Sharpen Your Negotiation Skills Starting Today With Tactical Empathy

Most negotiation advice tells you to push harder or hold your ground longer. Jonathan B. Smith says the real leverage is empathy.

Jonathan is a negotiation expert and trainer with The Black Swan Group. He trained directly under Chris Voss, co-authored the bestseller Fight Less, Win More, and has spent years teaching executives how strong negotiation skills come from understanding the other person before you ever state your ask.

Jamie and Jonathan break down how to read the room in a negotiation using a technique called labeling, why staying quiet after a hard question works better than filling the silence, and how a Chris Voss negotiation technique called a no-oriented question prompted a response just 11 hours after months of silence.

They also unpack tactical empathy as applied emotional intelligence, the exact phrasing Jonathan uses when a prospect or professional contact has gone quiet, and a simple daily habit that builds negotiation skills in low-stakes moments like a rideshare ride or a rental car counter. Jamie shares how 42 women in her program collectively added nearly a million dollars in compensation last year through their negotiation efforts.

If you've ever gone silent instead of asking for what you're worth, press play before your next hard conversation.

Episode Breakdown:

00:00 Why Empathy Beats Aggression in Negotiation

03:30 What Tactical Empathy Means

05:00 How to Hunt for Black Swans in Every Negotiation

08:33 The Label That Changed a Security Guard's Whole Demeanor

12:51 Why Dynamic Silence Makes People Talk

16:12 The Three Negotiation Tones and When to Use Each One

19:14 Why Data and Logic Alone Never Close a Deal

23:12 The CAVIAAR Method for Getting Into the Right Frame of Mind

26:58 The No Oriented Question That Beats Ghosting

34:39 Practicing Negotiation With an Uber Driver or a Rental Car Counter

Connect with Jonathan B. Smith:

Newsletter - Salary Negotiation - https://www.blackswanltd.com/newsletter/topic/salary-negotiation  CAVIAAR Method

Purchase your copy of Fight Less, Win More

Jonathan B. Smith is a negotiation expert and trainer with The Black Swan Group, and author of the best-selling book Fight Less, Win More. Trained in Tactical Empathy® by former FBI negotiator Chris Voss, Jonathan helps leaders navigate high-stakes conversations with clarity, confidence, and connection. In Fight Less, Win More, he and co-author Derek Gaunt reveal how to apply field-tested negotiation techniques, from active listening to uncovering hidden motivations, to everyday business and personal interactions. The book offers practical guidance for reducing friction, resolving conflict, and achieving better outcomes without manipulation or compromise. A former entrepreneur and seasoned business coach, Jonathan has helped thousands of executives scale with intention and communicate with impact. Whether working with CEOs or family-owned businesses, he teaches a simple truth: the key to negotiation isn’t talking more, it’s listening better. Jonathan is a Commercial Pilot, dog trainer, and avid offshore fisherman.

Connect with Jamie McKinney:

Enrollment is open for the 3 Pillars of Leadership course! Find more info and book your Discovery Call

Visit Jamie's website

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