Law://WhatsNext

🎙️ This week we sit down with Mary O'Carroll - the newly announced CEO of Legal Eng Consulting Group (LECG), and one of the most influential figures in the legal operations and legal technology industry.Mary's career arc is, by her own admission, a “portfolio” one. She built and led legal operations at Google. She founded and grew the CLOC community into the global home of legal ops. She moved into big law as Chief Operating Officer at Goodwin. She has sold legal technology (Ironclad), advises investors (she is an Executive in Residence at Signal Fire), technology companies (Sandstone), hosts her own podcast Pearls On Gloves Off, authors her own Newsletter, and — as of yesterday is now the full-time CEO of LECG, a boutique legal operations consulting and services firm focused on what she calls legal engineering. ---Alex and I are big fans and friends of Mary - few people in the legal industry benefit from her wide ranging experience and perspective. Even fewer can so succinctly distill the objectives, incentives, opportunities and competing priorities of the firms, teams, tech companies and individuals that make up our unique legal ecosystem, and none with the energy, candour and piercing intellect Mary brings to every conversation.  ---In the short time we spend together we get into:The CEO Announcement — Mary uses the episode to confirm she is joining LECG as full-time CEO. She explains why! What a Legal Engineer actually is? Mary defines the legal engineer as someone who can understand legal processes, re-engineer them, and then leverage technology to automate, accelerate, optimise and maintain them. The Billable Hour is the Operating System — Drawing on her recent Substack piece, Mary explains why everyone has been focused on the wrong half of the billable hour problem. Pricing on a fixed fee is the easy bit. The harder bit is the underlying incentive structure of a law firm.  If you give an associate a tool that turns eight hours into one and tell them they still need to hit hours, you have created a structure that is at odds with the technology itself. It is, she says, "a hundred percent the innovator's dilemma."The View from the VC Side — As an Executive in Residence at Signal Fire, Mary has watched venture capital wake up to legal in a serious way. ---Connect with Mary O'Carroll — through Legal Eng Consulting Group (LECG) | on Substack | or LinkedIn---If you enjoyed this conversation, please share it with someone or a community who you think would find it valuable . And if you have a moment, rate the show and tell us what landed — it helps us reach more people and keep getting brilliant guests like Mary.---For more conversations at the intersection of law and technology, head to⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠.

Google says it will be able to break RSA encryption by 2029. Third-party actors are already collecting encrypted data on the assumption they'll be able to read it later. The UK has just committed £2 billion to a quantum strategy. 🎙️This week we sit down with Rebecca Keating and Laura Wright — barristers at 4 Pump Court and the co-authors of A Practical Guide to Quantum Computing and the Law.Both are a rare breed of Barrister with technical credentials to complement their deep legal expertise. Rebecca worked in-house at Dropbox before being called to the Bar in 2017, sits on the ICO's Technology Advisory Panel, and has acted in one of the only quantum-related cases to pass through the UK courts. Laura took an MSc in Computing Science at Imperial mid-career — her final project was a new coding language for legal contracts — and now writes and speaks regularly on smart contracts, AI liability, and quantum risk.---What You'll LearnWhat is Quantum Computing — Alex surprises us all with his own definition and a sneak preview into how he likes to prepare for our podcast conversations! 👀The Quantum Paradox — Rebecca's framing for the central tension of the technology - the ability of quantum computers to upend the security systems that are the basis upon which we keep information safe, but there's also the capability to have even more secure systems than we have ever had.Harvest Now, Decrypt Later — This is not a future threat. Third-party actors are already collecting RSA-encrypted data they can't read today on the assumption they'll be able to decrypt it within a few years. NIST's quantum-readiness window of 2030–2035 is, in Rebecca's view, too late to start the conversation — particularly for anyone holding sensitive medical, political, or nationally significant data. Contracting for Quantum Computing as a Service — Customers won't own quantum computers — they'll access them remotely on a pay-as-you-go basis. Laura walks through what features are likely to make "QCaaS" contracts genuinely different from SaaS.---Connect with Rebecca Keating — Barrister at 4 Pump Court | Member, ICO Technology Advisory PanelConnect with Laura Wright — Barrister at 4 Pump Court | Co-host, 4 Pump Court podcastTheir book — A Practical Guide to Quantum Computing and the Law (Law Brief Publishing, December 2024).The Law of AI (2nd edition, Sweet & Maxwell) — Rebecca and Laura author the chapter on AI and Professional Liability.Society for Computers and Law (SCL) — Rebecca and Laura's recent SCL webinar on quantum legal issues was the catalyst for this episode.  Both (+ Tom) are members of the SCL - a leading educational charity for the tech law community in the UK.---If you enjoyed this conversation, please share it with someone or a community who you think would find it valuable . And if you have a moment, rate the show and tell us what landed — it helps us reach more people and keep getting brilliant guests like Rebecca and Laura.---For more conversations at the intersection of law and technology, head to⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠.

🎤 This week we sit down with Bilva Chandra — who has spent the bulk of her career working on AI safety, ethics, and governance at the places where it matters most.  Her CV reads like a guided tour of the AI governance landscape: she's worked at OpenAI, RAND, the US AI Safety Institute (now CAISI), and most recently Google DeepMind. She's been inside the frontier labs building the technology and inside the institutions trying to govern or influence its development — often thinking about the same problems from both sides of the table.---One of the catalysts for our conversation emanated from her recent contribution to a Google DeepMind paper — Architecting Trust in Artificial Epistemic Agents — exploring what happens when AI systems become active participants in how knowledge is created and shared. But it's Bilva's broader career at the intersection of AI and society that makes this conversation so compelling: she's someone who genuinely cares about getting this right, and isn't afraid to say when she's worried.We cover a lot of ground — from the practical challenge of making AI systems reliable enough for enterprise adoption, to the deeper worry about what happens to human judgment when cognitive work is increasingly offloaded to machines. What emerges is a picture of someone who is both genuinely optimistic about what AI can unlock and deeply clear-eyed about the societal fault lines it's accelerating. Bilva doesn't treat AI risk as a theoretical exercise. She frames it as a human problem — one tangled up with polarisation, declining trust in institutions, and an information environment that was already broken before the first LLM shipped.---Connect with Bilva Chandra — on LinkedIn | Or by subscribing to Role Model, her new newsletter on AI and society.---If you enjoyed this conversation, please share it with someone who you think would find it valuable — especially anyone grappling with how to govern AI responsibly in their organisation. And if you have a moment, rate the show and tell us what landed — it helps us reach more people and keep getting brilliant guests like Bilva.---For more conversations at the intersection of law and technology, head to⁠⁠ https://lawwhatsnext.substack.com/⁠⁠.

