Milestone Tracker

Track and monitor project milestone progress

Instructions

1. Check Available Tools

   • Verify Linear MCP server connection
   • Check GitHub CLI availability
   • Test git repository access
   • Ensure required permissions

2. Gather Milestone Data

   • Query Linear for project milestones and roadmap items
   • Fetch GitHub milestones and their associated issues
   • Analyze git tags for historical release patterns
   • Review project documentation for roadmap information
   • Collect all active and upcoming milestones

3. Analyze Milestone Progress For each milestone:

   • Count completed vs. total tasks
   • Calculate percentage complete
   • Measure velocity trends
   • Identify blocking issues
   • Track time remaining

4. Perform Predictive Analysis

   • Calculate burn-down rate from historical data
   • Project completion dates based on velocity
   • Factor in team capacity and holidays
   • Identify critical path items
   • Assess confidence levels for predictions

5. Risk Assessment Evaluate each milestone for:

   • Schedule risk (falling behind)
   • Scope risk (expanding requirements)
   • Resource risk (team availability)
   • Dependency risk (blocked by others)
   • Technical risk (unknowns)

6. Generate Milestone Report Create comprehensive report showing:

   • Milestone timeline visualization
   • Progress indicators for each milestone
   • Predicted completion dates with confidence
   • Risk heat map
   • Recommended actions for at-risk items

7. Track Dependencies

   • Map inter-milestone dependencies
   • Identify cross-team dependencies
   • Highlight critical path
   • Show dependency impact on schedule

8. Provide Recommendations Based on analysis:

   • Suggest scope adjustments
   • Recommend resource reallocation
   • Propose timeline changes
   • Identify quick wins
   • Highlight blockers needing attention

Prerequisites

• Git repository access
• Linear MCP server connection (preferred)
• GitHub milestones or project boards
• Historical velocity data

Command Flow

1. Milestone Discovery

1. Check Linear for project milestones/roadmap items
2. Scan GitHub for milestone definitions
3. Analyze git tags for release history
4. Review README/docs for project roadmap
5. Ask user for additional context if needed

2. Comprehensive Milestone Analysis

Data Collection Sources

Linear/Project Management:
- Milestone definitions and due dates
- Associated tasks and dependencies
- Team assignments and capacity
- Progress percentages
- Blocker status

GitHub:
- Milestone issue tracking
- PR associations
- Release tags and dates
- Branch protection rules

Git History:
- Commit velocity trends
- Feature branch lifecycle
- Release cadence patterns
- Contributor availability

3. Milestone Status Report

# Milestone Tracking Report - [Project Name]
Generated: [Date]

## Executive Summary
- Total Milestones: [Count]
- On Track: [Count] ([%])
- At Risk: [Count] ([%])
- Blocked: [Count] ([%])
- Completed: [Count] ([%])

## Milestone Dashboard

### 🎯 Current Sprint Milestone: [Name]
**Target Date**: [Date] (in [X] days)
**Confidence Level**: [High/Medium/Low]

Progress: ████████░░ 80% Complete

**Key Deliverables**:
- ✅ User Authentication System
- ✅ Database Schema Migration  
- 🔄 API Integration (75%)
- ⏳ Documentation Update (0%)
- ❌ Performance Testing (Blocked)

**Health Indicators**:
- Velocity Trend: ↓ Declining (-15%)
- Burn Rate: 🔴 Behind Schedule
- Risk Level: Medium
- Team Capacity: 85% allocated

### 📅 Upcoming Milestones

#### Q1 2024: Beta Release
**Target**: March 15, 2024
**Status**: 🟡 At Risk

Timeline:

Jan ████████████░░░░░░░░ 60% Feb ░░░░░░░░░░░░░░░░░░░░ 0% Mar ░░░░░░░░░░░░░░░░░░░░ 0%

**Dependencies**:
- Alpha Testing Complete ✅
- Security Audit (In Progress)
- Marketing Website (Not Started)

**Predicted Completion**: March 22 (+7 days)
**Confidence**: 65%

#### Q2 2024: Public Launch
**Target**: June 1, 2024
**Status**: 🟢 On Track

Key Milestones Path:
1. Beta Release → 2. User Feedback Integration → 3. Production Deployment

**Critical Path Items**:
- Infrastructure Setup (Start: April 1)
- Load Testing (Duration: 2 weeks)
- Security Certification (Lead time: 4 weeks)

4. Predictive Analytics

## Completion Predictions

### Machine Learning Model Predictions
Based on historical data and current velocity:

**Beta Release Probability**:
- On Time (Mar 15): 35%
- 1 Week Delay: 45%
- 2+ Week Delay: 20%

**Factors Influencing Prediction**:
1. Current velocity 15% below plan
2. 2 critical dependencies unresolved
3. Team member on leave next week
4. Historical milestone success rate: 72%

### Monte Carlo Simulation Results
Running 1000 simulations based on task estimates:

Completion Date Distribution: Mar 10-15: ████ 20% Mar 16-22: ████████ 40% Mar 23-31: ██████ 30% April+ : ██ 10%

