Law://WhatsNext

🎙️ 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.
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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 environment
What'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 take
The 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 materials
Why Building Makes You Better at Everything Else — From vendor negotiations to IT collaboration, how technical fluency transforms your effectiveness as in-house counsel
How to Get Started — Artur's practical advice: a Claude subscription, Google Antigravity, and the willingness to ask "how do I do this?"
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Connect with Artur: LinkedIn | Github
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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 layers
What Actually Drives Adoption — Survey data revealing that lawyers prioritise context management and verification over raw accuracy when choosing AI tools
Where Humans Still Win — High-judgment, context-sparse tasks requiring commercial reasoning remain firmly in human territory; routine, context-complete work is where AI excels
Prompt Injection in Practice — Live demonstrations of how attackers can trick AI models into revealing harmful information using low-resource languages and clever framing
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Connect with Anna: LinkedIn | LegalBenchmarks.ai
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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 matters
Where 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 apart
Connect 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 educators
Deep dives into the intersection of law, technology, and organisational behaviour
Practical 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/
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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 & trust
Dana 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 times
Jessica 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 working
Sigge 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 lose
Dan 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.