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July 15, 2026 By Staff

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

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.

Click here for more information or to purchase this On Demand CLE, Why Mediation Fails and How to Fix It: A Strategic, Political, and Practical Approach to Case Resolution (On-Demand) – LPCLE –.

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

  1. Why Parties Mediate — Identifying the real reasons parties seek mediation, from communication breakdowns and merit disputes to settlement validation and opposition research
  2. Mediator Selection — Key criteria for choosing an effective mediator, including credibility with opposing counsel, persistence, subject matter familiarity, and the ability to navigate roadblocks
  3. 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)
  4. Insured vs. Uninsured Defendants — How insurance coverage shapes the emotional and economic dynamics of negotiation on the defense side
  5. 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
  6. 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
  7. 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
  8. 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)
  9. 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
  10. Choosing the Right Forum — Comparing in-person, remote, and shuttle diplomacy formats, and evaluating which approach best fits the case and the parties
  11. 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
  12. Learning Through Mediation — Using the mediation session itself as an intelligence-gathering opportunity to pressure-test facts, legal theories, and unanticipated defenses
  13. 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
  14. Professionalism and Maintaining Relationships — Why the relationship with opposing counsel outlasts any single case, and why professionalism is the foundation of effective dispute resolution

Reuben Guttman, Esq.

Reuben Guttman, Esq. is a founding member of Guttman Buschner LLP and mediator with Resolute Systems who brings decades of complex litigation experience across fraud, breach of fiduciary duty, antitrust, environmental, and statutory claims. He has recovered billions of dollars for whistleblowers and the federal government, with qui tam settlements ranking among the largest in False Claims Act history, and serves as an Adjunct Professorial Instructor at American University, faculty member of the National Institute of Trial Advocacy, and Fellow of the American Bar Foundation.

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  • rguttmanReuben A. Guttman
    Senior Founding Partner


    (202) 800-3002
    rguttman@gbblegal.com

    Practice Areas
    Consumer Law
    Complex Litigation
    Complex Employment and Labor
    Civil Rights

    Education
    Emory Law School (J.D., 1985)
    University of Rochester (BA, 1981)

    Admissions
    The State of Georgia
    The District of Columbia
    The Commonwealth of Pennsylvania
    The State of New Jersey
    The Supreme Court of the United States
    The United States District Courts for the
    - District of Columbia
    - District of New Jersey
    - District of Nebraska
    - Northern District of Georgia
    - District of Maryland
    - Western District of Michigan
    -Eastern District of Pennsylvania
    The United States Courts of Appeal for the
    - Third Circuit
    - Fourth Circuit
    - D.C. Circuit.

    Boards/Memberships
    Fellow of the American Bar Foundation

     

    American Bar Association Fellows
     

    Reuben A. Guttman
    Rated by Super Lawyers


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On Demand CLE: Reuben Guttman, and Professor JC Lore present CLE covering topics in their book, Pretrial Advocacy, Wolters Kluwer-NITA (2021).”
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