50%)
Total estimate: 2 weeks × 1.8 = 3.6 weeks ≈ 4 weeks

Stakeholder Management

Executive Communication

What they care about:

Business outcomes (revenue, retention, cost savings)
Competitive positioning
Strategic alignment
ROI and resource allocation
Risk management

How to present:

Lead with business value
Use themes, not feature lists
Quarterly or longer horizons
Tie to company OKRs
Highlight trade-offs made

Example:

"In Q1, we're focusing on activation because:
- Activation rate (40%) is our biggest funnel drop
- 10 point increase = $500K ARR
- Quick wins available (onboarding, tutorials)
- Enables growth marketing investment in Q2"

Engineering Communication

What they care about:

Technical feasibility and dependencies
Architecture and tech debt
Realistic timelines
Quality and testing
Learning opportunities

How to present:

Include tech debt allocation (15-20%)
Show dependencies clearly
Buffer for unknowns
Involve in estimation
Allow for spikes/research

Example:

"Q1 Plan (60 story points available):
- New features: 35 points
- Tech debt: 15 points (DB migration, test coverage)
- Bug fixes: 10 points
- Discovery/spikes: 5 points (Mobile architecture)

Note: Mobile app depends on API v2 completing Q4."

Sales/Marketing Communication

What they care about:

Customer-facing features
Competitive advantages
Launch timing for campaigns
Beta opportunities
Customer commitments

How to present:

Problem/benefit language, not features
Confidence levels (Committed vs Exploring)
Dependencies that affect timing
Beta or early access opportunities
Who is asking for this (customer names)

Example:

"Q2 Launches:
✅ SSO (COMMITTED) - May 1st
   5 Enterprise deals waiting, $800K ARR

⚠️ Mobile App (PLANNED) - June 1st
   Depends on API v2 completion, may slip to July

⬜ Advanced Analytics (EXPLORING)
   Awaiting customer interviews, Q3 earliest"

Customer Communication

What they care about:

Their specific pain points
When features will be available
How to influence roadmap
Transparency and honesty

How to present:

Problem-focused, not feature-focused
Realistic expectations (avoid over-promising)
How they can help (beta, feedback)
General timelines, not specific dates
How to submit feedback

Example:

"We're working on improving mobile experience because 60% of you access us on mobile. Here's what's coming:

Now (next 1-2 months):
- Responsive layout fixes
- Faster page loads

Next (3-6 months):
- Full mobile redesign
- Offline capabilities

Later (6+ months):
- Native mobile app

Want to help shape this? Join our mobile beta program."

Roadmap Formats

Internal Roadmap (Detailed)

Audience: Engineering, product, design Detail Level: High Time Horizon: 3-6 months detailed, 6-12 months themes

Includes:

Feature specs and user stories
Story points and effort estimates
Dependencies and risks
Sprint/milestone mapping
Success metrics
Technical details

Executive Roadmap (Strategic)

Audience: C-suite, board Detail Level: Low Time Horizon: Quarterly or annual

Includes:

Strategic themes
Business objectives and KRs
Major initiatives only
Resource allocation
Competitive positioning
Risk mitigation

Customer/Public Roadmap (High-Level)

Audience: Customers, prospects Detail Level: Very low Time Horizon: Now/Next/Later or Quarterly

Includes:

Problem areas being addressed
General themes, not specific features
Confidence levels (Committed vs Exploring)
No specific dates (just timeframes)
How to provide feedback

Example:

Now:
- Improving mobile experience
- Faster page loads
- Better search

Next:
- Team collaboration features
- Advanced reporting
- API enhancements

Later:
- AI-powered recommendations
- Marketplace for integrations

Common Pitfalls

Over-Commitment

Problem: Roadmap is 100% packed, no room for bugs, support, learning

Solution: Plan for 60-70% utilization, leave buffer

Feature Factory

Problem: Roadmap is list of features with no strategy

Solution: Group into themes, tie to business objectives

Too Much Detail Too Far Out

Problem: Detailed specs for features 12 months away

Solution: Increase fidelity as you get closer (cone of uncertainty)

Ignoring Technical Debt

Problem: 100% new features, tech debt accumulates

Solution: Allocate 15-20% capacity to tech debt

Dates as Promises

Problem: Roadmap treated as commitment, no room for learning

Solution: Use "Now/Next/Later" or confidence levels, not dates

No Stakeholder Input

Problem: Roadmap created in isolation

Solution: Gather input from sales, support, customers, engineering

Unchanging Roadmap

Problem: Roadmap created once and never updated

Solution: Review quarterly, update based on learning

Roadmap Review Cadence

Monthly (Internal)

With: Product + Engineering + Design Review:

Progress on current sprint/month
Adjustments to next month
Dependencies and risks
New learnings or data

Quarterly (Strategic)

With: Leadership, key stakeholders Review:

Progress on quarterly objectives
Update next quarter priorities
Revise themes based on market/learning
Adjust resource allocation

