Splitting the Difference Can Leave Money on the Table

John Bradley "JJ" Jackson

14 Jan 2026 • 2 min read

Many of us have heard the classic orange negotiation story, but it is worth revisiting because it captures one of the most important lessons in negotiation. The difference between what people say they want and why they want it.

The story usually goes like this. Two sisters are in the kitchen and there is only one orange left. Both of them want it. Each insists on having the whole orange. That is their position: "I want the orange. Gimme."

Since neither is willing to give in, they argue and eventually reach what feels like a fair solution. They cut the orange in half. Each sister walks away with fifty percent. On the surface, this looks like a reasonable compromise.

But here is the problem. Compromise is not always optimal.

If someone pauses and asks a better question, everything changes. Instead of asking, “What do you want?” the question becomes, “Why do you want the orange?”

When that question is asked, the real story comes out. One sister needs the rind to bake a cake. The other needs the juice to make a drink. Suddenly, the conflict disappears. One person gets all of the peel. The other gets all of the juice. Both get one hundred percent of what they actually need from the same orange.

This is the moment where the lesson clicks. The original fight was not really about the orange itself. It was about two different interests hiding behind the same position.

When people focus only on their positions, they tend to argue, defend, and ultimately compromise. The best they can usually do is split the difference, which often leaves value on the table. When people explore interests, they open the door to creative solutions that were not obvious at first.

The orange story reminds us that great negotiation is not about winning more of a fixed pie. It is about understanding what actually matters to the other side and seeing whether the pie can be expanded. When we take the time to ask why, we often discover that a supposed conflict is really an opportunity for collaboration.

In real life, the orange might be money, time, control, or credit. The lesson is the same. Do not stop at what someone is demanding. Dig into why they are asking. That is where better outcomes live.

P.S. This story reminds us that it is not all about you. In fact, a skilled negotiator attempts to understand the wants and needs of other person. This can allow both parties to get what they want.