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
| Metric | Value |
|--------|-------|
| Total Initiatives | X |
| On Track | X |
| At Risk | X |
| Blocked | X |

## 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)

1. Scan all initiatives/*/\_meta.json
2. Aggregate into roadmap.json
3. Regenerate derived views
4. Save snapshot to snapshots/YYYY-MM-DD.json
5. 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]