Check Pipeline Health

Sales Leader, Revenue Operations, Executive and Founder.

• Start of a quarter or half.
• When the forecast and the pipeline tell different stories.
• Before committing a number to the board.

• Pipeline by stage with counts and value
• Historical win rate and average sales cycle by stage
• This period's target and how much is already closed

Best for one task. Copy it, add your information, and run it in your AI assistant.

You are a revenue operations analyst. Here is my current pipeline by stage: [paste]. Here are my historical win rates and cycle times by stage: [paste]. Target is [NUMBER] with [AMOUNT] already closed. Tell me plainly: does this pipeline support the number? Where are the three biggest leaks (stage where deals die, age past cycle, coverage shortfall)? What should I inspect this week? Use my numbers only. Where you make an assumption, name it.

Best for repeatable work. The file includes the process, required inputs, decision rules, quality checks, and output format.

---
name: check-pipeline-health
description: A blunt read on whether your pipeline can support the number, with the three leaks to fix first.
license: MIT
metadata:
  author: The Revenue AI Report
  version: 1.0.0
  last-reviewed: 2026-09-04
  source: https://www.therevenueaireport.com/skills/check-pipeline-health
---

# Check Pipeline Health

A blunt read on whether your pipeline can support the number, with the three leaks to fix first.

## When to use this skill

- Start of a quarter or half.
- When the forecast and the pipeline tell different stories.
- Before committing a number to the board.

## Inputs to collect

- Pipeline by stage with counts and value
- Historical win rate and average sales cycle by stage
- This period's target and how much is already closed

## Process

1. Export pipeline by stage with age in stage.
2. Add your real historical conversion and cycle numbers. Do not use benchmarks.
3. Ask for the read. Demand it use only your numbers.
4. Validate the three leaks with the managers who own those stages.
5. Pick one fix per leak and date it.

## Decision rules

- Coverage below your historical requirement is a pipeline problem, not a closing problem. Say so.
- Deals aged past twice the average cycle count as dead until a buyer action proves otherwise.
- If a stage converts under half the historical rate for two periods, inspect the stage definition, not the reps.

## Output requirements

- A yes or no on whether the pipeline supports the number, with the math shown.
- The three leaks, ranked by dollars at risk.
- An inspection list for this week.

## Quality checks

- All math uses your pasted numbers, not industry ratios.
- Assumptions are listed, not hidden.
- Each leak has an owner and a next step.

## Limitations

- Aggregates hide single-deal risk. A pipeline can look healthy and still miss on one big deal.
- Historical rates break when the market or your motion just changed. Say so if they did.

## Example input

Stage 2: 40 deals, $4.1M, avg age 61 days (cycle avg 38). Historical stage-2-to-close: 18%. Target $2.5M, closed $0.9M.

## Example output

Verdict: no. Stage-2 value at historical conversion yields about $740k, leaving a gap of roughly $860k against the remaining $1.6M. Leak one: stage 2 aging 60 percent past cycle, meaning a slice of the $4.1M is stale. Inspection: every stage-2 deal older than 60 days needs a buyer-verified next step this week.

## Review checklist

- Did the read use your numbers only?
- Are stale deals reclassified honestly?
- Does each leak have an owner and a date?

## Works with

- Playbook: Make conversation data do work (L3) (sales, L3) https://www.therevenueaireport.com/playbooks/conversation-data-to-work-l3
- Playbook: Put an answer layer on the warehouse you already paid for (L4) (revops, L4) https://www.therevenueaireport.com/playbooks/answer-layer-on-warehouse-l4
- Playbook: Point retrieval at the revenue corpus (L4) (enablement, L4) https://www.therevenueaireport.com/playbooks/point-retrieval-at-revenue-corpus-l4
- Tool: Cycle (Knowledge & Search) https://www.therevenueaireport.com/tools/cycle
- Tool: BoostUp (Sales & Revenue Intelligence) https://www.therevenueaireport.com/tools/boostup
- Tool: Gyaan (Data & Analytics) https://www.therevenueaireport.com/tools/gyaan
- Tool: Revenue.io (Sales & Revenue Intelligence) https://www.therevenueaireport.com/tools/revenue-io
- Tool: Salesforce (Sales & Revenue Intelligence) https://www.therevenueaireport.com/tools/salesforce

## Rules of conduct

- Write for a Director, VP, or operator. Short sentences. Explain uncommon terms.
- Separate facts from assumptions. Never hide uncertainty.
- Do not invent numbers, benchmarks, quotes, or customer names.
- Do not send messages, change CRM records, or publish anything unless the user explicitly asks.
- Flag when a decision needs human review.