🎤 This week we sit down with David Bushby — Head of Legal Operations at Canva and the voice behind In Counsel Weekly — for a conversation that's part provocation, part practical playbook, and part three mates who love this stuff catching up over a good topic.  David follows Sam Lewis as the second member of the brilliant Canva legal team to join us for a chat, and from our vantage it's easy to discern the talent, curiosity and sense of fun they must have coursing through their team.---David has spent the last couple of years at the forefront of AI adoption in legal — not as a commentator, but as a practitioner. Custom GPTs, Claude skills in Cowork, vibe-coded legal research tools, Chrome extensions that make SaaS platforms do things they were never designed to do. He's materially contributing to the building of an AI-native legal function in real time.---"I just started to feel, by the end of last year — we just really need to go it alone. We can control what tools we use... maybe the AI dividend is just up to us on the in-house side."Here's a big question David has been grappling with (and we get into it straight away during our catch up): are law firms passing on their AI productivity savings to clients? The invoice data says no. The rate increases — 12–16% in the US and UK, with individual partner hikes of 25–35% — say definitely not. And at the line-item level? Nothing. So what does a smart in-house legal ops team do? They begin to contemplate going it alone.  David walks through Canva's owners mindset approach to outsourcing, the vibe-coded tools his team is building in Claude Code, and why the AI dividend might just be something in-house teams have to take for themselves.---Connect with David Bushby — by subscribing to In Counsel Weekly — David's popular bite-sized weekly newsletter for in-house counsel | Or find him on LinkedIn ---If you enjoyed our conversation, please do share it with someone who you think would be interested in listening (or is equally passionate or enraged by law firm productivity). And if you've got a spare minute, please rate the show and tell us what landed 🙏 It helps us grow our audience and continue to attract great guests like David.---For more conversations at the intersection of law and technology, head to⁠ https://lawwhatsnext.substack.com/⁠.

🎙️Peter Duffy is back for our quarterly deep dive into the biggest stories from his ever-popular Legal Tech Trends newsletter (celebrating its recent 50th edition 🎉). This time around, the conversation is dominated by one name: Anthropic. Between a legal plugin that spooked public markets, a viral tweet showcasing a "Claude-native" law firm, and a principled stand-off with the US Defense Department that sent millions of users switching sides — it's been quite the quarter.What we else dive into:Vibe coding hits legal — From weekend hackathons to working prototypes in 30 minutes. Peter explains why it's transforming ideation and prototyping, but flags the considerable leap from "amazing demo" to "enterprise-ready." Plus, Alex reveals his salmon regulation app “Branchly” is storming the charts over at vibecode.law.The privilege and compliance watch-outs — An SRA investigation into a solicitor uploading client docs to ChatGPT, a US ruling that use of consumer Claude waived attorney-client privilege, and judges struggling with where "AI" begins and ends. Shadow IT is alive and well.The LLM numbers blind spot — Peter's public service announcement: LLMs are not designed for numerical calculations and it's one of the easiest ways to trigger hallucinations. The McKinsey security incident — A security researcher accessing 45 million+ internal chatbot messages. Not an AI-specific problem per se, but a timely reminder that vibe-coded tools and internal chatbots need proper security scrutiny — especially when you have client data and a reputation on the line.Harvey, Legora, and the question you shouldn't be asking — "Which one should I buy?" Maybe start with your problems, not the product. Talk to your users, define your requirements, understand the commercial value — then go to market with a structured evaluation. ---Listen if: You want a grounded, hype-free take on the quarter that put legal AI firmly in the mainstream spotlight.---Rate, subscribe, comment, and share if you enjoyed this chat with Peter!---For more conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/.

🎤 This week we sit down (for our first in-person episode) with Nick West — Partner and Chief Strategy Officer at Mishcon de Reya — who has spent two decades working at the intersection of law, technology and business model innovation.Nick’s path is one of the more unusual and instructive in the industry: competition lawyer at Linklaters, strategy consultant at McKinsey, product leader at LexisNexis, Managing Director of Axiom UK, and now the person responsible for technological transformation and R&D at Mishcon. He founded MDR Lab (one of the first legal tech startup incubators) and the MDR Group (collection of specialist consultancy businesses that sit alongside but separate from the core Mischon legal practice), built one of the industry’s first in-house data science teams, and has overseen the firm’s AI adoption journey from early experimentation through to commercial platform deployment.  There are few people in the legal industry who’ve thought as deeply — or as practically — about how law firms actually work and how they might need to change.The conversation is wide-ranging — we cover the full arc of Nick’s career, the evolution of innovation culture inside a law firm, how Mishcon adopted AI (and what they got wrong along the way), the productivity question everyone’s asking, what happens when clients start sending genuinely good AI-drafted documents, and the early “signals” for where the business model of law might be heading.---Connect with Nick West Partner and Chief Strategy Officer at Mishcon de Reya---If you enjoyed this conversation please do share it with someone or a community who you feel would benefit from listening. If you have any more time do tell us what resonated; what didn't; and, rate the show (it helps us grow the audience and get great guests like Nick)!---For more conversations at the intersection of law and technology, head to⁠ https://lawwhatsnext.substack.com/⁠.

🎙️This week Tom sits down with Matt Rogerson — Global Policy Director at the Financial Times and one of the more prominent and forceful voices in the UK press and publishing industry on the question of AI companies using copyrighted content without permission or payment.The timing could hardly be more significant. We recorded this conversation on the day the House of Lords Communications and Digital Committee published what may prove to be the most consequential UK report on AI and creative industries to date: AI, Copyright and the Creative Industries — an 85-page report drawing on testimony from Google, Meta, Microsoft, OpenAI and dozens of creative industry bodies, whose conclusions could not be clearer: the UK's copyright framework is not outdated, the problems stem from widespread unlicensed use, and the government should rule out a commercial text and data mining exception entirely.And just one week earlier, the FT helped launch SPUR — the Standards for Publisher Usage Rights coalition — alongside the BBC, The Guardian, Sky News and The Telegraph: a coalition not just defending the status quo, but getting on the front foot to build shared technical standards and licensing frameworks so AI developers can access quality journalism through rights-cleared channels.What provoked this conversation was a pamphlet published by Public First, a UK policy consultancy, titled "Text & Data Mining and its value to the UK economy" — which called for a broad commercial exception to UK copyright law, extending the argument to cover AI inference as well as training. Matt's reaction on LinkedIn was characteristically direct, and it got us talking.---During our conversation, Matt dismantles several of the core narratives being advanced by AI lobbyists — the anthropomorphisation of models to normalise unlicensed use; the claim that licensing infrastructure is too hard to build; and the idea that the UK must weaken copyright to remain competitive. He makes a compelling case that the real opportunity lies not in capitulating to US hyperscalers, but in building sovereign AI models with transparent training data and proper licensing — pointing to the Allen Institute, a US model co-funded by the government and Nvidia, as proof that this is already happening.Matt highlights the infrastructure already being built to support fair licensing: Microsoft's Publisher Content Marketplace, the FT's existing commercial API access, and emerging thinking from writers like Florent Daudens on what a post-browser, agentic news economy could look like. The claim that it's "too hard" for AI companies to pay for content is not just wrong — it's being actively disproved by the market.And we close on what may be the most consequential long-term argument of all: the slop spiral. If there is no economic incentive to produce high-quality journalism — because AI companies can take it for free — the supply of reliable information degrades. AI models trained on and retrieving from an increasingly polluted information environment produce worse outputs. Trust erodes. And we drift into a world where the information we consume is dependent wholly on the alignment of a particular model and the commercial interests of those administering it. Matt makes the case that secure news and information supply chains could become a national security issue if this dynamic starts to accelerate.---If you enjoyed this conversation please do share it with someone or a community who you feel would benefit from listening. If you have any more time do tell us what resonated; what didn't; and, rate the show (it helps us grow the audience and get great guests like Matt)!---For more conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/.

