Why Is Buying Legal AI So Painful? ft. Legal Benchmarks Founder Anna Guo | The Future of Law Is Today, Ep. 12

An In-House Lawyer’s Perspective on Buying AI, ft. In-House Counsel Travis Zollner | The Future of Law Is Today, Ep. 19

Summary Travis Zollner joins Ceschino to discuss the frustration of navigating the legal AI world as a practicing lawyer looking for reliable solutions and clear information about what any given solution does and doesn’t do. Travis discusses the challenges and opportunities of integrating AI into legal workflows, emphasizing the importance of accuracy and the need for human oversight. The conversation explores the push for AI in legal settings and where it’s coming from, the risks associated with overrelying on AI without human oversight, and the necessity for transparency in AI solutions, marketing, and sales. Ultimately, the discussion highlights the balance between leveraging technology for efficiency while ensuring legal integrity. Takeaways * Pressure to use and buy AI often comes without direction from leadership. * AI can create efficiencies but also introduces risks — hallucinations remain a problem. * Accuracy in AI outputs is a major concern for legal professionals. * Human oversight is essential when using AI in legal work. * The push for AI integration comes from a desire for efficiency, but the need to review every output compromises those gains. * AI vendors often lack transparency about their solutions’ limitations. * Legal teams need to understand in practical terms where AI can be beneficial and what its limits are. * The importance of context in legal agreements cannot be overstated. * Honesty in AI pitches is crucial for driving effective adoption. Chapters 00:00 Travis’s Career Journey 04:08 Navigating Legal Tech and AI as a Buyer 07:22 Where Is the Push for AI Coming From? 09:10 Understanding AI’s Limitations and Risks in Legal Work (Especially When You’re an AI) 14:12 A Call for Transparency in AI Product Pitches 19:09 Evaluating Risk at Scale 22:49 What Lawyers Want: The Perfect(ly Transparent) AI Pitch 27:02 Keeping It Human: Fantasy and Gaming Nerds Keywords legal tech, AI in law, buying AI, tech procurement, assessing vendors, in-house counsel, career journey, legal workflows, AI integration, accuracy in AI, human oversight, legal technology, future of law

AI Negotiation Agents and the New Law Career, ft. Ozeki Founder Kenneth Carter | The Future of Law Is Today, Ep. 18

Summary Kenneth Carter shares his journey from being a lawyer to founding Ozeki, a legal tech company focused on automating and enhancing negotiation processes. He discusses the limitations of generative AI in legal contexts and introduces the concept of “artificial discretion” as a more effective approach. The conversation explores the nuances of negotiation strategies, the role of trust in negotiation, and the evolving landscape of legal careers in the face of automation, emphasizing the need for a multidisciplinary skill set in the future of law. The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com [http://thelegaltechguide.com]). Takeaways * Generative AI has limitations in legal applications due to its tendency to hallucinate. * Effective negotiation requires understanding both parties' values and needs. * AI can augment human negotiators rather than replace them. * Negotiation is about creating value through trade-offs, not just redlining documents. * Building trust in negotiations involves sharing selective information. * A diverse skill set enhances problem-solving capabilities in law. * Young and future lawyers should embrace multidisciplinary approaches to their careers. * The legal profession is evolving with the tech. * Creativity and adaptability are essential for success in the changing legal landscape. Chapters 00:00 From Lawyer to Founder: A Journey of Optimization 02:57 AI Beyond LLMs and Language Generation 04:41 Agentic AI: the New Frontier 11:18 Agentic Legal Tech to Automate Negotiation, Not Document Generation 14:03 Creating Value by Fixing the Broken Negotiation Process 19:52 Building Trust in Negotiations: The Indifference Curve 22:18 Coming Up With the Ozeki Name 24:24 Advice for New and Aspiring Lawyers: Embrace Multidisciplinarity 28:55 Keeping It Human: Modeling for a Children’s Book Keywords legal tech, AI, negotiation, law, future of law, legal careers, technology in law, discretion, negotiation strategies

The Legal OS and Reshaping the Practice of Law, ft. 9to5 Founder Marla Calvert Miller and Legal Futurist Anastasia Boyko | The Future of Law Is Today, Ep. 17

