How can a mediation succeed when the parties are so entrenched in their positions emotionally?

It is a fair question, and it sits behind a good many decisions to postpone mediation or to skip it altogether. It deserves a direct answer, and the answer begins with a correction: emotional entrenchment is not the obstacle to mediation. It is the reason for it. Parties who hold their positions loosely settle their cases over the telephone. The families who need a mediator are precisely the ones who cannot imagine moving, and a mediation designed for reasonable people having a pricing disagreement will fail them. A mediation designed for entrenched people will not.

In an estate or trust dispute, the position a party refuses to abandon is almost never a number. It is a number standing guard over something else: loyalty to a parent who can no longer speak for themselves, the conviction of having been wronged for decades and never once believed, a place in the family that the will seems to have erased. When a son insists the trust amendment is invalid, he is rarely making only a legal argument. He is often saying that his mother would never have done this to him, and that agreeing to any other account of her intentions feels like betraying her. You cannot buy that position off with arithmetic, because it was never for sale in arithmetic’s currency.

Counsel and mediators alike reach instinctively for the merits: the verdict ranges, the burden of proof, the cost of continuing. All of that matters, and the day will come to it. But a position anchored in grief or grievance does not respond to risk analysis any more than a fever responds to a lecture. Argue with it early and it hardens. The party hears one more person telling them their pain is a math problem.

The emotion is heard first, on purpose and without a clock running in anyone’s face. In these matters I expect a real portion of the day to be spent on the loss and the history, not the ledger, and I plan for it. A party who has been allowed to talk for twenty minutes about their father, to a neutral who is actually listening, will often negotiate about his estate with a steadiness that surprises everyone in the building, including them. What looked like entrenchment was, in large part, the pressure of never having been heard. Relieve the pressure and the position underneath it turns out to be smaller than anyone thought.

Then the honest conversation about the case can land, and it lands privately. Nobody abandons a position in front of the family member they have spent two years fighting. Movement happens in caucus, one room at a time, where a party can hear a candid read of their theory from someone with no stake in flattering them, sit with it, and change their mind without an audience. Preserving that privacy is not a courtesy. It is the mechanism by which entrenched people move.

The pre-mediation calls with counsel map the emotional terrain along with the legal one: which wounds are oldest, which people cannot be in a room together at all, where the last negotiation actually broke down. I mediate these cases in caucus, with the sides in separate rooms from the start and a joint session only in the uncommon matter that calls for one. That is not a preference about style. It is what lets an entrenched party say the thing they would never say across a table. And the day must be given room to run long, because entrenched parties do not move on a schedule. They move when the grievances have been aired, the arithmetic has finally been done, and they are tired of carrying the fight. That moment tends to arrive in the evening, well after the hour when a box-checking mediation has already given up.

No mediator can promise that an entrenched party will move, and I would be wary of one who implies otherwise. Some positions hold to the end, and a small number of cases truly need a ruling. But after thirty years of practicing in these disputes and ten deciding them, I can tell you that where a party stands at nine in the morning tells you very little about where they will stand at six in the evening, provided the hours in between were designed for who they actually are.

Entrenchment is not the sign that mediation cannot work. It is the sign that the mediation must be built for the people in the room rather than the numbers in the file. That is not an obstacle to the process.

That is the job.