We sit down with Rok Popov Ledinski — an independent legal AI and data consultant whose background spans high-security enterprise engineering through to advising law firms on their AI and security strategy. Our initial interest in Rok's work was sparked by his YouTube channel, where he's been producing sharp, accessible breakdowns of the real risks underpinning today's AI tools.Within minutes, we're into a forensic dissection of Anthropic's Claude Cowork — the agentic tool pitched at non-developers that launched earlier this year. Rok walks us through the contradictions in Anthropic's own technical documentation: a tool demonstrated by its creators as a way to organise your desktop, while the same support pages advise against granting it access to sensitive local files. A tool marketed for running tasks autonomously in the background — while its activity isn't captured by audit logs. A tool whose safety guidance asks users to watch for "suspicious actions that may indicate prompt injections" — aimed at an audience that, as Rok points out, has largely never heard of prompt injections. Rok explains, in terms accessible to non-technical listeners, how hidden instructions embedded in an innocuous document can hijack an AI agent into exfiltrating sensitive client data. His hypothetical attack vector for law firms is disarmingly simple: find lawyers on LinkedIn who are openly using Cowork, send a document to their publicly available email address containing concealed instructions, and let the agent do the rest.But this isn't an anti-AI conversation. Rok is emphatic that these tools should be used — just not naively. Drawing on enterprise security frameworks from companies like Cisco, he advocates for a practical middle ground: map what your AI has access to, create sanitised copies of sensitive folders, scope permissions tightly, vet your MCP servers and plugins, and understand (physically, not just contractually) how data flows through your systems.Key TakeawaysThe Cowork Paradox: Anthropic's own documentation reveals a tension between how Cowork is marketed (autonomous, background task execution) and how it should be used (limited permissions, no sensitive files, manual monitoring for prompt injections). Security attacks are now a "When," Not an "If": Unlike traditional cybersecurity breaches, prompt injection attacks exploit a fundamental limitation of large language models — they can't distinguish instructions from data. Research shows success rates as high as 90% for some proprietary LLMs. Claude is among the more resistant, but not immune.Practical Security for Legal Teams: Rok's actionable advice for in-house teams and law firms includes: creating clean data environments separate from originals; using self-hostable workflow tools like n8n; scoping AI permissions to the minimum necessary; and conducting genuine due diligence on every plugin and MCP server before connecting it to your systems.Key ReferencesRok's YouTube Channel: where our interest in Rok's work began, and a recommended follow for anyone wanting to stay across the security dimensions of legal AI adoptionRok's LinkedIn — he hosts weekly live sessions every Saturday with a security expert specialising in air-gapped, offline AI deployments in regulated industriesThe Art of Modern Legal Warfare — Rok co authors with a former guest and friend of the show Anna Guo and Sakshi Udeshi a series of vulnerability types specific to legal AI use cases.If you enjoyed this conversation please do share it with someone or a community who you feel would benefit from listening. If you have any more time do tell us what resonated; what didn't; and, rate the show (it helps us grow the audience and get great guests like Rok)!

🎙️Alex and Tom step aside for this one — handing the mic to their friend Catie Sheret (General Counsel at Cambridge University Press & Assessment), who hosts a rich three-way conversation with Oliver Patel (Head of Enterprise AI Governance at AstraZeneca) and Peter Lee (Partner at Simmons & Simmons). Three very different vantage points — converging on the same question: how do you actually make AI governance work in practice?What begins with a definitional exercise (what is AI governance, anyway?) quickly evolves. Oliver draws a sharp line between AI ethics, responsible AI, AI governance and AI safety as related but distinct disciplines — and makes a passionate case that governance is fundamentally change management, not compliance theatre. Peter describes the "golden thread" he sees in the best organisations: corporate philosophy flowing from the boardroom right down into the tools people use every day. Catie grounds everything in context — arguing that your principles only stick when they're anchored to what your organisation actually does: content IP at Cambridge, medical ethics at AstraZeneca etc.The conversation builds through the practical mechanics — use case assessment, vendor oversight, committee structures, crisis preparation — before arriving at the question everyone's wrestling with: agentic AI. Peter frames it as a mindset shift from "can we trust the output?" to "what actions can this system initiate?" Oliver goes further: the fundamental logic of agentic AI, he argues, is to take the human out of the loop — and organisations need to confront that honestly rather than pretending otherwise.There's a wonderful thread on human flourishing running throughout — Peter's insistence that philosophers have never been more important, Oliver's pride in AstraZeneca's "Thriving in the Age of AI" literacy programme, and a closing round of book recommendations that ranges from Richard Susskind's How to Think About AI to Jenny O'Dell's How to Do Nothing (Oliver's brilliantly contrarian pick about the importance of stepping away from screens entirely) to Governing the Machine by Ray Eitel-Porter, Paul Dongha, Miriam Vogel.It's a masterclass in how to think about governance as something that enables rather than constrains — hosted with warmth and real expertise by Catie.If you enjoyed this episode, please do share it with another friend, team or community who might also enjoy it! Please do let us know what resonated (by comment) and rate the show (if you haven't already)! We appreciate your time, attention and support!For more conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/ for: (i) insights from leading practitioners, technologists, and educators; (ii) deep dives into the intersection of law, technology, and organisational behaviour; and (iii) practical analysis and visualisation of how AI is augmenting our potential.

The vibe coding conversation in legal has gone full culture war: one side says they've built a billion-dollar startup in 10 minutes, the other says don't bother. The truth — as usual — is far more interesting than either extreme.🎙️This week we sit down with Chris Bridges (Co-Founder & COO, Tacit Legal) and Matt Pollins (Co-Founder & CPO, Lupl) — two legal technologists who live in the same small town in West Sussex and who've channelled that proximity into building vibecode.law, an open-source platform where the legal community can share, discover and upvote vibe-coded legal tech projects.The platform launched just over a week before we recorded and already had 18 projects — from a SaaS inflation calculator for contract lawyers to a Harvey for Mongolian law to a tool that unlocks track changes when a passive-aggressive opposing lawyer has locked them down.During our chat, we explore:Why vibe coding's real value is compressing the feedback loop between idea and prototype — not replacing developers The structural gap: how 25 years of developer tooling (linting, testing, documentation, standards) gives engineering focussed AI tools a head start that legal tech can't shortcut Why the adversarial nature of law makes standardisation fundamentally harder than in software vibecode.law: what it is, the projects landing on it, and the product thinking behind building a two-sided community Responsible vibe coding and why we're probably 6–12 months from a data exposure incident The T-shaped lawyer: curiosity as the defining skill for the next generationConnect with our guests:Chris Bridges — tacit.legal | author of When will legal vibe like codeMatt Pollins — agents.law | lupl.comCheck out vibecode.law to explore or submit your own projects.---If you enjoyed this episode, please like, subscribe, comment, and share! For more conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/

