Mediation is one of the most powerful tools in a litigator’s arsenal — but only when approached with strategic intent. This course goes beyond the mechanics of the mediation process to examine the political, psychological, and practical forces that determine whether a case resolves or falls apart. Drawing on decades of complex litigation experience, Reuben Guttman walks practitioners through how to diagnose why parties come to the table, how to select and prepare the right mediator, how to identify and overcome roadblocks, and how to reframe settlement in terms that resonate with clients and opposing parties alike. Attendees will leave with a sharper understanding of the hidden dynamics that drive — or derail — case resolution, and concrete strategies for making mediation work.
Principles
- Successful Mediation Begins Long Before the Session
- Settlement Is Driven by People, Politics, and Interests—Not Just Legal Merits
- Effective Negotiation Requires Adaptability and Strategic Communication
- Professionalism Creates Better Outcomes
Syllabus
- Why Parties Mediate — Identifying the real reasons parties seek mediation, from communication breakdowns and merit disputes to settlement validation and opposition research
- Mediator Selection — Key criteria for choosing an effective mediator, including credibility with opposing counsel, persistence, subject matter familiarity, and the ability to navigate roadblocks
- Understanding Case Baggage — How case type affects settlement dynamics, from highly polarizing claims (fraud, discrimination, family law) to cases more naturally suited to resolution (negligence, breach of contract)
- Insured vs. Uninsured Defendants — How insurance coverage shapes the emotional and economic dynamics of negotiation on the defense side
- Recognizing and Overcoming Roadblocks — Common barriers to settlement, including plaintiffs reluctant to part with their case, unrealistic damages models, parties overconfident in their own positions, attorney-client control issues, and adversarial lawyer dynamics
- The Politics of Bargaining — Mapping where negotiation actually happens: within each side, between counsel, and between attorney and client; why mediators must understand these internal politics
- Reframing Settlement for the Client — How to translate dollar figures into concrete, meaningful terms that connect with a client’s real-world goals and priorities
- The Corporate Rubik’s Cube — Analyzing how settlement or verdict affects a corporate defendant’s external exposure (further litigation, securities risk, regulatory scrutiny, reputational harm) and internal dynamics (profit center allocation, accountability)
- Reverse Engineering the Settlement — Working backward from a realistic resolution: who controls the decision, how settlement impacts the business, and how even contentious disputes get reduced to a business calculation
- Choosing the Right Forum — Comparing in-person, remote, and shuttle diplomacy formats, and evaluating which approach best fits the case and the parties
- Preparing and Educating the Mediator — Strategies for getting the mediator up to speed efficiently, including deselecting extraneous facts, focusing on dispositive issues, and using timelines and witness cheat sheets
- Learning Through Mediation — Using the mediation session itself as an intelligence-gathering opportunity to pressure-test facts, legal theories, and unanticipated defenses
- Zealous vs. Offensive Advocacy — Drawing the line between effective fact-based advocacy and conduct that poisons the process; how to inoculate the room against information that is difficult to receive
- Professionalism and Maintaining Relationships — Why the relationship with opposing counsel outlasts any single case, and why professionalism is the foundation of effective dispute resolution
