Summary

Ryan Anderson, co-founder and CEO of Filevine, joins Ceschino to discuss how AI is moving from a one-question-at-a-time tool to an always-on, matter-aware system for legal work. The conversation covers a broad range of topics including the advent of agentic AI, how AI can anticipate legal teams’ needs, simulation of judicial reasoning for litigation strategy, and why anti-hallucination tooling is becoming not just essential, but possible in legal practice.

Takeaways

• AI in law is shifting from occasional use to an always-on layer that anticipates needs before lawyers ask.

• An agent is an AI system tasked with pursuing a goal through multiple steps, not just answering a single prompt.

• Multiplayer, agentic systems could coordinate work across an entire matter or case team.

• AI can uncover insights teams may not have found manually, rather than simply accelerating existing tasks.

• Research agents can simulate how different judge archetypes might reason through a case.

• AI tools such as LOIS for Word can plan, ingest case files, analyze prior drafts, and help produce stronger briefs.

• Anti-hallucination technology is becoming essential for verifying legal research and citations.

• Legal AI must detect fabricated cases, misquoted cases, and quotes taken from the wrong part of an opinion.

• Lawyers still need professional judgment even as AI improves search, drafting, and citation checking.

• Junior lawyers may struggle to develop foundational research and writing skills if they rely on AI too early — the profession needs a plan for how to train new entrants.

• The future of legal AI may involve many highly specialized models instead of one dominant system.

• AI is more likely to expand lawyer capacity than replace lawyers entirely.

Chapters

00:00 AI in law and the “cold fusion” moment

05:30 Transforming legal work, not just accelerating it

08:45 What is an AI agent?

13:18 Developing anti-hallucination technology in legal AI

16:29 Three common types of legal AI hallucinations

21:15 Drawing inspiration from the people who shape law and justice

23:57 Testing anti-hallucination tech and legal aI

26:26 The importance of context engineering

30:19 Ryan’s controversial opinions on the legal tech industry

30:42 Controversial opinion #1: millions of custom AI models

31:24 Controversial opinion #2: AI won’t replace lawyers

32:36 Controversial opinion #3: AI creates a training challenge for the legal profession

39:06 Ryan’s fun fact and closing thoughts

Keywords

AI, legal tech, legal AI, AI hallucinations, legal research, AI agents, agentic AI, legal innovation, justice, law practice, AI models, legal ethics

Summary

Benjamin shares his transformative journey from a successful career in law to becoming a depth coach for high-performing professionals. He discusses the concept of depth coaching, emphasizing the importance of understanding the unconscious and the ego's role in personal development. The dialogue explores themes of midlife transitions, the search for meaning beyond external success, and the necessity of embracing imperfection in creativity. Benjamin also highlights the significance of recognizing life's mysteries and the interplay between our inner and outer worlds.

Takeaways

• Benjamin transitioned from law to coaching high-performing professionals.

• He identifies as an anti-executive coach, focusing on those who feel stuck despite success.

• Depth coaching involves engaging with the unconscious to achieve personal growth.

• The ego plays a crucial role in how we perceive ourselves and our achievements.

• Burnout can signal a need for deeper change and self-exploration.

• Creativity often requires permission to be imperfect and messy.

• Life's challenges can be seen as opportunities for growth and self-discovery.

• The unconscious can manifest in our external experiences, often termed fate or luck.

• Midlife can be a time to reevaluate one's identity and purpose.

• Embracing the unknown can lead to unexpected and meaningful life paths.

Chapters

00:00 From Law to Coaching: A Personal Journey

05:09 Understanding Depth Coaching and the Role of the Ego in Personal Development

10:21 Embracing Imperfection in Creativity and Expression of the True Self

13:37 What Causes Burnout and Midlife Crises

17:28 Finding Meaning Beyond Professional Success

21:18 How the Unconscious Connects to Life's Challenges and Opportunities

26:23 Living Authentically by Proactively Being True to Oneself

30:13 The Mystery: Embracing That Some Things Are Beyond Our Control

Keywords

Coaching, high achievers, midlife crisis, personal transformation, depth psychology, identity, purpose, mythology, somatic embodiment, professional success, personal development, meaning, creativity, self-discovery

Summary

Mathieu Bouillon starts the conversation by discussing the adoption of legal AI in Europe compared to the US, highlighting the emergence of legal tech startups and diminishing language barriers. Mathieu also addresses the impact of AI on legal education, stressing the importance of critical thinking and a hybrid approach to learning that incorporates both AI tools and traditional methods. Mathieu and Ceschino discuss the evolving landscape of professional skills in the age of AI, exploring the necessity of continuous learning and unlearning, the impact of AI on professional expertise, and the challenges of maintaining skill levels without becoming overly reliant on technology. The discussion also touches on the future of junior hiring and the importance of mentorship and human connection in a technology-driven world.

Takeaways

• European law firms are adopting AI at a similar pace to US firms.

