Roadmap Analysis Skill

Procedural knowledge for analyzing and reporting on product roadmap health.

When to Use

• Running /roadmap command and subcommands

• User asks "what should I work on?", "what's the priority?"

• Checking roadmap health and blockers

• Planning work allocation

Data Sources

Primary source of truth:

pm-workspace-docs/roadmap/roadmap.json

Derived views (regenerated from JSON):

pm-workspace-docs/roadmap/roadmap.md # Narrative pm-workspace-docs/roadmap/roadmap-gantt.md # Mermaid Gantt pm-workspace-docs/roadmap/roadmap-kanban.md # Table kanban pm-workspace-docs/roadmap/snapshots/ # Historical snapshots

Initiative details:

pm-workspace-docs/initiatives/active/[name]/_meta.json

Roadmap JSON Schema

{ "generated_at": "ISO8601", "initiatives": [ { "id": "initiative-name", "name": "Human Readable Name", "phase": "discovery | define | build | validate | launch", "status": "on_track | at_risk | blocked | paused", "priority": "P0 | P1 | P2 | P3", "personas": ["sales-rep", "revops"], "strategic_pillar": "pillar-name", "owner": "name", "days_in_phase": 5, "created_at": "ISO8601", "updated_at": "ISO8601", "blockers": [], "next_action": "description" } ], "summary": { "total": 10, "by_phase": { "discovery": 2, "define": 3, ... }, "by_status": { "on_track": 7, "at_risk": 2, ... }, "stale_count": 1 } }

Analysis Procedures

Health Assessment

Calculate health score based on:

Metric Healthy Warning Critical

Stale initiatives (>14d) 0 1-2 3+

Blocked initiatives 0 1 2+

At-risk initiatives <20% 20-40%

40%

Missing owners 0 1-2 3+

Overall Health:

• 🟢 Healthy - All metrics in healthy range

• 🟡 Needs Attention - 1-2 warnings

• 🔴 Critical - Any critical metric

Phase Distribution Analysis

Ideal distribution (adjust based on team capacity):

• Discovery: 10-20% (pipeline)

• Define: 15-25% (specification)

• Build: 30-40% (active development)

• Validate: 10-20% (testing)

• Launch: 5-10% (shipping)

Flag imbalances:

• Too much in discovery → "Pipeline building but not shipping"

• Too much in build → "Risk of context switching"

• Nothing in validate → "Skipping validation?"

Priority Analysis

Check for:

• Multiple P0s (should be rare)

• P0/P1 items blocked or at-risk (escalate)

• P3 items in build phase (misalignment?)

Staleness Detection

Days in Phase Status

0-7 Normal

8-14 Monitor

15-21 ⚠️ Stale

22+ 🔴 Very stale

Work Recommendations

Based on current state, recommend:

Recommended Focus

This Week

1. [P0/P1 item] - [phase] - [specific action]
2. [Stale item needing attention] - [what to do]

Blockers to Resolve

• [Initiative]: [blocker description]

Quick Wins Available

• [Low-effort items ready to advance]

Output Formats

Default Summary (/roadmap )

Product Roadmap

Generated: YYYY-MM-DD Health: 🟢/🟡/🔴 [status]

Overview

Phase Distribution

[Bar chart or table]

Top Priorities

1. [P0/P1 items with next actions]

Needs Attention

• [Stale/blocked items]

Quick Actions

• /status [name] - View initiative details
• /roadmap refresh - Regenerate from initiatives

By-Phase View (/roadmap by-phase )

Group initiatives by phase with key details.

By-Persona View (/roadmap by-persona )

Group initiatives by target persona.

By-Pillar View (/roadmap by-pillar )

Group initiatives by strategic pillar.

Stale Report (/roadmap stale )

Focus on items needing attention:

• Stale (>14 days)

• At risk (7-14 days)

• Blocked

• Missing owner

Refresh (/roadmap refresh )

• Scan all initiatives/*/_meta.json

• Aggregate into roadmap.json

• Regenerate derived views

• Save snapshot to snapshots/YYYY-MM-DD.json

• Compare to previous snapshot and report changes

Snapshot Comparison

When refreshing, compare to previous snapshot:

Changes Since [previous date]

New Initiatives

• [name] added in [phase]

Phase Changes

• [name]: discovery → define

Status Changes

• [name]: on_track → at_risk

Completed

• [name] launched

Integration

After roadmap analysis:

• Deep dive on initiative → /status [name]

• Initiative stuck → /iterate [name] or resolve blocker

• Missing research → /research [name]

• Ready to build → /proto [name]