Law://WhatsNext

Tom Rice and Alex Herrity
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Aug 14, 2025 • 17min

GPT5 - Pt 2 with Sigge Labor (CTO) and Jacob Johnsson (Legal Eng) of Legora

Rapid dispatch: we pulled in Sigge Labor (CTO) and Jacob Johnsson (Legal Engineer) from Legora - one of the fastest-growing AI companies in the world (and one of the few with early access to GPT-5) for a chat about OpenAI's recent model release.They share what it’s already unlocking for legal reasoning, why their “battle evals” put GPT-5 ahead 80%+ of the time across a host of legal tasks, and how its new steerability could reshape the way lawyers (and the tools they use) interact with the model (including through Legora).This is part two and concludes our GPT-5 launch mini-series - snappy, unpolished, and recorded while the paint’s still wet. If you like these hot-off-the-press deep dives, tell us (and more importantly… tell the algorithm by: rating, reviewing, and telling your friends).
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Aug 12, 2025 • 23min

GPT5 - Pt 1 with Jake Jones (CPO & Co-Founder, Flank)

Emergency drop: we grabbed Jake Jones (CPO & Co-Founder, Flank) for a quick-fire reaction to OpenAI’s ChatGPT-5 launch. We cover his day-one impressions, what it means for legal products (including Flank), and the downstream implications for how legal work gets done. A short detour from our usual programming—did you enjoy this rapid-response format? If yes, please like, rate, and share to help Law://WhatsNext reach more people.
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Jul 29, 2025 • 49min

The Future Lawyer

In this compelling episode of Law://WhatsNext, hosts Tom & Alex dive into the transformative shifts underway in legal education and junior lawyer development. Joined by three visionary voices - Lucie Allen (Managing Director, Barbri), Rob Elvin (Partner, Squire Patton Boggs), and Sophie Correia (Trainee Solicitor, TravelPerk) - the discussion explores provocative ideas reshaping what it means to be a lawyer.Do Lawyers Even Need to Know the Law?Sophie Correia challenges the traditional emphasis on memorisation and technical rules in legal education. Reflecting on her real-world experiences at a tech scale-up, Sophie argues that success hinges more on human skills such as communication, empathy, and trust-building, rather than recalling obscure statutes.The Flawed Incentives of Legal TrainingRob Elvin sheds light on systemic issues stemming from the billable hour model, which prioritises short-term profitability over effective mentoring. He advocates for a groundbreaking solution: linking career progression directly to the quality of trainee supervision, potentially transforming mentorship from a luxury into an essential career catalyst.The AI DisconnectLucie Allen identifies a critical gap in legal education - the absence of meaningful engagement with AI and technology. Despite these tools reshaping the profession, current frameworks like the SQE neglect to equip trainees adequately for technological realities, posing a substantial risk to their future readiness.Three Ideas to Transform Legal Education:Continuous Learning as the New Norm: Education doesn't stop at qualification. Lucie emphasises the necessity of lifelong learning, driven by relentless curiosity and adaptation to change.Human Skills Set Lawyers Apart: Sophie highlights the enduring value of human-centric capabilities—understanding people, navigating complexity, and ethical reasoning—as indispensable traits lawyers must cultivate.Systemic Change through Collective Responsibility: Rob, Lucie, and Sophie underline the importance of personal agency and collaborative effort in driving substantial reform across education, training, and regulatory frameworks.A Hopeful Path ForwardUltimately, the podcast champions a future in which tomorrow’s lawyers blend ethical judgment, technological proficiency, and interpersonal insight, prompting listeners to reconsider not whether lawyers need to know the law, but rather what precisely they need to know—and how to prepare them best for the evolving landscape.Join us for an inspiring conversation that challenges conventional wisdom and points toward an empowered, adaptable, and human-centred future for the legal profession.
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Jul 18, 2025 • 37min

Quarterly Legal Tech Trends with Peter Duffy (Q2, 2025)

In this quarterly deep-dive, we reconnect with Peter Duffy, the brilliant mind behind the Legal Tech Trends newsletter, for our regular temperature check on what's actually happening in the legal technology landscape. Peter's ability to cut through the hype and identify real trends, combined with his practical experience helping organisations actually adopt AI, makes this a masterclass in separating signal from noise.Whether you're trying to understand why adoption is lagging despite the excitement, wondering about the strategic implications of billion-dollar acquisitions, or simply want to understand what Silicon Valley's sudden fascination with legal really means, this conversation hopefully delivers some insight.The episode kicks off with a sobering look at AI adoption across the legal profession, and the numbers might surprise you. Peter walks us through recent surveys from Bain and BCG that paint a picture quite different from the hype we're all hearing about at conferences/or on LinkedIn.The acquisition and partnership landscape is absolutely wild right now, and we break down the strategic implications of:Clio's $1 billion acquisition of vLexEudia's acquisition of the Irish ALSP Johnson HannaHarvey's strategic alliance with LexisNexisWe end discussing some personal topics of interest, including:Y Combinator's explicit call-out for startups to build "full stack AI companies" – using law firms as their prime example;The Builders Playbook: 2025 State of AI Report; andthe implications of the recent order in the New York Times v. OpenAI caseIf you found this episode interesting, please do like, subscribe, comment, and share! It helps the show rank and reach more people.. Best, Alex & Tom
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Jul 8, 2025 • 32min

