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Law://WhatsNext

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by Tom Rice and Alex Herrity

45 episodes

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Podcast Overview

How are leading practitioners leveraging emerging technologies and ways of working to pursue their passion and objectives, and as a by product what are the implications for the future of legal practice? Let’s explore this together. What to expect: - Focused conversations with leading practitioners; technologists and educators - Deep dives into the intersection of law, technology, and organisational behaviour - Practical analysis and visualisation of how AI is augmenting our potential - Insights from adjacent industries that might inform our own

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Recent Episodes

June 10, 2026

Return on Token: Shawn Curran on Lawyer-Builders, Open Source, and the Real Cost of AI

🎙️ This week we sit down with <a href="https://www.linkedin.com/in/shawn-curran-b5b5858/">Shawn Curran</a>, CEO of <a href="https://jylo.ai/">Jylo</a> — for a conversation that starts where a lot of legal teams and law firms are quietly stuck: Now that almost anyone can build software, should they?Shawn is unusually well placed to answer. He spent the best part of two decades as a technologist inside private practice — McGrigors, Latham & Watkins, Freshfields, then head of legal tech and later director at Travers Smith, before spinning Jylo out of the firm two and a half years ago. ---He's watched the industry crawl from paper files 📄 to systems of record 🗄️ to systems of productivity ⚙️ and now to what he calls "systems of intelligence" 🧠. So when he says the barrier to building software is "literally on the floor" 📉, it lands with some authority. And he's thrilled about it. The open-source wave of lawyer builders democratising access to their products — Will's <a href="https://mikeoss.com/">MikeOSS</a>, Antti Innanen's <a href="https://lavern.ai/">Lavern</a> — is, to Shawn, a long-overdue correction. Now the person who actually understands the work describes it in plain English and watches it take shape.---This discussion plays out against a legal technology market that refuses to sit still. One week it's a new open-source release; the next, Kirkland & Ellis commits half a billion dollars to its own platform; the week after, a frontier lab ships a legal plugin. Shawn admits he loses a faintly ridiculous amount of time to "is this Jylo for free?" emails. Which brings us to Shawn’s stand out observation from our conversation - we talk endlessly about ROI; Shawn would rather we talked about ROT (return on token). If a firm spends thirty grand vibe-coding something nobody ever opens, it hardly matters that it would have cost two hundred grand in engineers; it's still money set on fire. "Return on token. What's the return on token? 'Rot.' … There's a lot of rot out there." Shawn warns that as token prices climb rather than fall, the honeymoon phase of trying everything is going to give way to harder questions about what's actually worth the spend. ---Connect with <a href="https://www.linkedin.com/in/shawn-curran-b5b5858/">Shawn Curran</a> — CEO of Jylo ---If you enjoyed this conversation, please do share it with a colleague or community wrestling with the same questions — and if you have a moment, tell us what resonated, what didn't, and rate the show. It genuinely helps us grow the audience and land great guests.---For more conversations at the intersection of law and technology, head to<a href="https://lawwhatsnext.substack.com/">⁠⁠⁠⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠⁠⁠⁠</a>.

June 2, 2026

AI-Native Hiring and Organisational Alignment with Stephanie Dominy

🎙️ This week we sit down with <a href="https://www.linkedin.com/in/stephaniedominy/" rel="ugc noopener noreferrer" target="_blank">Stephanie Dominy</a> — General Counsel and Head of Ops at <a href="https://tessl.io/" rel="ugc noopener noreferrer" target="_blank">Tessl</a>. Stephanie has practised law for nearly three decades, but at Tessl she hires across the whole organisation, including against one of its operating principles: "Be AI Native." What begins as "how do you spot an AI-native engineer?" becomes "how do you hire an AI-native lawyer?" — and then a deeper question still: if AI can already draft, research and build, what is the irreducibly human part of legal work? Stephanie's answer is taste and judgment. She explains why Tessl keeps iterating on how it hires, most recently reverse-engineering its interviews (inspired by <a href="https://sierra.ai/blog/the-ai-native-interview" rel="ugc noopener noreferrer" target="_blank">Sierra's AI-native interview framework</a>). From there we touch on cognitive surrender, the commoditisation of knowledge, legal training pathways, and her observation that those with humanities backgrounds are often better equipped to interrogate AI than purely data-driven minds.---Tom is equally sceptical of organisational efforts to adopt this technology. He points to <a href="https://www.anthropic.com/constitution" rel="ugc noopener noreferrer" target="_blank">Claude's Constitution</a> — the document Anthropic uses to steer a probabilistic model through competing demands via a clear order of precedence — and argues it isn't so different from a legal constitution, and is a surprisingly useful mirror for any company trying to go AI-native. (It's also humbling, he suggests, to work out where you sit in the "model stack.") His argument: every organisation is made up of teams with competing priorities, so be deliberate about where to go all-in. His example — the overzealous sales team optimising for deals while legal supercharges risk prevention. Today those incentives collide only occasionally, and human leaders resolve them. But as each team is amplified by AI, the collisions get faster, and their resolution is quietly outsourced to the model — piling on competing instructions that degrade its performance. ---Tom and Stephanie are taking this one to the stage — Wednesday 3 June 2026, at Crafty Fest, Regent's University London. <a href="https://crafty-counsel.com/events/crafty-fest/" rel="ugc noopener noreferrer" target="_blank">Crafty Fest</a> is Europe's largest festival for the in-house legal community, and their session picks up exactly where this episode leaves off.---Connect with <a href="https://www.linkedin.com/in/stephaniedominy/" rel="ugc noopener noreferrer" target="_blank">Stephanie Dominy</a>, General Counsel & Head of Ops at Tessl. And the open question Stephanie left us with: if you've built something that actually works for testing taste and judgment — an interview question, a practical test, anything — we want to hear it. Bring it to Crafty Fest, or drop it in the comments 👇---For more conversations at the intersection of law and technology, head to<a href="https://lawwhatsnext.substack.com/" rel="ugc noopener noreferrer" target="_blank">⁠⁠⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠⁠⁠</a>.

