In every mediator’s career, there are many moments when negotiations stall.

I call that moment: “IN THE DITCH”.

Sometimes it’s in the final round. Other times, it happens right at the start—before the first offer even lands properly. Counsel arrives with their client, and instead of advancing the discussion, they open by backing up their previous offer. Why? Because they’ve spent more time, more money, and more emotional capital since the last exchange, and they believe it justifies a revised position.

The result? The other side sees it as bad faith. Walls go up. Trust drains. You’re in the ditch before you’ve even started moving.

At times, the breakdown isn’t just about numbers—it’s about perceptions that precede the session. Counsel may come into the mediation with an entrenched view of the other side as being difficult or untrustworthy. This perception may stem from prior encounters—perhaps the other lawyer has a history of starting negotiations with outrageous numbers, only to fold near the end of the day. That history becomes baggage, and it’s carried into the room before a word is even spoken. It informs tone, posture, and expectations. The problem is, the client may not even be aware of this dynamic, yet they’re instantly caught up in it.

In other scenarios, the mediation gets derailed when a party shows up with unrealistic expectations set by a previous counsel, a rogue expert report, or online research that promises huge money outcomes for minor injuries. Once the reality check lands, the disappointment bleeds into the process. The client feels misled, the lawyer feels exposed, and the entire tone shifts from cooperative to defensive. Suddenly, settlement is no longer about fair value—it’s about saving face.

Sometimes, it’s not either party that drives the session into the ditch—it’s the dynamic between the lawyers themselves. Maybe they’ve litigated against each other for years. Maybe there’s bad blood, bruised egos, or a professional rivalry that infects the negotiation. As a mediator, you can feel the tension before anyone speaks. Sarcasm replaces strategy. Offers are delivered with bite. Even good proposals get rejected because of who made them.

Another common derailment comes when an insurer’s representative lacks true settlement authority. A claims adjuster attends with a low ceiling, pre-approved by head office, but without flexibility. The lawyer may be ready to move, but their client is handcuffed. When the plaintiff side senses this limitation, frustration mounts. Momentum dies. To get out of this particular ditch, a good mediator makes the most of the available room to move, sometimes structuring conditional proposals that allow the adjuster to go back to their supervisors with something tangible: a framework, a capped demand, or a written rationale to request more discretion. Keeping the adjuster in the game—while managing the plaintiff’s expectations—is a delicate dance, but a necessary one.

A different kind of stall occurs when a party’s counsel isn’t aligned with their client. Maybe the lawyer is pushing hard for resolution, but the client wants their day in court. Or maybe the client is emotionally ready to settle, but the lawyer is framing every move as weakness. The mediator’s job here is to identify that misalignment quietly and help counsel recalibrate. In caucus, I may separate the client for a brief one-on-one conversation because I have gained their trust—never to undercut counsel, but to gauge readiness, clarify goals, and offer space for candid reflection. Sometimes, giving the client permission to settle is the most powerful move of the day.

Then there are mediations that go sideways due to outside pressure. A party may arrive distracted or distressed by unrelated events—a know-it-all relative, a major financial strain, a pending job loss. These real-life stressors bleed into their judgment. They become rigid, irritable, or erratic. The mediator must be perceptive enough to catch these cues and adjust the pace accordingly. In such moments, the process must accommodate the person before the position.

This is where the mediator’s judgment becomes the most valuable tool in the room. In caucus, I don’t just shuttle numbers. I manage try to manage psychology. I name what’s going on—carefully. Counsel needs to hear that they’re not negotiating in a vacuum. The other room is watching posture, tone, timing, and consistency. They’re deciding whether to trust, whether to believe, whether to compromise. And if that trust erodes early and goes “in the ditch”, it’s almost impossible to repair without a structural shift.

Sometimes, that shift means changing the format. When positions harden, I might float a mediator’s proposal—framed not as my opinion, but as a tool for progress. When frustration builds, I might propose brackets that give both sides a sense of control without demanding immediate vulnerability. And when I see that neither side wants to blink first, I might suggest a time-limited round of conditional offers to test appetite without full exposure.

In emotionally charged files, especially wrongful death or catastrophic loss cases, the ditch appears when grief overwhelms logic. A client who lost a loved one doesn’t care about deductions, structured settlements, or comparative fault percentages—not at first. They want acknowledgment. They want the other side to see their pain. In those moments, I slow everything down. I don’t rush to dollars. I let the story breathe. I create space for dignity before I ask for compromise.

I also know when to stop. Sometimes, the reset doesn’t happen in real time. If a mediation breaks down, I ensure it falls forward. I can offer a summary of where we were and where we can still go. I often propose an adjournment and a second session, as a cooling-off period. I stay available, because closure doesn’t always happen in one day.

Mediators aren’t neutral observers. We are active stewards of process, tone, and progress. When negotiations go in the ditch—early, late, or repeatedly—it’s our job to recognize the slope, pump the brakes, and guide both vehicles back onto the road. That’s not magic. It’s skill. And it’s what separates a facilitator from a force multiplier.

Because in mediation, stalling isn’t neutral. It’s directional. And if you can’t turn breakdowns into breakthroughs, you’re not driving the process—you’re just along for the ride.

Fortunately, I don’t do this alone. I have an edge when things go sideways: I have Dan. As my Online Dispute Resolution Coordinator, Dan quietly keeps the structure tight, the information flowing, and the parties grounded. When the process starts to slip, Dan ensures the logistics hold firm. But Dan’s value goes well beyond technical support. He offers something equally vital—a steady, objective voice. As a non-lawyer, Dan brings a practical, outsider perspective that often helps reframe the problem when legal instincts aren’t cutting it. He’ll ask the question no one else is asking, or highlight how a move might be perceived outside the echo chamber of litigation. His calm, measured presence gives me the space to focus on momentum, tone, and nuance—because while I’m working the human elements of the dispute, Dan is anchoring the practical ones. When a mediation goes in the ditch, having “The Reasonable Dan” in the passenger seat makes all the difference in getting it back on the road.