Don't Split the Difference — Win It

Every business owner faces high-stakes conversations — a partnership dispute, a key hire negotiation, a client threatening to walk, a vendor who has you over a barrel. Most go in armed with facts and a number. Chris Voss would tell you that’s the wrong preparation entirely. The owners who consistently win difficult conversations aren’t better arguers. They’re better listeners — and they show up with a plan that most people never think to build.

Here is a practical field guide drawn from Voss, from Roger Fisher and William Ury’s Getting to Yes , and from what the best negotiators actually do before, during, and after a difficult conversation.

Before the Conversation

• Know your BATNA — and theirs Fisher and Ury coined it: your Best Alternative to a Negotiated Agreement. Before any high-stakes conversation, get clear on what you will do if this falls apart entirely. Then think hard about their alternative. Whoever has the stronger BATNA has more leverage — but knowing yours keeps you from making a desperate deal.
• Separate the people from the problem Another principle from Getting to Yes . The vendor who missed the deadline is not your enemy. The late delivery is the problem. Keeping that distinction clear — especially when emotions are high — protects the relationship and keeps the conversation focused on resolution rather than blame.
• Write down what they want — not just what you want Voss is relentless on this point. Most people walk in knowing their position cold and having spent almost no time genuinely considering the other side’s needs, pressures, and fears. Write it out. What do they actually need from this conversation? What would make this a win for them? That preparation changes everything.
• Set a range, not a number Voss recommends anchoring with a range rather than a single figure. It signals reasonableness, reduces defensiveness, and — if calibrated well — the floor of your range becomes the starting point for the other side.

During the Conversation

• Listen to understand, not to respond The most common mistake in high-stakes conversations: people spend the time the other person is talking building their next argument. Voss calls this “collecting information.” Real listening — the kind that changes outcomes — means staying genuinely curious about what the other person is actually telling you.
• Label the emotion in the room Voss’s labeling technique is disarmingly effective: “It seems like you’re frustrated with how this was handled.” You’re not agreeing. You’re not apologizing. You’re acknowledging. When people feel their emotion has been recognized, the intensity drops and problem-solving becomes possible.
• Ask calibrated questions instead of making demands “How am I supposed to make that work?” “What would need to be true for us to move forward?” These questions are not evasions — they are invitations. They shift the burden of creative problem-solving to the other party and almost always surface options you hadn’t considered.
• Silence is a tool — use it After a label, a question, or a key statement, stop talking. Most people rush to fill silence because it feels uncomfortable. Let it sit. The other person will almost always fill it with something useful — a concession, a concern, a piece of information you needed.
• Watch for the Black Swan Voss’s term for the hidden piece of information that changes the entire dynamic. It might be a deadline you didn’t know about, a constraint they’re embarrassed to admit, or a priority that has nothing to do with the stated issue. Stay curious long enough and it usually surfaces.

After the Conversation

• Confirm understanding in writing — immediately Lencioni’s commitment research and Voss both point to the same problem: people leave conversations having heard different things. A brief follow-up email — “Here is what I understood us to agree to” — closes that gap before it becomes a new conflict.
• Debrief yourself honestly What did you learn about what they actually needed? Where did you get defensive? What question could you have asked earlier? The owners who get consistently better at high-stakes conversations treat each one as a data point, not just an outcome.

The Shark Sense Insight

Most business owners prepare for a difficult conversation by building their case. The best ones prepare by building their curiosity — about what the other side needs, fears, and hasn’t said yet.

Facts matter. Preparation matters. But in the room, the owner who listens better, labels accurately, and stays genuinely curious about the other side almost always comes out ahead — not just with a better deal, but with a stronger relationship on the other side of it.

Winning the conversation is good. Winning it in a way that keeps the relationship intact is leadership.

This work starts with a conversation. Reach out at jredmon@redmonlaw.com.