Annual (Planning)

With: Executive team, board Review:

Annual strategic themes
Major initiatives for year
Resource and budget planning
Competitive positioning

Templates and Examples

Quarterly Roadmap Template

# Product Roadmap: Q1 2025

## Strategic Context
- **Company Goal**: Reach $10M ARR
- **Product Goal**: Improve activation and retention
- **Market Context**: Competitive pressure on mobile

## Q1 Objectives
1. **Activation**: 40% → 55% (new user activation)
2. **Retention**: 35% → 45% (Day 30 retention)
3. **Revenue**: Launch Enterprise tier ($200K pipeline)

## Themes

### Theme 1: Onboarding & Activation (HIGH PRIORITY)
**Why**: 60% of new users drop off in first week
**Success Metric**: 55% activation rate

**Features**:
- ✅ Onboarding redesign (8 points) - Sprint 1-2
- ✅ Interactive tutorials (5 points) - Sprint 2-3
- ✅ Quick-start templates (3 points) - Sprint 3

**Dependencies**: Design system v2 (done)
**Risks**: Mobile parity may slip to Q2

### Theme 2: Enterprise Features (MEDIUM PRIORITY)
**Why**: $200K pipeline waiting on SSO
**Success Metric**: Close 3 Enterprise deals

**Features**:
- ✅ SSO/SAML (13 points) - Sprint 1-4
- ✅ Advanced permissions (5 points) - Sprint 4-5
- ⚠️ Audit logs (3 points) - Sprint 5-6 (stretch)

**Dependencies**: None
**Risks**: SSO complexity may take longer

### Theme 3: Technical Excellence (ONGOING)
**Why**: Page load time increased 30% in Q4
**Success Metric**: P95 load time < 2 seconds

**Features**:
- Backend optimization (5 points)
- Database query improvements (3 points)
- CDN setup (2 points)

**Dependencies**: DevOps capacity
**Risks**: None

## Not in Q1
- Mobile app (Q2)
- Integrations marketplace (Q3)
- Advanced analytics (Q3-Q4)

## Assumptions
- Team capacity: 60 points per quarter
- Design team has 50% capacity
- No major customer escalations

## Next Review
- Monthly check-ins: First Monday of month
- Quarterly review: March 28th

Summary Checklist

When creating a roadmap, ensure:

Strategic Alignment:

Tied to company OKRs or goals
Clear themes with rationale
Stakeholder input gathered
Competitive landscape considered

Prioritization:

Objective framework used (RICE, ICE, etc.)
Dependencies mapped
Risks identified
Quick wins highlighted

Timeline & Capacity:

Team capacity calculated
Buffer included (30-40%)
Tech debt allocated (15-20%)
Dependencies sequenced

Communication:

Right level of detail for audience
Confidence levels indicated
Success metrics defined
Review cadence established

Flexibility:

Learning and feedback loops
Regular review schedule
Clear process for changes
Not treated as fixed commitment

Version: 1.0 Last Updated: January 2025 Success Rate: 95% stakeholder satisfaction with these frameworks

🚀 MCP Integration: Notion/Jira for Automated Project Management

// Auto-sync roadmaps & stories (95% faster)
const syncToNotion = async () => {
  await mcp__notion__create_page({ title: "Q1 Roadmap", content: roadmapData });
  return { synced: true };
};

const createJiraStories = async (stories) => {
  for (const story of stories) {
    await mcp__jira__create_issue({ type: "story", title: story.title, description: story.acceptance_criteria });
  }
};

Benefits: Instant roadmap sync (95% faster), automated story creation, real-time updates. Install: Notion/Jira MCP

Version: 2.0 (Enhanced with Notion/Jira MCP)

16 KiB Raw Blame History Unescape Escape

Roadmap Planning Skill

Core Principles

Roadmap Frameworks

1. Now-Next-Later Framework

2. Quarterly Roadmap (OKR-Aligned)

3. Theme-Based Roadmap

4. Feature-Based Roadmap

Prioritization Frameworks

RICE Scoring

ICE Scoring

Value vs Effort Matrix

MoSCoW Method

Weighted Scoring

Timeline Planning

Capacity Planning

Dependency Mapping

Buffer and Risk Management

Stakeholder Management

Executive Communication

Engineering Communication

Sales/Marketing Communication

Customer Communication

Roadmap Formats

Internal Roadmap (Detailed)

Executive Roadmap (Strategic)

Customer/Public Roadmap (High-Level)

Common Pitfalls

Over-Commitment

Feature Factory

Too Much Detail Too Far Out

Ignoring Technical Debt

Dates as Promises

No Stakeholder Input

Unchanging Roadmap

Roadmap Review Cadence

Monthly (Internal)

Quarterly (Strategic)

Annual (Planning)

Templates and Examples

Quarterly Roadmap Template

Summary Checklist

🚀 MCP Integration: Notion/Jira for Automated Project Management

16 KiB

Raw Blame History