Pipeline Health Analyzer

Pipeline Health Analyzer

Identify pipeline risks, predict deal outcomes, and prescribe specific actions to accelerate stalled opportunities.

Contents

• references/output-template.md - Full report skeleton to populate.
• references/stage-analysis.md - Per-stage deep-dive patterns (Discovery, Demo, Proposal) and why deals stall.
• references/forecasting.md - Forecast tables, probability calibration, AI re-scoring, scenario planning.
• references/email-templates.md - Re-engagement email templates for stalled and dark deals.
• references/examples.md - Trigger phrases, a worked example request, and best practices.

Workflow

1. Obtain the pipeline data. Request a CSV export with deal name, stage, value, rep, deal age, days in current stage, last activity date, close date, and probability if not provided. 2. Compute pipeline-by-stage metrics: deal count, total value, average deal size, average days in stage, and stage-to-stage conversion rates. Compare each against historical benchmarks. 3. Score each deal across six health dimensions: stage velocity, engagement level, qualification depth, stakeholder coverage, competitive position, and 30-day momentum. 4. Identify stalled and at-risk deals. Flag deals exceeding benchmark time in stage, with no recent activity, with slipped close dates, or with single-threaded contacts. 5. For each critical deal, determine the root cause and prescribe prioritized actions (immediate, this-week, backstop). Pull re-engagement copy from references/email-templates.md. 6. Build the forecast: categorize deals (Commit/Best Case/Pipeline/Upside), calculate weighted and risk-adjusted value, check probability calibration against actual close rates, and re-score outliers. Follow references/forecasting.md. 7. Model best-case, expected, and worst-case scenarios against quota, with a mitigation plan for the downside. 8. Produce strategic recommendations across immediate, short-term, and long-term horizons. 9. Assemble the report using references/output-template.md. Use plain status words (Healthy / At Risk / Critical) and trend words (Up / Flat / Down); never use emoji. 10. Close with the report card, next-review date, and week-over-week KPIs to track.

Operating Principles

• Run weekly, not monthly; pipeline health degrades fast.
• Base assessments on activity metrics, not rep intuition.
• Disqualify dead deals early; a flowing pipeline is healthy.
• Always end with concrete next steps, not just analysis.
• Coach with the insights; do not weaponize them against reps.

See references/examples.md for trigger phrases, a worked example, and the full best-practices list.

Re-engagement Email Templates

Adapt these templates when prescribing actions for stalled or dark deals. Replace bracketed placeholders with deal specifics.

Stalled deal check-in

Use for a deal that has gone quiet after a prior interaction.

Subject: [Company] - Quick check-in

Hi [Name],

I haven't heard back since our [last interaction] on [date].

I know [current stage/topic] can involve [common challenge in this stage].

Two questions:
1. Is [project/initiative] still a priority for Q[X]?
2. If so, what's changed since we last spoke that I should know about?

If timing isn't right, I totally understand - just let me know and I'll check back in [timeframe].

[Your Name]

Dark proposal re-engagement

Use when a proposal was sent 30+ days ago with no response.

Subject: [Company] proposal - did we miss the mark?

Hi [Name],

I sent over the proposal [X] days/weeks ago and haven't heard back.

Usually when I don't hear back, it means one of three things:
1. Timing isn't right (totally fine, just let me know)
2. We missed the mark on something in the proposal
3. You're evaluating internally and I'm being impatient

Which is it? And if it's #2, what would you change?

[Your Name]

Trigger Phrases, Example Request, and Best Practices

Trigger phrases

• "Why do my deals get stuck in demo stage?"
• "Analyze my Q3 pipeline health"
• "Which deals should I focus on this week?"
• "Why is my forecast accuracy so bad?"
• "Predict which deals will close this quarter"

Example request

"I have 45 deals in my pipeline worth $3.2M. My quota is $2.5M this quarter. 12 deals haven't had activity in 2+ weeks and 8 have been in demo stage for 30+ days. Analyze my pipeline health and tell me what to do."

Response approach: 1. Request the pipeline export (CSV with all deal data) if not provided. 2. Analyze stage distribution and velocity. 3. Identify stalled deals and patterns. 4. Calculate the risk-adjusted forecast. 5. Provide specific next actions for top deals. 6. Recommend process improvements.

Best practices

1. Run weekly: Pipeline health degrades quickly; review weekly, not monthly. 2. Be honest: Identify bad deals early; disqualifying is healthy. 3. Use data: Do not rely on a rep's gut; look at activity metrics. 4. Take action: Analysis is worthless without concrete next steps. 5. Track trends: One snapshot is useful; trends over time are powerful. 6. Coach, do not criticize: Use insights to help reps improve, not punish. 7. Celebrate wins: When a stalled deal closes, share what worked.

