Library/AI-Era / Emerging Sales Work/Deal & Account Intelligence/Stress-test your own deal before the review
TestedAI-Era / Emerging Sales WorkSame-Day Use (under 30 min)

Stress-test your own deal before the review

Get a skeptical inspection of your deal that finds the gaps before your manager or a slipped quarter does.

About this prompt

This prompt is a skeptical inspector for an AE or sales manager who wants to find what's wrong with a deal before a review or a slip exposes it. It scans the deal's vital signs, calls out wishful thinking, and delivers an honest verdict on whether the deal is as real as you think. Use it before a deal review or whenever a deal feels softer than your forecast says.Reps believe what they want to believe about their own deals, which is exactly why they get caught flat in a deal review or surprised by a slip. This prompt plays the skeptical inspector you need instead of a cheerleader, finding the weaknesses first. You provide the opportunity (ACCOUNT, SIZE, PRODUCT, STAGE, EXPECTED CLOSE), what you know about the buying side (CHAMPION, ECONOMIC BUYER, OTHER STAKEHOLDERS, THEIR PROCESS), the compelling event (WHAT'S DRIVING URGENCY — or your honest admission there isn't one), where you think it stands (MY READ), and the assumptions holding the deal together (THE ASSUMPTIONS HOLDING THIS DEAL TOGETHER). It returns a risk scan of the deal's vital signs, a wishful-thinking check that calls out optimistic assumptions treated as facts, the single points of failure, a stage-reality check on sandbagging, the hardest questions a manager will ask, a prioritized action list, and an honest verdict. Be candid in WHAT'S DRIVING URGENCY — admitting there's no compelling event is exactly the gap this is built to surface. Distinct from a buying-committee map, this inspects whether the whole deal is real before someone else does it for you.

The prompt

I want to inspect my own deal hard and find what's wrong with it before my manager does in a deal review — or before it slips. Be the skeptical inspector I need, not a cheerleader. The deal: - The op
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Variables to replace

ACCOUNT, SIZE, PRODUCT, STAGE, EXPECTED CLOSE | CHAMPION, ECONOMIC BUYER, OTHER STAKEHOLDERS, THEIR PROCESS | WHAT'S DRIVING URGENCY — OR MY HONEST ADMISSION THERE ISN'T ONE | MY READ | THE ASSUMPTIONS HOLDING THIS DEAL TOGETHER

How to run it

  1. Copy the prompt and paste it into Claude, ChatGPT, Gemini, or Copilot — it's tuned to run in any of them.
  2. Replace the variables — swap each bracketed token for your deal's specifics. The variables list above explains every field.
  3. Make it yours — run it, keep what's strong, and tighten your inputs on the next pass. The prompt improves with your context.

What good output looks like

Make it yours

StagePipeline Management
SeatAE,Sales Manager
DifficultyAdvanced
Time to valueSame-Day Use (under 30 min)
Works withAI-Agnostic
CategoryAI-Era / Emerging Sales Work
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