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Every organization running a transformation has people who see exactly what's going to fail. Most of them stay silent. Not because they lack courage, but because they lack permission. 

In this episode, Jackson breaks down the red team pre-mortem: a structured way to surface uncomfortable truths before they become expensive failures. 

He shares a real example from his time at Nestlé Dryer's, explains why most pre-mortems produce nothing useful, and walks through five plays that actually work.

What You'll Learn:

• What a red team pre-mortem actually is and why it matters now more than ever
• The five reasons most pre-mortems fail before they start
• Why "staffing with believers" guarantees you'll miss the real risks
• The difference between a leader explaining intent and defending a decision
• How to use the People, Process, Technology frame to structure the conversation
• Why your incentive structure might be rewarding the wrong behavior
• Five actionable plays to build a red team that captures real intelligence

Key Moments: 

[[02:15] Why most organizations never get the benefits 

[04:30] The Nestlé Dryer's story: "Is this going to go perfect?" 

[07:45] The five reasons pre-mortems fail 

[12:30] Psychological safety defined: belonging after dissent 

[15:00] The People, Process, Technology frame 

[17:20] Five plays to make your red team work 

[22:00] The flaw-finder problem: who gets celebrated? 

[24:30] Four takeaways to put into practice

Quotable Moments:

• "You're asking people to find the fatal flaws before they become fatal. That's the genius of this."
• "The person who catches a problem before launch gets a polite thank you. The person who heroically fixes it afterward gets celebrated."
• "One defensive reaction teaches everybody what's actually welcome."
• "Psychological safety means you can put an uncomfortable truth on the table, argue about it, maybe even be wrong, and still belong to the team."
• "You already have the diversity. The question is whether you've built a structure that lets it speak."

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Resources

• My Talent Sherpa: mytalentsherpa.com
• Talent Sherpa Substack: talentsherpa.substack.com
• Scott Morris / Propulsion AI: getpropulsion.ai
• Dripify: try.dripify.com/talentsherpa