In ten years on the probate bench I do not recall a single party who came to court expecting to lose. Both sides arrived with sincere conviction, prepared by able lawyers, certain that a fair hearing meant a favorable ruling. Then I ruled, and roughly half of them learned that sincerity is not evidence.

That experience is the single most useful thing I bring into a mediation room, so let me share what it taught me about how cases actually get decided, because it is not how parties think.

The client experiences the dispute as the whole history: decades of family life, sacrifices unacknowledged, promises made in kitchens. The court experiences the dispute as two or three legal questions with burdens of proof attached. Most of what the client considers the heart of the matter is, legally, atmosphere. It is painful to hear and essential to know: the story that would move a brother does not move a bench.

Parties imagine their testimony as the moment the truth comes out. What I saw from the bench was narrower: a witness caught shading one answer loses the court on every answer after it. And in estate litigation, where the central witness is deceased and the documents must speak for them, a living witness’s overreach against a paper record is the most common way a strong case becomes a weak one by lunch.

Undue influence, incapacity, breach: each comes with a burden, sometimes a heavy one, and the burden decides close cases. A party can be right about what happened and still lose because right and provable are different things. Every trial lawyer knows this. Very few clients do, until it is too late to matter.

I could not split differences, honor moral claims the instrument ignored, or order the creative arrangement everyone privately preferred. A court chooses between the pleaded outcomes, and appellate review then measures that choice against standards no family member has ever read. Parties who expect wisdom from a courtroom often receive, instead, correctness. They are not the same thing, and the appeal takes another two years either way.

The largest obstacle in a mediation is often not the gap between the numbers. It is the gap between each party’s estimate of their chances and the estimate a neutral decision-maker would actually make. Counsel usually know the sober number. But there are things a client cannot fully hear from their own advocate, because the advocate’s job description is belief.

So part of my work, in the privacy of the caucus, is to be the first neutral audience the case has ever had: to tell a party, kindly and specifically, how their theory would likely have fared in front of someone whose job was to decide it. Not a prediction dressed as certainty, no honest mediator offers those, but a decision-maker’s read of the strengths, the exposures, and the arithmetic of pressing on. Delivered by someone who spent ten years making exactly those calls, that conversation tends to land differently than it does from anyone else in the case.

What parties do with it is theirs. That is the point, and it is the quiet advantage mediation holds over the courtroom I used to run: a verdict is a stranger’s decision about your family. A settlement is your own.

I spent a decade handing down the first kind. I have come to believe most families deserve the chance at the second.