A healthy pipeline is constantly flowing. Deals either progress, close, or get disqualified; they should not sit still.

Probability, Forecast, and Scenario Planning

Use these sections when the analysis includes a forecast or quota-attainment question.

Current forecast table

• Quota: $[X]M
• Gap to Quota: $[X]M ([X]% short/over)
• Deals Needed to Close Gap: [X] deals at avg size of $[X]K

Probability calibration

Compare forecasted probability vs. actual outcomes over the last 90 days to surface over/under-confidence.

Probability assessment guidelines:

• 90%+ = Contract sent, legal review only remaining
• 70-89% = Verbal yes, pending paperwork/approvals
• 50-69% = Strong interest, still evaluating options
• 10-49% = Early stage, many unknowns

AI-driven close probability scoring

Apply historical win/loss patterns to revise per-deal probabilities, then report the forecast delta.

Deals to INCREASE probability:

Deals to DECREASE probability:

Impact on forecast:

• Original Forecast: $[X]M
• AI-Adjusted Forecast: $[X]M
• Difference: $[X]M ([+/-X]%)

Scenario planning

Provide three scenarios with assumptions, revenue, and quota delta.

Best case (20% probability)

• Assumptions: all Commit deals close; 80% of Best Case; 60% of Pipeline; 2-3 surprise Upside wins.
• Report revenue, vs. quota, and the specific deals that must close.

Expected (60% probability)

• Assumptions: 85% of Commit; 65% of Best Case; 45% of Pipeline; 10% of Upside.
• Report revenue, vs. quota, and the normal-execution conditions.

Worst case (20% probability)

• Assumptions: 70% of Commit; 40% of Best Case; 20% of Pipeline; 0% of Upside.
• Report revenue, vs. quota, the causes, and a mitigation plan (accelerate Best Case to Commit, add top-of-funnel opportunities now, consider price flexibility).

Pipeline Health Analysis Output Template

Produce the report in this structure. Replace bracketed placeholders with real values. Use plain status words (Healthy / At Risk / Critical) and plain trend words (Up / Flat / Down). Do not use emoji.

# Pipeline Health Analysis

**Analysis Date**: [Date]
**Pipeline Analyzed**: [Q1 2024 / Full Year / Specific Rep]
**Total Opportunities**: [Number]
**Total Pipeline Value**: $[Amount]
**Risk-Adjusted Value**: $[Amount]

---

## Executive Summary

**Overall Pipeline Health**: [Healthy / At Risk / Critical]

**Key Findings**:
- [Positive finding 1 with metric]
- [Concern 1 with metric]
- [Critical issue with metric]

**Bottom Line**: [2-3 sentence summary of pipeline state and urgency]

**Forecast Confidence**: [High/Medium/Low] - [Explain reasoning]

---

## Pipeline Overview

### Pipeline by Stage

| Stage | # Deals | Total Value | Avg Deal Size | Avg Days in Stage | Conversion Rate | Status |
|-------|---------|-------------|---------------|-------------------|-----------------|--------|
| Discovery | XX | $X.XM | $XXK | XX days | XX% to Next | Healthy/At Risk/Critical |
| Demo | XX | $X.XM | $XXK | XX days | XX% to Next | Healthy/At Risk/Critical |
| Proposal | XX | $X.XM | $XXK | XX days | XX% to Next | Healthy/At Risk/Critical |
| Negotiation | XX | $X.XM | $XXK | XX days | XX% to Closed | Healthy/At Risk/Critical |
| **Total** | **XXX** | **$X.XM** | **$XXK** | **XX days avg** | **XX% overall** | |

**Stage Health Indicators**:
- Healthy: Moving at or above benchmark velocity
- At Risk: Slower than benchmark, needs attention
- Critical: Significant slowdown, immediate action required

**Benchmarks** (based on historical data):
- Discovery to Demo: [X] days average
- Demo to Proposal: [X] days average
- Proposal to Negotiation: [X] days average
- Negotiation to Closed: [X] days average

---

## Deals Requiring Immediate Attention

### Critical - High Value Stalled Deals ([N] deals)

#### Deal #1: [Company Name] - $[Amount]

**Why It's Critical**:
- Deal size: $[Amount] ([X]% of quarter)
- Stalled in [Stage] for [X] days ([X]x longer than average)
- No activity in last [X] days
- Close date slipped [X] times
- At risk of being lost to [competitor/status quo]

**Deal Details**:
- **Rep**: [Name]
- **Stage**: [Current stage]
- **Days in Stage**: [Number] (benchmark: [X] days)
- **Deal Age**: [Number] days total
- **Last Activity**: [Date] - [Type of activity]
- **Close Date**: [Date] (originally [Date])
- **Probability**: [X]% (down from [X]% last month)

**Symptoms of Stall**:
- [Symptom 1: e.g., "Champion stopped responding"]
- [Symptom 2: e.g., "Can't get meeting with economic buyer"]
- [Symptom 3: e.g., "Competitor mentioned for first time"]

**Root Cause Analysis**:
- **Primary Issue**: [What's really causing the stall]
- **Contributing Factors**: [Secondary issues]
- **Pattern**: [Have we seen this before? What happened?]

