by Andra B. Greene
I just celebrated my fourth anniversary as a neutral. Before that, I spent forty years as a Big Law litigator. In those four decades, I sat through hundreds of mediations, represented sophisticated clients, negotiated hard cases, and thought I understood the process. I didn’t; not really.
Sitting in the neutral’s chair has changed how I think about mediation. Some of what I’ve learned seems obvious in hindsight. Other things look entirely different from the middle than they did from one side of the table. More than once, I’ve caught myself thinking: I wish I’d understood this when I was practicing. I would have been a far more effective advocate.
Here are ten things I see differently now.
1. The Mediator Really Is Neutral
As an advocate, it’s tempting to treat the mediator as one more person to persuade. Convince the mediator your client is right, the thinking goes, and the mediator will walk into the other room, make your case for you, and bring back a surrender. That is not the job.
Mediation is a voluntary process. My role is to help both sides reach a resolution they
can each live with. The merits matter—I need to understand the strengths of your case and the weaknesses of theirs. But I also need to understand the strengths of their case and the weaknesses of yours. I have to be able to talk candidly with each side about the risks they face and where a resolution might actually live. My effectiveness depends entirely on my credibility with both rooms. The moment the other side decides I’m your advocate, I lose most of my ability to move them.
So, the useful question isn’t, “How do I get the mediator on my side?” It’s “What does the
mediator need from me to move this case?” Those are very different questions, and only one of them helps you.
2. Candor With the Mediator Builds Credibility
Every case has warts. Even the good ones. As an advocate, I was reluctant to admit mine— often under client pressure. But that instinct works against you in mediation. When counsel presents a case in caucus as though it has no problems at all, I don’t conclude the case is unusually strong. I wonder whether counsel has actually reckoned with its weaknesses, or whether they’re serious about resolving the case at all.
Here’s what I want from you in our pre-mediation calls and in caucus: tell me where you’re exposed. Which witness worries you. Which document you wish didn’t exist. Which legal argument might not hold up. And then tell me how you plan to manage it. That candor changes how I hear everything else you tell me. It doesn’t make me think less of your case—it helps me understand it. And it’s precisely what makes me believe you when you tell me your case is strong where it’s strong. You will not convince me your case is perfect. Don’t try. Help me understand it as it actually is.
3. Prepare Your Client for the Mediation, Not Just the Litigation
Looking back, I wish I’d spent more time on this. Most of my clients had been through mediation before, so we assumed we didn’t need to prepare for the process itself. That was a mistake. Even sophisticated, repeat clients forget what mediation actually is and how it unfolds.
Before the mediation, talk candidly with your client about risk and weakness. Set realistic expectations for the outcome. Tell them the mediator will likely push on their position—not because the mediator has taken the other side, but because testing assumptions is the job. I typically send each side a confidential list of tough questions before mediation, so they know what they’ll need to be able to explain to me.
Prepare your client for the pace, too. Mediation can feel tedious. Prepare them for an opening number that may strike them as absurd or insulting. Prepare them for the reality that if the case is going to settle, compromise isn’t optional.
Above all: the mediation should never be the first time your client hears the case has real weaknesses. A client who arrives expecting vindication, rather than negotiation, makes everyone’s job harder—including yours.
4. Don’t Spring Things on People at the Mediation
I’ve had clients want to hold something back—a document, a new case, an expert opinion, a damages theory—for a dramatic reveal at the mediation table, hoping it would force the other side to capitulate. Surprise can be a good trial strategy. It is almost never a good mediation strategy.
If information is significant enough to change how the other side values the case, give them time to absorb it. A decisionmaker or insurer confronting major new information for the first time mid-mediation often doesn’t have the authority—or the composure—to respond to it productively.
The same goes for me as the mediator. If there’s something I need to know to do my job well, I’d rather hear it before the mediation than stumble onto it late in the day. Surprises burn time, breed distrust, and make decisions harder. None of that helps settle a case.
5. Be Deliberate About What’s Truly “Mediator Eyes Only”
As a litigator, I was hesitant to exchange briefs with the other side at all, and when I did, I often layered on a Mediator Eyes Only sub-mission for good measure. Now I encourage parties to exchange pre-mediation submissions and to keep MEO material to a minimum.
Before you designate something MEO, ask a practical question: what do I actually want the mediator to do with this? If the information would help move the other side, but I’m barred from using it, its value to you is limited. I’ve had counsel hand me the single most important fact in the case and then instruct me not to touch it. There are legitimate reasons for confidentiality. But it should be a strategic choice, not a reflex. Tell me what I can share, what I can’t, and whether there’s a way to convey the substance of an issue without revealing the protected detail itself. Give me the tools to actually do the job.
6. Think Carefully About What the Mediator Needs to Read
I used to submit mediation briefs with hundreds of pages of exhibits, sometimes entire motions attached. Now that I’m on the receiving end—and I do read everything each side sends me—I understand how little of that volume actually helps.
A mediation brief has one audience and one purpose: helping me understand your position well enough to help resolve the case. Before you attach the full summary judgment record, ask what you really need me to understand. Identify what matters. Explain why. Give me a roadmap, not an archive. A tight brief that flags the pivotal facts, the key legal issues and rulings, the settlement history, the important personalities, and the real obstacles to resolution will serve you far better than an exhaustive record of the litigation. If I want more, I’ll ask for it before the mediation—and when I do, please send it. You’re not trying to prove the case has been heavily litigated. You’re trying to equip me to help resolve it.