P50 Date: March 19 P90 Date: March 28

### Risk-Adjusted Timeline
Recommended buffer: +5 days
Confident delivery date: March 20

5. Dependency Tracking

## Milestone Dependencies

### Critical Path Analysis
```mermaid
gantt
    title Critical Path to Beta Release
    dateFormat  YYYY-MM-DD
    section Backend
    API Development    :done,    api, 2024-01-01, 30d
    Database Migration :active,  db,  2024-02-01, 14d
    Security Audit     :         sec, after db, 21d
    section Frontend  
    UI Components      :done,    ui,  2024-01-15, 21d
    Integration        :active,  int, after ui, 14d
    User Testing       :         ut,  after int, 7d
    section Deploy
    Infrastructure     :         inf, 2024-03-01, 7d
    Beta Deployment    :crit,    dep, after sec ut inf, 3d

Dependency Risk Matrix

Dependency	Impact	Likelihood	Mitigation
Security Audit Delay	High	Medium	Start process early
API Rate Limits	Medium	Low	Implement caching
Team Availability	High	High	Cross-training needed

### 6. Early Warning System

```markdown
## ⚠️ Milestone Alerts

### Immediate Attention Required

**1. Performance Testing Blocked**
- Blocker: Test environment not available
- Impact: Beta release at risk
- Days blocked: 3
- Recommended action: Escalate to DevOps

**2. Documentation Lagging**
- Progress: 0% (Should be 40%)
- Impact: User onboarding compromised
- Resource needed: Technical writer
- Recommended action: Reassign team member

### Trending Concerns

**Velocity Decline**
- 3-week trend: -15%
- Projected impact: 1-week delay
- Root cause: Increased bug fixes
- Recommendation: Add bug buffer to estimates

**Scope Creep Detected**
- New features added: 3
- Impact on timeline: +5 days
- Recommendation: Defer to next milestone

7. Actionable Recommendations

## Recommended Actions

### This Week
1. **Unblock Performance Testing**
   - Owner: [Name]
   - Action: Provision test environment
   - Due: Friday EOD

2. **Documentation Sprint**
   - Owner: [Team]
   - Action: Dedicate 2 days to docs
   - Target: 50% completion

### Next Sprint
1. **Velocity Recovery Plan**
   - Reduce scope by 20%
   - Focus on critical path items
   - Defer nice-to-have features

2. **Risk Mitigation**
   - Add 5-day buffer to timeline
   - Daily standups for blocked items
   - Escalation path defined

### Process Improvements
1. Set up automated milestone tracking
2. Weekly milestone health reviews
3. Dependency check before sprint planning

Error Handling

No Milestone Data

"No milestones found in Linear or GitHub.

To set up milestone tracking:
1. Define milestones in Linear/GitHub
2. Associate tasks with milestones
3. Set target completion dates

Would you like me to:
- Help create milestone structure?
- Import from project documentation?
- Set up basic milestones?"

Insufficient Historical Data

"Limited historical data for predictions.

Available data: [X] weeks
Recommended: 12+ weeks for accurate predictions

Current analysis based on:
- Available velocity data
- Industry benchmarks
- Task complexity estimates

Confidence level: Low-Medium"

Interactive Features

What-If Analysis

"Explore scenario planning:

1. What if we add 2 more developers?
   → Completion date: -5 days
   → Confidence: +15%

2. What if we cut scope by 20%?
   → Completion date: -8 days
   → Risk level: Low

3. What if key developer is unavailable?
   → Completion date: +12 days
   → Risk level: Critical"

Milestone Optimization

"Optimization opportunities detected:

1. **Parallelize Tasks**
   - Tasks A & B can run simultaneously
   - Time saved: 1 week

2. **Resource Reallocation**
   - Move developer from Task C to Critical Path
   - Impact: 3 days earlier completion

3. **Scope Adjustment**
   - Defer features X, Y to next milestone
   - Impact: Meet original deadline"

Export & Integration Options

1. Gantt Chart Export (Mermaid/PNG/PDF)
2. Executive Dashboard (HTML/PowerBI)
3. Status Updates (Slack/Email/Confluence)
4. Risk Register (Excel/Linear/Jira)
5. Calendar Integration (ICS/Google/Outlook)

Automation Capabilities

"Set up automated milestone monitoring:

1. Daily health checks at 9 AM
2. Weekly trend reports on Fridays
3. Alert when milestones go off-track
4. Slack notifications for blockers
5. Auto-create Linear tasks for risks

Configure automation? [Y/N]"

Best Practices

1. Update Frequently: Daily progress updates improve predictions
2. Track Dependencies: Most delays come from dependencies
3. Buffer Realistically: Use historical data for buffers
4. Communicate Early: Flag risks as soon as detected
5. Focus on Critical Path: Not all tasks equally impact timeline
6. Learn from History: Analyze past milestone performance