AI-Native Hiring and Organisational Alignment

A quick reminder: Law://WhatsNext is our vehicle to explore through dialogue (or occasional reflection) how leading lawyers, educators and technologists are using emerging tech to evolve how we practice and administer legal services. No hype — just practical conversations. Hi Friends 👋 🎙️ This week we sit down with Stephanie Dominy — General Counsel and Head of Ops at Tessl for a conversation that begins with a deceptively simple question: Stephanie has practised law for nearly three decades, but her remit at Tessl runs well beyond legal risk: as Head of Ops she hires across the whole organisation, including against one of Tessl’s 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?“ which provokes a deeper introspection 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, and we learn why Tessl keeps iterating on how it hires most recently reverse-engineering its interviews (inspired by Sierra’s AI-native interview framework). From there we grapple with cognitive surrender, the commoditisation of knowledge, legal training pathways, and Stephanie’s observation on the rising significance of those with humanities backgrounds and why they’re frequently better equipped to interrogate AI than purely data-driven minds. If we’re all still working out how to assess and develop AI-native skills at the individual level, Tom is equally sceptical of organisational efforts to adopt this powerful technology. He points to Claude’s Constitution: the document Anthropic uses to steer a probabilistic model through competing demands via a clear order of precedence and argues it is: Not so different from a legal constitution; and A surprisingly useful mirror for any company trying to go AI-native. It’s a humbling exercise, he suggests, to work out where you sit as an organisation in the “model stack,” so everyone understands their real influence over what the system produces. Every organisation is made up of teams with competing priorities, so Tom believes you have to be deliberate about where to go all-in: if everyone is going to be amplified, decide consciously what each team should optimise for, and debate the abundance-versus-scarcity question of internal deployment honestly. Listen Now Available here or on Spotify, Apple Podcasts, or wherever you enjoy your podcasts. His tangible example: the overzealous sales team optimising for deals while legal supercharges its risk-prevention programme. Today those incentives collide only now and then, and human leaders usually resolve them. But as each team is amplified and accelerated by AI, the collisions become more frequent and their resolution is being quietly outsourced to AI to resolve (piling competing instructions onto a model that ultimately impede and degrade its performance). Tom argues that Legal sits in a unique vantage point: work flows to it, it operates bilaterally across the business, and it is unusually well placed to see the friction coming - and therefore well placed to provoke the conversation nobody else is having 👀 Crafty Fest: See This Conversation Live 🎪 Tom and Stephanie are taking this one to the stage — Wednesday 3 June 2026, at Crafty Fest, Regent’s University London. Crafty Fest is Europe’s largest festival for the in-house legal community, and their session picks up exactly where this episode leaves off. Connect with Stephanie Dominy — General Counsel & Head of Ops at Tessl 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. 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 (and Stephanie) want to hear it. Bring it to Crafty Fest, or drop it in the comments 👇 We hope you have a great week and we hope to see you tomorrow in London! Tom & Alex Thanks for reading Law://WhatsNext! This post is public so feel free to share it. Share