Podcast Summary: Confessions of an Implementer

S2E31 | Simple Negotiating: Win More By Fighting Less with Jonathan B. Smith

Host: Ryan Hogan
Guest: Jonathan B. Smith
Date: January 14, 2026

Episode Overview

This episode of Confessions of an Implementer dives into the art of everyday negotiation with Jonathan B. Smith—renowned business strategist, EOS implementer, and author of the upcoming book Fight Less, Win More. Host Ryan Hogan probes Jonathan’s unique approach to negotiation, which is rooted in tactical empathy and is designed to help anyone—from entrepreneurs to everyday people—achieve better outcomes while reducing friction and conflict. The two also discuss Jonathan’s journey with EOS, lessons on building a consulting practice from scratch, how to market a book in the modern era, and why impact and connection lie at the heart of both negotiation and implementation work.

Key Discussion Points & Insights

1. Everyday Negotiation & Tactical Empathy

[00:00 - 04:12]

• Negotiation is everywhere: Jonathan reframes negotiation as essentially any interaction where "I want or I need" is in your head.
  • Not just for high-profile deals or hostage negotiations, but for daily life—getting an upgrade, talking to your kids, requesting at work, etc.
• Tactical empathy: The backbone of Jonathan's approach, borrowed and adapted from Chris Voss and the Black Swan Group.
  • "The basis of the negotiation we do is called tactical empathy. It's basically you have an intuition about what's going on in the other person's head and then you're going to verbalize that intuition and not be afraid that you're going to get it wrong." (Jonathan, 05:08)
• Listening as the core: By truly listening and acknowledging the other party's perspective, we disarm threats and open doors to better outcomes, often surpassing our initial goals.
  • “We go into the negotiation hunting black swans. The idea is people are desperate to be heard. Most people are not listened to. So the whole thing is about listening.” (Jonathan, 08:48)

2. The Book Strategy: Accessibility and Practical Value

[01:16 - 04:12, 54:04 - 57:14]

• Jonathan’s book, Fight Less, Win More, is positioned as a practical, everyday companion to the best-selling Never Split The Difference, making top-tier negotiation skills accessible for all.
• Inspired by the structure of EOS books—just as “What the Heck is EOS?” is the primer for “Traction,” so Fight Less, Win More breaks down complex negotiation tactics into usable, approachable strategies.
• The book focuses on real, relatable scenarios and includes a field guide and logbook for skill-building.

3. The Core Four Negotiation Tools

[26:02 - 28:49]

1. Labeling: Articulate your observation or intuition (“it looks like, it seems like, it feels like”) to acknowledge someone’s emotional or mental state.

2. Mirroring: Repeat the last few words or key phrases the other person uses to signal active listening and encourage them to elaborate.

3. Dynamic Silence: Use intentional pauses after labeling or mirroring, giving space for others to process and respond.

4. Summary: Recap ("So far, you told me...") to demonstrate deep listening, aiming for the other party to say, "That's right," signifying they've felt heard.

   “Summary is so far. You told me… If you didn't, don't agree with what I said, the urge to correct is irresistible.” (Jonathan, 27:20)

• Clarification on Intent:
  • Jonathan distinguishes tactical empathy from manipulative 'yes-momentum' sales tactics, emphasizing genuine understanding over engineered agreement.

4. Building Skills: Mindset and Habit Formation

[15:04 - 20:06; 17:52 - 18:17]

• Negotiation skills are learnable, but require discipline and practice:

  • Use “low-stakes practice” daily (i.e., coffee shop interactions, elevator conversations).
  • Keep a log/journal of each practice, review outcomes regularly.
  • The process follows the Japanese Shu-Ha-Ri model: learn by imitating, adapting, then internalizing until it becomes second nature.

  “It’s a learned skill, but it requires lots of discipline… The only way you can get good at the skills is through low-stakes practice.” (Jonathan, 15:12) “It’s really and truly a new language. It’s a new, different way of putting language together.” (Jonathan, 17:46)

5. Negotiation Preparation: Research, Dossiers, and AI

[20:06 - 23:09]

• For high-stakes deals, Jonathan uses detailed briefings and AI-powered tools to prepare—mapping out the other party’s worldview and priorities.

  • “I created something with… a Google Chrome plugin that you can actually put the negotiation into that tool and it will spit out their point of view as well as spit out the negotiation one sheet…” (Jonathan, 21:08)

• “Proof of life”: Quickly determine if a deal is viable, to avoid wasting time on dead ends.

