SimonTheSalesBooster Skill: Pipeline Health Analyzer
What This Skill Does
Performs a deep diagnostic of a sales pipeline to identify stuck deals, coverage gaps, forecast risk, and velocity issues. Outputs an actionable pipeline review with prioritized deal recommendations, next steps, and a pipeline health score.
When to Use
- You're doing a weekly or monthly pipeline review
- Your forecast feels unreliable or you're missing your number
- Deals are sitting in stages too long with no movement
- You want to coach your team on which deals to prioritize
Inputs Required
Before running this skill, ask the user to provide (can be pasted as text or uploaded as CSV/export):
- Deal list — company name, deal value, stage, close date, last activity date, next step
- Sales cycle benchmark — average days per stage (if known)
- Monthly/quarterly revenue target
- Current month/quarter close date
- Number of reps (if team pipeline)
Step-by-Step Instructions
Step 1 — Calculate Pipeline Coverage Ratio
Pipeline Coverage = Total Pipeline Value ÷ Revenue Target
Healthy coverage ratios:
- 3x = minimum (you need 3x pipeline to hit your number)
- 4–5x = healthy
- 6x+ = risk of sandbagging or poor qualification
- Under 2x = red alert — pipeline emergency
Output: Coverage ratio + color-coded status (red/yellow/green)
Step 2 — Stage Velocity Analysis
For each pipeline stage, calculate:
- Average days in stage (from deal data provided)
- Compare to benchmark (or industry standard if no benchmark)
- Flag stalled deals — any deal sitting 1.5x longer than average in its stage
Standard B2B SaaS benchmarks (adjust based on user's context):
Stage | Healthy Duration | Stalled Threshold
Discovery/Qualify | 3–7 days | >14 days
Demo/Evaluation | 7–14 days | >21 days
Proposal/Pricing | 5–10 days | >21 days
Negotiation | 5–14 days | >30 days
Verbal Commit | 3–7 days | >14 days
Step 3 — Deal-Level Risk Scoring
Score each deal from 1–10 on probability of closing this period:
| Risk Factor | Points Deducted |
|---|---|
| No activity in 14+ days | -2 |
| No defined next step | -2 |
| No economic buyer engaged | -2 |
| Close date is "end of quarter" with no urgency | -1 |
| Deal has been pushed from previous period | -2 |
| No champion confirmed | -1 |
| Missing mutual close plan | -1 |
| Competitor present with no differentiation | -1 |
Score 8–10 = commit | 5–7 = upside | Under 5 = pipeline (not forecast)
Step 4 — Identify Priority Actions
For each deal, recommend a specific next action based on its risk profile:
If stalled at Discovery: → "Re-engage with a relevant insight or trigger. Send the 'Have things changed?' message."
If stalled at Proposal: → "Schedule a proposal review call — proposals don't close themselves. Get the economic buyer on a call."
If missing next step: → "Reach out today. Use: 'Hey [Name], I want to make sure this stays on track for [date]. Can we confirm [next step]?'"
If close date keeps slipping: → "Have a direct conversation about what's really in the way. Fake close dates are a forecast killer."
If no economic buyer: → "Ask your champion: 'When we're ready to move forward, who else would need to weigh in?'"
Step 5 — Generate Pipeline Health Score & Summary
Pipeline Health Score (0–100):
- Coverage ratio: 25 points
- Average deal velocity: 20 points
- % of deals with defined next step: 20 points
- % of deals with economic buyer engaged: 20 points
- Close date distribution (not all stacked at quarter end): 15 points
Output Summary:
PIPELINE HEALTH REPORT — [Date]
Overall Health Score: [X/100] — [RED / YELLOW / GREEN]
Coverage: [X]x — [Status]
Total Pipeline: $[X]
Target: $[X]
Gap to target: $[X]
CRITICAL DEALS (must close to hit number):
1. [Deal] — $[X] — Action: [...]
2. [Deal] — $[X] — Action: [...]
STALLED DEALS (at risk of slipping):
1. [Deal] — In [Stage] for [X] days — Action: [...]
FORECAST COMMITS:
[List of deals scored 8–10]
THIS WEEK'S FOCUS:
Priority 1: [Specific deal action]
Priority 2: [Specific deal action]
Priority 3: [Specific deal action]
Output Format
Deliver:
- Pipeline Coverage Ratio with status
- Stage Velocity Analysis (by stage)
- Deal Risk Scores (all deals)
- Priority Action List (top 5 this week)
- Pipeline Health Score with summary report
Pro Tips
- Run this review every Monday morning — 30 minutes of pipeline hygiene prevents missed quarters
- Any deal without a next step isn't a deal — it's a wish
- The fastest way to improve forecast accuracy is to ruthlessly remove deals that haven't had activity in 30+ days
- The best indicator of a deal closing is whether the prospect is doing work (sending docs, scheduling calls, looping in stakeholders) — not whether you are
- A pipeline review is a coaching tool, not a status update — always end with "what's the next step and when?"