pipeline-health

Purpose

Analyze pipeline coverage, conversion rates, velocity, and forecast accuracy to ensure you're on track to hit targets and identify where to focus attention.

Usage

/pipeline-health - Full pipeline analysis
/pipeline-health [timeframe] - Focus on specific period (e.g., "this quarter", "Q1")
/pipeline-health forecast - Forecast-focused view

Step 1: Gather Pipeline Data

Collect deal information from 04-Projects/:

For Each Deal Extract:

Company name
Deal value/size
Current stage
Entry date to current stage (or last modified date)
Close date (if specified)
Confidence level (if mentioned)

Read Targets:

Check 01-Quarter_Goals/Quarter_Goals.md or user files for revenue targets
Check for quota information
Typical sales cycle length (or calculate from historical data)

Step 2: Calculate Pipeline Metrics

Coverage Metrics

Pipeline coverage ratio = Total pipeline value / Target

3x coverage = Healthy
2-3x coverage = Adequate
<2x coverage = At Risk

Weighted pipeline = Sum of (Deal value × Stage probability)

Discovery: 10%
Demo: 25%
Proposal: 50%
Negotiation: 75%
Contract: 90%

Velocity Metrics

Average time in stage:

For each stage, calculate average days deals spend there
Flag deals exceeding average by 50%+

Average sales cycle:

From discovery to close
Compare current deals to average

Conversion Metrics

Stage conversion rates:

Discovery → Demo: X%
Demo → Proposal: X%
Proposal → Negotiation: X%
Negotiation → Contract: X%
Contract → Close: X%

(Calculate from historical closed deals if data available)

Step 3: Analyze Forecast

Commit vs Best Case vs Pipeline

Commit forecast:

Contract stage deals (90% probability)
Total commit value

Best case forecast:

Negotiation + Contract (75%+ probability)
Total best case value

Pipeline forecast:

All active deals weighted by stage probability

Gap Analysis

Target: [Quota or goal] Commit: [Amount] - [Gap to target] Best case: [Amount] - [Gap to target] Coverage: [Pipeline / Target ratio]

Step 4: Identify Issues

Red Flags

Insufficient coverage - Pipeline < 3x target
Slow velocity - Deals stuck in stages too long
Low conversion - Stages with poor conversion rates
Forecast risk - Heavy reliance on few large deals
Stage bunching - Too many deals in one stage
Aging deals - Deals past typical sales cycle

Opportunities

Quick wins - Deals close to closing that need push
Stuck deals - Deals that could move with attention
New pipeline needed - If coverage insufficient

Step 5: Generate Pipeline Health Report

Present findings in this format:

markdown

# 📊 Pipeline Health Report

**Period:** [Timeframe]
**Target:** $[Target amount]
**Report date:** [Today]

---

## 🎯 Forecast Summary

### Current Position

| Forecast Type | Amount | % of Target | Gap to Target |
|---------------|--------|-------------|---------------|
| **Commit** (90%+) | $XXX,XXX | XX% | $XX,XXX |
| **Best Case** (75%+) | $XXX,XXX | XX% | $XX,XXX |
| **Pipeline** (weighted) | $XXX,XXX | XX% | $XX,XXX |

**Overall health:** [On Track / At Risk / Behind]

---

## 📈 Pipeline Coverage

**Total pipeline:** $XXX,XXX
**Coverage ratio:** X.Xx (Total pipeline / Target)

**Status:**
- ✅ 3x+ coverage = Healthy
- ⚠️ 2-3x coverage = Adequate (yours: X.Xx)
- 🚨 <2x coverage = At Risk

**Action needed:** [Yes/No - if <3x, need more pipeline generation]

---

## ⏱️ Velocity Analysis

**Average sales cycle:** XX days
**Deals exceeding cycle:** [X deals] - [List if important]

**Time in stage (average):**
- Discovery: XX days
- Demo: XX days
- Proposal: XX days
- Negotiation: XX days
- Contract: XX days

