TLOP 2.0, Ep. 9 - Anna Guo, LegalBenchmarks.ai

Anna Guo joins the Legal Ops Podcast, talks about LegalBenchmarks.ai, AND...1) Lawyers Don’t Actually Need 100% Accurate AI (but... Here’s What They Want Instead).2) Honest Career Paths in the AI Era: Spray & Pray, Personal Brand, or the Connect?3) The Pigeon Gap, and the potential modern-era strategic genius of having a Fax machine.LegalBenchmarks.ai was a project born from conversations with in-house teams who wanted to understand what actually works, beyond the marketing taglines and vendor demos. It is a collaborative effort powered by lawyers, researchers, and builders who believe in open, practical evaluation. They provide legal teams with unbiased, practical AI performance insight and share real-world findings that help legal teams adopt AI safely and effectively.https://www.legalbenchmarks.ai/home

Brittany Arthur (Design Thinking Japan) join the Legal Ops Podcast.Q:What? A: Design thinking is a process for solving complex problems by focusing on human needs first, then exploring possibilities, prototyping solutions, and iterating. Q: Why? A: In an increasingly AI-driven conversation where people are pushing solutions that may not be adopted (especially in legal technology), push back and stay focused on the human (in the loop or otherwise!) that has a business problem to be solved.Q: When? A: Right now. Do it. Push play.---Other notable highlights: - Strategy and effective rollout of AI in large organizations (hint: value multipliers and strategic enablers like legal and legal ops can accelerate a lot of this)- How to think about AI- Questioning "What comes after AI"?- Shohei Ohtani- Brittany's ability to generate value with a bat...

Phil drops by the Legal Ops Podcast. Once an aspiring artist and comicbook-preneur, he moved on to become a tech-savvy law dragon, and most recently - ambidextrous dad. This episode features:-The secret origin of his ambidexterity: chopsticks, parenting, and boiled eggs, all starring his left hand (and sometimes, his right—blowing minds at family dinners).\- Epic tales from the legal trenches: from being told he’d never make management to turning down director gigs.- Behind-the-scenes insights from his role building a cutting-edge e-discovery department.- Community building, networking, and the (in)famous "Legal Tech Mafia": early morning runs, big ideas, and laughs.- Servant leadership in action: why giving his time to team members means more than any process or checklist.- How imposter syndrome pops up—and how creativity makes problems solvable and tech solutions cheaper (like, $480k cheaper).Bonus round: secret art skills, geeky tattoo stories, and candid banter that proves legal technology can actually be fun, fast, and friendly.

Matt Lhoumeau, the CEO of Concord Worldwide, joins the Legal Ops Podcast.You should listen if you want to hear about:- His interesting story in the United States- The (un)importance of previous accomplishments and certifications- The CD v. MP3 shift- Controversial opinions on contracts (yes, really)- The value of the human touch in the age of AI- 0 legal teams, data trading, and NDA absorption?Also available on Youtube!Concord: https://eu1.hubs.ly/H0lTSrr0

Harry Borovick, GC of Luminance, Author and Educator joins the Podcast. Highlights:1. “People don’t want drills, they want holes.” -Richard SusskindHarry channels Richard Susskind, and then notes that clients care about outcomes, not the tools or processes behind them. A mindset shift towards results seems more relevant than ever in the age of AI, but is this all so simple?“The idea is...people are more interested in the outcome than the process to achieve it. That’s why you often hear the terminology, you know, the black box problem...”2. The Rise of the Tech-Enabled, Emotionally Intelligent LawyerHarry gets real about the future of law: it’s not just about knowing the law or using AI, but about soft skills and empathy. Lawyers are often a powerful support system for clients, and the argument here is: AI—no matter how advanced—can’t replace the human touch.“What most people want from their lawyer is one of two things: the correct answer delivered rapidly, concisely, in an applicable manner, and...an emotional crutch essentially, an emotional support system for the client.”3. Why Legal Education Needs a RevolutionHarry critiques traditional legal education, arguing that law schools are failing to prepare students for the realities of modern practice. He calls for universities to embed technology and practical skills into the curriculum, and shares how he’s actively working to bridge that gap.“There are an enormous amount of academic institutions and very few preparing students...(for what the) professsion is going to be...Learning lots of cases doesn’t actually make you able to... have a great deal of experience interviewing a client to Why Listen?1) Fresh perspectives on what it means to be a lawyer in 2025 and beyond.2) Actionable insights for law students, educators, and hiring managers.3) Real talk about the intersection of tech, empathy, and business in legal practice.

Jane Oxley, the Chief Revenue Officer of Smokeball joins the Legal Ops Podcast. Highlights:- What is pizza anyway? - How well do you know legal trivia? (a.k.a. Do you recognize the name Smokeball?) - The early days of a startup can be hard, but that is harder if you don't have a good winter coat. - How important is it to stay focused? How critical are early adopters? (Spoiler: Very. Very very.) - Legal professionals may be more prone to use advanced technology when it is baked into things in a seamless way. - Are there differences in approach to when dealing with a small law firm v. a larger corporation? - Can this all be easy peezy?

In this Pulse episode, Daryl and Elliot discuss:DonglesWho first introduced the idea of LLMs "talking" to LLMs?LLMs actually "talking" to LLMsMaking AIMI a thing DeepseekResearch LLMs (specialization v. generalization)Using words with imperfect definitions, and rabbitholes"Probabilistic loops" and "thinking"

JP Biard, the Chief Global Strategy Officer at LegalOn Technologies joins the Legal Ops Podcast. Highlights:- How much has LegalOn grown?- Why do people go to law school? What does technology have to say about that?- Are lawyers reluctant to adopt new technology?- What has LegalOn's evolution been, and how is that different from other players in this space?- What is the real impact of contract lifecycle management systems? Or, who gets the most benefit?- Isn't the art of the possible just a flowery way to say "education"?- What is the power of playbooks?- What are the differences in lawyers across geographies?

After a long break, Elliot and Alex are back. Where did they go? What were they doing? And who is this other guy? This episode features... 1). Who is this other guy? Introducing Daryl Osuch. 2). 2024 Year in Review: a lookback that features highly critical and mostly arbitrary scores on a scale of 1 (Wrong, and you will laugh about this later) to 10 (Right, and I am scared of your apparent prescience). Alex spent Christmas building small language model apps, Daryl defends LLM mistakes, and Elliot determines we all did pretty poorly. 3). 2025 Predictions: Daryl holds a surprise spelling quiz, We make oblique references to 80's movies that you may or may not catch, and Elliot opines on the GenAI hype cycle. 4). What's next?

Dee Venello is a senior operations professional at Commvault. She has implemented contracting systems and other legal technology in multiple organizations, carefully managing diverse stakeholders with a variety of interests and workflows. She also has experience in general business operations, providing her with insight into the issues and concerns faced by teams that the legal department supports. A big thanks to LinkSquares for sponsoring this episode and for recommending Dee as a guest of the show. We discussed with Dee why LinkSquares was selected by two of her employers as the primary contracting solution for the organization. We also discussed a range of related issues, including: * The importance of CLM in general * Why change management is vital in any technology implementation * The value of cross-functional understanding and partnerships * How CLM liberates data, and what to do with it * Driving continuous improvement and "planning to plan" LINKS LinkSquares website: https://linksquares.com Dee on LinkedIn: https://www.linkedin.com/in/dee-venello-74090a40/