## Evidence

This skill is grounded in The Revenue AI Report research:
- https://www.therevenueaireport.com/research/proof-gap
- Related analysis: https://www.therevenueaireport.com/blog/pipeline-truth-test-for-ai




Source and updates: https://www.therevenueaireport.com/skills/check-pipeline-health

1. 1.Export pipeline by stage with age in stage.
2. 2.Add your real historical conversion and cycle numbers. Do not use benchmarks.
3. 3.Ask for the read. Demand it use only your numbers.
4. 4.Validate the three leaks with the managers who own those stages.
5. 5.Pick one fix per leak and date it.

• Coverage below your historical requirement is a pipeline problem, not a closing problem. Say so.
• Deals aged past twice the average cycle count as dead until a buyer action proves otherwise.
• If a stage converts under half the historical rate for two periods, inspect the stage definition, not the reps.

• A yes or no on whether the pipeline supports the number, with the math shown.
• The three leaks, ranked by dollars at risk.
• An inspection list for this week.

Stage 2: 40 deals, $4.1M, avg age 61 days (cycle avg 38). Historical stage-2-to-close: 18%. Target $2.5M, closed $0.9M.

Verdict: no. Stage-2 value at historical conversion yields about $740k, leaving a gap of roughly $860k against the remaining $1.6M. Leak one: stage 2 aging 60 percent past cycle, meaning a slice of the $4.1M is stale. Inspection: every stage-2 deal older than 60 days needs a buyer-verified next step this week.

• Did the read use your numbers only?
• Are stale deals reclassified honestly?
• Does each leak have an owner and a date?

What does the Check Pipeline Health skill do?

A blunt read on whether your pipeline can support the number, with the three leaks to fix first.

Who is the Check Pipeline Health skill for?

Sales Leader, Revenue Operations, Executive and Founder. It sits at the intermediate level and takes about 45 minutes.

What do I need before I start?

Collect these first: Pipeline by stage with counts and value; Historical win rate and average sales cycle by stage; This period's target and how much is already closed.

What is the difference between the quick prompt and the SKILL.md file?

The quick prompt is for one task. Copy it, add your information, run it. The SKILL.md file is for repeatable work: it carries the process, required inputs, decision rules, quality checks, and output format so an AI assistant runs the same way every time.

What should I check before trusting the output?

Did the read use your numbers only? Are stale deals reclassified honestly? Does each leak have an owner and a date?

Is it free to use?

Yes. Every skill on The Revenue AI Report is free and published under the MIT license. Attribution is welcome, not required.

• Aggregates hide single-deal risk. A pipeline can look healthy and still miss on one big deal.
• Historical rates break when the market or your motion just changed. Say so if they did.

Run the skill, then roll it out with a playbook. Vendor links are supporting context, not a recommendation.

• Playbook: Make conversation data do work (L3) (sales, L3 L3 Integrated)
• Playbook: Put an answer layer on the warehouse you already paid for (L4) (revops, L4 L4 Orchestrated)
• Playbook: Point retrieval at the revenue corpus (L4) (enablement, L4 L4 Orchestrated)
• Tool: Cycle (Knowledge & Search)
• Tool: BoostUp (Sales & Revenue Intelligence)
• Tool: Gyaan (Data & Analytics)
• Tool: Revenue.io (Sales & Revenue Intelligence)
• Tool: Salesforce (Sales & Revenue Intelligence)

• Research: proof gap
• Related analysis