🎙️ This week we sit down with Artur Serov — a Senior Commercial Counsel working in-house across corporate, commercial, and AI compliance — who has been quietly vibe coding legal tech solutions that rival features in commercial platforms.  This is a practical, how-I-did-it episode. Artur walks us through his journey from first principles — the failed early experiments, the tools that unlocked progress, and the specific steps any curious lawyer could follow to start building.  Artur shares his screen during our conversation to demo a Word add-in with features he couldn't find in commercial legal tech (party-aware context, risk appetite dials, AI-powered negotiation prep), and previews a more ambitious workspace prototype where AI retains memory across an entire transaction lifecycle.  Since publishing this prototype has evolved, and you can read more about that here.  Artur is candid about what's now possible: with Claude Opus 4.5 and Gemini 3, self-built solutions can get remarkably close to enterprise-grade. But he's equally honest about the remaining hurdles — deployment, maintenance, security — and his belief that a growing community of "vibe lawyers" will help solve them together.---What you might take from this conversation:The First Principles Path to Technical Fluency — How Artur went from zero coding experience to working prototypes, using Claude as a teacher and Google Antigravity as his development environmentWhat's Missing from Commercial Legal Tech — Why context is the killer feature, and how Artur built deal-aware AI that knows who you represent, what you're negotiating, and what risks you're willing to takeThe Workspace Vision — A prototype where AI memory persists across NDAs, partnership agreements, and every document in a transaction — with your playbooks and policies embedded as reference materialsWhy Building Makes You Better at Everything Else — From vendor negotiations to IT collaboration, how technical fluency transforms your effectiveness as in-house counselHow to Get Started — Artur's practical advice: a Claude subscription, Google Antigravity, and the willingness to ask "how do I do this?"---Connect with Artur: LinkedIn | Github---If you found this episode interesting, please tell us and do share it with a friend, colleague or community who might take something from it! For more, head to⁠ lawwhatsnext.substack.com⁠ for: (i) Focused conversations with leading practitioners, technologists, and educators; (ii) Deep dives into the intersection of law, technology, and organisational behaviour; and (iii) Practical analysis of how AI is augmenting our potential.

We sit down with Anna Guo — a Singapore-based lawyer, startup advisor, and founder of LegalBenchmarks.ai — who has quietly built one of the most rigorous practitioner-driven evaluation frameworks for legal AI tools in the industry. Her community now spans close to 900 legal and AI professionals. Her research has produced findings that challenge industry assumptions: that legal-specific AI tools don't always outperform general-purpose models, that accuracy isn't actually the top driver of lawyer adoption, and that in some drafting tasks, AI is already matching or exceeding human reliability.This is a watch-don't-only-listen episode. Anna shares her screen throughout — running us through a live, double-blind benchmarking exercise where we rank outputs from legal AI, general-purpose AI, and human lawyers without knowing which is which. She also demonstrates how prompt injection attacks can bypass AI guardrails using techniques as simple as low-resource languages (Vietnamese or ASCII code?), surfacing security risks that become particularly acute as we move closer toward widespread agentic AI adoption.What You'll Learn:The Three Dimensions of Tool Evaluation — Why measuring accuracy alone misses the point, and how Anna assesses output reliability, output usefulness, and platform workflow support as distinct layersWhat Actually Drives Adoption — Survey data revealing that lawyers prioritise context management and verification over raw accuracy when choosing AI toolsWhere Humans Still Win — High-judgment, context-sparse tasks requiring commercial reasoning remain firmly in human territory; routine, context-complete work is where AI excelsPrompt Injection in Practice — Live demonstrations of how attackers can trick AI models into revealing harmful information using low-resource languages and clever framing---Connect with Anna: LinkedIn | LegalBenchmarks.ai---If you found this episode interesting, please tell us and do share it with a friend, colleague or community who might take something from it! For more, head to lawwhatsnext.substack.com for: (i) Focused conversations with leading practitioners, technologists, and educators; (ii) Deep dives into the intersection of law, technology, and organisational behaviour; and (iii) Practical analysis of how AI is augmenting our potential.

Season 2 is here.In our opener, we sit down with Anson Lai — commercial counsel by day, relentless tinkerer by night — who walks us through how he built and published a document review tool as a Microsoft Word add-in that rivals offerings from legal AI startups raising hundreds of millions.The kicker? He did it in weeks. And he's giving it away.This isn't theoretical. Anson shares his screen, shows us the tool live, and opens the hood on what makes it work. No mystique. No black box. Just a lawyer who got tired of copy-pasting contracts into ChatGPT tabs and decided to do something about it.What You'll Learn:"Vibe Coding" — How conversing with AI tools (not just instructing them) shaped better technical decisions"Bring Your Own Key" Architecture — Why your documents going straight to Google's API (with no middleman) actually mattersWhere the Real Moat Lives — If building software now takes hours not months, differentiation lies in the refinements — the nested lists, tables, and edge cases where most AI tools quietly fall apartConnect with Anson: LinkedIn | GitHub (Open Source Project)If you found this episode interesting, please like, subscribe, comment, and share! For more, head to lawwhatsnext.substack.com for:Focused conversations with leading practitioners, technologists, and educatorsDeep dives into the intersection of law, technology, and organisational behaviourPractical analysis of how AI is augmenting our potential

Welcome to Law://WhatsNext - the show where we catch up with leading practitioners (lawyers; technologists; educators and more) who are leveraging emerging technologies to pursue their passion and objectives, and as a by product we get nerdy trying to understand the implications for the future of legal practice (and more broadly, knowledge work). To keep up with the pace of change and developments subscribe to this channel or to our newsletter at: https://lawwhatsnext.substack.com/----In this episode, we've distilled a year of extraordinary dialogue into one 20-minute highlights reel. We've spent 2025 in conversation with legal industry pioneers — the general counsels, technologists, and educators redefining how law is practised, learned, and delivered. These are some of our standout moments from a series of compelling global conversations. What made the reel (this could honestly be a multi-part series):Part 1: Hype vs. Reality — Is AI progress real?Kevin Cohn (the soon to be CEO of Brightflag) provokes that the trough of disillusionment is coming but that shouldn't blight the reality that the value in the skills and expertise we used to highly prize are dramatically eroding Part 2: Agency, authenticity & trustDana Rao (the former GC & Chief Trust Officer at Adobe) demonstrates that we can be the agents (rather than mere subjects) of positive change, and we loved learning more about the work he and his team at Adobe invested to build the Content Authenticity Initiative (to counter the ever increasing proliferation of deepfakes)Part 3: Leading in disruptive timesJessica Block (EVP at Factor) used a recent read (Notes on Complexity by Neil Theise) as the lens through which she explained the importance of cultivating the right environment (over systems) for the emergent properties of transformational change to "bubble" up. Part 4: Evaluating what's actually workingSigge Labor (President at Legora) explained for us the work that Legora performs to understand frontier model performance and how they react to new developments and assess leaps in capabilities. We anticipate that in 2026 more and more legal teams and firms will invest in their evaluation capabilities, and this conversation (that accompanied the release of GPT5 in the summer) is one to check out if you haven't already. Part 5: The skills we might loseDan Hunter (Executive Dean, The Dickson Poon School of Law, King's College London) talked of the "terrifying bind" we encounter as we offload more and more cognitive work to compute - the work may get easier and more efficient but our cognitive development doesn't replicate (in terms of resilience) the old training training pathway. He has immediate concerns in the classroom and anticipates a coming gap in law firm talent pipelines.These are just glimpses. Check out our Spotify, Apple Podcasts, or Substack pages for the full conversations. Thank you for listening, supporting, and championing the show. We wish you a happy new year — Series 2 is coming soon 👀