May 19, 2026

The Defensibility Question: Helen Fan on What Survives When Frontier Models Climb the Stack

🎙️ This week we sit down with <a href="https://www.linkedin.com/in/helenfanlegalai/">Helen Fan</a> — California lawyer, Chief AI Officer at a Silicon Valley boutique firm, and one of the most original voices currently writing and building in legal AI.What makes Helen unusual is the combination. She is a practising cross-border lawyer who is also genuinely technically literate — building, testing and writing about agentic systems at a level most lawyers (and a fair few engineers) do not reach. And she sits squarely on the bridge between the US and China technology frontiers (building legal tech communities in each)."My role is really about being a bridge — between tech people and legal professionals, and between the US and Asia."It is a rare vantage point — and one that has produced one of the more original frameworks we have come across in the legal AI conversation this year. Our conversation is in two halves. First, we ground the conversation in the Legal AI Value Stack — Helen's five-level framework for thinking about defensibility in a world where frontier models keep climbing the stack. Then we get into the fun part: OpenClaw LLP, her public experiment to actually walk the roadmap herself. We get into the design choices behind her two AI associates, the four-layer security framework she has built, the Argument Report skill, her custom debrief skill which has her agents look back over recent work and recommend tweaks, why she ended up on Discord, and her honest reflections after the first 60 days. Key ReferencesConnect with Helen Fan — California lawyer & Chief AI Officer | <a href="https://www.linkedin.com/in/helenfanlegalai/">LinkedIn</a> | <a href="https://helenfan1.substack.com/">Substack</a> | <a href="https://helenlab.com/">Personal site</a><a href="https://helenfan1.substack.com/p/the-legal-ai-value-stack-five-levels">The Legal AI Value Stack — Five Levels of Defensibility</a> — Helen's now widely-shared framework. Start here if you have not read it yet.<a href="https://helenlab.com/openclawlaw/">The OpenClaw LLP AI-Native Law Firm Experiment</a> — Helen's public 100-day project, documented on LinkedIn and her site.<a href="https://www.youtube.com/watch?v=ZG1Js1LT86I">Helen's Stanford Presentation</a> — A quick video run-through of the talk Helen gave at Stanford a few weeks before this recording. 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 Helen.---For more conversations at the intersection of law and technology, head to<a href="https://lawwhatsnext.substack.com/">⁠⁠⁠⁠⁠ https://lawwhatsnext.substack.com/⁠⁠⁠⁠⁠</a>.

45 total episodes available

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Frequently asked questions

Have a different question and can't find the answer you're looking for? Reach out to our support team by sending us an email and we'll get back to you as soon as we can.

What is Law://WhatsNext?: How are leading practitioners leveraging emerging technologies and ways of working to pursue their passion and objectives, and as a by product what are the implications for the future of legal practice? Let’s explore this together. What to expect:

Focused conversations with leading practitioners; technologists and educators

Deep dives into the intersection of law, technology, and organisational behaviour

Practical analysis and visualisation of how AI is augmenting our potential

Insights from adjacent industries that might inform our own
How often does this podcast release new episodes?: This podcast updates daily.
Where can I listen to this podcast?: This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
Does this podcast accept guests?: No, this podcast does not typically feature guests.

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