Library/Deal Strategy & Stakeholder Management/Deal Desk & Commercial Approvals/Stress-test a deal request as deal desk and CFO
TestedDeal Strategy & Stakeholder ManagementSame-Day Use (under 30 min)

Stress-test a deal request as deal desk and CFO

Role-play a skeptical deal desk lead and CFO to find the holes in your approval request before they do.

About this prompt

This prompt plays a sharp deal desk lead and CFO reviewing your non-standard request and tries to reject it. It runs a three-pass grilling, an economics-and-precedent verdict, and a prioritized fix list so you can strengthen the case before submitting. Use it when a deal needs an exception and you want the weaknesses surfaced by a tough rehearsal rather than in the live approval meeting.Most deals get bounced because the rep never pressure-tested the request before submitting. This prompt runs that rehearsal by playing the people who'll try to reject you. Give it ACCOUNT and DEAL SIZE, THE NON-STANDARD ASK, MY CURRENT RATIONALE as it stands, the GIVE-GETS you're offering, and your close DATES, and it runs three passes: a deal desk grilling with the five to seven hardest questions and whether your justification answers each, a CFO lens that returns approve, approve-with-conditions, or reject with the single biggest reason, and a fix list with the specific give-gets to go collect and a tightened justification that survives both reviewers. Use this to harden a request before submission, then build the actual paperwork with the deal-desk submission prompt. For best results, paste your real current rationale rather than an idealized version, so the gaps it finds are the gaps a reviewer will actually find.

The prompt

Before I submit this deal for approval, I want it stress-tested by someone who'll actually try to reject it. Play a sharp, slightly skeptical deal desk lead and CFO reviewing my request. Poke holes.
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Variables to replace

ACCOUNT, DEAL SIZE | THE NON-STANDARD ASK | MY CURRENT RATIONALE | GIVE-GETS | DATES

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

StageNegotiation
SeatAE,Sales Manager
DifficultyAdvanced
Time to valueSame-Day Use (under 30 min)
Works withAI-Agnostic
CategoryDeal Strategy & Stakeholder Management
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