Mediation Pro Tip: Preparing for Mediation

[This article was published in the September 2025 issue of the Palm Beach County Bar Association Bulletin, which can be viewed by clicking here.]

Mediation is a powerful opportunity to craft a creative settlement that serves your client’s interests, potentially making you their go-to problem solver for future disputes.  Even if you don’t settle, mediation is a useful tool for engaging deeply with your case, connecting with your client, and gaining insights that could benefit you at trial.  Lawyers who treat mediation as “checking a box” so they can get to trial risk missing out on these advantages.  Of course, your ability to prepare may be limited by the case's value, time constraints, or other factors.  But like many things in life, getting the most out of mediation requires time and thoughtful preparation. 

Here are some pro-tips for effective mediation preparation:

Do Your Homework

Cases often don’t reach mediation until months or even years after filing.  By then, factual and legal issues may have evolved significantly.  A critical part of mediation preparation is knowing your case thoroughly: the witnesses, evidence, legal claims, defenses, and the remedies each side is seeking. 

Start by reviewing the current operative pleadings - the complaint, answer, counterclaims, and defenses - and understand the elements that must be proven at trial.  Assess the evidence obtained through discovery and determine how well each side can meet its burden of proof.  Then, evaluate the remedies being sought and consider the best, worst, and most likely outcomes.  If mediation occurs early in the litigation not all those issues may be fleshed out, but a solid grasp of the available information will make you as effective as possible. 

Be sure to calculate the fees and costs already incurred and estimate the cost of taking the case to trial.  Even if attorneys’ fees aren’t recoverable, this information can influence settlement strategy and decisions at mediation.

Don’t overlook the decision-makers.  Gather intel on the judge, arbitrator(s), or potential jury pool, and how they’ve ruled in similar cases.

Communicate With Your Client

Once you’ve reviewed the case, meet with your client to prepare them for mediation.  If they’re unfamiliar with the process, explain what to expect.  Clarify whether the session will begin jointly or in separate rooms, and explain the mediator’s role.

Emphasize that mediation isn’t adversarial, but rather a chance to find common ground.  Let the client know that your tone in a joint session may be more conciliatory than it would be at trial.  Also, set your client’s expectations around time: mediation can be slow and require patience, with long waiting periods while the mediator speaks with the other side.

It’s important to be candid about the case’s strengths and weaknesses, and the risks of proceeding to trial.  An honest discussion will help your client be realistic about potential outcomes and possibly more open to compromise.  You don’t want your client to learn about weaknesses in the case for the first time from the mediator or opposing counsel during mediation.

Crucially, talk strategy.  What settlement terms are acceptable? What should the opening offer be?  Are there any insurance or third-party considerations?  Encourage flexibility - your client may hear things that challenge their assumptions and require reevaluation.  Make sure they come with sufficient settlement authority and a clear understanding that any agreement is voluntary - they should never feel pressured to settle.

Clients often have valuable insight into how the opposing party views the case.  Use that to anticipate offers or demands and identify potential paths to resolution.  (For more information, check out my blog post on this issue.)

Finally, brainstorm creative settlement options. with your client.  Mediation allows for more flexible solutions than litigation, such as a business benefit that can be conferred in lieu of damages or other relief sought in the case.  Be sure to allow your client enough time to raise outside-the-box settlement solutions with others in their organization and obtain any necessary approvals.

Communicate With Opposing Counsel

Engaging opposing counsel in advance can greatly improve the likelihood of settlement at mediation.  Even if you haven’t exchanged formal offers, any prior dialogue can give the mediator a helpful starting point.

Consider sharing your mediation statement - or at least a non-confidential version - with opposing counsel.  It allows the other side to understand your perspective and better prepare their client.

Sending opposing counsel a draft settlement agreement with blanks for the key issues that need to be resolved can also be extremely helpful.   It’s a great way to focus and streamline the mediation, and will enable quicker documentation of a settlement at the end of mediation.  (See my blog post on drafting mediation settlement agreements.)

Communicate With the Mediator

Arming the mediator with information in advance about your case expedites mediation and increases the likelihood of settlement.  I provide parties a list of 13 items to address in their pre-mediation statements to help me prepare for a successful mediation (the list is available on the Procedures page of my website).  After reviewing the parties’ submissions, I conduct a short private call with each side’s counsel to ask questions about the case, discuss any sensitive interpersonal dynamics between the parties or counsel, and identify any issues to emphasize or avoid with your client. 

If the case does not settle at mediation, the mediator should stay in contact with counsel (if they agree) and continue to look for opportunities to resolve the case, such as a court ruling or a development in discovery.  Many cases that do not settle at mediation ultimately resolve with continued mediator involvement.

I hope this information helps you prepare for your next mediation more effectively.  Feel free to contact us if you have questions or are ready to schedule a mediation.