We're joined by Peter Duffy for our quarterly ritual of dissecting the big headlines of Peter's popular Legal Tech Trends newsletter and ruminating on their potential implications for legal service delivery.  Peter returns wide eyed and optimistic fresh off some time in the US, where he enjoyed attending TLTF in Austin.What gets covered:The eternal "legal-specific vs. frontier model" debate — With Gemini 3 dropping and capabilities proliferating into vertical spaces, Peter weighs in on whether specialised legal AI still has an edge.PE is coming for BigLaw — McDermott exploring MSO structures to let private equity in; 20% of UK firms eyeing PE money; we explore the uncomfortable questions: (i) does outside capital corrupt lawyer independence? (ii) does PE change the fabric of the firm and its operation?  The vibes have shifted — Wild stat emanating from the PWC Law Firm Survey - Top-100 law firms expecting AI to boost revenue dropped from 69% (2023) to 31% (2025). Meanwhile, in-house teams are having their main character moment with a 24-point jump in AI optimism. Is this gap telling? Product chaos continues — Norm AI spinning up an actual law firm (!), Crosby raising $20M for Slack-native contract review, Legora's client portal coming Q1 2026, and Linklaters designating 20 "AI lawyers" to build workflows.Listen if: You’re worried your LinkedIn feed isn’t giving you enough legal technology news 😂  OR maybe you’re curious to experiment to see what else is going on out there (beyond this platform)? Rate, subscribe, comment, and share if you enjoyed this chat with Peter!For more conversations at the intersection of law and technology, head to⁠ https://lawwhatsnext.substack.com/⁠ for: (i) discussions with leading practitioners, technologists, and educators; (ii) Deep dives into the intersection of law, technology, and organisational behaviour; and (iii) Practical analysis and visualisation of how AI is augmenting our potential.

Hot off the heels of breaking legal LinkedIn last week, we caught up with Jamie Tso - a Hong Kong-based lawyer who's been building-in-public and sparking conversations across the legal community with his viral AI creations. This is a watch (don't only listen) episode. Jamie screen-shares his way through Google AI Studio, live-coding lightweight versions of legal tech tools we all know. Jamie walks through his "SpellPage" contract editor (inspired by a novel-writing app, naturally), demonstrates real-time AI-powered redlining, and casually drops the concept of an open-source "legal AI operating system" built from first-principles that could democratise access to common technology workflows we are building to support common practices across legal. His philosophy? The barrier to entry is now so low that sophisticated AI tools "should be free, more or less."Key moments:Live demo of AI-powered contract editing with natural language instructionsWhy Google AI Studio is the ultimate one-stop shop (native API keys, version control, GitHub integration, no coding required)The shift from chatting with AI → AI using tools → AI spinning up mini-apps on the goJamie's vision for consolidating legal workflows into reusable, customisable modulesMust-read context: Check out Jamie's viral posts that sparked this conversation:The contract editor build"Gemini 3 is basically AGI at this point"This is what building in the age of AI looks like - experimental, exhilarating, unnerving and transformative.  If you enjoyed this episode with Jamie, please like, subscribe, comment, and share!For more conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/ for: (i) Focused conversations with leading practitioners, technologists, and educators; (ii) Deep dives into the intersection of law, technology, and organisational behaviour; and (iii) Practical analysis and visualisation of how AI is augmenting our potential.

Alex and Tom step aside for this one—no hosts, no scripts—just Andy Cooke (CLO of Perk) and Sam Ross (CLO of Remote) in conversation. What begins with nursery vomiting bugs quickly evolves into a refreshingly honest exploration of what it means to lead a legal function in disruptive technology companies. They dissect the tension between being "bold, brief, and gone" versus staying in the room to build genuine relationships, challenge the limiting "trusted advisor" archetype, and wrestle with when precision matters less than context and authentic communication. Andy and Sam don't just theorise—they get personal about the moments that test you: deciding whether someone's lying on an expense claim, navigating board dynamics when you're the least financially fluent person in the room, and maintaining ethical standards when the stakes are existential. But this isn't a heavy-handed meditation on professional responsibility. The conversation crackles with levity and self-awareness - from Sam's admission that he deliberately uses humour to "pierce through" hierarchy, to their shared recognition that being fallible and human is part of doing the job right. Both find genuine joy in what they do, drawing energy from learning from others and building networks that pay dividends years later. It's a masterclass in thoughtful leadership wrapped in the warmth of two friends who clearly respect each other's craft - and aren't afraid to acknowledge when they get it wrong. If you enjoyed this episode, please like, subscribe, comment, and share! It gives us a warm fuzzy feeling and helps make our podcast more discoverable to other podcast aficionados! For more thought-provoking conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/ for: (i) Focused conversations with leading practitioners, technologists, and educators; and (ii) Deep dives into the intersection of law, technology, and organisational behaviour; and (iii) Practical analysis and visualisation of how AI is augmenting our potential.

Creating content has never been easier. With both LLMs and world models (Sora 2, Veo 3, Marble) the fidelity of what we can produce at the tip of a prompt is getting genuinely scary.  Guy Shahar is the CEO and founder of Blee, a Y Combinator-backed AI content compliance platform that helps companies review and oversee marketing materials at scale. Before founding Blee nearly four years ago, Guy led marketing operations at Adobe for five years, and he has been witnessing firsthand the explosion of AI-generated content and deliberating on the implications. We sit down with Guy in this short conversation to discuss: (1) the rising proliferation of AI generated content; (2) the cyber-like threat of deepfakes and bad actor impersonation; and (3) the new opportunities large language and world models present for some of the world's largest brands in how they generate and manage their production of compelling content.Key TakeawaysThe "Content Tsunami" is here and it's only getting bigger - Content creation has exploded with AI, fundamentally changing the speed and volume at which companies can produce marketing materials. What used to take weeks now happens in hours. Guy calls this the "content tsunami" - a relentless wave of content being generated across all digital channels. But the gap between how fast content can be created and how fast it can be safely approved is widening, creating significant risk exposure for companies and their brands.Deepfakes aren't just a detection problem - they're a trust problem - One real danger of deepfakes isn't just that bad actors can create convincing fake content - it's that they're eroding trust in everything we see online. The recent deepfake of Irish presidential candidate Catherine Connolly which went viral in Ireland, which falsely showed her withdrawing from the race just days before the election and remained live for 12 hours, demonstrates how sophisticated and damaging this content has become. AI compliance creates new opportunities for how teams work - While AI-generated content creates new risks, it also opens unprecedented opportunities to transform workflows and team structures. Guy promotes the potential for companies to rethink their entire "content supply chain" - testing 50 or 100 versions of marketing materials instead of just two, delivering hyper-personalised content at scale, and breaking down silos between marketing, legal, GTM and compliance teams. Key References from Our ConversationCatherine Connolly Deepfake Incident: An AI-generated video falsely depicting Irish presidential candidate Catherine Connolly withdrawing from the race surfaced just days before the October 2025 election, viewed nearly 30,000 times over 12 hours before Meta removed it - a stark example of how deepfakes can threaten democratic processes and why rapid content monitoring matters.Content Authenticity Initiative (CAI): an open standard verification system with over 900 member companies working to authenticate digital content and combat deepfakes through content credentials and metadata tracking.Dana Rao: Adobe's former General Counsel and Chief Trust Officer, is mentioned for his perspective on deepfakes and the transition from trying to detect fakes to proving authenticity - Dana appeared on an earlier episode of Law://WhatsNext which you can access here. If 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: (i) Focused conversations with leading practitioners, technologists, and educators; (ii) Deep dives into the intersection of law, technology, and organisational behaviour; and (iii) Practical analysis and visualisation of how AI is augmenting our potential.

