What I've Learned About Moving Parties Past Impasse

There is a moment in almost every difficult mediation when it feels like the case is not going to settle. The offers and demands are too far apart. Someone has said something that offended the other side. A party has dug into a position and will not budge. What I have come to appreciate is that this moment is not the end of the mediation—it is often where the real mediation begins. The cases that feel most meaningful to me are not the ones that came together easily. They are the ones where everyone in the room—the attorneys, the parties, and I—had to work for it.

I want to share a few things I have learned about what can help move cases past impasse, because I think it is useful for the attorneys who entrust cases to me to understand how I think about these moments. And I will be candid: some of what I have learned has come from mediations that did not settle, where I went home and asked myself what I could have done differently.

The first thing I have learned is that impasse is almost never about the numbers alone. When parties say they are "too far apart," what they usually mean is that one or both sides has not yet accepted a fundamental reality about their case. Maybe the plaintiff has not fully internalized the risk that a jury might find comparative fault. Maybe the defense has not grappled with how sympathetic the plaintiff will be on the stand. The mediator's job at that point is not to split the difference. It is to help each side see the case more clearly—and that takes patience and, frankly, some courage, because it means having honest conversations that people do not always want to hear.

I had a case recently, a business dispute between two former partners, where by the fourth hour neither side had moved more than ten percent from their opening positions. The plaintiff was furious about what he saw as betrayal. The defendant felt she had been falsely accused and was not going to "reward" the plaintiff by paying a significant settlement. When I sat with the plaintiff in caucus, I did not start with the numbers. I asked him what he wanted this to look like a year from now. Did he want to be sitting in a courtroom, spending more money on attorneys' fees, reliving this conflict in front of a judge? Or did he want it behind him? That question helped shift the conversation from "what am I owed" to "what do I actually need." On the other side, I worked with the defendant's attorney to walk her through a realistic trial cost analysis. When she saw what 18 more months of litigation would actually cost in legal fees, expert costs, and lost productivity, the settlement numbers started to look very different. To be clear, the attorneys on both sides deserve a great deal of credit for that resolution—they had prepared their clients well, and they were willing to have tough conversations when it mattered.

The second lesson I have learned is about the power of listening—and I mean really listening, not just waiting for someone to finish talking so I can pivot to my next point. In an employment discrimination case I mediated, the plaintiff spent the first 45 minutes of our initial caucus telling me about the 15 years she had given to the company, the promotions she had earned, and how the termination had shattered her sense of professional identity. Some of that was legally relevant. A lot of it was not. But all of it mattered to her. And by the time she had finished, she was calmer, more focused, and ready to have a realistic conversation about settlement value. If I had cut her off after ten minutes and tried to steer the conversation to numbers, I do not think that case would have settled that day.

Third, I have found that the best results tend to come when the mediator works closely with the attorneys, not around them. The attorneys in the room know their clients, they know the case history, and they often know exactly what the obstacle to settlement is—they just need a little help getting past it. Some of the most productive conversations I have during a mediation happen in quiet sidebar moments with counsel, where we can talk candidly about what their client needs to hear and how best to deliver that message. In a personal injury case involving disputed liability, plaintiff's counsel and I worked together to develop a presentation for the plaintiff that acknowledged her frustration with the defense's position but walked through the specific evidence a jury would see on comparative fault. Coming from her own attorney, reinforced by the mediator's independent assessment, the message landed in a way it never would have if I had delivered it alone. That case settled because of the attorney's relationship with her client and her willingness to have a difficult conversation—I just helped set the table.

Fourth, and this is something I think about a lot, there are cases where the obstacle is not legal analysis but personality. Every litigator has dealt with a party—or sometimes an adjuster or a corporate representative—who approaches mediation as a zero-sum game. They view any movement as weakness. They want to win, and they define winning as the other side losing. With those individuals, traditional appeals to reason and compromise do not always work. What I have seen work, in some situations, is reframing the settlement as the party's own strategic decision. In a personal injury case, I helped an insurance representative think through the risk that a trial in a plaintiff-friendly jurisdiction could produce a significantly larger result. I did not tell him his evaluation was wrong. I tried to help him see that settling might be the smarter play—and I let him be the one to recommend it to his supervisor. Whether the reframing made the difference or whether he would have gotten there on his own, I honestly cannot say. But the case resolved.

Fifth, I have learned never to give up too early. Some of the cases I have been involved in that ultimately settled did so after the point where most people in the room thought the case was dead. In one case, the parties were genuinely packing up to leave. I asked each side for 15 more minutes. In those 15 minutes, I proposed a structured settlement that neither side had considered—a partial payment now with the balance contingent on a specific event—and it helped break the logjam. I have also had cases where the mediation did not settle on the day, but because I stayed in touch with counsel afterward and continued to facilitate dialogue, the case settled within a couple of weeks. Mediation does not have to end when the session ends, and I try to follow up on every case that does not resolve at the table.

I share these stories not to suggest that I have all the answers—I certainly do not. There are cases I have not been able to settle, and there are cases that settled despite my involvement rather than because of it. The truth is that when a case resolves, it is usually the product of many forces: the attorneys' preparation, the parties' willingness to be realistic, the timing, and sometimes just plain luck. But I do believe that a mediator who is prepared, patient, and genuinely engaged with the people in the room can make a meaningful contribution in the hard cases—the ones where the parties are entrenched, the emotions are high, and the path to resolution is not obvious. Those are the cases that keep me motivated to keep doing this work.