In a conversation with Arthur Rothrock on The Litigator's Path, Reuben explains why he's shifting from a career built on courtroom combat to full-time mediation work, what makes trial lawyers better mediators than many retired judges, how AI is changing the economics of associate training, and why the emotional pace of modern litigation is burning out lawyers and clients alike. He also describes how he wrote a novel in the margins of a busy practice by replacing cocktail hour with short writing sessions. The thread connecting all of it: after four decades of fighting, Reuben has come to believe that most disputes should never reach trial, and that the skills required to settle them are the same advocacy skills he spent a career building.
Why Tim Reuben Believes Trial Lawyers Make Better Mediators Than Retired Judges
Reuben's position is blunt and, by his own admission, "perhaps a tad controversial": the assumption that a retired judge will be an effective mediator is wrong. He has seen it fail repeatedly across decades of practice. His reasoning is structural. Judges spend their days managing calendars with 18 or more items, acting as what Reuben calls "a traffic cop" trying to clear a docket. That is a real skill, he says, but it is not a mediation skill.
What mediation requires, in Reuben's view, is advocacy on behalf of resolution. A mediator needs to understand both sides and then persuade each party that settlement serves their interests. Lawyers who spent careers as advocates can slide back into that mode. Judges who went straight from law school to clerkships to the bench, or who spent limited time in trial practice, often default to telling parties their case is weak rather than drawing them toward agreement. Reuben recalls one judge-mediator who spent the session citing published opinions, and another who flatly told a party their case was "garbage." Neither approach moved anyone toward settlement. "Most people don't react well to that," Reuben says. "You're just going to react and say, well, you go jump in the lake."
His own style is interactive and directive. He asks questions designed to get parties to identify their own risks rather than lecturing them about weaknesses. He divides mediation into two stages: a first phase where each side tells enough of their story to feel heard, followed by a deliberate pivot toward the future. Reuben warns against letting stage one run too long. When parties spend too much time reliving grievances, they become more emotionally entrenched and less willing to compromise. "All they can do is wallow in it," he says, and wallowing is the enemy of resolution.
How Reuben Structures Mediation Around Risk Analysis and Forward-Looking Negotiation
Reuben frames every mediation as a risk analysis exercise. The question he pushes parties to answer is not who was right or wrong, but what they stand to lose by continuing and what they gain by stopping now. He has settled cases that ran past midnight because, as hours pass, parties slow down and begin thinking more practically.
The backdrop to this approach is a court system under severe strain. Reuben cites LA Superior Court Judge Riff's observation that civil filings have more than doubled in recent years. In his own practice, Reuben filed a straightforward motion to compel that sat unheard for a full year because the court lacked capacity. "Justice delayed is justice denied," he says, and the practical consequence is that clients face open-ended timelines with no guarantee of resolution. One of Reuben's own cases ran for 10 years, went to the Court of Appeal, received Supreme Court review, and was tried twice. He won and recovered all legal fees for his clients, but even he acknowledges that a decade of litigation is something "people can't last that long" through.
That experience is part of what drives his transition to mediation. He still litigates and oversees cases at Reuben, Raucher & Blum, but he is deliberately shifting the balance. He also notes a practical advantage of running mediation from within an active litigation firm: he has access to his own attorneys, research capabilities, and institutional knowledge in ways that a solo mediator or one housed at a large mediation company may not.
Tim Reuben's Take on AI, Associate Training, and Why Lawyers Must Educate Themselves Now
Reuben recently required every attorney at his firm to devote significant time to AI education, covering available tools, appropriate use cases, and limitations. He compares AI's impact to two earlier shifts he witnessed firsthand: the arrival of Lexis and Westlaw, which replaced physical law libraries and hours of manual research, and the rise of email, which transformed how evidence is created and discovered. Jason Horst predicts a related downstream effect: as AI accelerates the pace of litigation, more disputes will migrate to private mediation precisely because courts cannot absorb the added volume.