**Recommended Actions** (Prioritized):
1. **[Immediate Action]** (Do Today)
   - **What**: [Specific action to take]
   - **Why**: [Why this will help]
   - **How**: [Tactical approach]
   - **Expected Outcome**: [What you'll learn/achieve]

2. **[Short-term Action]** (This Week)
   - **What**: [Specific action]
   - **Who**: [Who should be involved]
   - **Success Metric**: [How to measure]

3. **[Backstop]** (If 1 & 2 Don't Work)
   - **What**: [Last-ditch effort or disqualification]
   - **Timing**: [When to execute]

**Re-engagement Email Template**: see references/email-templates.md

**Escalation Path**:
- If no response in 3 business days, [Manager reaches out to their executive]
- If still no response, [Consider disqualifying]

**Forecast Recommendation**:
- Move from [Current %] to [New %] probability
- Flag as "At Risk" in forecast call
- Develop backup deals to cover potential loss

---

#### Deal #2: [Company Name] - $[Amount]

[Repeat structure for each critical deal]

---

### At Risk - Deals Losing Momentum ([N] deals)

**Common Patterns**:
- [X] deals stuck in Demo stage for 30+ days
- [X] deals with decreasing engagement (less frequent contact)
- [X] deals with upcoming close dates but missing key milestones
- [X] deals where champion has gone silent

**Bulk Actions to Consider**:
1. **Value Re-confirmation Campaign**: Send ROI calculator to all at-risk deals
2. **Executive Engagement**: Get your VP to reach out to their C-level
3. **Event Invitation**: Invite to exclusive webinar/dinner to re-engage
4. **Competitive Intelligence**: Share relevant case study of competitor customer switching to you

**Individual Deal Summary**:

| Deal | Value | Stage | Days Stalled | Issue | Recommended Action |
|------|-------|-------|--------------|-------|-------------------|
| [Company 1] | $XXK | Demo | 45 | Can't get 2nd meeting | Multi-thread: Find another contact |
| [Company 2] | $XXK | Proposal | 32 | Awaiting legal review | Offer to connect legal teams directly |
| [Company 3] | $XXK | Discovery | 28 | "We're busy with X" | Create urgency: Limited time offer |

[Continue for all at-risk deals]

---

## Probability Analysis & Forecast

Insert the current forecast table, probability calibration, AI-driven re-scoring, and the three scenarios here. See references/forecasting.md for the full tables and assumptions.

---

## Stage-Specific Analysis

Insert a per-stage deep dive (Discovery, Demo, Proposal) here when stage-level data is available. See references/stage-analysis.md for the structure.

---

## Strategic Recommendations

### Immediate Actions (This Week)

1. **Address [X] Critical Stalled Deals**
   - **Owner**: [Sales Manager]
   - **Action**: Personal outreach to top [X] stalled deals
   - **Goal**: Get meetings rescheduled or disqualify
   - **Impact**: $[X]M at risk

2. **Demo Stage Intervention**
   - **Owner**: [Sales Enablement]
   - **Action**: Audit next [X] demos for "right people" attendance
   - **Goal**: Increase Demo to Proposal conversion from [X]% to [X]%
   - **Impact**: [X] more deals per month

3. **Forecast Recalibration**
   - **Owner**: [Sales Ops]
   - **Action**: Review AI probability adjustments with reps
   - **Goal**: Improve forecast accuracy by [X]%
   - **Impact**: Better planning and resource allocation

---

### Short-term Actions (This Month)

4. **Implement Stage Duration Alerts**
   - Set automatic alerts when deals exceed benchmark time in stage
   - Manager reviews all deals >30 days in any stage

5. **Multi-Threading Initiative**
   - Deals with only 1 contact have [X]% lower close rate
   - Require 3+ contacts per deal in CRM
   - Train reps on "economic buyer" access strategies

6. **Competitor Win/Loss Analysis**
   - [X] deals lost to [Competitor] in last 90 days
   - Interview lost prospects to understand why
   - Adjust competitive positioning

---

### Long-term Improvements (This Quarter)

7. **Optimize Deal Stages**
   - Current 5-stage pipeline may need adjustment
   - Consider: Discovery -> Technical Validation -> Business Case -> Proposal -> Negotiation
   - Clearer exit criteria for each stage

8. **Predictive Deal Scoring**
   - Build model on historical win/loss data
   - Auto-score deals weekly on health dimensions
   - Surface at-risk deals before reps recognize them

