Product Roadmap Skill

Version: 1.0.0 Category: Product Triggers: Planning work, checking priorities, roadmap questions

Quick Reference

Current Capabilities (Phase 0 Complete)

• ✅ 77 AI agent definitions across 23 categories

• ✅ 106+ automation scripts

• ✅ 88+ documentation files

• ✅ Full CLI tooling (workspace, repository_sync)

• ✅ O&G Knowledge System with RAG

• ✅ Claude Flow MCP integration

• ✅ Compliance propagation framework

Strategic Focus Areas

• Foundation strengthening (configuration, testing)

• Enhanced automation and parallel operations

• Monitoring dashboards and visibility

• Cross-repository intelligence

• Team collaboration features

• Advanced CI/CD orchestration

Phase Overview

Phase Focus Timeline

1 Foundation Strengthening Weeks 1-3

2 Enhanced Automation Weeks 4-7

3 Monitoring & Dashboards Weeks 8-11

4 Cross-Repository Intelligence Weeks 12-16

5 Team Collaboration Weeks 17-20

6 Advanced CI/CD Weeks 21-26

Phase 1: Foundation (Critical)

Goal: All repos configured, 80%+ test coverage, zero broken integrations

Must Complete

• Configure all 25 repository URLs in config/repos.conf

• Verify all 5 MCP servers operational

• Finalize config/sync-items.json settings

• Establish cross-repository test framework

• Populate docs/api/ directory

Phase 2: Enhanced Automation

Goal: 50% reduction in manual sync time

Must Complete

• Smart conflict resolution with auto-merge

• Enhanced parallel operations (10-repo)

• Automated dependency updates across repos

• Branch strategy templates

Phase 3: Monitoring Dashboards

Goal: Real-time dashboard operational, 90% issue auto-detection

Must Complete

• Real-time web dashboard (Plotly visualizations)

• Health score metrics per repository

• Alerting system (build failure, stale branches)

• Activity timeline visualization

Effort Scale

Code Duration Examples

XS 1 day Config change, single script update

S 2-3 days New utility script, docs update

M 1 week New feature module, integration

L 2 weeks Major feature, cross-repo changes

XL 3+ weeks System-wide changes, new subsystems

Domain-Specific Initiatives

Energy & O&G

• O&G Knowledge System enhancement

• BSEE data integration

• Lower Tertiary analysis automation

Marine Engineering

• Marine analysis standardization

• Engineering verification system

Web & Applications

• Full-stack templates (Rails 8 + React)

• Component library sync

Success Metrics

Phase 1

• All 25 repositories configured

• 80% baseline test coverage

• Zero broken MCP integrations

Phase 2

• 50% reduction in manual sync time

• 80% auto-resolution of common conflicts

Phase 3

• Dashboard operational with real-time data

• 90% issue auto-detection rate

Repository Count

• Total: 25+ repositories

• Work: 15 repositories

• Personal: 11 repositories

Full Reference

See: @.agent-os/product/roadmap.md

Product Roadmap Frameworks

Now / Next / Later

The simplest and often most effective roadmap format:

• Now (current sprint/month): Committed work. High confidence in scope and timeline. These are the things the team is actively building.

• Next (next 1-3 months): Planned work. Good confidence in what, less confidence in exactly when. Scoped and prioritized but not yet started.

• Later (3-6+ months): Directional. These are strategic bets and opportunities we intend to pursue, but scope and timing are flexible.

When to use: Most teams, most of the time. Especially good for communicating externally or to leadership because it avoids false precision on dates.

Quarterly Themes

Organize the roadmap around 2-3 themes per quarter:

• Each theme represents a strategic area of investment

• Under each theme, list the specific initiatives planned

• Themes should map to company or team OKRs

• This format makes it easy to explain WHY you are building what you are building

When to use: When you need to show strategic alignment. Good for planning meetings and executive communication.

OKR-Aligned Roadmap

Map roadmap items directly to Objectives and Key Results:

• Start with the team's OKRs for the period

• Under each Key Result, list the initiatives that will move that metric

• Include the expected impact of each initiative on the Key Result

• This creates clear accountability between what you build and what you measure

When to use: Organizations that run on OKRs.

Timeline / Gantt View

Calendar-based view with items on a timeline:

• Shows start dates, end dates, and durations

• Visualizes parallelism and sequencing

• Good for identifying resource conflicts

• Shows dependencies between items

When to use: Execution planning with engineering. NOT good for communicating externally (creates false precision expectations).

Prioritization Frameworks

RICE Score

Score each initiative on four dimensions, then calculate RICE = (Reach x Impact x Confidence) / Effort

• Reach: How many users/customers will this affect in a given time period?

• Impact: How much will this move the needle for each person reached? Score: 3 = massive, 2 = high, 1 = medium, 0.5 = low, 0.25 = minimal.

• Confidence: How confident are we in the estimates? 100% = high, 80% = medium, 50% = low.

• Effort: How many person-months of work?

MoSCoW

• Must have: Non-negotiable commitments.

• Should have: Important and expected, but delivery is viable without them.

• Could have: Desirable but clearly lower priority.

• Won't have: Explicitly out of scope for this period.

ICE Score

Simpler than RICE. Score each item 1-10 on Impact, Confidence, and Ease.

ICE Score = Impact x Confidence x Ease

Value vs Effort Matrix

• High value, Low effort (Quick wins): Do these first.

• High value, High effort (Big bets): Plan these carefully.

• Low value, Low effort (Fill-ins): Do these when you have spare capacity.

• Low value, High effort (Money pits): Do not do these.

Dependency Mapping

Identifying Dependencies

• Technical dependencies: Feature B requires infrastructure work from Feature A

• Team dependencies: Feature requires work from another team

• External dependencies: Waiting on a vendor, partner, or third-party integration

• Knowledge dependencies: Need research or investigation results before starting

• Sequential dependencies: Must ship Feature A before starting Feature B

Managing Dependencies

• List all dependencies explicitly in the roadmap

• Assign an owner to each dependency

• Set a "need by" date

• Build buffer around dependencies -- they are the highest-risk items

• Flag dependencies that cross team boundaries early

• Have a contingency plan: what do you do if the dependency slips?

Capacity Planning

Allocating Capacity

A healthy allocation for most product teams:

• 70% planned features: Roadmap items that advance strategic goals

• 20% technical health: Tech debt, reliability, performance, developer experience

• 10% unplanned: Buffer for urgent issues, quick wins, and requests from other teams

Capacity vs Ambition

• If roadmap commitments exceed capacity, something must give

• Do not solve capacity problems by pretending people can do more -- solve by cutting scope

• When adding to the roadmap, always ask: "What comes off?"

Communicating Roadmap Changes

How to Communicate Changes

• Acknowledge the change: Be direct about what is changing and why

• Explain the reason: What new information drove this decision?

• Show the tradeoff: What was deprioritized to make room?

• Show the new plan: Updated roadmap with the changes reflected

• Acknowledge impact: Who is affected and how?

Avoiding Roadmap Whiplash

• Do not change the roadmap for every piece of new information

• Batch roadmap updates at natural cadences (monthly, quarterly)

• Distinguish between "roadmap change" (strategic reprioritization) and "scope adjustment" (normal execution refinement)

• Track how often the roadmap changes

Sources

• Original: workspace-hub product roadmap

• Enriched: anthropics/knowledge-work-plugins (2026-02-03)

Use this when planning work, checking priorities, or understanding product direction.