Product Counsel(ling) in the Age of AI with Sam Lewis

We sit down with Sam Lewis, Senior Product & Privacy Counsel at Canva, who kicks things off by asking us the most important question of 2025: "If you had to be a piece of cutlery, what would you be?" Spoiler alert: Sam's a spoon (warm, empathetic, part of the emotional support crew), while Tom and Alex predictably went fork (practical go-getters with zero patience for fluff).Beyond the viral TikTok personality tests, Sam delivers cutting-edge insights into product counsel work at a company that's been building AI since 2017 - well before it was trendy. With Canva's community using AI tools over 18 billion times, Sam has become a thought leader on navigating the complex intersection of law, privacy, and AI-native product development.What makes this conversation essential listening:Sam reveals how legal teams at AI-first companies don't just manage risk - they can drive growth. Three Key Takeaways:1. Trust is the Ultimate Competitive Advantage: In an era where AI capabilities are rapidly commoditizing, trust becomes the differentiator. Sam reveals how Canva aims to be one of the world's most trusted platforms, this isn't just about compliance - it's about building products people love and companies trust.2. Privacy Instincts Are Non-Negotiable in AI-First Companies: Sam makes it clear: "I don't think it's possible to advise on AI without understanding privacy." AI is built on data, and privacy laws determine what's fair, legal, and ethical - making strong privacy instincts essential for knowing when to green light and when to pause in AI-native environments.3. Product Counsel Is Risk-Aware, Not Risk-Averse: Sam champions a philosophy that's become essential for AI-first companies: taking a risk-aware rather than risk-averse approach. To Sam this means asking the right questions, reducing unnecessary friction, and helping teams figure out how to move forward safely - often saying "how can we" instead of "we can't."The conversation touches on Canva's pioneering "AI everywhere" culture (where AI impact is now part of performance reviews), Sam's love for loud parenting, and her admiration for @sophworkbaby on Instagram (a fellow Aussie and ex-Googler) delivering plain unfiltered career insights.If you found this episode interesting, please do like, subscribe, comment, and share! It helps the show rank and reach more people.. Best, Alex & Tom
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Jun 24, 2025 • 48min

Building to Last: Legal AI & Engineering with Ross McNairn

Ross McNairn, CEO and Founder of Wordsmith, brings a rare perspective to legal tech - lawyer turned software engineer turned CTO at companies like Skyscanner and TravelPerk. Our conversation spans Ross's transition from being a trainee solicitor navigating Scottish estate law to leading one of the world's fastest-growing legal AI companies, his philosophy on building lasting products over quick wins, and why he believes we're entering the era of "legal engineering."What We Cover:Building Philosophy: Why Ross spent a year quietly iterating rather than rushing to market with an MVP wrapper.The UK Opportunity: How Britain's legal heritage and technical talent create untapped advantages in the AI race.Legal Engineering Revolution: Ross's five-level competency framework transforming lawyers into product-minded operators.Market Evolution: Why the generalist legal AI era is ending and specialization is the future.Three Key Takeaways:1. Quality Over Speed Wins Long-Term: Ross's mantra: "I don't want to be the first tool that everybody buys. I want to be the last tool that they buy." While competitors rush wrappers to market, disciplined product development with 95% engineers and lawyers creates lasting competitive advantages through superior reliability and user experience.2. Legal Engineering is the New Frontier: The future belongs to lawyers who think like product managers. Ross describes customers building sophisticated systems with 50+ interconnected agents—a glimpse into legal practice where workflow orchestration, not individual task automation, drives value for in-house teams managing constant business demands.3. Invisible Quality Creates Unbeatable Moats: While everyone debates model capabilities, Wordsmith are developing rigorous "evals" testing frameworks defining world-class legal outputs. If you found this episode interesting, please like, subscribe, comment, and share!
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Jun 12, 2025 • 50min

Building Beyond the Hype with KD and Priyam (HashiCorp)

