How to Win Every Mediation

Any article on winning must start by defining the term. Unlike most of what we do as litigators, mediation never results in an absolute “win.” Some settlements feel more like wins than others and settlement alone is not the right judge of win or loss.  With motions, trial, or arbitration it is usually possible to distinguish a win from a loss, even when there is some kind of compromise verdict. However, in mediation if the parties reach an agreement, it is always a function of compromise. So, how do you define a win in mediation? Of course there are many possible definitions of a win: e.g., Fisher & Ury would define a win as a negotiated settlement that is better than your BATNA.  After hundreds of negotiations as both a neutral and an advocate, I do not believe there are any universal definitions of win and loss; each party goes into a mediation with different expectations. Finality at any cost is a win for some but totally unacceptable for others.  For the purposes of this article, we will define winning as achieving a resolution (e.g., finality, beating BATNA, or crafting a result unavailable in a civil judgment).

In this article, I suggest that there are two keys or differentiators that are present in most “winning” negotiations: 1) a different mindset than the one advocates take into court or even an arbitration and 2) preparation beyond researching the law and discovery of the facts — although these are also necessary prerequisites. Litigation is naturally competitive but successful mediations often require a more cooperative mindset. I do not suggest by this that this requires any compromise of your ethical obligation to zealously represent your client. However, you are much more likely to “win” at mediation if you put aside all notions of winning or losing. If the definition of winning involves a beatdown, mediation probably is not the right place to resolve the dispute.

Win-Win and the Collaborative Mindset

To say that the system that creates and nurtures lawyers is competitive is a gross understatement. Law schools are competitive places where lawyers’ future opportunities most often are defined by the law school’s ranking and the lawyer-in-training’s ranking in his or her class. After law school most of what we do reflects a competition within our law firms and with lawyers outside our law firms.

Most clients seek litigation counsel because they expect aggressive advocacy. Rational decision-makers (those who have been through litigation and know the costs and benefits), though, want more than blinders-on, hard-nosed advocates.  They want counselors who are capable of helping them reach a solution in the most effective way possible. In some cases that may require blinders-on, no holds barred litigation. For most cases, however, negotiating in a collaborative, problem-solving environment is the better alternative.  Unfortunately, more times than not, advocates approach mediation the same way they approach a hearing, cross-examination, or trial. Trial lawyers come into mediation with the intent of convincing the other party that they face insurmountable obstacles.  Although, this may be the only chance you have to speak directly to the other side, that mindset presupposes that counsel for the other party is not being honest with their client.  There is nothing wrong with advocating forcefully for your client but there are ways to accomplish that task without losing the ability to collaborate toward a resolution.

Negotiation texts describe techniques such as active listening, affirming the other side’s position etc. I believe the “skills” we are talking about, however, are the natural offshoot of a cooperative mindset. Approaching a negotiation or mediation as a problem-solving opportunity instead of “our one chance to talk directly to the other side,” i.e., drive home our belief that your case is worthless, will naturally lead to the kind of empathy that the texts describe in action verbs. Very few people are fooled in an adversarial context by this kind of pretense. In fact, you are more likely to harden the other side than you are to weaken their resolve.

In the words of Steven Covey, “seek first to understand, then to be understood.” In every mediation I have conducted both parties come in believing their narrative and their interpretation of how the law treats that narrative.  Unless you assume the opposing party is lying and/or the opposing lawyer is incompetent or worse, there is value in trying to understand where they are coming from.   Good negotiators seek first to understand, great negotiators not only understand but convince the other side that they understand.  If you can do that you might even be able to persuade.

Can collaborative problem-solving be taught? My short answer is not only can it be taught, you already know how to do it. Its more mindset than specific skills.

A few years ago, I served as a mediator in a business divorce case in which both counsel were well prepared, respectful of the other side, and forceful, articulate advocates for their clients’ positions. In spite of this — or perhaps because of it — we made little progress throughout the day until we met outside the presence of the clients. In this setting, with a little prodding, both counsel were able to concede an understanding of where the other side was coming from; a concession they could not make in the presence of their clients. Once that happened, counsel was in a much better position to get past positional bargaining and start exploring the interests that were preventing resolution.

Future posts will explore how to get to a collaborative mindset in more detail but I strongly recommend that every advocate take a DRC-approved mediation training course. Even if you have no desire to ever serve as a neutral, the skills taught should be in your repertoire as an advocate. Short of full-blown mediator training, watch how good mediators approach the parties. Seek first to understand. Not only will you find alternatives you had not thought of before but the other side might actually listen to you.

