Library/Sales Operations, CRM & Productivity/Performance Improvement & Self-Coaching/Steelman Devil's Advocate Plan Review Framework
TestedSales Operations, CRM & ProductivityQuick Win (under 10 min)

Steelman Devil's Advocate Plan Review Framework

Stress-test your deal assumptions by generating the strongest possible case against your current forecast position.

About this prompt

This prompt runs a structured devil's advocate review against a deal you believe is on track, surfacing the best arguments for why it will slip, stall, or be lost. It's designed for AEs, sales managers, and directors preparing for forecast calls or deal reviews. Use it when a deal feels solid but you want to identify blind spots before they become surprises.

The prompt

I'm about to share a [strategy / decision / plan]. After I share it, I want you to: (1) Spend 1 paragraph steelmanning it — make the best possible case FOR it, (2) Then spend 2 paragraphs being a toug
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Variables to replace

STRATEGY / DECISION / PLAN | DESCRIBE

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

StageOngoing/Cross-Stage
SeatAE, Sales Manager, All Roles
DifficultyIntermediate
Time to valueQuick Win (under 10 min)
Works withAI-Agnostic
CategorySales Operations, CRM & Productivity
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