Is AI making legal writing too easy—and too cheap? In this episode, Jen Leonard and Bridget McCormack explore how generative AI tools are reshaping writing as a professional skill. They discuss the paper “Making Talk Cheap,” which argues that when anyone can generate polished text, writing loses its value as a signal of skill, effort, or merit. What does this mean for hiring, advancement, and lawyering in the AI era? Plus, they unpack a new Wharton study showing how enterprise AI use is soaring—with real ROI—while sharing personal stories of AI’s practical impact.

Topics Covered:

• Wharton’s 2025 report on enterprise AI adoption and ROI (vs. the “failed pilots” narrative)
• How generative AI is leveling the playing field in writing quality
• The Making Talk Cheap study on devalued written work and hiring signals
• Implications for legal hiring, promotion, and skill development in the AI era

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Can AI make the nation’s largest trial court more accessible, trusted, and just? In this episode, LA Superior Court CEO, David Slayton joins hosts Jen Leonard and Bridget Mary McCormack to unpack how generative AI is already reshaping court services—and why “effective” beats “efficient.” 

We explore Court Help on LACourt.gov, change-management tactics that stick, and the delicate balance between moving too slowly (and getting overwhelmed) and too fast (and losing public trust). Practical, candid, and grounded in real operations, this conversation offers a roadmap for legal leaders navigating AI.

Topics covered:

• Court Help and responsible gen-AI design
• Serving self-represented litigants at scale
• Change management in high-trust institutions
• Risks of moving too slow—or too fast—on AI
• Predictive analytics, triage, and future workflows

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Can an AI fairly decide a dispute—and win party trust? Recorded live at MAICON 2025, this episode dives into the American Arbitration Association’s first AI arbitrator, a documents-only two-party workflow designed for construction cases with a human in the loop. AAA President Bridget McCormack explains the multi-agent architecture, why procedural fairness matters, and how the tool reflects a century of arbitration expertise. We also unpack OpenAI’s Sora 2 rollout, likeness/IP controversies, and the shift from opt-out to permission-first models—and what deepfakes mean for courts and the rule of law.

Topics covered:

• How AAA’s AI arbitrator works (and when to use it)
• Human oversight, speed, and cost gains
• Sora 2’s IP backlash and policy reversal
• Deepfakes, watermarking limits, and courtroom risk

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How should law schools teach judgment, writing, and readiness in the age of AI? Georgetown’s Jonah Perlin and Suffolk’s Dyane O’Leary join hosts Jen Leonard and Bridget McCormack to explore how generative AI is reshaping legal education—from 1L writing and grading to ethics, policy, and professional judgment.

They share real classroom experiments that reveal how professors are using AI to teach reasoning and curiosity, and how schools are balancing innovation with integrity through redesigned assessments and “AI literacy” curricula. The conversation also dives into multimodal and voice-based tools transforming how students learn, communicate, and prepare for modern practice.

Topics covered:

• How AI is transforming legal writing and pedagogy
• Grading, integrity, and fairness in the AI era
• What “practice-ready” means for future lawyers
• The rise of multimodal and voice-driven learning
• Building judgment and curiosity through AI

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Can state‑court judges safely use generative AI? In this episode, Jen Leonard and Bridget McCormack unpack Pennsylvania’s interim policy for courts—what it allows, what it restricts, and how human review and confidentiality guardrails work in practice. They compare real AI workflows from their own desks—editing a book with Claude and turning a long essay into slides—and dissect the “AI pilots are failing” storyline versus the reality of high adoption and slower ROI. You’ll also hear why court labs, enterprise access, and judge‑focused guidelines matter now.

We cover:

• Pennsylvania Supreme Court’s interim AI policy and guardrails
• AI Aha!: Claude as editor; ChatGPT vs. Claude vs. Gemini for slides
• MIT “AI pilots” narrative vs. actual adoption and ROI timelines
• Court “AI labs,” enterprise licenses, and chatbots for self‑represented litigants
• Michigan pilot with Learned Hand and practical guidance for judges

Episode Highlights:

02:56 AI Aha! Moments

10:10 What Just Happened: MIT Report

21:55 Main Topic: PA Supreme Court’s Interim AI policy

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What does it take to modernize a 100-year-old legal institution and prepare lawyers for the AI era? In this episode, Jen Leonard and Bridget McCormack sit down with Jae Um (Lumio) and Ilona Logvinova (Cleary Gottlieb) to explore how legal organizations move from AI experiments to real impact. From acquisitions and change management to digital agents and legal education reform, this conversation breaks down what actually drives innovation in law.