  “It’s not a tragedy to not do a deal. It’s a tragedy to spend a long time not working through a deal and not getting the deal.” (Jonathan, 33:36)

6. EOS Implementation & Jonathan's Backstory

[36:17 - 47:28]

• Jonathan’s journey with EOS began after a chance meeting with Gino Wickman, leading to early involvement in the EOS community, and building and selling multiple Inc. 500 businesses using the system.

• Discusses the difficulties and persistence required in starting a consulting practice from scratch (240 coffees before his first client).

  • “Selection begins daily, assessment is ongoing.” (Jonathan, 41:57)

• The strength of building deep expertise, niche authority, and combining those with unique skills (negotiation + EOS) to create exceptional client value.

7. Marketing, Publishing, and Launch Strategy

[48:04 - 57:14]

• Decision to use a hybrid publisher (Amplify Publishing) for greater control and better economics, later securing a UK/Commonwealth deal with Penguin Random House as an anchor for foreign rights.
• The importance of quality (“If it’s not five star, don’t review”), and a long-term outlook for impact and sales.
• Multi-pronged marketing strategy: podcasts, speaking engagements, PR, LinkedIn Learning, coaching, and being the keynote at Black Swan events.

8. EOS & Negotiation in Practice: Real-World Impact

[57:14 - 69:57]

• Jonathan chooses clients who are collaborative, ambitious, and can both teach and learn ("easy, lucrative, and fun"—ELF clients).

• Application of negotiation skills in EOS session rooms: facilitating breakthroughs during tense or stagnant leadership meetings with tactics like accusations audits, labels, and dynamic silence.

• EO’s true power: 70% team health, 15% content, 15% facilitation. Customization and flexibility trump strict dogma for real client impact.

  “I do EOS freestyle. I run special operations… At the end of the day, I have a client, a Syrian client in the city. He said, ‘I don’t care what it’s called. Put cash money in my pocket.’ That’s what your clients care about.” (Jonathan, 69:04)

9. Personal Mission & Legacy

[61:05 - 62:22]

• Jonathan’s driving goal is to make a lasting, transformational impact for his clients—often changing lives and businesses at pivotal moments.
  • “Every client I start with, I say… my goal is that we’re friends for life and I make an impact on you. It changes your life…” (Jonathan, 61:05)

Notable Quotes & Memorable Moments

• On Negotiation as Life:

  • "Anytime I want or I need is in your head. It is [a negotiation]." (Jonathan, 07:56)
  • "We actually go into a negotiation without necessarily having a desired outcome... we go in hunting black swans." (Jonathan, 08:16)

• On Empathy vs Sympathy:

  • "Sympathy is about you. Empathy is about them. So we say tactical empathy." (Jonathan, 13:32)
  • "People can smell intent. This is not the intent to manipulate people into Yes Momentum." (Jonathan, 30:26)

• On Low Stakes Practice:

  • “The only way you can get good at the skills is through low stakes practice. So you need to actually be willing to do the low stakes practice and get it wrong because it’s gonna feel awkward at first.” (Jonathan, 15:15)

• On The Hard Road To Impact:

  • “240 coffees, no clients… sheer will. Selection begins daily, assessment is ongoing.” (Jonathan, 41:57)

• On Client Selection:

  • “I want only clients that are easy, lucrative, and fun. ELF. Not hard, annoying, lame, and frustrating.” (Jonathan, 71:07)

• On Legacy:

  • “My goal is that we’re friends for life and I make an impact on you. It changes your life.” (Jonathan, 61:05)

Timestamps for Important Segments

• Understanding Negotiation & Tactical Empathy: [00:00 – 08:48]
• Core Negotiation Tools Overview: [26:02 – 28:49]
• Negotiation Preparation & AI Dossier: [20:06 – 23:09]
• The Publishing Journey & Book Strategy: [48:04 – 57:14]
• Building a Consulting Practice & Early EOS Days: [36:17 – 47:28]
• Applying Negotiation Skills in EOS Sessions: [64:25 – 68:09]
• Legacy and Client Impact: [61:05 – 62:22]
• Selecting the Right Clients (ELF framework): [71:07 – 71:26]

Final Thoughts

Jonathan B. Smith’s approach offers a masterclass in practical negotiation—rooted in empathy, deep listening, and disciplined daily practice, not hackneyed tricks or adversarial tactics. This episode distills actionable frameworks and mindset shifts that listeners can use immediately, whether they're closing deals or just navigating everyday life. It’s not about fighting harder or out-muscling your counterpart, but about hearing, understanding, and co-creating better outcomes for everyone involved—“fighting less, winning more.”

For More

• Jonathan’s Site: staycurious.jbs.com
• Book: Fight Less, Win More (Release: Jan 13, 2026)
• EOS Info: eosworldwide.com

“Eat off menu.” — Jonathan B. Smith (72:44)