How Will I Know When We've Won?
The question I learned to ask every client — because their first answer is almost never the real one
I fancy myself a thoughtful and experienced negotiator. That's my big thing. That's a way that I can bring value to a client — the ability to negotiate, or to help them negotiate. Here's the elephant in the room: people often don't really and truly know what they want. That's true in a lawsuit, a real estate deal, or an argument at the dinner table.
I want to explore how a lawyer/mediator digs into what a person really wants. Finding out what's actually motivating people, I've come to believe, is the secret sauce to resolving conflict successfully. As we all kind of intuitively know, sometimes the argument about who didn't take out the trash isn't always about who didn't take out the trash.
Two different problems, same client
In the words of Joe Biden, "Here's the deal." By the time a dispute makes it to court, the entire controversy is usually reduced to a dollar figure. The procedural details take over — technicalities become the focus. The case takes on a life of its own. The fight becomes about the fight.
The winner is never completely made whole, and the loser is in a real hole. A court can award money. It can issue an injunction. It cannot make someone sorry. It cannot make someone understand what they cost you. It cannot give you back the two years you spent angry. And then there are the fees and costs. Unless it's a tort, often the parties are dividing a pie with other folks also taking a bite.
That's the legal problem. Then there's a human problem underneath it too — and a court is only built to solve the first one. The psychological side never gets addressed, and in the end nobody leaves happy.
Why the first answer may not be the real one
Sometimes the honest answer to "What are we fighting over?" really is the money. Plenty of disputes are exactly what they look like on the surface — a car wreck, a debt, a broken contract. Those are the easy ones.
But often, especially once hurt feelings, embarrassment, or shame is involved, the first answer is a proxy for something the client hasn't said out loud yet — sometimes hasn't even said to themselves.
The client who says they want a judgment on the record, when what they actually want is for one specific person — a family member, a former friend, a business partner they trusted — to admit what they did and be exposed.
The client who wants to take a case all the way to trial "on principle," when what's actually driving them is the fear that settling will feel like agreeing they were foolish to trust the other side in the first place. They feel betrayed.
The client who wants the other side to hurt — not just to pay, but to suffer — because they themselves are hurting, and some part of them believes that if the other person hurts too, it will finally feel fair. Sometimes these folks are hurting for all kinds of reasons completely unrelated to the dispute at bar.
Mediation isn't just refereeing two stated positions until they meet in the middle. A good mediator needs to find out what each party actually needs to hear, or to walk away with — which means figuring out what wants and needs live deep down in the secret places in their heart.
Where this is going
This is the first piece in a series about a question I think doesn't get asked enough, by lawyers or by anyone else sitting across from a person in conflict: what does this person actually want, beyond what they're saying? How will I know when we've won?
In upcoming posts, I'll dig into ways to get a client — or the parties to a dispute — to actually open up about what they really want or need. Sometimes you have to help them figure out what that is. It's crucial for an advocate or a neutral to fully understand the dispute, and often the parties' history, in order to craft a solution that actually resolves it, not just settles it on paper. Good advocates and neutrals have techniques for this — ways to make people comfortable enough to actually say what they need.
One of those techniques is something called T-funnel questioning. You start with something broad enough that the party can answer however they want, not however you'd frame it. "Tell me about your relationship with your business partner before this happened," not "Did he shortchange you on the March invoice?"
As the party talks, you listen for the gaps and threads worth pulling, then progressively ask more specific, more closed questions to pin down the actual facts. Dates, specific conversations, who else was in the room. Before moving to the next topic, you summarize your understanding to verify accuracy, then open a new T-funnel for the next subject.
That's one tool. There are others — ways to defuse an angry party without agreeing with them, questions that get someone to reveal what they actually value without ever asking directly. I'll get to those.
Next time, though, I want to go somewhere a little less comfortable — the party who doesn't just want to win, but wants the other side to lose and hurt. Occasionally I'd run across a juror like that. They were angry or hurt. They wanted other people to hurt. We used to call those folks "punitive jurors," and they are dangerous. There's genuinely interesting research on why some people are wired that way, why it rarely gives them what they're hoping for, and what a good mediator does when that's the party sitting in front of them.
How Will I Know When We've Won?
If you've ever walked out of a negotiation, a lawsuit, or an argument with someone you love — technically "ahead," but still feeling like something wasn't finished — you already know why this question matters. We'll dig into it more, next time.