How Tactical Empathy Improves Difficult Conversations with Jonathan B. Smith (Ep. 11)
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Deezer Most people think negotiation is about getting what you want. In reality, it’s about understanding what the other person needs.
In this episode of The Pleasant Street Pod, host Taylor Nissi, CFP®, CEPA, welcomes negotiation expert and Black Swan Group trainer Jonathan B. Smith for a conversation about tactical empathy, active listening, and how better communication can improve leadership, business decisions, and relationships.
Taylor and Jonathan discuss:
- Why tactical empathy creates better outcomes by helping people feel heard and understood, even when you disagree.
- The five levels of listening and how deeper listening uncovers information that can change the direction of a conversation.
- Practical negotiation tools like labels, mirrors, and calibrated questions that help entrepreneurs navigate difficult conversations with more confidence.
- And more!
Resources:
- Strategic Wealth Scorecard (2-minute assessment): Strategic Wealth Score Card
- Fight Less, Win More by Jonathan B. Smith
Connect with Taylor Nissi:
- Pleasant Street Wealth Advisors
- LinkedIn: Taylor Nissi CFP®, CEPA
- Book some time with Taylor (Book 20 Minute Strategy Call)
Connect with Jonathan B. Smith:
About our Guest:
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.