On AI specifically, Reuben sees both promise and danger. He points to a recent appellate opinion in which a lawyer was sanctioned $10,000 for submitting AI-generated work product without verification. The tool, he notes, can fabricate citations even when instructed not to. His position is that AI will likely take over certain associate-level tasks, particularly legal research and initial memo drafting, but that a human lawyer must still read every case, verify every citation, and apply independent judgment. "When you read those cases and use independent thought, you find new arguments, new ideas, new approaches," he says. The worry is that if firms stop hiring junior associates because AI handles their traditional work, there will be no pipeline of trained lawyers to become the senior litigators and mediators of the next generation. Reuben sees this as a genuine threat but not an inevitable one, provided firms continue to invest in training.
The document review problem is where Reuben sees AI's most immediate value for practicing litigators. Modern cases routinely involve thousands of emails and text messages. His firm has handled matters requiring recovery of deleted texts through forensic experts, including one case where deleted photographs told "a different story than what was in the pleadings." Loading that volume of communications into the right system and using AI to surface relevant material could dramatically reduce review hours – the kind of workflow that platforms like Legion are designed to address.
The Advocacy Skills That Connect Tim Reuben's Litigation, Mediation, and Fiction Writing
Reuben wrote Tequila during what he calls cocktail hour – the 5:00 to 6:00 p.m. window after leaving the office. Rather than unwinding with a drink, he sat down and wrote. His method was to keep chapters short, two to four pages each, so he could complete one in a single sitting. The structure also serves the reader: each chapter shifts characters and locations, keeping the plot moving quickly. "Instead of drinking a whole lot of tequila, I worked on writing Tequila," he says.
He traces the impulse back to creative writing in high school, but career building, firm management, and raising children pushed the project back for decades. Now an empty nester with his youngest in college, he found the time. He is roughly 80 to 90 percent through a first draft of a second novel, which includes a full jury trial sequence.
What connects all three pursuits – litigation, mediation, and writing – is the same mental process. Each requires research, idea generation, and persuasion. In litigation, Reuben persuades judges and juries. In mediation, he persuades opposing parties. In fiction, he persuades readers to care about his characters. He is a believer in clarity of narrative: his books feature unambiguous heroes and villains because, after a career spent navigating shades of gray, he finds value in art that draws clean moral lines. The main character, Brian Youngman, is a lawyer with "some quirks and some faults," but there is no confusion about which side he is on.
Reuben also stresses the value of humor in advocacy – and in life. He recalls making a bankruptcy judge laugh in a New York courtroom while representing a client with $50 million at stake, a relative "peanut" in that proceeding. The opposing big-firm lawyers, he says, were "immediately traumatized." His advice: the safest joke is one you make about yourself. It signals approachability without risking offense, and it reads the room without demanding anything from it.
What Litigators Can Take Away
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Reuben requires every lawyer at his firm to spend dedicated education time on AI tools, treating it with the same seriousness as learning Lexis or Westlaw when those platforms first arrived – because the lawyers who understand AI's limits will avoid the sanctions that are already hitting those who don't.
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When mediating, Reuben deliberately limits how long parties spend recounting past grievances, then pivots the conversation toward future interests and practical risk analysis – a structure that prevents emotional entrenchment and moves cases toward resolution.
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Reuben evaluates mediators not by whether they held a judicial title but by whether they spent meaningful time as advocates; his experience is that the ability to persuade, not the authority to decide, is what drives settlement.
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Before sending any written communication – an email, a brief, a demand letter – Reuben tells his associates to reread it, and ideally read it aloud, because the few seconds of friction that creates is often enough to catch tone problems and half-formed arguments before they cause damage.
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Reuben treats his fiction writing the same way he treats case preparation: short daily sessions with a defined scope, so that the work compounds over months without requiring large blocks of uninterrupted time that a practicing lawyer rarely has.
Listen to the Full Episode
Tim Reuben's full conversation with Arthur Rothrock covers everything from the economics of decade-long litigation to why Aesop's fables belong in trial preparation. Listen on Spotify or Apple Podcasts. Learn more about Reuben's mediation practice at reubenmediation.com or his novel at timreuben.com.