Why Mediation Fails and How to Fix It: A Strategic, Political, and Practical Approach to Case Resolution

This session explores the fundamental reasons parties enter mediation, from bridging communication gaps to validating resolutions. Participants will learn how to assess whether clients genuinely want to settle and how court-ordered mediation impacts party attitudes.

Learn which types of disputes are inherently difficult to settle due to emotional baggage, including fraud, discrimination, and family law matters. The session contrasts these with straightforward business disputes and insurance cases that tend toward easier resolution.

This session examines the critical back story behind disputes and the stakeholders who truly call the shots. Participants will identify common roadblocks including lawyers who won’t part with cases, clients drinking their own Kool-Aid, and decision-makers with personal stakes.

Timing is an art—cases can be mediated too soon or too late. This session explores strategic timing considerations from defense and plaintiff perspectives, with attention to case-specific factors like domestic disputes and complex litigation.

Discover why your opponent’s respect for the mediator may matter more than your own preferences. Key selection criteria including persistence, subject matter familiarity, and the counterintuitive benefits of selecting mediators from the opposing practice area are examined.

A short break to refresh before continuing with the remaining sessions on mediation formats, techniques, and settlement processes.

Traditional joint opening statements have evolved as many mediators now avoid confrontational formats that impede resolution. This session covers alternative approaches including staggered arrivals, separate caucuses, and considerations for remote versus in-person mediation.

Learn what critical information to provide mediators, emphasizing back stories over legal technicalities. Participants will discover how to present efficiently using chronologies and cheat sheets rather than overwhelming with exhaustive documentation.

Mediation involves multiple concurrent negotiations between lawyers, clients, and insurers. This session addresses the bulldog lawyer problem and the importance of preparing clients for difficult conversations they will encounter during the process.

Beyond resolution, mediation serves as a mechanism to test facts, theories, and defenses. Learn how mediators can help educate clients about case weaknesses and conduct essential risk assessments that go beyond simply delivering numbers.

This session identifies the four critical pinch points where mediations fail and provides strategies for navigating each. Topics include describing resolutions creatively, leveraging non-monetary terms, and avoiding the dangerous term sheet stage pitfalls.