**Slow movers:** (50%+ over average)
- [Company] - XX days in [stage] (avg: XX days)
- [Company] - XX days in [stage] (avg: XX days)

---

## 🔄 Conversion Health

**Stage conversion rates:**

| From Stage | To Stage | Rate | Benchmark | Status |
|------------|----------|------|-----------|--------|
| Discovery | Demo | XX% | ~50% | ✅/⚠️/🚨 |
| Demo | Proposal | XX% | ~50% | ✅/⚠️/🚨 |
| Proposal | Negotiation | XX% | ~60% | ✅/⚠️/🚨 |
| Negotiation | Contract | XX% | ~75% | ✅/⚠️/🚨 |
| Contract | Close | XX% | ~90% | ✅/⚠️/🚨 |

**Bottleneck stages:** [Stages with low conversion]

---

## 🚨 Risk Factors

### High-Risk Items

1. **Heavy deal concentration**
   - Top 3 deals = XX% of commit
   - Risk: If one slips, major impact

2. **[Deal Name] - $XXX,XXX**
   - Risk: [Specific risk]
   - Mitigation: [Action needed]

### Stage Issues

- **Too many in [stage]:** [X deals]
  - Bottleneck indicator
  - Action: Review what's blocking progression

- **Aging deals:** [X deals over XX days old]
  - May never close
  - Action: Qualify out or re-engage

---

## 💡 Opportunities

### Quick Wins (Focus Here)

**[Company] - $XX,XXX**
- Stage: Contract Review
- Days in stage: 5
- Action: One call away from close
- Impact: Closes gap by XX%

**[Company] - $XX,XXX**
- Stage: Negotiation
- Days in stage: 8
- Action: Address pricing concern
- Impact: High confidence, near close

### Stuck Deals That Could Move

**[Company] - $XX,XXX**
- Stage: Proposal (15 days)
- Issue: Waiting on champion response
- Action: Executive reach-out

---

## 📊 Pipeline Distribution

**By Stage:**
- Discovery: [X deals] - $XXX,XXX
- Demo: [X deals] - $XXX,XXX
- Proposal: [X deals] - $XXX,XXX
- Negotiation: [X deals] - $XXX,XXX
- Contract: [X deals] - $XXX,XXX

**By Close Date:**
- This week: [X deals] - $XXX,XXX
- This month: [X deals] - $XXX,XXX
- This quarter: [X deals] - $XXX,XXX
- Beyond quarter: [X deals] - $XXX,XXX

---

## 🎯 Recommended Actions

### Immediate (This Week)

1. **[Action]** - [Deals affected] - [Impact]
2. **[Action]** - [Deals affected] - [Impact]
3. **[Action]** - [Deals affected] - [Impact]

### Strategic (This Month)

1. **Generate new pipeline** - Coverage at X.Xx, need X.Xx
2. **Accelerate [stage]** - X deals stuck, average XX days
3. **Improve [stage] conversion** - Currently XX%, need XX%

### Health Tracking

- **Next review:** [Suggested date]
- **Metrics to watch:** [Key metrics that need improvement]

Step 6: Offer Actions

After presenting the report, ask:

"Want me to:

Deep dive on specific deals or stages?

Create action plan for pipeline generation?

Draft forecast update for leadership?

Review deals to qualify out?"

Timeframe Filtering

When user specifies timeframe:

"this quarter" - Deals closing this quarter
"Q1" - Deals in Q1 specifically
"this month" - Deals closing this month

Filter metrics and analysis to that window.

Forecast Mode

When user runs /pipeline-health forecast:

Focus exclusively on:

Commit vs Best Case vs Target
Gap analysis
Risk factors in commit deals
Actions to close gap
Deals likely to slip
Upside opportunities

Integration with Other Skills

After running: Suggest /deal-review for deal-level deep dive
If coverage low: Suggest reviewing lead generation strategy
If velocity slow: Suggest /process-audit on sales process
Before leadership meeting: Run this + prepare summary

Example Output