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. 

We will be launching the Hello Monday Book Club soon. If you’re interested in joining, send us an email at [email protected] and let us know!