12 Ways to Help You “Win” at Your Next Mediation

Whether you're representing a plaintiff, defendant, business owner or insurer, thoughtful preparation can significantly increase the likelihood of a successful outcome. The following checklist highlights 12 practical ways to get the most out of your next mediation.

1. If you need their money or approval, then get decision-makers involved early in the process.

• Insurance carriers
  • If you expect insurance carriers to participate in the settlement process, then:
    • Give plenty of notice so that internal timelines can be met and procedures can be followed
    • Provide detailed information
    • Make sure that the carrier is not surprised by the strategy or tactics you plan to use at the mediation session
• Board members, owners, family members and financial partners
  • Have they been informed about possible outcomes, risks, costs, and goals for the mediation? If the dispute poses a significant risk (existential?), then you should take steps to avoid surprises.
  • Do they feel differently about risks than the executive, family member or general counsel who has been your primary point of contact?

 A missing or uninformed decision-maker can delay or derail settlement efforts. 

2. Talk about money with your client

• What has been spent?
  • Any cost/benefit/risk analysis should start with reviewing what has been spent. A sometimes painful, but necessary, discussion.
• What is the range of possible outcomes?
  • Are there any similar cases? Are there any verdicts or judgments that could help guide the client’s expectations?
  • Consider all the possibilities, including:
    • Is a Sec. 998 offer pending? Should one be made?
    • Is there any risk of being required to pay the other side’s attorneys’ fees and costs?
    • Is there any risk of punitive damages or claims that won’t be covered by an insurance carrier?
    • Are there any liens that must be satisfied?
    • Could a bad outcome lead to the need for bankruptcy protection?
    • Are there any tax liabilities that need to be considered?
• How much will be spent going forward?
  • Can the client really afford a full-blown legal battle? Strong emotions shouldn’t trump practical limitations. 
• Be ready to cut a check.
  • If a case does not settle at the mediation, the client may be required to immediately cut a large check as a deposit for anticipated litigation costs. This can be a difficult discussion.

Mediation works best when decisions are grounded in economic reality—not just legal positions or strong emotions.

3. Discuss the delays and uncertainties that will follow if a settlement is not reached.

It is important to maintain a realistic view of what happens if the case doesn’t settle.

• Months or years of delay just getting to trial, then appealing a verdict or ruling
• An outcome determined by a third party (judge, jury, or arbitrator)

Mediation provides control. Litigation surrenders that control to others.

4. How does the possibility of continuing or ending litigation affect the business?

Discuss how the dispute could have an impact on the following:

• Investors
• Plans to go public
• Potential acquisitions or the sale of a company
• Public relations or reputation
• The potential to create an unfavorable precedent
• The distraction, expense, lost time and stress that litigation can impose on owners and key executives, particularly in smaller organizations

 In some cases, these factors outweigh legal outcomes in driving resolution.

5. Have a solid understanding of the other side’s position.

• What “ballpark” is the other side playing in?
• Are settlement expectations wildly misaligned?
• Are there fundamentally different views of the facts that need to be reconciled?

 Knowing what to expect can avoid unnecessary impasses early in the process.

6. Discovery: Formal discovery is focused on what you need in the courtroom; mediation is focused on resolution.

• If your opponent has raised a challenging argument, or hints at damaging evidence, the mediation session can provide an opportunity to informally obtain information that would otherwise require months of expensive, formal discovery.
• Arm the mediator with the arguments and evidence that you want the other side to consider. 
• Don’t hold out for “perfect information” when sufficient information exists to support a settlement.
• “Smoking guns” are sometimes most effective when revealed during a mediation. If they will help to settle the case, use them.
• Experts: Before investing the money, evaluate whether they are needed to clarify, question or substantiate important issues that are critical to settlement discussions.
• Are you managing expectations properly? 
• Have you provided enough information to the other side to support your client’s damages claims?
• Are you appropriately discounting your damages based on the liability arguments you will face at trial or arbitration? 

The most productive mediations often involve the informal exchange of information, saving a lot of time and expense for the parties. 

7. Given potential costs and risks, be clear on overall goals.

• What does success look like?
• What is acceptable?
• What is off the table?

Without clarity on goals, even productive discussions can stall.

8. Use mediation briefs strategically.

• A clear, concise brief will help to frame the issues and set expectations.
• Consider whether two versions are appropriate:
  • One for the opposing party
  • One for the mediator, with additional sensitive/confidential information

A strong brief can accelerate progress before the mediation even begins.

9. Give the mediator a heads-up

Make sure that the mediator is aware of any unique considerations that could affect the mediation:

• Behavioral issues
• Personality dynamics
• Emotional or sensitive topics
• Financial or business limitations
• Concerns involving the case, opposing counsel or the client
• Challenges in the client’s assessment of litigation risks and potential outcomes

The mediation will be more productive if the mediator knows what to expect and how to best communicate with the parties.

10. Be ready with creative alternatives.

Not all disputes are resolved through a payment. Consider:

• Alternative deal structures and business solutions (e.g., teaming, licensing, payments over time, etc.)
• If there will be any ongoing relationships

Often, the best outcomes come from expanding the options—not narrowing them.

11. Be ready with a draft settlement agreement.

It can be difficult after a long day of mediation discussions to start editing a settlement agreement. Both parties will save a lot of time and money if you prepare beforehand and are ready with an agreement that just requires some minor tweaks.

This is especially important if there are any unique considerations or terms that need to be taken into account to resolve the dispute.

12. Treat mediation as trial preparation.

Being well prepared for mediation can strengthen your trial or arbitration posture. It can:

• Clarify themes
• Test arguments
• Reveal strengths and weaknesses

Even if the case does not settle, the process can add value.

Final thoughts

Mediation is an important strategic opportunity. The parties who get the most out of it:

• Prepare thoughtfully
• Align internally and have the difficult discussions with the client before the session begins
• Engage realistically
• Remain open to both legal and business solutions

The parties who achieve the best outcomes are typically those who arrive prepared—not only with a strong understanding of the legal issues, but also with a realistic assessment of the business, financial and personal considerations at stake.

When approached thoughtfully, mediation can do more than resolve a dispute. It can help parties avoid unnecessary costs, preserve important relationships and reach resolutions that better reflect their business objectives, financial realities and long-term interests.