Summary This episode explores an emerging concept in legal tech and AI: the legal operating system. 9to5 Legal Docs founder Marla Calvert Miller and legal futurist Anastasia Boyko share insights earned over a varied pair of careers in legal practice, legal tech, and legal education and training. They join Ceschino to discuss how AI and the concept of the legal OS are giving lawyers a chance to reshape legal services and rethink what they want their careers as lawyers to be. The discussion also addresses the importance of a systems-based approach to tech and legal operations, and strategies for managing change in legal practices. The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com [http://thelegaltechguide.com]). Takeaways * AI gives us a chance to rethink legal service delivery as a profession * 9to5 is building a legal operating system for transactional law * The legal OS needs to do more than just handle documents, matters, and intake * Different types of practice need their own tailored operating systems * Empathy and human connection are core competencies in legal tech and legal practice, now more than ever * Lawyers should reflect on their career goals and personal values when making decisions, from adopting new tech to choosing career paths * Lawyers must prioritize security and privacy in legal AI implementations * Practice managers need to engage with clients to understand their needs and preferences * Leaders should develop a North Star to guide change management in legal practices Chapters 00:00 Introduction to Marla’s and Anastasia’s Legal Journeys 04:10 Shaping Legal Careers 09:00 Reimagining Legal Services With AI 14:20 The Legal Operating System Concept 17:10 Putting Lawyers’ Clients Front and Center in Legal Tech 20:11 Reacting to Claude for Legal 24:38 Substance in Legal AI Marketing: What Do The Tools Really Do? 27:19 Navigating Security When Trying Legal AI 30:12 Business of Law: Shifting to Alternative Billing Arrangements 35:23 Nobody Wants to Talk to Your AI Bot 37:44 Fixing the Empathy Blind Spot in Legal Services 39:57 Defining Your Team's North Star to Guide Tech Adoption 42:59 Keeping It Human: Keep It Weird Keywords Legal Tech, AI, Legal Innovation, Legal Practice, Legal Operating System, Legal Careers, Legal Tech Adoption, Legal AI Tools

Staying Composed Even With Ambitious Goals, ft. Paragon Tech Founder Jay McAllister | The Future of Law Is Today, Ep. 16

Summary Jay McAllister joins Ceschino to share his experience working in high-pressure environments of his own creation, and how he maintains focus and composure while targeting ambitious goals. Jay discusses the inspiration behind and results of his 100x social experiment. The conversation also explores the psychology of personal motivation, pressure, and the desire for achievement, and how to balance goal-oriented ambition with a productive level of appreciation for the progress that’s already been made. The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com [http://thelegaltechguide.com]). Takeaways * Before starting a new business initiative, it’s crucial to define parameters for success * Business initiatives should focus on eliminating the largest constraints, not pet projects * The best way to elevate performance is with consistent processes and systems * Jay challenged himself to 100x his output on social media to source new clients * He established accountability and set up systems and support to make scaling possible * Self-assessment is often overly negative — it’s important to acknowledge the gains made as well as remaining goals * Mindset matters: believing you can do something new is a prerequisite to doing it * Taking on greater responsibility can force people to become more productive in general Chapters 00:00 Jay’s Focus as an Entrepreneur and Advisor to Attorneys 05:45 Defining Success in Business Initiatives 10:56 Elevating Performance With Consistent Processes and Systems 11:54 The 100x Social Experiment: Inspiration 16:02 Purpose and Structure of the 100x Experiment 19:42 The Gap Versus the Gain: Learning to Reframe Self-Assessment 24:40 Desire as a Personal Contract to Be Unhappy 26:33 Never Say “Can’t” 29:43 Setting Up the 100x Experiment 35:16 Productivity Hack: Take on More Work 38:07 Results of the 100x Experiment 43:06 Keeping It Human: Fun Economics and Science Facts Keywords Law, legal tech, AI, productivity, motivation, inspiration, scaling, discipline, business operations, legal operations, systems thinking, process improvement

What Is AI, Anyway? A Primer for Lawyers, ft. 2nd Chair Co-Founder Austin Brittenham | The Future of Law Is Today, Ep. 15

Summary Austin Brittenham, a lawyer and legal tech founder who started his legal AI company while still in law school, provides a thorough overview of AI – what it is, how the tech has evolved, and where it’s going. He dives into the implications of AI for lawyers and the practice of law, from everyday document automation to fabricated images presented as evidence in court. Ceschino and Austin also examine what people building AI for lawyers need to keep in mind, whether as tech vendors or in-house within legal practices. The conversation concludes with a reflection on how reinforcing critical thought can help future generations maintain their mental acuity in the age of AI. Takeaways * The arc of AI has progressed from if-then logic to machine learning to generative AI * AI has recently evolved from small language models developed by machine learning startups to large language models powering generative AI applications * Large language models may be plateauing in terms of the information that can be gained from web scraping, but alternative teaching methods such as reinforcement learning may lead to future advancements * Legal tech may be moving toward broad platforms that host specialized add-on solutions, or toward a future where legal practices bring in engineering talent to build bespoke solutions * AI and vibe coding raise the risk of people reinventing the wheel with custom apps * Whether building legal AI as a tech vendor or in-house, you need to stay plugged in with the people who will use it every day Chapters 00:00 Introduction to Austin and His Legal AI Journey 03:35 Navigating Legal AI as an Entrepreneur 06:55 The Types of AI Lawyers Should Know About 13:09 Practical Applications of Generative AI 22:10 The Platformization of Legal Tech 23:46 Alternative Future: Building In-House Tech Capabilities 28:07 Reinventing the Wheel With AI and Vibe Coding 32:28 The Importance of Legal Expertise When Building Legal Tech 38:05 The Need to Stay Plugged In With End Users When Building Tech 42:51 What’s Next, Beyond LLMs and Gen AI? 48:38 Keeping It Human: Developing Critical Thought Through Debate Keywords Generative AI, large language models, machine learning, small language models, legal tech, law, litigation, tech procurement, cybersecurity, ethics, compliance, vibe coding, critical thinking