𝗪𝗵𝗮𝘁 𝗶𝗳 𝘆𝗼𝘂 𝗰𝗼𝘂𝗹𝗱 𝗳𝗼𝗿𝗺𝗮𝘁 𝗮 𝗹𝗲𝗴𝗮𝗹 𝗱𝗼𝗰𝘂𝗺𝗲𝗻𝘁 𝗷𝘂𝘀𝘁 𝗯𝘆 𝗮𝘀𝗸𝗶𝗻𝗴?

At #ILTACON2026, David Woolstencroft sat down with Chris Cangero, co-founder of DocStyle, who has spent 25 years in legal tech. He grew up with Wang terminals in the family garage, and he and co-founder Adrian Bailey have now bootstrapped the business for almost 17 years.

Their latest launch is DocStyle AI. It connects their mature document tools to the LLM of your choice through an MCP server. The interesting part is how they got there. Their first attempt was to build AI into the product. Three months in, they scrapped it and started over. Now the LLM handles the conversation, and DocStyle's deterministic tools do the precise work.

The result: you can say "style this in our house template and add a table of contents using level one headings only" and it gets done. You don't need to know which button to press. In their internal benchmarks, it's 99.3% more token efficient than using an LLM on its own, and a full paper is coming soon.

Chris's message to firms was clear: don't replace your word processing teams. Free them up for the documents only they can fix, and let lawyers handle the other 80% themselves, even at midnight.

#LegalTech #ILTACON #PeopleInLegal #LegalAI #DocumentAutomation

"There had to be a better way than PowerPoint."

At #ILTACON2026, Tim Kenney sat down with Tim Follett and Neal Chatrath of StructureFlow, and that line is where it all started.

Tim was a corporate lawyer doing private equity fund structuring, building structure charts by hand. So he built a data-driven, AI-enabled platform that turns complex relational information (entities, documents, assets, people) into structure charts, flow charts and timelines automatically.

Neal brings something unusual to a legal tech conference: a career in fintech, across hedge funds and the service providers behind PE funds and investment banks. He's now StructureFlow's first senior hire in North America, based in New York, where most of their revenue already comes from. His job: go deeper with law firms, and build the bridge to their clients. One month in, those clients are already asking their lawyers, "How are you doing this?"

The biggest takeaway? The AI conversation is shifting. It's less about the models and more about the context we give them. "Ontology" was the word of the week, and structured, mapped data is something both a human and a machine can navigate.

Next up for StructureFlow: a graph-based data layer you can point at your document repositories and systems of record. Diagramming is where it started. It's not where it ends.

Thanks Tim and Neal for joining us on People in Legal, and congratulations on the North America expansion.

Is AI finally going to kill the billable hour?

People have been predicting its death for decades. Maurice Tunney thinks this time might actually be different.

David Woolstencroft had a great conversation with Maurice, Director of Technology and Innovation at Keystone Law, about AI, technology and the very different platform model behind Keystone.

Maurice has worked in legal for 25 years and has heard the “death of the billable hour” conversation throughout his career. But with AI now dramatically reducing the time needed for certain types of legal work, his view is that something fundamental has to change. If the time required to do the work is being slashed, can firms really keep charging for time in the same way?

They also talk about Keystone’s unique operating model, building technology around how lawyers actually work, practical AI adoption, and one lawyer who has grown his practice by around 60–70% with AI helping, under close supervision, with drafting, analysis and chronology work.

A fascinating conversation about what AI might really change inside a law firm, beyond simply adding another tool to the tech stack.

Chapters
0:00 Intro
0:31 Meet Maurice
3:46 The 15% Referral Incentive
5:06 The Happiest Law Firm
6:22 Why Lawyers Join
8:14 Building From Scratch In The Cloud
13:00 Choosing The Tech Stack
17:40 The AI Pressure
19:43 Keybot And Secure ChatGPT
23:00 When Clients Use ChatGPT
24:44 The Death Of The Billable Hour
27:42 AI As The Junior
28:45 Picking The Big AI Tools
30:31 Rolling Out AI Without Overload
32:29 A Year From Now

Guest: Maurice Tunney, Director of Technology and Innovation, Keystone Law
Host: David Woolstencroft

People in Legal — where legal leaders and legal technology meet.
https://www.peopleinlegal.com/
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