We sit down with Kevin Cohn, Chief Customer Officer at Brightflag, who occupies one of the most unique vantage points in legal services – the interface between corporate legal departments and their outside counsel. We’re sure any AI start up would pay a premium to understand the work that is going to law firms and the value and time it takes to deliver that, right? By processing billions of dollars in legal invoices, Kevin and his team have unprecedented visibility to spot macro trends – from law firm partner utilisation patterns to staffing changes. In this lively but familiar conversation (we’ve each all known one another for a few years) Kevin reveals some emerging trends very relevant to the technological revolution we are all experiencing. Beyond the predictable conversation about rising law firm rates, Kevin shares two interesting developments the Brightflag team are noticing: increased partner utilisation (which might actually be good news if total hours are decreasing?)something more troubling – what Kevin diplomatically calls "not the most above board" AI-enabled billing practices, with ever more invoices showing suspicious six-minute increments.We also talk about the evolution of skills and relationships in an era when both clients and counsel are being shaped by automation and analytics.Kevin is also our first Law://WhatsNext guest to have an AI version of himself shipped and deployed to give Brightflag customers on-demand access to his expertise on legal operations and spend management. While Kevin Clone can handle questions about invoice review and matter management workflows with ease, we discover its limits when we request an Italian wine pairing. The Clone politely deflects: "I'm here to focus on legal operations and Brightflag." Some things simply can't be replicated by AI. The real Kevin remains irreplaceable.Key ReferencesBrightflag LinkedIn Post — Introducing Kevin CloneAsk Kevin Clone a Question — BrightflagIf you enjoyed this episode, please like, subscribe, comment, and share! It helps more people discover conversations like this.  For more thought-provoking content at the intersection of law and technology, head to https://lawwhatsnext.substack.com/ for: (i) Focused conversations with leading practitioners, technologists, and educators; (ii) Deep dives into the intersection of law, technology, and organisational behaviour; and (iii) Practical analysis and visualisation of how AI is augmenting our potential.

In a twist to what has probably become our “normal” programming, this episode features just the two of us in conversation. We explore the implications of technological progress - from the shift we’re contemplating from AI-infused linear workflows to fully agentic ones, to the risks and vulnerabilities baked into today’s LLM architectures. Essentially, it’s the kind of discussion we often have offline, brought into the open.The following pieces ground our discussion:From linear AI-infused workflows to fully agentic - new skills and orchestration challengesLegal AI’s Future Is Railroads, But Speeding Up Canals Still Makes Sense For Now by Alex Herrity  The Problem with Agentic AI in 2025 by Sangeet Paul Choudary - The original article featuring the canals vs railroads analogy that inspired Alex's piecePrompt Injection Attacks & AI Governance:The Lethal Trifecta for AI Agents by Simon Willison - defining the three dangerous elements that enable prompt injection attacksPrompt Injections as Far as the Eye Can See by Simon Willison - Johann Rehberger's "Month of AI Bugs" research demonstrating widespread prompt injection vulnerabilitiesI Accidentally Became a ChatGPT Surveillance Node by Juliana Jackson - The article Tom and Alex discuss revealing OpenAI's buggy infrastructure leaking private conversationsChatGPT Scrapes Google and Leaks Your Prompts - Quantable Analytics - Technical breakdown of the ChatGPT prompt leakage issueIf 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: (i) Focused conversations with leading practitioners, technologists, and educators; (ii) Deep dives into the intersection of law, technology, and organisational behaviour; and (iii) Practical analysis and visualisation of how AI is augmenting our potential

This week we sit down with Memme Onwudiwe for a conversation that starts in a Harvard Law classroom - transitions to his building an AI company before ChatGPT was a thing - and ends up in outer space 🚀Memme co-founded Evisort while at Harvard Law School in 2016, building AI-powered contract intelligence from the Harvard Innovation Lab years before it became mainstream. Workday acquired the company in October 2024, where Memme now serves as an AI Evangelist. Memme returns to Harvard each spring to teach legal entrepreneurship alongside co-founder Jerry Ting, and he’s a published space law scholar whose paper “Africa and the Artemis Accords” examines how emerging nations can secure their stake in the space economy.Key ReferencesAcademic ResearchAfrica and the Artemis Accords — Memme Onwudiwe & Kwame Newton, New Space (2021)Legal FrameworksArtemis Accords — Non-binding bilateral space exploration principles (2020, 55+ signatories)Outer Space Treaty — Foundational UN space law treaty (1967)Moon Agreement — “Common heritage” framework (1979, 18 signatories)OrganizationsHarvard Innovation Labs — Where Evisort was foundedCLOC — Corporate Legal Operations Consortium (6,300+ members)Space Beach Law Lab — Annual space law conference, Feb 24-26, 2026, Long BeachCorporateWorkday-Evisort Acquisition — ~$310M, closed Oct 2024If 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.

Nicole Braddick needs no introduction - but if you had to rush one for the purposes of publishing a podcast 👀 you might say she’s the Global Head of Innovation at Factor Law, following the February 2025 acquisition of her company, Theory & Principle, where she served as CEO and Founder. A former trial lawyer who transitioned into legal tech 15 years ago, Nicole has been one of the industry's most persistent advocates for bringing modern design and development practices to legal technology. Her team has worked with leading law firms, legal tech companies, corporate legal departments, non-profits and public sector organisations to build custom solutions focused on user experience - transforming an industry that, when she started, was "purely functional" and "engineering-led" into one where good design is finally recognised as essential.We get into all of that and more during our discussion, and lean in hard for Nicole’s system wide view and perspective on what’s happening at present.. Key TakeawaysNicole advocates that the calculation around build versus buy has fundamentally changed with generative AI. She argues that corporate legal departments should consider getting enterprise accounts with providers like Anthropic or OpenAI and should be building their muscles for developing internal customised solutions rather than defaulting to SaaS products. The proliferation of chatbots in law was appropriate when everyone was experimenting with generative AI, but Nicole believes the industry has overcorrected. Chat interfaces place enormous cognitive load on users who must craft effective prompts, whereas traditional point-and-click UIs make things easier by guiding users through structured workflows. Nicole sees the future as lying in hybrid experiences.While the AI industry races toward autonomous agents, Nicole sounds a cautionary note for legal applications. The entire value proposition of agents is "getting rid of control"- but lawyers have to wrestle with their ethical obligations and duties to control, to check, and to approve. Nicole sees this as a fascinating design challenge: where previous UX best practices focused on removing friction to create seamless experiences, Nicole and her team are actively considering where they must now strategically add friction and interruption points, believing the goal is to prevent lawyers from blindly clicking "yes, yes, yes" while avoiding so much friction that they abandon the tool. If 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

