AI Reshapes Legal Practice: ClioCon 2025 Delivers a Wake-Up Call

Jeff Lewis reports from the 2025 Clio Cloud Conference in Boston. Day 1 was encouraging, but Jeff reports feeling Day 2 as a “gut punch”: within about 5-10 years, many fundamentals of legal practice will be unrecognizable.

Here are a few ways legal industry leaders suggest you can skate to where the puck is going—rather than finding yourself behind by skating to where it is now.

• The $5 Billion Opportunity: Clio CEO Jack Newton says there are billions in untapped legal services—and AI tools can help lawyers tap it.
• 74% of Billable Tasks Automatable: Clio's research suggests nearly three-quarters of current billable work could be automated. The game: find the redundancy, or else be the redundancy.
• AI Becoming Standard: 79% of legal professionals are now using AI tools (up from just 19% two years ago).
• Time-Tracking Revolution: Before AI replaces your billables, let it enhance them: AI-powered tools like Point One and Tempello automatically capture and enter your time—you might be surprised how much money you’re leaving on the table.
• Context-Aware Legal Research: Clio's new "Vincent" platform combines practice management data with comprehensive legal research to produce AI responses grounded in both case facts and applicable law, reducing hallucinations and providing verifiable citations.
• The Neurosurgeon Analogy: Susskind's provocative comparison suggests that just as AI might make brain surgery obsolete through prevention and precision, traditional legal services may be replaced by more efficient, AI-driven alternatives that clients prefer.

True, there are shiny objects out there, and as Tim says many will get “Sherlocked”—become obsolete as the underlying AI tech improves. But getting in the game is key—the sidelines are going to be a very unhappy place very soon.

Few lawyers and LRW instructors write and think more about AI than Professor Jane Woods of Mizzou Law, who offers this most important AI advice: If you haven’t read the case, don’t cite the case.

• The Boies Schiller Cautionary Tale: That would have saved Boies Schiller’s bacon. We discuss the high-profile Scientology/Masterson appeal, and whether the Court of Appeal is going to strike plaintiff’s respondent’s brief because of the Boies Schiller attorneys hallucinated cases and otherwise wrong legal citations.
• AI's Ideal Applications: Most effective AI uses include drafting standard legal sections, style polishing, fact organization, and processing large records.
• How to AI in Legal Practice: Avoid garbage-in-garbage-out by feeding case opinion PDFs from authoritative legal databases directly into AI projects—don’t let AI search the internet on its own.
• Don’t hate the "Em Dash"! Some firms have reportedly banned em dashes in legal writing because they're seen as indicators of AI-generated text, highlighting how AI's stylistic preferences (even good ones!) may be reshaping legal writing conventions.
• Should lawyers disclose AI use? It depends. But if you’re thinking about charging $900/hour and to outsource to a robot, maybe don’t do that.

Jeff thinks our business and even this podcast will be aped by robots by this time next year. Until then, tune in for tips on how best to resist or suck up to the robot overlords.

Just a couple years ago when we talked with Ernie Svenson, the attorney who talks tech fluently, AI was not even a thing. Now in late 2025, it’s the only thing. Ernie joins Tim and Jeff to discuss the rapidly evolving landscape of AI in legal practice, why AI gives small firms an advantage, and how attorneys can safely leverage these tools without falling victim to “hallucinations.”

We discuss how to embrace AI tools without anxiety (or with the appropriate amount of anxiety), starting with inconsequential applications before moving to more consequential legal work.

• Pattern Recognition on Steroids: AI excels at pattern recognition and language expression, ideal for first drafts and oral argument prep.
• Not an AI Problem: Recent sanctions for citing hallucinated cases reflect a longstanding due diligence issue. AI just exposes attorneys who don't verify sources.
• Small Firm Advantage: AI works best as a force multiplier for individual cognitive ability, giving solo practitioners and small firms who master these tools an edge over larger organizations.
• Agentic AI on the Horizon: While fully autonomous AI agents need careful supervision, basic applications like data entry are already available, with complex applications developing rapidly for case prioritization and KPI extraction.

Teaching Judges: Appellate Expert Cherise Bacalski on Brief Writing and the Human Side of Law

Appellate specialist Cherise Bacalski teaches appellate writing at NYU Law's New Appellate Judges Program, and in this interview we discuss her insights from both sides of the bench and how her background in rhetoric shapes her approach to appellate advocacy.

• Training new judges: At NYU, Cherise teaches newly appointed appellate judges how to make their opinions more readable through proper structure, headings, and organization—skills that help both judges and practitioners.
• The rule is king: What is the rule in your case? Cherise explains that, whatever it is, that rule should inform every part of your brief.
• Write for a “hostile reader”: Reading your brief—your trenchant, brilliant, erudite, sparkling brief—is the last thing any judge wants to do. Forget being brilliant. Just be clear, concise, skimmable, and easy to digest.
• Lead with old information: One of the most effective writing principles is beginning each new point with familiar information to propel readers forward at the speed of thought, reducing the need for excessive explanation.
• The human element: Cherise views the law as fundamentally human. Understand you are talking to humans, not picking a lock.
• AI is an amazing tool, but not a replacement: Use AI to test arguments and identify weaknesses in briefs. But AI sometimes misses critical "smoking gun" evidence in case analysis.

