Business negotiation skills are essential for entrepreneurs who want to close better deals, build partnerships, and grow their companies. In this episode of The WealthAbility Show, host Tom Wheelwright sits down with negotiation strategist Jonathan Smith to break down practical techniques that help business owners negotiate more effectively.
Jonathan Smith works with the Black Swan Group and collaborated closely with negotiation expert Chris Voss. His book Fight Less, Win More translates high-level negotiation strategies into practical tools that entrepreneurs can apply in everyday business situations.
The conversation begins with one of the most important negotiation principles: making the conversation about the other party rather than yourself. Jonathan explains how “tactical empathy” allows negotiators to reduce resistance and build trust during difficult conversations.
Tom and Jonathan also explore several key negotiation techniques entrepreneurs can immediately apply:
- Why listening is the most powerful skill in negotiation
- How “labels” help people feel heard and understood
- The power of silence to encourage deeper responses
- How to identify hidden information during conversations
- Why negotiations often require multiple conversations rather than a single deal
Jonathan introduces the concept of “black swans,” unexpected pieces of information that can dramatically change the outcome of a negotiation. Skilled negotiators stay curious and look for these insights because they often reveal motivations that were hidden at the beginning of the discussion.
The episode also addresses how entrepreneurs should approach negotiation preparation. Instead of trying to force a deal, effective negotiators define their parameters, listen carefully, and determine whether a real opportunity exists before investing significant time in the negotiation process.
This topic matters today because entrepreneurs negotiate constantly—with partners, clients, vendors, employees, and investors. Developing strong negotiation skills allows business owners to create better agreements, avoid costly misunderstandings, and build long-term business relationships that generate consistent growth.
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00:00 – Intro.
01:40 – Tactical Empathy & Emotional IQ: Successful Negotiations Are About Them. Not You.
03:43 – The Simple Truth: Listening for Logic & Acknowledge Their Point of View.
06:59 – 5 Levels of Listening: For The Jist, Hijack, Logic, Logic & Emotion, Their POV.
09:30 – Negotiation Is Learning (and Practicing) Another Language.
11:37 – Dynamic Silence.
18:24 – D.O.S. Conversation: Dangers, Opportunities, and Strength.
26:10 – How AI Impacts Negotiations.
29:04 – First Steps to Make You a Better Negotiator.
32:49 – Closing Statements.
Looking for More on Jonathan B. Smith?
Book: “Fight Less Win More: How Master Negotiators Influence, Hearts, Minds, And Deals”
Website: staycuriousjbs.com
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