We sit down with Stephan Breidenbach, co-founder of the Rulemapping Group and a German scholar who's been quietly revolutionising how we think about law, technology, and democratic governance since the early 2000s.What started as a teaching tool to help law students visualise complex legal reasoning has evolved into something far more ambitious: a comprehensive system for transforming laws into executable code that maintains human oversight while dramatically improving access to justice.Stephan's present work spans three critical areas: decision automation (turning legal rules into fast, transparent systems), rule-based AI (supporting human lawyers with explainable reasoning), and law as code (drafting legislation that's both human and machine-readable from day one).Some of our highlights from the conversation:The Transparency Imperative: "I would never trust an LLM with a legal process because it's confabulating" Stephan declares, highlighting why the Rulemapping approach prioritises explainable AI over black-box solutions. Their system lets human decision-makers see exactly how the AI reached its conclusions – a "zoom in, zoom out" process that mirrors how lawyers naturally think.Democracy-First Technology: Unlike Silicon Valley's "move fast and break things" mentality, Stephan advocates for keeping humans in the loop even when AI becomes more accurate: "I think it's very important for trust in the legal system and therefore in a democratic system that there are human beings, even if they make worse decisions."Access to Justice at Scale: Through real-world deployments like processing 500,000 diesel emission scandal cases and serving as Europe's first certified Digital Services Act dispute resolution body, Rulemapping demonstrates how thoughtful automation can make legal systems accessible to everyone, not just those who can afford lawyers.We also explore the behavioural risks of over-relying on automated systems, the potential for "law as code" to improve democratic participation, and Stephan's vision of embedded law that serves citizens rather than bureaucracy.If 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 more of the same.

We catch up with Ben Martin, the former Director of Privacy at Trustpilot and author of "GDPR for Startups," who's currently living his best life somewhere in the Estonian wilderness with a camper van, fishing rod, and blessed freedom from subject access requests. Having built privacy programs at high-growth companies like Trustpilot, Ovo Energy, and King Digital Entertainment, Ben brings a refreshingly practical perspective to privacy law that goes way beyond compliance theatre.From his sabbatical perch in the Nordics, he reflects on everything from why GDPR hasn't quite delivered its promised outcomes to how privacy lawyers are uniquely positioned to lead AI governance.What We Cover:The Sabbatical Chronicles: Ben's epic Nordic adventure and why stepping away from work sometimes gives you the clearest perspective on itPrivacy Program Building: Moving from compliance theatre to business enablement, and why good privacy programs start with genuine curiosity about productsGDPR Reality Check: Why the regulation might not have quite yet delivered its intended outcomes and the types of privacy lawyers and approaches Ben sees in practiceAI Governance Evolution: How privacy professionals are naturally stepping into AI oversight roles and what new skills they need to developTechnical Literacy: The importance of understanding what your business actually builds and Ben's practical approach to learning complex technical conceptsKey References:GDPR for Startups - Ben's practical guide to building privacy programs in high-growth companiesField Fisher Privacy Newsletter - Legal developments summary that Ben recommends for staying currentHard Fork Podcast - Ben's go-to for broad tech and AI developmentsLovable - The AI coding platform Ben's been experimenting with to build his habit tracker (and recruit his girlfriend as user number one)If you found this episode interesting, please like, subscribe, comment, and share! For more thought-provoking conversations at the intersection of law and technology, head to https://lawwhatsnext.substack.com/.

This week we sat down with Dan Hunter, Executive Dean of the Dickson Poon School of Law at King's College London and serial legal tech entrepreneur. Dan's journey spans academia across three continents, four successful startups (including his current venture GraceView), and decades of research on the cognitive science of legal reasoning. As both an educator training the next generation of lawyers and an entrepreneur building AI-powered legal solutions, he offers a unique dual perspective on the transformation underway across knowledge work.Key Takeaways1. The Learning Paradox: AI Makes Us Feel Smarter While Making Us DumberStudents using large language models consistently perform better on assignments and believe they're learning more - but when the AI is removed, they've retained virtually nothing. This creates a dangerous illusion of competence (sycophantic models propagate this!) that law schools and firms must address through new assessment methods and training approaches.2. We're Heading Toward a "Barbell" Legal ProfessionTraditional pyramid law firm structures will collapse as AI automates much of the work. Dan believes the future involves senior lawyers managing client relationships at the top, AI agents handling routine tasks in the middle, and "legal engineers" swarming around validating AI outputs and steering the models.3. Entry-Level Legal Jobs Are Already DisappearingWe discuss the recent Stanford research "Canaries in the Coal Mine? Six Facts about the Recent Employment Effects of Artificial Intelligence" by Erik Brynjolfsson, Bharat Chandar, and Ruyu Chen, Stanford Digital Economy Lab (2025) - The landmark study using ADP payroll data showing 13% employment decline for young workers in AI-exposed occupations.Interested in more?If you found this episode interesting, please like, subscribe to the show, comment, and share! For more thought-provoking content at the intersection of law and technology, head to our Law://WhatsNext home 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

We have fun sitting down with Dana Rao (the former General Counsel and Chief Trust Officer at Adobe) - where we cover the implications of AI progress on: regulatory frameworks and geopolitics; copyright law; deepfakes - including content proliferation and authenticity; fair use and Dana’s take on the current class action lawsuits in the US; and Dana’s proposals for a new impressionistic right for creators to stave off the economic harms of their work being imitated. The conversation provided us with a fascinating insight into life at Adobe at the moment the performance of these generative models really began to take-off, and it was clear to us that Dana and his team played a pivotal role in shaping not only what kind of products Adobe went on to develop but how they would be distributed and consumed by their users!This episode draws on Dana's extensive experience at the intersection of technology, law and policy. Here are the key references and cases we discussed:Legal Cases:Andy Warhol Foundation for Visual Arts, Inc. v. Goldsmith, 598 U.S. 508 (2023) -  The Supreme Court case that Dana argues will have an influence in the outcome of AI fair use battles (which are focussed on economic competition between uses)Thomson Reuters Enterprise Centre GmbH v. Ross Intelligence Inc., No. - 1:20-CV-613-SB (D. Del. Feb. 11, 2025) - The "Westlaw case" Dana mentioned where the judge initially ruled for the AI company but changed his mind after better understanding the technologyDana's Policy Work:Senate Judiciary Committee Testimony (July 12, 2023) - Dana's appearance before the Senate Subcommittee on Intellectual Property hearing titled "Artificial Intelligence and Intellectual Property – Part II: Copyright"Adobe's Proposed Anti-Impersonation Law - Dana's legislative proposal for federal protection against AI-powered style imitationContent Authenticity Standards:Content Authenticity Initiative (CAI) - Adobe-founded initiative with over 5,000 members working to establish content provenance standardsCoalition for Content Provenance and Authenticity (C2PA) - The formal standards organization co-founded by Adobe, Microsoft, Intel, Arm, BBC, and Truepic under the Linux FoundationC2PA Implementation in Google Pixel Phones - Recent adoption of content authenticity standards in consumer devicesIf you found this episode of Law://WhatsNext interesting, please rate, subscribe, comment, and share!

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).

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.

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.

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

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

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!