We cover:

• Practical AI workflows and tools in legal practice
• Culture, incentives, and strategy in firm innovation
• Inorganic vs. organic growth (acquisitions and beyond)
• Digital agents and the future of early-career legal work
• How law schools must evolve for AI-native practice

Episode Highlights:

02:15 AI Aha! Moments

10:39 Inorganic Growth & Innovation Strategy

32:50 Law Schools & Learning in the AI Era

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Is GPT-5 good enough to practice law? This episode dives into OpenAI’s newest model and its implications for legal practice, including how it compares to previous models and where human oversight remains essential. Jen Leonard and Bridget McCormack also unpack a groundbreaking report from IAALS on regulating AI in legal services, shifting the focus from lawyers to consumers.

Episode Highlights:

(2:22) AI Aha! Moments: AI and human error in court

(12:52) What Just Happened: Key features and legal benchmarks of GPT-5

(20:50) IAALS phased approach to AI oversight

(28:13) How courts and communities are adapting to AI tools

Read the IAALS report on regulating AI in law here: https://iaals.du.edu/sites/default/files/documents/publications/ulr_regulating_ai.pdf

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What happens when a litigator and a quantum physicist build a law firm from the ground up with AI at its core? In this episode, hosts Jen Leonard and Bridget McCormack speak with Phillip Young and Daniel Long of Garfield Law, the UK’s first fully AI-native, regulator-approved law firm. They share how Garfield streamlines small debt claims, navigated unprecedented regulatory scrutiny, and solved AI hallucination risks with a hybrid expert system. Along the way, they explore what AI integration could mean for lawyers, courts, and access to justice worldwide.

Episode Highlights:

(2:38) AI Aha! Moments: Using Claude as a Lifestyle Assistant

(5:01) Origin of Garfield Law

(13:00) Regulation, Ethics, and Tech Safeguards

(26:07) The Future of Law

Topics include:

-Building the Garfield AI platform

-Winning regulatory approval in the UK

-Tackling hallucination in legal AI

-Future of API-integrated courts

-Implications for legal training and the profession

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Could AI make you a better advocate than a lawyer?

In this episode, Jen Leonard and Bridget McCormack explore real-world stories of self-represented litigants using AI tools to win cases, plus a bold proposal to allow “robot lawyers” in appellate arguments. From century rides powered by ChatGPT to experiments in legal education innovation, this conversation tackles the evolving role of AI in justice.

Episode Highlights

(3:02) AI Aha! Moments: Fitness and food ordering hacks

(7:41) ChatGPT Agents explained

(19:37) Self-represented litigant wins appeal with AI

(22:17) Adam Unikowski's jaw-dropping experiment

Topics covered:

– A self-represented litigant’s AI-assisted appellate victory

– Adam Unikowsky’s robot lawyer experiment at SCOTUS

– ChatGPT Agents and task-based automation

– AI for legal research, CLE, and gamification

– Why courts should pilot AI-supported oral arguments

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What happens when a top litigation firm lets lawyers truly experiment with AI?

In this episode, Jen and Bridget sit down with Jen Reeves and Chris Kercher of Quinn Emanuel to explore how one of the world’s top law firms is embracing AI from the inside out. From launching a grassroots Skunk Works group to using Claude and ChatGPT in high-stakes litigation, they share how culture, leadership, and curiosity are driving real results. Perfect for lawyers, tech leaders, and anyone wondering how AI is actually being used in practice today.

Episode Highlights

(2:17) AI Aha! Moments: ChatGPT Planned the Roadtrip and Made the Punchlist.

(5:13) How Quinn Emanuel Built an AI Culture That Stuck

(15:40) The Mindset Shift That Unlocks AI Use

(23:54) AI for Small Firms: Where to Start and What to Skip

Topics include:

– Building an AI culture without mandates

– Using Claude to manage real litigation workflows

– Why context beats prompts

– Advice for small firms and solos

– How AI is making law more fun (and faster)

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