Civil Litigation,
Alternative Dispute Resolution
Jul. 8, 2025
Complex case mediation: 6 essential tips for attorneys to succeed
Court-ordered mediation in complex cases can feel like a detour, but by applying the six CIRCLE strategies, attorneys can turn it into a powerful advantage for resolution and insight.





Jill M. Manning
Mediator, Arbitrator, Special Master, Neutral Evaluator and Discovery Referee
JAMS
Phone: (415) 433-9000
Email: JManning@jamsadr.com
University of San Francisco SOL; San Francisco CA
She handles antitrust and competition, business and commercial, class action and mass torts, cybersecurity and privacy, education, employment, entertainment and sports, health care and securities matters.

Choose
Identify
Range
Calm
Learn
Evaluate
You are representing a client in a complex case that is making its
way through the court system when -- boom -- the judge orders the parties to
mediation. It may not feel like welcome news. Mediation can seem like an
unexpected detour, one that delays litigation and pulls focus from trial
preparation. But in truth, it presents a powerful opportunity. First, mediation
allows your client to explore resolution without signaling any weakness -- your
client did not initiate the process, beyond checking a box on the mandatory ADR
form. Second, by approaching the session strategically and applying the six key
tips that follow, you will leave the mediation in a stronger position than when
you started. Whether or not a settlement is reached, you will walk away with
valuable insights into the opposing party's strategy, a fresh perspective on
your case from a neutral, and a clearer path forward. CIRCLE up your team and
apply these six tips to conquer complex case mediation.
Choose
It may seem straightforward, but selecting the mediator is one of
the most important decisions you will make in the entire process, particularly
in complex cases. A successful mediation often hinges on the mediator's
neutrality, experience, subject matter knowledge and style. Take the time to
evaluate each candidate's background and approach in light of
the specific dynamics of your case, your client's priorities and your strategic
goals. A well-matched mediator can build trust, manage conflict effectively and
significantly increase the chances of reaching a meaningful resolution. Factors
to consider are:
Neutrality: Neutrality
means that the mediator has no stake in the outcome, holds no predetermined
opinions about the case and demonstrates no favoritism toward any party.
Carefully vet proposed mediators by asking specific, targeted questions
designed to identify potential biases.
Subject
matter knowledge: Consider whether it would be helpful to select a mediator with
experience or knowledge in the area of law or industry
relevant to the dispute, particularly in complex or technical cases (e.g.,
antitrust, intellectual property).
Experience
in complex cases: In high-stakes or multiparty cases, it is essential to select a
mediator with proven experience managing complex disputes. A mediator familiar
with the dynamics of large-scale or multifaceted conflicts will be better
equipped to navigate the legal, logistical and interpersonal challenges these
cases present.
Style: Is the
mediator facilitative (guiding parties to find their own solutions), evaluative
(offering opinions on strengths and weaknesses) or transformative (focused on
relationship repair)? The effectiveness of the process often depends on
choosing a mediator whose approach aligns with the nature of the dispute, the
parties' dynamics, and the goals of the mediation.
Identify
Once the parties have selected a mediator, begin preparing your
case thoughtfully. Identify the strengths and weaknesses of your position. A
clear understanding of both allows you to set realistic expectations for
settlement. This balanced perspective helps you avoid the pitfalls of
overconfidence or unnecessary pessimism, enabling you to negotiate from a
well-informed, strategic position. Leverage your case's strengths by
emphasizing key arguments and supporting evidence. At the same time,
acknowledging weaknesses enables you to anticipate likely counterarguments and
plan measured responses. It also helps you distinguish between core issues and
those that are more flexible. With this clarity, you can make targeted
compromises that protect your client's essential interests while giving ground
on less critical points. Being prepared to negotiate from this foundation
increases the chances of reaching a resolution that meets your client's goals.
Range
Develop a range of potential settlement options. Prepare multiple
solutions that could meet both your client's needs and those of the opposing
party. Consider creative and non-monetary terms -- such as payment plans,
changes to policies or practices, confidentiality or nondisparagement clauses,
or future business arrangements. Based on your assessment of the case's
strengths and weaknesses, establish a realistic settlement range. Identify both
your client's ideal outcome and the minimum acceptable terms. Have an honest
conversation with your client about likely outcomes and the risks of continued
litigation. Set practical expectations for what mediation can achieve,
including the possibility that the parties may not reach an agreement. Finally,
make sure that all necessary decision-makers are available and authorized to
contribute to discussions and approve any proposed terms.
Calm
Mediation can be emotionally charged, especially if the dispute
involves personal animosities or high stakes. Prepare yourself and your client
to stay calm, focused and open-minded during the mediation. Be prepared to
address emotional responses without letting them derail the mediation process.
When tensions flare, don't get furious; get curious. Ask the mediator "W"
questions: Why is this person acting this way? What are they really trying to
say? What is underneath their position or emotion? Who is driving the process?
In the context of mediation, anger can shut down communication, but curiosity
opens it up. When attorneys get curious, they are more likely to uncover hidden
interests, misunderstandings and opportunities for compromise. Maintaining a
solution-focused mindset, not an emotional one, is key.
Learn
Consider asking for a joint session with the mediator. While joint
sessions have become less common, they still provide a valuable chance to
observe opposing counsel firsthand and gain important insights. During a joint
session, you can learn important information from opposing counsel about their
view of the important facts and applicable law. Pay close attention to opposing
counsel and their client, and evaluate their strengths and weaknesses: How
effective and persuasive is opposing counsel? Is the client credible,
sympathetic or likeable? A joint session can offer a preview of what opening
statements at trial might look like and how a jury could perceive the case.
Take detailed notes and think critically about how these dynamics might
influence the courtroom. Use these observations to refine your negotiation
strategy and develop a more informed, targeted settlement offer.
Evaluate
After a joint session, the mediation will proceed to separate
caucus sessions, and the mediator will shuttle between parties to communicate
offers, explore concerns, and facilitate negotiation. When your client receives
a settlement offer, evaluate it carefully. Consider if the proposed outcome is
better than what the client is likely to achieve at trial by analyzing the
strength of the case, the likelihood of success and the potential costs of
continued litigation -- including attorneys' fees, expert costs, delays and
appeals. Assess the quality of the evidence, key witnesses, factual disputes,
and any procedural or judicial factors that may influence the outcome.
Consider your client's broader goals and values. Does the offer
align with what truly matters to them -- whether that's financial recovery,
confidentiality, speed, or closure? Help the client understand not just the
legal implications but also the emotional and practical trade-offs of settling
versus litigating. Ask for the mediator's neutral perspective. They may provide
insight into how the offer compares to similar cases or suggest creative
options for bridging gaps. If the negotiation stalls, consider asking the
mediator to make a settlement proposal. Because they're engaging privately with
both sides, they may have a unique vantage point to craft a solution that meets
the core interests of both parties.
Armed with these six tips for mediating complex cases, you are
well positioned to make the most of the mediation process. Depending on the
complexity of the issues involved, the case may be resolved in a single session
or require multiple meetings. Some outcomes may feel like true win-win
resolutions; others may simply represent a practical compromise -- acceptable to
both sides and far preferable to the uncertainty, expense, and time demands of
continued litigation. Most importantly, mediation allows you to shape the
outcome rather than leaving it in the hands of a judge or jury.
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