When A Cooperator Faces A Competitor

A cooperative negotiator will inevitably encounter a competitive adversary who believes it his or her duty to come at the problem with a competitive attitude. In this situation there is a legitimate fear that the competitive negotiator will “win” because the collaborative negotiator will need to concede too much in order to collaborate.

A number of years ago I took a course on mediation strategies that involved negotiation role-playing. One of the role plays was a famous scenario called the prisoners’ dilemma, which addresses this concern regarding collaboration and competition. In short, two prisoners, without the ability to determine what the other is doing have the opportunity to cooperate (collaborate) with each other or betray (compete with) each other. There have been more than 2,000 articles written on the Prisoners’ Dilemma and most pundits came to the conclusion that the best outcomes came from not cooperating. That is that the best strategy was to betray the other party. In our world, competitive negotiators get the better deal, right?

Turns out that is not right. In 1984, Professor Robert Axelrod published The Evolution of Cooperation.  Evolution is a report of Axelrod’s study of the Prisoners’ Dilemma. Professor Axelrod invited academics from all over the world to devise strategies for an “iterative” prisoners’ dilemma tournament. In the iterative version, the participants play the game repeatedly with the assumption that each has knowledge of the others’ actions in previous scenarios and can change their strategy based upon past performance. In short, it mimics a multi-step mediation negotiation.  Professor Axelrod discovered that the best strategy — the winner of the tournament — was what he called the “tit for tat” strategy. The winner — the algorithm with the best outcomes overall — was a strategy that called for the player to cooperate at first and then match the opponents moves in each subsequent iteration. More on this in subsequent posts.


Assuming you can learn to become a collaborative advocate, the single biggest differentiator between mediations that are successful — by whatever definition — and those that are not is the preparation of the parties and their counsel. This is sometimes a function of timing — early mediation has many benefits but may also preclude adequate preparation. Too often it is a function of not knowing how to prepare for mediation. Obviously, good litigators research legal issues and engage in discovery to understand the strengths and weaknesses of the case. This is critical but not enough.

In addition to the legal research, factual investigation, and discovery needed to understand the legal position, it is very important that you take the time to understand the negotiating strengths and weaknesses of your case. In my experience, most counsel come into mediation with a good understanding of the legal position but rarely fully understand their client’s bargaining position.

Interests Not Positions

Earlier we discussed the need to understand the other side’s interests. The difference is best described by Fisher & Ury but for a brief description click here. Fully understanding the other side’s motivations (their driving interests) is usually not possible prior to mediation but getting to your client’s underlying interests is imperative. Many times even understanding your own client’s interests may be difficult because many times your client may not fully understand the forces behind the positions he or she is taking. Exploring with your client the acceptability or unacceptability of various settlement scenarios is a very good way to begin helping them get at the underlying interests. Good mediators help adversarial parties do this in part to try and get at the real issue. Doing it ahead of time will allow you to set up the negotiation to point toward that goal.

A Good Agreement / Unacceptable Terms

I have already suggested that you explore acceptable and unacceptable options with your client before the mediation. That exercise may help both of you determine the interests driving the positions but do not stop there. Thorough preparation requires an exploration of what a good agreement looks like and the trade-offs that may be necessary. If your client wants confidentiality what must she concede to get it. If she wants to minimize or maximize the financial side of the deal what can she trade. This exploration may lead to the discovery of concessions that mean more to the other side than they do to you. On the flip side, explore what terms are absolutely unacceptable.


Your preparation should also include an attempt to find external standards that can be used to persuade the opposing party that the settlement you are proposing is legitimate. Can you really recover what you are demanding? If the recovery of fees is a part of your demand, how likely are you to recover those fees in a judgment? Legitimacy in this exercise should include an attempt to evaluate the other side’s alternatives to settlement.


Preparing for mediation should always include a detailed analysis and discussion about the alternatives to a settlement. Start with a detailed budget of the cost of continued litigation. But the cost of litigation always is higher than the amount paid in fees and litigation costs. Your client should fully understand the disruption to their lives or their business and employees to go through discovery and trial. Of course, this discussion should include a realistic assessment of the best case, most likely case, and worst case alternatives to settlement. Deciding to accept or reject a settlement offer or to make a settlement offer cannot be rational without understanding the alternatives. You simply cannot rely on a mediator to provide your client with these assessments.

More From My Blog

The Bottom Line

Should you tell your mediator your bottom line? This post from an experienced mediator explores that question.

Read More »
Mediation 2.0

The default model for mediation has produced excellent results in most cases. For complex, multi-faceted, or multi-party mediation, this article suggests re-thinking the process.

Read More »