Mediation Preparation as a Litigation Strategy

Thomas P. Cunningham, Esq. | Partner

Friday, May 29, 2026

Cases that settle at mediation almost always do so because at least one side was well prepared. The attorney who walks in with a well-constructed submission, a clear theory of the case, and a realistic path to resolution can often control the room. That dynamic is worth examining, because the habits that lead to good trial preparation do not automatically translate into good mediation preparation. The goals are different, the audience is different, and the measure of success is different. 

The Mediation Submission Is Not a Courtesy

Some attorneys treat the mediation submission as an administrative formality without much strategic thought. That approach wastes a significant opportunity to influence the mediator's approach before the session begins.   

The submission is your first and most reliable communication with the mediator. It is not only a first impression but can provide the mediator with the roadmap to your ideal settlement. It deserves the same care as a brief. It should be concise enough that a busy mediator reads it in full, and substantive enough that reading it actually moves the needle: the core factual dispute identified without being buried in background, the legal and damages issues that cut against your position acknowledged (mediators will find them anyway), and your client's view of resolution explained.

Credibility with the mediator is a resource that gets spent across the entire session. Submissions that inflate damages figures or omit significant weaknesses in the damages analysis can erode it before the session begins. Mediators who find inflated, or unfairly deflated figures, can result in a lack of credibility for the attorneys.

A Theory of the Case Built for Settlement

A trial theory of the case is designed to carry a verdict. A mediation theory of the case serves a different purpose: it is designed to produce a number or non-monetary terms that both sides can accept. That distinction matters in practice.

A trial theory tends to suppress the weaknesses in your position. A mediation theory must account for those weaknesses because the mediator will raise them in caucus, and your client needs to be prepared to hear them. Attorneys who have not developed a realistic assessment of their vulnerabilities before the session often find themselves negotiating from a position of weakness when the mediator begins exploring the other side's arguments.

Building a mediation theory of the case requires answering three questions honestly before the session. First, what is the best outcome your client can realistically expect at trial, accounting for litigation risk and appellate exposure? Second, what does the other side's best case cost your client if it prevails? Third, given those two endpoints, what range of outcomes at mediation is more favorable than continued litigation?

Attorneys who have done that analysis can negotiate purposefully within the rational settlement zone. Those who have not tend to anchor on a monetary settlement position rather than on case theory.  Mediations that anchor on positions rarely settle.

Preparing the Client for the Process

Attorney preparation and client preparation are related but distinct tasks. An attorney can have a sophisticated mediation strategy and a client who undermines it in the first joint session.

Clients need to understand what mediation is not: it is not a hearing, the mediator will not render a decision, and offers that feel inadequate at various points do not mean the session is failing. A client who understands this going in is far less likely to derail a session that is actually making progress.  They need to understand that mediation is a process.  It ebbs, flows and ultimately builds toward a resolution.

Clients also need a realistic picture of the litigation alternative. A client who has heard an honest accounting of trial risk from their own attorney before the session is far better positioned to make a rational settlement decision than one hearing it for the first time from a mediator in caucus.  

Finally, settlement authority should be resolved before the session, not during it. Attorneys and representatives who arrive without clear authority to settle within a given range (or who need to consult someone unavailable during the session) create delays that mediators and opposing counsel may read as bad faith, regardless of intent.  It can also derail the momentum of the mediation.  

The Path to Settlement as a Tactical Document

Beyond the submission and client preparation, the most useful pre-mediation exercise is mapping a specific path to settlement: 

• Where to open

• How much to move on each exchange

• At what point to call for a mediator's proposal

Opening positions matter more than attorneys sometimes acknowledge. An opening so far from a realistic number that it reads as bad faith signals to the mediator that the party is not serious. An opening too close to the target eliminates room to move. The right position is calibrated to the facts, the mediator's style, and what you know about the other side's likely approach.

A mediator's proposal is worth thinking through in advance. When both sides are close but neither wants to move first, a mediator's proposal can bridge the gap without either party visibly conceding. Knowing when to call for one, and whether your client would accept the mediator's likely range, is a decision best made before the session rather than in the middle of it.

Plan to settle the case.  Confidentiality provisions, payment timing, and nonstandard release terms, must be addressed early on.  Identifying those terms before the session and introducing them at an appropriate time early in the session, can prevent an issue later on when the parties are close to a monetary resolution of the case.  

Preparation Checklist for Mediation Counsel

• Submission: concise, credible, strategically framed; not a recitation of the pleadings and discovery. Identify the core dispute, acknowledge material weaknesses, and explain what resolution looks like from your client's perspective.

• Damages analysis: stress-tested against the other side's best case, not just your own.

• Theory of the case: built around a realistic settlement range derived from honest trial risk assessment, not the best possible trial outcome.

• Client preparation: process explained, litigation risk assessed honestly, settlement authority confirmed before the session.

• Negotiation map: opening position, movement sequence, non-monetary terms available, and a considered view on when to request a mediator's proposal.

Kenney Shelton Liptak Nowak LLP represents clients across a broad range of civil litigation matters. Tom Cunningham is a member of the National Academy of Distinguished Neutrals (nadn.org).  He has a well-established mediation practice where he has assisted parties in the resolution of hundreds of disputes involving complex personal injury cases and insurance coverage matters. 

For questions about mediation strategy or dispute resolution in pending matters, contact our civil and commercial mediation team.