7. Don’t Shoot the Messenger
At some point in every mediation, I’m going to bring you news you don’t want to hear. The other side won’t move. They’ll make a demand you consider absurd. They’ll characterize your evidence in a way you find insulting. They may say something about your case, or your client, that lands badly. Delivering that message doesn’t mean I agree with it. Part of my job is carrying information between rooms, including the unpleasant kind. Taking it out on the messenger doesn’t move the negotiation forward—it just costs you time.
Instead, ask what the message actually tells you. Is it posturing? Is there a real obstacle behind it? What does their reaction reveal about what they care about? What would it take for them to move? The message is data. Use it—and put me to work helping you craft the response.
8. Mediation Is a Process—Settlement Isn’t the Only Measure of Success
Litigators are impatient by training. I certainly was. I found the pace of mediation maddening: everyone knows the case, everyone knows why we’re here, so why can’t we just get to the real numbers?
Because negotiation isn’t arithmetic. People need time—to absorb information, recalibrate expectations, consult with people outside the room, test positions, and get comfortable with a decision. Sometimes the same point has to land three different ways before it registers. Sometimes an insurer needs more authority. Sometimes a client needs time to let go of an outcome they’ve been expecting for years. What looks like dead time in one room is often real work happening in another. And sometimes, despite all of that, the case doesn’t settle that day. Complex or emotionally charged cases often don’t. That’s not a failed mediation—it’s an unfinished one.
Even without an agreement, the day is rarely wasted. You learn how the other side actually sees the case, which arguments worry them and which don’t, where their real priorities sit, how their decisionmakers react under pressure. You may learn the true obstacle isn’t money at all—it’s timing, authority, principle, or something more personal. You learn things about your own case, too: a good mediator will pressure-test assumptions you’ve been carrying for months, and your client may hear that same assessment differently coming from someone with no stake in the outcome.
My job doesn’t end when the day does. If a case doesn’t settle, I stay engaged and keep working it as it ripens. So, the right question after a mediation that doesn’t resolve isn’t just “why didn’t we settle?” It’s “what did we learn, and what do we do with it?”
9. Every Number Sends a Message
There’s a real difference between leaving room to negotiate and opening from a position so extreme it stalls the negotiation before it starts. Lawyers often treat an aggressive opening as costless—start high, leave room, work toward the “real” number eventually. But an unrealistic opening can cost you. It signals to the other side that you may not be serious. It can burn hours just getting both parties into a workable range. In the worst cases, it causes the other side to disengage entirely.
And it’s not just the opening number. Every move after it sends a signal—its size, its timing, the explanation attached to it, or the absence of one. A small move can mean you’re near your limit, or it can be a tactic to draw out a bigger one from the other side. A large move can show seriousness, but without context it can also set an expectation that another one is coming.
Before the mediation, think through the entire negotiation. Who moves first? Where will the other side likely start? How will your client react to it? What does your opening say, and what will your subsequent moves say? Where do you actually believe this case settles? And tell me what you’re trying to communicate. I can often convey the meaning behind a move in a way the number alone can’t. Your numbers should move the negotiation forward, not just mark territory.
10. Help the Mediator Understand the People, Not Just the Case
I spend real time with the briefs before a mediation. But cases settle because of people, not paper, so I need to understand the human dynamics at play.
Tell me about the decisionmakers. Is the client angry? Worn down? Worried about precedent? Does someone need to feel heard before they can talk seriously about money? Are non-monetary factors important to resolution? Is there a business relationship worth protecting? Is there an insurer, a board, an executive, or a spouse whose view will shape the ultimate decision?
Tell me about opposing counsel, too. What’s the relationship? Have past negotiations gone smoothly or badly? Has opposing counsel sued the client before? Is there history I should know before I walk into that room? None of this shows up in the complaint or the summary judgment papers. It’s often more important to resolution than another ten pages of legal analysis.
The best mediation advocates understand there are two problems to solve: the legal dispute and the human decision-making that has to happen for it to resolve. I hold a pre-mediation call with each party for exactly this reason. Use that call to tell me who I’m dealing with.
What I See Differently From the Middle
After forty years as a litigator, the biggest shift in my thinking is this: mediation is not a trial with a neutral instead of a judge. The objective is different. The audience is different. And effective advocacy looks different. The best mediation advocates are persuasive, but they’re also candid, strategic, patient, and pragmatic. They know when to argue and when to listen. They prepare their clients for compromise, not vindication. They give the mediator the information—and the room— to work the other side effectively. They know how to be the Secretary of State, not just the Secretary of War. And they understand that success isn’t always measured by whether everyone signs before leaving the room. Sometimes the mediation resolves the case that day. Sometimes it simply changes how the parties understand the case, in a way that lets it resolve later. Both are real outcomes. Both are worth the day.
Andra B. Greene is a mediator, arbitrator, and independent panelist with Phillips ADR Enterprises. She can be reached at AGreene@phillipsadr.com
This article first appeared in Orange County Lawyer, October 2026 (Vol. 68 No. 10), p. 43.