• Language barriers in legal tech are diminishing due to AI.

• AI can enhance productivity but may lead to skill decay and dependency, so skilled professionals must avoid using AI as a crutch.

• Critical thinking is essential in the age of AI.

• The future of legal work will involve both AI and human expertise, so legal education must adapt to include AI training.

• Quality output requires human creativity and critical thinking alongside AI.

• A hybrid approach to education is necessary for future lawyers.

• Change is the new normal, and professionals must adapt continuously.

• The illiterate of the 21st century will be those who cannot learn, unlearn, and relearn.

• The future of junior hiring may involve fewer positions due to AI efficiency.

• Mentorship and hands-on experience are crucial for junior professionals in the age of AI.

• Companies risk long-term viability by not hiring juniors.

• AI should be viewed as an assistant, not a replacement for human skills.

Chapters

00:00 Matthew Bouillon's Journey in Law and AI

03:51 AI Adoption in Europe vs. the US

07:32 Building in Legal AI

10:37 AI's Impact on Legal Education and Training

18:44 The Importance of Adapting by Learning and Unlearning

20:04 AI's Impact on Experienced Professionals’ Skills

24:20 Avoiding AI Dependency While Using AI

27:50 The Future of Junior Hiring and Training in the AI Era

32:29 Keeping It Human: A Missed Opportunity

Keywords

AI, legal tech, law firms, education, organizational transformation, AI adoption, critical thinking, future of law, learning, professional development, junior hiring, productivity, creativity, mentorship, technology, legal practice, sustainable business practices, talent strategy, talent management

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

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).

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

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).

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

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).

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

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

Summary

Elisa Silverglade discusses her journey in legal automation, emphasizing the importance for lawyers of client relationships over simply getting paperwork done. She distinguishes between AI and automation, explaining how automation can enhance efficiency in law firms. The discussion also covers the significance of change management in implementing automation, the deterministic nature of robotic process automation as opposed to the probabilistic nature of generative AI, and the evolving roles of employees in the legal field. The conversation concludes with a focus on the human element in automation and the potential for technology to create more fulfilling work environments.

Takeaways

• Automation can significantly reduce repetitive tasks in law firms.

• The core value in law is the client relationship, not just paperwork.

• AI mimics human thought, while automation replicates human behavior.

• Deterministic applications ensure consistent execution and accuracy.

• Change management is crucial for successful automation implementation.

• Automation can enhance job satisfaction by reducing grunt work.

• Younger employees will need to adapt to new roles as automation increases.

• The legal profession must focus on client relationships to provide value.

• Technology should augment human work, not replace it.

Chapters

00:00 Introduction to Legal Automation and AI

04:58 The Difference Between Automation and AI

07:00 The Role of Automation in Legal Processes

16:29 Deterministic Vs. Probabilistic Applications

22:03 The Impact of AI on Work Quality and Customer Experience

27:10 Automation: Enhancing Work, Not Replacing It

34:34 Transforming Junior Roles in the Workforce

40:11 Keeping It Human: The Most Statistically Complex Game in History

Keywords

legal automation, AI, robotic process automation, law firms, change management, deterministic applications, client relationships, technology in law, future of work, human element

Summary

Grant Taylor and Scott Tandoi discuss their journey into legal tech, focusing on the integration of large language models in law. They explore the limitations of LLMs, the importance of context engineering, and how AI can augment human expertise rather than replace it. The discussion also touches on the future of AI in legal work, and personal insights into parenthood and including your children in what you do.

Takeaways

• Large language models can process legal language but can’t analyze it.

• Context engineering is crucial for effective AI use in law.

• AI should augment human expertise, not replace it.

• The role of AI in legal work is to assist, not to take over.

• Prompt engineering is different from context engineering.

• AI can help with mundane tasks, freeing up human time.

• The future of AI in law involves more workflow automation.

• Understanding the limitations of LLMs is essential for legal professionals.

• Personal interests and experiences shape professional journeys.

Chapters

00:00 The Genesis of Legal Tech Collaboration at Opine

03:42 Parsing the First Legal Case With AI: Hanson Brothers

05:11 Understanding LLMs: Parsing New Information vs. Built-In “Knowledge”

08:18 The Reliability of LLMs in Legal Contexts

10:13 Probabilistic vs. Deterministic Applications

12:50 Context Engineering: Enhancing AI Accuracy

17:03 The Importance of Backend Prompt Structure in AI Applications

20:30 Legal-Specific AI vs. General Purpose AI

22:43 Shepardization and Its Role in Legal AI

27:10 Finding the Balance: AI and Human Collaboration

39:46 The Shift to AI in Workflows

44:56 Keeping It Human: Sharing Sports, Work, and Interests With Kids

Keywords

legal tech, large language models, AI in law, context engineering, prompt engineering, legal work, AI limitations, generative AI, augmented intelligence