Li spoke on the CL Talk podcast about lessons learned from piloting tech tools and managing change
AI is pushing law firms to rethink how they operate, and the legal sector’s next leap forward will come from those who are prepared to adapt, says Derrick Li, chief operating officer at Lawson Lundell. “Winter is coming,” he says, quoting Game of Thrones to capture the urgency and anxiety that artificial intelligence brings to the legal industry. “We as a legal industry need to be prepared.”
Li’s perspective is shaped by a career that began in external auditing, moved through management consulting during the Sarbanes-Oxley era, and led to roles as chief internal auditor, CFO, and now COO. “I realized I really strive or enjoy the world of grey rather than black and white.” The transition from a public sector organization with thousands of employees to a 500-person law firm gave him the chance to make decisions faster and focus on what he calls “running a business,” while letting lawyers “do what they do best, which is lawyering.”
For Li, every technology investment, especially in AI, must serve two goals: supporting lawyers and delivering for clients. “We invest a lot of our time and resources to ensure that our lawyers are equipped with the best fit-for-purpose technologies, including AI, to ultimately solve our clients' problems as effectively and efficiently as possible,” he says. He likens his role to Alfred in Batman, equipping heroes with the right tools: “When Gotham City shines the bat signal, Batman is called to action. And my favourite part is always when Alfred equips Batman with the coolest technologies to help Batman ultimately save Gotham City. So, when we apply this concept of Batman at Lawson Lundell, our clients signal that they need help, our lawyers immediately respond to action, and our back office functions are ready to equip our lawyers with the latest technology and tools,” he says.
Li’s approach to AI at Lawson Lundell is systematic and relentless. “Not surprisingly, AI has been a recurring topic at our firm's strategic planning sessions…” He spearheaded the formation of an AI governance committee and a multi-year AI strategy. The firm benchmarks against other large law firms and the Big Four accounting firms, encourages staff to suggest products to pilot, and takes a phased approach to evaluating what he calls the “mega foundational AI solutions, or the big dogs.” The firm is currently piloting Thomson Reuters Co-Counsel and Microsoft Copilot, narrowing down options through use-case demos and internal expertise. “A lot of the technologies don't necessarily integrate in a seamless way with our existing infrastructure, like our document management system. So I work daily with our internal team... and we've got many exciting developments in our pipeline,” he says.
Negotiating with AI vendors has revealed a landscape in flux. “One of the challenges that I saw, at least even as far as last year, was that these large companies... they're investing significant R&D dollars. So they're wanting to recuperate that cost. … In the legal world, they have models that you have to pay for subscriptions for your whole firm, whether your lawyers use it or not…” Li pushes for subscription models that reflect actual usage, arguing, “If your product works well, people are going to use it and you'll … gain entry that way.” He notes a shift this year, with vendors seeking strategic relationships as adoption lags. “The legal industry has said that the technology isn't where it needs to be. Do I think it'll get there? Yes, but today it's not so,” he says.
Driving AI adoption inside the firm is as much about change management as it is about technology. “We're really trying to go back to the basics…” Li says, pointing to lessons learned from a previous management system rollout. The firm’s “AI Central” intranet portal, micro sites, and newsletters are designed to cut through the noise and deliver what staff need. “We've got weekly surveys, [where] we are really trying to promote when people have success stories... It's really a balancing [act], because the amount of information that goes with a firm, you're always balancing noise versus what they really need to know about,” he says.
Li’s finance background drives his focus on data. “Business analytics is something that's near and dear for me…” The firm mines data from across the lawyer lifecycle to build dashboards for partners and clients. “We have a concept called the ‘easy button,’ where you press the button and it can generate emails to your clients... [or] outstanding invoices in the click of a button…” he says. The next step is integrating large language models and machine learning to drive better decisions, combining external data from Statistics Canada with internal firm data.
Li has direct advice for firms starting their AI journey: “You have to decide… where do you want to play in the sand?” Firms must choose whether to be early adopters, wait-and-see followers, or ignore the trend entirely. For Lawson Lundell, the aim is to stay ahead of client needs without getting swept up in hype. “There is a hype curve in the AI…” Li warns, noting that flashy demos can exaggerate what AI can deliver. Ultimately, it’s a business decision – firms must weigh real benefits against costs.
Looking ahead, Li sees AI’s biggest impact coming from document analysis and integration with legal databases. The idea of simply dropping a document into a tool and asking it questions is close, but not quite a reality yet. The key risks? Accuracy and trust. “It is a credibility and trust business…” he emphasizes. That’s why Lawson Lundell is developing policies to ensure junior lawyers always double-check AI outputs. “You’re saving time on non-value tasks, but you must ensure the output is accurate and reliable – because clients rely on us.”
This conversation can also be found here:
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