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

Jessica Block thinks about the technological transformation we are all experiencing the way physicists think about quantum mechanics – as a system where observation changes the outcome and where the most interesting things happen at the edge of possibility.In this episode of Law://WhatsNext, we catch up with Jess, Executive Vice President at Factor – a former theatre major turned legal tech executive who's spent her career electrifying complex systems. From her early days in eDiscovery at FTI Consulting to her multifaceted roles at Factor (including a stint as CFO), she embodies the kind of cross-functional thinking and leadership that thrives in periods of rapid transformation.What makes this episode essential listening is Jessica's ability to articulate the delicate balance between structure and emergence when leading through technological upheaval. "We're constantly stitching together partial insights to get to coherence," she explains, describing how Factor is approaching the GenAI moment not as a traditional tech rollout but as a complex system that requires cultivation rather than control.The conversation takes unexpected turns as Jessica reflects on Factor’s strategic pivot into AI-first legal solutions. The Sense Collective, formed during what she calls "that constant loop of discovery and disappointment" in early 2023, has positioned Factor at the center of a community exploring how generative AI will reshape legal work. We venture into philosophical territory when Jessica references complex systems theory and Neil Theise's "Notes on Complexity" drawing parallels between consciousness as a transducer and the kind of emergent organisational change Factor is nurturing. These moments of introspection reveal why building and leading in this space requires not just technical expertise but a willingness to confront existential questions about how we approach work itself.If you found this episode interesting, please like, subscribe, comment, and share!

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!

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!

We dive into the machine room of AI-native legal tech with Jake Jones, co-founder of Flank (formerly Legal OS) – a designer-turned-entrepreneur who's building digital colleagues to serve as the front line between corporate legal teams and the businesses they support.What makes this episode essential listening is Jake's ability to demystify complex concepts that many of us encounter but few truly understand – from RAG (Retrieval Augmented Generation) to context windows and vector databases."We're in the era of workarounds," Jake explains, describing how companies are building complex technical solutions that will likely become obsolete within 12-24 months as AI capabilities advance. His breakdown of how these systems actually function – chunking documents, creating embeddings, and using similarity search – provides a rare glimpse into the machinery behind today's AI applications and why this technical debt is both necessary and temporary.The conversation takes fascinating turns as Jake drops provocative insights throughout: "I think SaaS is going to die," he declares, predicting that today's point-and-click applications will seem as primitive as telegrams once model-based applications become the norm. "We will look back in 20 years and think, how did the older generations manage to get anything done?"We venture into unexpectedly philosophical territory when Jake reflects on why interactions with AI can sometimes feel spookily conscious: "What we're seeing is our own consciousness projected into it and being reflected back." These moments of introspection reveal why building in this space requires not just technical expertise but a willingness to confront existential questions about intelligence and humanity itself.This episode embodies exactly why we started Law://WhatsNext – to capture raw, unfiltered conversations with the people building our future while it's still being shaped. Jake's candid admission that he initially "metamorphosed into fear" about AI's implications before finding a more optimistic path forward mirrors the journey many of us are on.Whether you're a legal professional trying to navigate the AI revolution or simply curious about the machinery behind the magic, Jake's insights will help you separate signal from noise in a rapidly evolving landscape. And fair warning: his hot takes on everything from hiring practices ("a single marketer who understands how to use AI can do the work of five") to the future of autonomous agents might just fundamentally change how you think about technology's role in legal practice.If you found this episode interesting, please like, subscribe, comment, and share!

We explore responsible AI governance with Hadassah Drukarch, former Director of Policy and Delivery at the Responsible AI Institute and current PhD researcher at Leiden University.Hadassah shares her journey into AI ethics and governance, driven by her interest in problem-solving and recognizing that traditional top-down legal approaches are insufficient for emerging technologies – we need bottom-up perspectives as well.The conversation centers on a critical disconnect: regulatory frameworks for AI are often too generalised and detached from practical implementation contexts. While frameworks like the EU AI Act provide baseline standards, Hadassah expresses serious doubts about their effectiveness, noting that implementing responsible AI looks dramatically different across industries like healthcare and finance.Perhaps most compelling is Hadassah's work testing healthcare robotics, which revealed significant gaps between regulatory standards and real-world performance. Her team's experiments showed that exoskeleton technology designed primarily for elderly users had been tested predominantly on male subjects and was often uncomfortable or unusable for women – demonstrating how policy development frequently lacks critical real-world testing with diverse user populations.Hadassah advocates for creating infrastructure that incorporates practical, on-the-ground testing directly into the regulatory process, replacing theoretical frameworks with evidence-based governance.The conversation concludes with reflections on the value of peer-to-peer knowledge sharing and practical conversations – like this podcast – as essential resources in this rapidly evolving field.If 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

In this episode of Law://WhatsNext, we sit down with Sean West, co-founder of Hence Technologies and author of the soon-to-be-released book Unruly, available for preorder ahead of its official release on 25 March 2025. Drawing on Sean’s experience as a globetrotting CEO , political advisor and legal technology founder, our conversation dissects the implications of a rapidly evolving geopolitical landscape - what Sean refers to as a new “unruly” world order.Key Themes & HighlightsGeopolitical Deconvergence: Why old-world certainties are fracturing, and how that puts legal professionals on the front lines of assessing and mitigating global risk.Law as a Techno-Political Force: Sean spotlights how law and law firms are no longer mere service providers but active shapers of strategic conversations in boardrooms and beyond.AI and the ‘Legal Singularity’: Referencing seminal works like Personalized Law: Different Rules for Different People by Omri Ben-Shahar and Ariel Porat, and The Legal Singularity: How Artificial Intelligence Can Make Law Radically Better by Abdi Aidid and Benjamin Alarie, Sean provokes us to imagine a future where legal frameworks adapt at the speed of technology—and the profound implications it holds for practitioners and society at large.A Special Offer for Our ListenersSean also shares how his team at Hence Technologies is forging new ways to track and interpret global events—so your legal function or organization can stay ahead of the curve. Want to give it a try? Head to global.hence.ai, and enter the code “lawwhatsnext” at checkout to receive a one-off promotional offer on the new product.If this conversation resonates with you, like, subscribe, comment, and share this episode! For more deep dives at the intersection of law, technology, and organizational behavior, visit https://lawwhatsnext.substack.com/ where we feature:Focused conversations with leading practitioners, technologists, and educatorsInsights on navigating geopolitical risk, AI regulation, and the future of legal practicePractical analysis of how emerging technologies can augment (not just automate) the work we do

In this episode, we chat with Sam Flynn, COO of Josef – a friend we've known for years who brings a rare blend of technical expertise, legal insight, and authentic enthusiasm to every conversation. Sam takes us through the development of "Roxanne," an AI chatbot created with Housing Court Answers and New York Law School to help NYC tenants understand their rights. It's a perfect full-circle moment from his early days in Australia where a weekend project to help people navigate unfair laws led...

Steph is the Legal Director at JUSTICE (all caps to distinguish it from the system itself), a human rights and law reform organisation working to make the justice system fairer and more accessible. JUSTICE’s fresh off the press report "AI in our Justice System" led by Sophia Adams Bhatti proposes the first rights-based framework for AI implementation, arguing that human rights—concrete, established, and enforceable—provide better guardrails than nebulous ethics principles, particularly in ...

In this episode of Law://WhatsNext, we sit down with Laurie Ehrlich, who made the bold move from Chief Commercial Counsel at Datadog to Chief Legal Officer at Dioptra, an AI native legal tech startup revolutionising contract negotiation. Laurie takes us through her fascinating journey over the past 12 months, sharing the thoughtful decision-making process that led her to leave the security of a public company for the dynamic world of AI startups. She reveals how she reframed the risk by givin...