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Why do Mediations fail and what you can do to prepare for Success

On Behalf of | Sep 14, 2025 | Firm News

As a mediator and a trial attorney, I see mediations from both sides — many successful and some not. Almost every practitioner agrees a “fair” settlement is preferable to a trial and that mediation can be an important tool in getting to a settlement. We all generally feel we need to pick the “best” mediator. I regularly hear complaints that one or another mediator was a disappointment because the case did not settle. As a practitioner and as a mediator, I have experienced a number of mediations that did not move the parties any closer to resolution.

There are a number of factors a mediator can control, but, in my experience, mediations fail because one or more of the parties (or counsel) did not come prepared or, more likely, did not have the proper preparation or expectations.

As an initial matter, mediation as discussed in this article is not synonymous with “settlement conference,” although they are similar and can even occur concurrently. Yes, a mediator can listen to the parties and establish a point or a range where a case “should” settle or what a value might be at trial. These are more often than not part of the discussion. However, mediation also involves exploring risks and motivations. More importantly, it encourages parties to explore options outside of the box of a verdict. I have settled cases that have included apologies, revised policies going forward, new business structures and relationships, and creative solutions to unquantified future liabilities.

Come with a mindset to settle the case

Prepare your client. As a mediator, I require accessibility to the decision maker on each side. In most cases, this means they must actually present throughout the mediation. Discuss settlement and the mediation process with your client before agreeing to mediate. It is important that each party understands the role of a mediator as a neutral and is prepared to resolve the litigation.

Prepare yourself. Have access to important pleadings, documents, and depositions. More importantly, prepare your own mindset. Advocacy at a mediation must be in the context of considering settlement itself to have some value. Yes, you should put out your best case but also be prepared to consider weaknesses. Mediation is not a not a trial. The purpose of hiring a third party is to explore facts, arguments, and law to hopefully come to an agreement. Be prepared to provide rationale for your settlement positions and offers. Be prepared to be asked to see the case from your opponent’s perspective.

At the mediation, present your arguments dispassionately and without accusation. If an issue has an important emotional aspect, say as much, but don’t feel the emotion must be demonstrated. People respond predictably to confrontation presentations, and emotional arguments beget a response in kind. As an advocate for your client, you need to approach the other party with openness.

Prepare the meditator. As a mediator, although I do not give legal advice, I will prepare myself on the substantive area of law and give forethought to potential strategies to bring the parties together. To those ends, well thought out mediation briefs are incredibly helpful. Mediation briefs should be short and succinct; the mediator will have follow-up questions. Specific citations are not helpful, unless a fact or legal proposition is central to the case and actually in dispute. Hit the important highlights, but don’t make it a legal brief. If the mediator needs more “proof” than your word, they will ask. Along with material facts, a mediator often needs context for those facts. Mediation is not a trial and mediators are not there to render a verdict; nor are their opinions subject to appellate review. Prepare your mediator by providing any particular points of emotion or “principle” that are significant to your client.

No surprises

Make sure you have shared key information, but do not mediate too early. Sufficient discovery must be completed so that there is substantial agreement as to what facts are in dispute and some confidence in what evidence is available on those facts. You are mediating to settle the case; if there is important evidence get it out there. Also, make sure both sides have considered key legal issues. Mediation is not the time to introduce a previously undisclosed affirmative defense or a unique theory of legal liability. Surprises can be effective at trial, and occasionally in a deposition, but in a mediation, they only halt the negotiation.

Consider contingencies

Make sure you have a plan to address any liens or third-party interests and inform the mediator of any such issues. Will there be an ongoing relationship between the parties going forward? Are there any concerns regarding current litigation? Are there any potential liabilities that may not have been identified or quantified? Too often, what appears to be a settlement quickly unravels when the parties have either not considered a significant issue or have proceeded under different assumptions as to who would be responsible for related matters outside of the lawsuit.

Every case, every client, and every mediation is different. However, the right mindset and thoughtful preparation are always an advantage for coming to an agreement and can save the parties from wasting time and mediator fees.


William Earnhart is a Partner at Birch Horton Bittner & Cherot. He has been a member of the Alaska Bar since 1994 and has practiced as a civil litigator, trial attorney, and labor negotiator throughout his career. He is also a member of the Professional Mediators of Alaska.

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