Tune in for a masterclass in appellate advocacy that bridges the gap between academic rhetoric and practical legal persuasion from an attorney who's seen the system from multiple perspectives.

Appealing in the 9th Circuit? Your deadline is 30 days. Don’t let Rule 58’s “separate document” extension lead you astray. Appellate specialists Tim Kowal and Jeff Lewis also discuss ChatGPT 5 (a “market disruptor”), and sanctions strategies in federal court.

• Appeal Deadline Alert: The 9th Circuit in McNeil v. Guitare held that Rule 58's 150-day extension for appeal deadlines applies only to final judgments, not collateral orders like qualified immunity denials.
• Anti-SLAPP Motion Timing: Mora v. Menjivar confirms that filing just a notice of anti-SLAPP motion within the 60-day deadline is insufficient—supporting documents must be filed concurrently.
• Out: Res Judicata. In: Claim Preclusion.
• Sanctions Strategy: 28 U.S.C. § 1927 can be used for sanctions without Rule 11's cumbersome 21-day safe harbor.
• AI Ethics: California courts confirmed in Nolan v. Land of the Free that attorneys must personally read all cited authorities, regardless of whether AI tools were used in brief preparation.

And more practical insights on navigating procedural pitfalls, avoiding sanctions, and ethically incorporating AI tools into your appellate practice.

Failing to cite your secondary sources in briefs is poor form. But is it plagiarism? Jeff and Tim debate. And when the Supreme Court The publishes a case, should it explain itself? PJ Gilbert and Tim say yes, Supreme Court and Jeff disagree.

Also in this episode:

• Can copying from a CLE article really get you sanctioned? Kelly v. Tao suggests… maybe.
• Presiding Justice Gilbert rails (again) against the Court's silent de-publishing practices.
• Deny a request for admission in a one-way fee-shifting case? You might still owe fees—Gammo v. Morrell.
• $105k in sanctions after failing to abandon claims disproven in discovery—Atlantic v. Baroness.
• The perils of citing the wrong fee statute—Martin v. Hogue.
• Gibson Dunn bills $1.8M for May alone in public interest litigation over LA homelessness.
• Can ChatGPT testify against you? OpenAI’s CEO says maybe.
• How AI tools are reshaping billing, ethics, and expectations for appellate lawyers.

Tune in for AI ethics, briefing blunders, and why even your RFA denials could cost you.

Patrick Hagen is a man of the people—he still proudly uses Times New Roman! But he also has the ear of LinkedIn’s legal-writing elite, with over 36,000 followers as of August 2025.

Patrick sits down with Jeff and Tim to share the source and method behind his viral legal-writing tips, how his judicial clerkships shaped his voice, how to hone good writing even when writing “by committee” under senior associates and partners, and why good writing—even in a losing case—is always worth the effort.

We discuss:

• Why it is axiomatic that you should pause and think before using the word “axiomatic.”
• How AI tools like ChatGPT, ClearBrief, and CoCounsel can be the road to sharpened prose—or the road to ruin.
• Can a legal writing critic still be gracious?
• And the lightning round: TNR, Arial, two spaces, Oxford commas, and “Comes now….”

Stay for the writing tips, return for the wit, and if you don’t want Patrick’s 36,000 followers laughing at your writing foibles behind your back, follow him on LinkedIn.

Unlike any other state, California effectively deputizes employees to act as “Private Attorney Generals” to sue employers for PAGA claims—both for themselves, and for their co-workers. But since the individual claims can get compelled to arbitration, employees started to file claims only on behalf of the “body” of co-workers, asserting no claim on behalf of themselves as the “head” of the case.

Employer litigator Monte Grix explains how PAGA evolved into their “headless” form. Monte, Tim, and Jeff discuss the four cases currently on review before the California Supreme Court, including Leeper v. Shipt. Monte offers an inside view from the defense side, explaining why employers see these actions as a threat to arbitration agreements and the subject of growing appellate friction.

Also in this episode:

• How Viking River Cruises and Adolph v. Uber set the stage for today’s headless-PAGA storm.
• Strategic pleading: why some plaintiffs drop their individual claims to avoid arbitration.
• The standing trap: can a plaintiff assert representative PAGA claims without showing personal harm?
• The stakes in the four pending California Supreme Court cases: if a plaintiff can skip arbitration by asserting only representative claims, is PAGA immunity from arbitration complete?
• Turrieta v. Lyft: why copycat plaintiffs can’t intervene in pending PAGA settlements.
• Rodriguez v. Packer Sanitation and the Fifth District’s lesson in reading "and" as "and/or".

Plus: a side quest into unconscious bias, tenure-track discrimination, and why arbitration clauses remain a sore spot for appellate lawyers.

Then: the California Supreme Court's recent ruling in Hohenshelt eases the "30-day rule" for arbitration payments. Employers who pay a day late haven’t necessarily waived their rights—and Monte predicts the U.S. Supreme Court may eventually weigh in.

Tune in for appellate nuance, strategic pleading, and the headless claims keeping California employers (and the courts) up at night.