Fight Less, Win More: How Tactical Empathy Changes Every Work Negotiation

Hello Monday with Jessi Hempel

Careers, Business

4.7 • 1.1K Ratings

🗓️ 2 February 2026

⏱️ 23 minutes

🔗️ Recording | iTunes | RSS

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Summary

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!

Transcript

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0:00.0	From LinkedIn News, I'm Jesse Hempel and this is Hello Monday.
0:07.0	It's our show about the changing nature of work and how that work is changing all of us.
0:12.0	So last fall, I had this former hostage negotiator in the studio.
0:16.0	We were talking about negotiation.
0:18.0	It was a pretty awesome episode and that's because the guest, you
0:22.6	probably remember him, he was Chris Foss.
0:25.6	So I'm going to gather information about you. I want to be very curious about you. I want you to
0:30.6	feel like I am actually intensely curious about you as a human being. Because the negotiation
0:36.6	has begun. We're negotiating for trust. We're negotiating
0:39.2	for a long-term relationship. Chris's book has never split the difference. It's become something
0:43.8	of a Bible for people who want to get better at asking for what they want, and most importantly,
0:49.4	at getting what they want. He's built this philosophy into a full consultancy. It's called the Black Swan Group.
0:56.1	He trains leaders and teams to negotiate with less friction and better outcomes. And now their
1:01.5	work is evolved into a new book. It's called Fight Less, Win More. And today in the studio,
1:08.3	we have one of this book's authors, Jonathan Smith.
1:11.6	If you don't do low-stakes practice, you won't be able to do the high-stakes negotiation.
1:15.6	You're going to fall back to whatever your training level is, and these are depreciable skills.
1:19.6	If you're not practicing, they go away.
1:21.6	Jonathan is a business strategist, a negotiation instructor.
1:25.6	He has spent years teaching people to listen in moments that
1:28.9	matter. And listening, it's the skill that separates great salespeople from average ones.
1:34.4	It's what distinguishes managers people trust from managers they endure. It's what keeps
	...

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