9. **Sales Process Consistency**
   - [X]% variation in how reps work deals
   - Document best practices from top performers
   - Create playbooks for each stage

---

## Pipeline Health Report Card

| Metric | Current | Target | Status | Trend |
|--------|---------|--------|--------|-------|
| Overall Pipeline Value | $X.XM | $X.XM | Healthy/At Risk/Critical | Up/Flat/Down |
| Weighted Pipeline | $X.XM | $X.XM | Healthy/At Risk/Critical | Up/Flat/Down |
| # Deals in Pipeline | XXX | XXX | Healthy/At Risk/Critical | Up/Flat/Down |
| Avg Deal Size | $XXK | $XXK | Healthy/At Risk/Critical | Up/Flat/Down |
| Avg Sales Cycle | XX days | XX days | Healthy/At Risk/Critical | Up/Flat/Down |
| Win Rate | XX% | XX% | Healthy/At Risk/Critical | Up/Flat/Down |
| Forecast Accuracy | XX% | XX% | Healthy/At Risk/Critical | Up/Flat/Down |
| Stage Conversion | XX% | XX% | Healthy/At Risk/Critical | Up/Flat/Down |

**Overall Grade**: [A/B/C/D/F]

---

## Next Pipeline Review

**Schedule next review for**: [Date, 1 week from now]

**Focus areas for next review**:
- Status update on [X] critical stalled deals
- Demo stage conversion rate (target: improve to [X]%)
- New deals added to top of funnel
- Forecast accuracy check

**KPIs to track week-over-week**:
- Deals moved to Commit status
- Deals closed vs. forecast
- Deals disqualified (healthy pipeline management)
- New opportunities created

Stage-Specific Analysis

Include a deep dive per stage when the pipeline export contains stage-level data. Use the patterns below.

Discovery Stage Deep Dive

Health: [Healthy / At Risk / Critical]

Metrics:

• Deals in stage: [X]
• Total value: $[X]
• Avg time in stage: [X] days (benchmark: [X] days)
• Conversion to Demo: [X]% (benchmark: [X]%)

Issues Identified: 1. Issue: [X] deals over 21 days in Discovery

• Impact: Discovery should take 7-14 days max
• Root Cause: Reps not asking hard qualification questions early
• Fix: Implement MEDDIC scorecard requirement to move to Demo

2. Issue: [X]% of Discovery deals have no next step scheduled

• Impact: Deals go dormant
• Fix: Make "scheduled next meeting" required field to save opp

Recommendations:

• Train reps on faster qualification (see Sales Methodology Implementer skill)
• Set stage duration alerts: if >14 days in Discovery, flag to manager
• Require next meeting date before advancing stage

---

Demo Stage Deep Dive

Health: [Healthy / At Risk / Critical]

Metrics:

• Deals in stage: [X]
• Total value: $[X]
• Avg time in stage: [X] days (benchmark: [X] days)
• Conversion to Proposal: [X]% (benchmark: [X]%)

Why Deals Get Stuck Here:

Based on analysis of [X] stalled deals in Demo stage, the top reasons are:

1. Wrong People in Demo ([X]% of stalls)

• Showed demo to users, not decision-makers
• Decision-makers didn't see value firsthand
• Fix: Require economic buyer on demo or do 2-tier demo approach

2. Demo Didn't Address Pain ([X]% of stalls)

• Generic demo, not tailored to their specific problem
• Prospect said "interesting" but didn't see immediate relevance
• Fix: Discovery call summary required before scheduling demo

3. No Clear Next Steps ([X]% of stalls)

• Demo ended with "we'll get back to you"
• Rep didn't book follow-up meeting before ending call
• Fix: Never end demo without next meeting scheduled

Action Plan for Demo Stage:

• Audit next 5 demos: are right people attending?
• Create "Demo Success Criteria" checklist (must-haves for demo)
• Role play: "Booking the next meeting" before demo ends

---

Proposal Stage Deep Dive

Health: [Healthy / At Risk / Critical]

Metrics:

• Deals in stage: [X]
• Total value: $[X]
• Avg time in stage: [X] days (benchmark: [X] days)
• Conversion to Negotiation: [X]% (benchmark: [X]%)

Red Flag Alert: [X] proposals sent over 30 days ago with no response

Why Proposals Go Dark: 1. Sent Too Early - Sent before they were ready to evaluate 2. Sent Wrong Format - PDF when they needed live presentation 3. Too Generic - Didn't address their specific pain/use case 4. No Champion - Sent to contact who can't advocate internally

Immediate Actions: 1. Re-engage all [X] dark proposals (see references/email-templates.md, "Dark proposal re-engagement"). 2. For proposals going to negotiation smoothly: document what they did right. 3. Create "Proposal Readiness Checklist" so reps don't send too early.