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

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

Opportunities

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

---

Step 5: Generate Pipeline Health Report

Present findings in this format:

# 📊 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:

1. Deep dive on specific deals or stages?
2. Create action plan for pipeline generation?
3. Draft forecast update for leadership?
4. Review deals to qualify out?"

---

Timeframe Filtering

When user specifies timeframe:

1. "this quarter" - Deals closing this quarter
2. "Q1" - Deals in Q1 specifically
3. "this month" - Deals closing this month

Filter metrics and analysis to that window.

---

Forecast Mode

When user runs /pipeline-health forecast:

Focus exclusively on:

1. Commit vs Best Case vs Target
2. Gap analysis
3. Risk factors in commit deals
4. Actions to close gap
5. Deals likely to slip
6. 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

# 📊 Pipeline Health Report

**Period:** Q1 2026
**Target:** $500,000
**Report date:** 2026-01-28

---

## 🎯 Forecast Summary

### Current Position

| Forecast Type | Amount | % of Target | Gap to Target |
|---------------|--------|-------------|---------------|
| **Commit** (90%+) | $235,000 | 47% | $265,000 |
| **Best Case** (75%+) | $430,000 | 86% | $70,000 |
| **Pipeline** (weighted) | $580,000 | 116% | +$80,000 |

**Overall health:** At Risk (Commit is 47% of target with 8 weeks left in quarter)

---

## 📈 Pipeline Coverage

**Total pipeline:** $847,000
**Coverage ratio:** 1.7x (Total pipeline / Target)

**Status:** 🚨 At Risk
- ✅ 3x+ coverage = Healthy
- ⚠️ 2-3x coverage = Adequate  
- 🚨 <2x coverage = At Risk **(You are here: 1.7x)**

**Action needed:** YES - Need $400K+ in new pipeline to reach 3x coverage

---

## ⏱️ Velocity Analysis

**Average sales cycle:** 45 days
**Deals exceeding cycle:** 3 deals (TechStart - 62 days, GlobalCo - 58 days, OldCo - 71 days)

**Time in stage (average):**
- Discovery: 7 days
- Demo: 10 days
- Proposal: 12 days ⚠️ (2x typical)
- Negotiation: 10 days
- Contract: 6 days

**Slow movers:** (50%+ over average)
- **TechStart** - 18 days in Proposal (avg: 12 days) - STALE
- **InnovateCo** - 18 days in Discovery (avg: 7 days) - Needs qualification

---

## 🔄 Conversion Health

**Stage conversion rates:**

| From Stage | To Stage | Rate | Benchmark | Status |
|------------|----------|------|-----------|--------|
| Discovery | Demo | 67% | ~50% | ✅ Good |
| Demo | Proposal | 75% | ~50% | ✅ Good |
| Proposal | Negotiation | 40% | ~60% | 🚨 **Issue** |
| Negotiation | Contract | 80% | ~75% | ✅ Good |
| Contract | Close | 100% | ~90% | ✅ Good |

**Bottleneck stages:** Proposal → Negotiation (40% conversion, should be ~60%)
- Issue: Deals getting stuck after proposal sent
- Root cause: Pricing concerns OR lack of follow-up

---

## 🚨 Risk Factors

### High-Risk Items

1. **Heavy deal concentration**
   - Top 3 deals (Acme, DataFlow, TechStart) = 68% of commit
   - Risk: If one slips, we miss target by 20%+

2. **DataFlow - $120,XXX** (25% of commit)
   - Risk: Evaluating ProductX competitor, concerned about dashboards
   - Mitigation: Executive call Friday - prep competitive positioning NOW

3. **TechStart - $75,XXX** (18% of commit)
   - Risk: 18 days stale, no response to proposal
   - Mitigation: Last-chance outreach today

### Stage Issues

- **Too many in Proposal:** 4 deals ($295K)
  - Bottleneck indicator (40% conversion rate)
  - Action: Review what's blocking progression - pricing? timeline? features?

- **Aging deals:** 3 deals over 60 days old ($215K)
  - TechStart, GlobalCo, OldCo - may never close
  - Action: Qualify out or re-engage with fresh approach

---

## 💡 Opportunities

### Quick Wins (Focus Here)

**StartupX - $40,XXX**
- Stage: Contract - Signatures received
- Days in stage: 1
- Action: Process payment today
- Impact: Closes gap to target by 8%

**NewCorp - $55,XXX**
- Stage: Negotiation
- Days in stage: 4
- Action: Final terms call tomorrow
- Impact: High confidence, contract by end of week

### Stuck Deals That Could Move

**GlobalCo - $95,XXX**
- Stage: Discovery (9 days)
- Issue: Waiting on champion Sarah to schedule demo
- Action: Executive reach-out to Sarah's boss to create urgency
- Impact: Could close this quarter if we move fast

---

## 📊 Pipeline Distribution

**By Stage:**
- Discovery: 3 deals - $220,000 (26%)
- Demo: 2 deals - $105,000 (12%)
- Proposal: 4 deals - $295,000 (35%) ⚠️ **Bottleneck**
- Negotiation: 2 deals - $175,000 (21%)
- Contract: 1 deal - $52,000 (6%)

**By Close Date:**
- This week: 1 deal - $40,000
- Rest of month: 1 deal - $55,000
- Feb: 4 deals - $285,000
- March+: 6 deals - $467,000

---

## 🎯 Recommended Actions

### Immediate (This Week)

1. **Save at-risk commit deals** - TechStart ($75K) + DataFlow ($120K) = $195K at risk
2. **Close StartupX** - $40K ready to process, no-brainer
3. **Push NewCorp to contract** - $55K, final call tomorrow

### Strategic (This Month)

1. **Generate $400K+ new pipeline** - Coverage at 1.7x, need 3.0x (gap: $1M in gross pipeline)
2. **Fix Proposal stage** - 4 deals stuck, 40% conversion vs 60% benchmark
3. **Qualify out aging deals** - 3 deals over 60 days, likely dead

### Health Tracking

- **Next review:** Friday (before week ends)
- **Metrics to watch:** 
  - Commit forecast (need to hit 70%+ by mid-Feb)
  - Proposal conversion rate
  - New pipeline adds per week