Episode 117 – Sales Lessons from Spies, Negotiators & Radical Empathy with Jeremy Hurewitz

Sales isn’t just about scripts and closing techniques—it’s about influence, trust, and understanding motivation on the deepest level. Who better to learn that from than spies and hostage negotiators?

In this episode, I sit down with Jeremy Hurewitz, journalist-turned-corporate intelligence professional, speaker, and author of Sell Like a Spy. Jeremy has spent years learning from ex-CIA officers, FBI negotiators, and intelligence experts—then translating those lessons into the sales world.

We dig into how spies use rapport, empathy, and vulnerability to turn the coldest conversations into cooperative relationships, and how you can use the same methods in sales to build trust, disarm resistance, and close deals with confidence.

 

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🔥 Episode Highlights

• The “sale that almost was” after 9/11 – how a near handshake deal between the CIA and Taliban leadership could have changed history.
  
  

• Why spies are the best salespeople – convincing someone to commit treason is the ultimate close.
  
  

• Radical empathy in action – learning to see the human side, even in people you don’t like or agree with.
  
  

• Mirroring done right – using verbal and physical mirroring to prove you’re truly listening and aligned.
  
  

• The power of vulnerability – why sharing small, human details can bridge the intimacy gap and spark deeper trust.
  
  

• Motivation as the key to influence – uncovering what people really want beneath the surface (status, security, recognition, legacy).
  
  

• Elicitation vs. interrogation – subtle ways to get prospects to reveal valuable insights without grilling them.
  
  

• Negotiation lessons from hostage crises – how to separate instrumental goals, emotional goals, and high-risk situations—and know when to walk away.
  
  

• Social recon for sales pros – using LinkedIn and social media as intelligence tools to personalize every conversation.
  
  

 

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💡 Key Takeaways

• Every objection hides motivation. A “no” often points to the real reason someone may need your help.
  
  

• Empathy wins in tough conversations. Seek common ground, even with prospects who resist you.
  
  

• Small signals build trust. Mirroring words, tone, and posture proves you’re tuned in.
  
  

• Show humanity, not perfection. A little vulnerability makes you relatable and opens doors.
  
  

• Do your recon. Sales professionals have access to massive intelligence via social media—use it wisely.
  
  

• Use elicitation. Frame statements that invite prospects to volunteer details instead of interrogating them.
  
  

• Not every negotiation is worth it. Some prospects or deals are “high risk”—know when to walk away.
  
  

• Sales isn’t zero-sum. The best outcomes leave both sides feeling like they’ve won.
  
  

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🔗 How to Connect with Jeremy Hurewitz

📖 Book: Sell Like a Spy – Available in print, e-book, and audiobook (read by Jeremy himself).
🌐 Website: challengerhillconsulting.com (Company) – speaking, training, and articles.

💼 LinkedIn: Jeremy Hurewitz

 

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📣 Call to Action

Call The Damn Leads
“By sales professionals, for sales professionals.” Each week, Drewbie Wilson, a sales vet with 20+ years in the game, brings you humor, real-world stories, and powerful strategies to help you excel in your sales career.

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• Proven Tactics: Practical tips for boosting your sales game
  
  

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