Fight Less, Win More: How Tactical Empathy Changes Every Work Negotiation
Mon Feb 02 2026
Every day is filled with negotiations. Here’s how to start winning them. Any conversation that has a want or a need is a negotiation. It's critical to approach even the low stakes negotiations with the same tools that will win high stakes conversations. But what if the key to better outcomes isn’t pushing harder, but listening better?
In today’s episode of Hello Monday, Jessi Hempel sits down with Jonathan Smith, negotiation instructor and co-author of Fight Less, Win More, to break down why negotiation is really about empathy, trust, and disciplined listening. Drawing on The Black Swan Group’s negotiation framework—made famous by Never Split the Difference—Jonathan shares practical tools for navigating conflict, building influence, and getting what you need without damaging relationships.
Jonathan is a business strategist and negotiation expert who has spent years teaching leaders, managers, and teams how to communicate in moments that matter most. His work focuses on tactical empathy, emotional intelligence, and the everyday negotiations that shape our careers and lives.
Jonathan and Jessi discuss:
Why every difficult conversation is a negotiation
Tactical empathy and how to help people feel truly heard
The “core four” negotiation skills: labels, mirrors, dynamic silence, and summaries
How low-stakes practice builds confidence for high-stakes conversations
Managing tone, emotion, and self-regulation
Why listening is a discipline—and how it improves trust and influence
Using AI as a preparation tool without losing human connection
If you want to go deeper on these tools listen to our episode from September, 2025 with The Black Swan Group's founder and CEO, Chris Voss.
Watch on YouTube: https://bit.ly/chrisvoss-hm-youtube
Listen on Apple: https://bit.ly/chrisvoss-hm-apple
Watch/Listen on Spotify: https://bit.ly/chrisvoss-hm-spotify
We will be launching the Hello Monday Book Club soon. If you’re interested in joining, send us an email at hellomonday@linkedin.com and let us know!
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Every day is filled with negotiations. Here’s how to start winning them. Any conversation that has a want or a need is a negotiation. It's critical to approach even the low stakes negotiations with the same tools that will win high stakes conversations. But what if the key to better outcomes isn’t pushing harder, but listening better? In today’s episode of Hello Monday, Jessi Hempel sits down with Jonathan Smith, negotiation instructor and co-author of Fight Less, Win More, to break down why negotiation is really about empathy, trust, and disciplined listening. Drawing on The Black Swan Group’s negotiation framework—made famous by Never Split the Difference—Jonathan shares practical tools for navigating conflict, building influence, and getting what you need without damaging relationships. Jonathan is a business strategist and negotiation expert who has spent years teaching leaders, managers, and teams how to communicate in moments that matter most. His work focuses on tactical empathy, emotional intelligence, and the everyday negotiations that shape our careers and lives. Jonathan and Jessi discuss: Why every difficult conversation is a negotiation Tactical empathy and how to help people feel truly heard The “core four” negotiation skills: labels, mirrors, dynamic silence, and summaries How low-stakes practice builds confidence for high-stakes conversations Managing tone, emotion, and self-regulation Why listening is a discipline—and how it improves trust and influence Using AI as a preparation tool without losing human connection If you want to go deeper on these tools listen to our episode from September, 2025 with The Black Swan Group's founder and CEO, Chris Voss. Watch on YouTube: https://bit.ly/chrisvoss-hm-youtube Listen on Apple: https://bit.ly/chrisvoss-hm-apple Watch/Listen on Spotify: https://bit.ly/chrisvoss-hm-spotify We will be launching the Hello Monday Book Club soon. If you’re interested in joining, send us an email at hellomonday@linkedin.com and let us know!