In our first "on record" informal coffee-style conversation with a fellow in-house team, we catch up with Kshitij (KD) Dua (Director of Legal Ops) and Priyam Bhargava (Senior Corporate Counsel) from HashiCorp (an IBM company). Having witnessed HashiCorp's extraordinary journey from startup through series rounds, IPO, and ultimately IBM acquisition, this dynamic duo bring unique insights and perspectives on the importance of the lawyer x legal ops dynamic/relationship; legal AI adoption and what happens when traditional SaaS metrics meet an intelligence explosion.Our conversation emerges following their super engaging "Influencing Without Authority" presentation at CLOC CGI in Las Vegas last month.What We Cover:Partnership Genesis: How their collaboration began with Priyam's proactive approach to improving a core revenue workflow.The ROI Challenge: Why traditional SaaS metrics may become meaningless as AI inference costs reshape enterprise economics.AI Integration: How curiosity trumps linear thinking, from brainstorming negotiations to governance frameworks.Career Evolution: International journeys from banking to law firms to HashiCorp's hypergrowth environmentIf you found this episode interesting, please like, subscribe, comment, and share! For more thought-provoking content at the intersection of law and technology, head to https://lawwhatsnext.substack.com/ for:Focused conversations with leading practitioners, technologists, and educatorsDeep dives into the intersection of law, technology, and organisational behaviourPractical analysis and visualisation of how AI is augmenting our potential
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May 15, 2025 • 54min

Leading, Complex Systems, and AI with Jessica Block

Jessica Block, Executive Vice President at Factor, is a former theater major turned legal tech innovator. She discusses the complexities of leading in a tech-transforming environment, comparing it to quantum mechanics. Jessica shares insights on Factor's AI-first approach to legal workflows, emphasizing collaboration and discovery. She reflects on her unique journey from theater to eDiscovery, highlighting invaluable skills acquired along the way. The conversation also dives into innovative tools for contract management and the need for adaptability and strategic thinking in the evolving legal landscape.
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Apr 29, 2025 • 53min

Zero to One: A Builder’s Journey with Jenn McCarron

In this episode of Law://WhatsNext, we welcome legal ops guru, pioneer, visionary and friend, Jenn McCarron - President of CLOC, former Director of Legal Operations at Netflix and Spotify - for a conversation about her renaissance year and visions for the future of legal operations.We go light, deep, introspective and playful around:“writing your own funeral” on jobs and being honest with yourself around your strengths, ambitions and (as a by product) your limitations (we all spend a lot of time at work)The discipline, rigour, humility and vulnerability that comes with honing the craft of “writing” (Jenn and a mystery co-author might be building some provocative frameworks for reimagining how we might perceive our current roles and their potential)Using the odd job interview to sharpen your intuition and feeling for who you are and what you doBecoming more intentional with the time, energy and attention Jenn is dedicating to her creative pursuits and passions Staying sharp with a couple of high profile consulting commitments at a prominent private equity firm and social media business, the CLOC Presidency and observing the market and how its evolving from a different vantage pointJenn’s influential Legal Ops 3.0 framework, which envisions legal operations evolving beyond implementing foundational systems to becoming data-powered enterprise wide strategic partnersSome recent reading, including Jevons Paradox: A Personal Perspective by Tina He, where we reflect on the idea that technology meant to create efficiencies often paradoxically increases workload (rather than creating more space) and we consider that legal ops professionals often "sell efficiency" without controlling what happens with the time saved.The episode concludes with a preview of the upcoming CLOC Global Institute, where Jenn hints at exciting new programming developments.  We will report back our thoughts and reflections from the event in Las Vegas next week!We covered a lot but the time came and went in a blink.  Jenn always brings bright, bold and effusive energy to every touchpoint, conversation and interaction.. We hope (but secretly suspect) you’ll find something in this chat to inspire a creative thought (or two) or reframe a perspective.If you found this episode interesting, please like, subscribe, comment, and share!
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Apr 17, 2025 • 45min

Q1 2025 Legal Tech Trends with Peter Duffy

Peter drops the quote of the quarter: "Legal is sexy now when it comes to people working in technology and innovation". In our latest episode, we're mixing things up by taking Peter Duffy's wildly popular Legal Tech Trends newsletter and diving deeper into the hottest headlines from Q1 2025. Peter joins us to unpack what's actually happening behind the email blasts and LinkedIn posts we've all been scrolling through.We explore four key trends:1. Voice as the new frontier - Why typing is "super slow" compared to how fast we think and speak, and how voice interfaces are becoming the preferred way for experts to unlock their domain knowledge when working with AI.2. Law firms rolling out Harvey & Legora - The rush to deploy these AI-native tools firm-wide and the cultural challenges of making them stick in an environment Peter describes as "a collection of islands."3. The Axiom & DraftPilot case study - A rare deep dive into actual, measurable results from AI implementation across 27 legal departments (with Peter confirming these stats are "totally legit").4. The economics of "product-led" law firms - How firms like MacFarlanes and A&O Shearman are experimenting with subscription models and profit-sharing arrangements that challenge the billable hour.Alex brings the heat with his skepticism about law firms' tech initiatives, comparing them to "drug dealers giving free samples" to hook clients – while we debate whether AI might finally change that dynamic.Want to stay on top of these trends yourself? Check out Peter's newsletter where he delivers regular shots of insights and personal recommendations after "scouring the web for mentions of LegalTech and listening to legal tech podcasts at 2x speed."If you found this episode interesting, please like, subscribe, and share!

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