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4.9IntermediateModule 04 · Sell Like a Pro

Pipeline Review - Deal Health Check

Your pipeline looks healthy but your close rate is lower than expected. Deals sit in the same

The prompt

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4.9Pipeline Review - Deal Health Check
Act as a sales pipeline analyst conducting a deal health review. For each deal I describe, score it against six criteria (Yes / Partial / No) and give a health rating: CRITERIA: 1. Confirmed problem : Do they acknowledge the pain clearly? 2. Decision-maker : Have I spoken directly to the buyer? 3. Budget : Is budget confirmed or realistically available? 4. Timeline : Is there a defined date with stakes attached? 5. Objections : Have key objections been surfaced and handled? 6. Next step : Is there a mutual commitment with a date? Deal 1 : [STAGE, LAST CONTACT, WHAT WAS AGREED, WHAT IS BLOCKING] Deal 2 : [STAGE, LAST CONTACT, WHAT WAS AGREED, WHAT IS BLOCKING] For each : Health rating (Strong / At Risk / Stalled) and one specific action to take this week. Deal health check ranges from healthy to at risk. Decision-Maker Timeline with Contacted Consequences Mutual Next Step Real decision-maker Timeline with clear No mutual next step has been reached consequences is set with a date Healthy At Risk Confirmed Problem Budget Defined Objections Surfaced Problem is clearly Budget for the deal Significant objections have identified is established been raised
LabelsReplace theseSwap the role below

LabelsReplace theseSwap the role below

Pro tip, from the book

The most honest pipeline review question is: 'If this deal were to close, what would have to happen in the next 7 days?' If you can't answer that specifically, the deal has no momentum. Deals without momentum don't close, they disappear.

Who should run this prompt

Module role profile

Who should prepare and run your sales conversations? Every stage of a sale requires a different mindset. The person who writes great cold outreach thinks differently from the person who closes enterprise deals. The buyer's procurement officer thinks differently from both. Use internal roles to prepare and execute. Use outside perspectives to find the objections, hesitations, and real decision criteria before they surface in a live conversation.

Choose any role to drop it into the prompt above. Only the highlighted opening clause changes — the rest of the prompt stays exactly as printed.

Internal rolesThink from inside the organisation
Outside perspectivesChallenge your blind spots

◆◆◆◆◆ → ◆ seniority, board level down to specialist outside the organisation

How to make any role sharper

  1. Add years of experience: "...with 15 years in enterprise SaaS" produces different depth than just the title.
  2. Add what they care most about: "You care most about [X]" shapes every word of the output.
  3. Add their communication style: "Be direct. Flag risks first. No jargon." changes the tone entirely.
See also: 1.3 Role Prompting - The Expert Chair

Use this when

The problem it solves

stage for weeks. You discover deals are stuck or dead - too late to recover them.

How the framework works

From the printed page

A Deal Health Check is a structured review of each active opportunity against a set of objective criteria: Is there a confirmed problem? Have you spoken to the real decision- maker? Is there a defined budget? Is there a timeline with consequences for missing it? Have objections been surfaced and addressed? Is there a mutual next step with a date? Deals that can't answer all six questions are at risk regardless of what the CRM stage says. AI can conduct a deal health review when you describe the deal's current state.

The method, in four moves

Do these in order
1

Review every deal over 21 days old against the six criteria every week.

2

Any deal without a confirmed next step with a date is not active it is stalled.

3

Move stalled deals to a nurture sequence rather than leaving them in the active pipeline.

4

Use the output to identify your one highest-risk deal and take action this week. Know which deals will close before your forecast does Six yes-answers don't guarantee a close, and one "no" doesn't mean walk away. Deals are made by people, not checklists - a stalled deal with a strong relationship can still move. Use the health check to focus your attention, not to make the decision for you. Don't let a scorecard replace your judgment.

Where the framework comes from

Salesforce / CRM methodology — pipeline management best practice

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Prompt extracted18 Sept 2026
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