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Why your biggest deals keep slipping
This AI pre-mortem spots deal killers before they strike.
Difficulty: Easy | Impact: Saves monster deals | Read Time: 1 min
Before:
Your white whale just got away.
18 months hunting this beast. 400% of quota swimming into the sunset.
You're left empty-handed while your manager asks the painful questions you can't answer.
"Did we qualify the right stakeholders? What about the competition? Why didn't we see this coming?"
After:
You're spotting what kills whale deals before they surface.
Your biggest opportunities have bulletproof qualification and clear next steps.
When managers ask tough questions, you've got answers. Because you hunted down the problems first.
The Workflow:
Pick your biggest active deal (the whale that would make your year)
Open ChatGPT and use this prompt:
"I'm a B2B sales rep selling [YOUR SOLUTION] to [TARGET MARKET]. Run a pre-mortem analysis on my biggest deal: [DEAL NAME]. I want to identify potential failure points before they happen so I can take preventive action. Ask me diagnostic questions about the deal one at a time, wait for my response, then provide the 5 most likely reasons we'll lose and specific actions I can take now to prevent each one."
Answer AI's questions honestly about your deal situation
Review the 5 failure scenarios and recommended actions
Build those actions into your deal strategy immediately
Pro Tip: Run this analysis monthly on your top 3 whales. Patterns will emerge.
Why it works:
Charlie Munger said it best: "All I want to know is where I'm going to die… so I'll never go there."
Hunting big game requires different tactics.
AI forces you to face the brutal questions you avoid. It spots qualification gaps and competitive threats without the emotional attachment that blinds you to red flags.
Try it with:
What sales challenge should we tackle next? Comment below and let us know.
Darryl and the Leveraged Team