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Adam D.H. Chisholm and Robert Shore on using AI to sharpen legal thinking

Adam D.H. Chisholm and Robert Shore on using AI to sharpen legal thinking

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Adam D.H. Chisholm and Robert Shore bring perspectives from very different areas of law at McMillan LLP. Adam is a partner in Litigation & Dispute Resolution, focused on high-stakes disputes across capital markets, intellectual property, and administrative law. Robert is a partner in Commercial Real Estate, advising developers on complex, data-heavy projects that shape cities.

Their work sits in different parts of the legal landscape, but their approach is closely aligned. Both are drawn to complexity and problem-solving, and both are helping shape how McMillan embeds AI into legal practice through the firm’s purpose-built AI committee.

How AI enhances both litigation precision and real-time transactions

For both Adam and Robert, AI is deeply woven into the fabric of their teams’ day-to-day work.

In Robert’s practice, the impact is shaped by scale and complexity. Transactions involve large volumes of information, multiple stakeholders, and constantly shifting inputs. AI provides a way to navigate that. “We’ve been able to speed up our operations dramatically,” he says. “AI has given us the bandwidth and the tools to keep the client more tightly in the loop in real time, so they can understand what’s going on with much better granularity.”



“It gives you a kind of extreme visibility on complicated transactions,” he says. “You can bring in all of the information, navigate it, and then pull it back to the client in a way that is very clear.”

It also connects to what drew Robert into law in the first place: “It’s always been about the people. And the transparency afforded through AI means that we’re able to effectively improve relationships with clients. It’s improving the way people work together.”

That clarity is tied to how Robert defines the role of a lawyer. “Lawyers are hired to deliver an outcome,” he says. “AI is a way to improve the service of delivering those outcomes.”

In litigation, Adam has seen a shift play out over time. “Going into a hearing, you would have summaries of every transcript to sift through. Now, with AI, you can query the documents at issue, find what you need on the spot a lot faster and with more precision.”


“It’s changing everything that I do to some extent,” he says. “There isn’t a single day that I’m not using Legora for something. It makes the work I do more efficient and higher in calibre and output.”

Adam also shares how AI supports drafting: “Before I deliver any substantial piece of legal writing, I can ask Legora to do a sort of gap analysis and identify any issues that might exist. It helps me create a better product.”

“But more important than how technology has affected my own work is how I see it changing the work around us,” Adam says. “I see AI as empowering all of our team members to enhance their training, development, and success.”

That team dynamic is central in litigation. “Most meaningful litigation is a team sport,” he says. “It’s really interesting to think about how technology facilitates and helps improve the products of those teams and how we can use it collectively to strengthen our teams.”

It’s also where their shared thinking comes through. “Even though we have very different practices, that’s something that Robert and I spend a lot of time talking about,” Adam says, “how to improve our teams and our group’s abilities using new technology.”

The lean AI Committee driving firm-wide adoption

To achieve this, McMillan’s AI Committee brings together Management, Innovation, Technology and a small number of partners from different practice areas, each responsible for significant client work. It meets weekly to focus on the firm’s AI strategy, including identifying areas of the business where AI can drive meaningful transformation, as well as how AI is used across the firm, how training is delivered, and how new capabilities are introduced into existing workflows.

“Everyone on the firm’s committee is really passionate about leading in the Canadian market in how we approach this,” Adam explains. The structure of the committee has been designed with this in mind: “We’re small in number, which is important for us to be able to be nimble enough to get things done.”

Robert elaborates: “We very deliberately designed it to include key leadership from legal, business and operational sides of the firm. The idea was to include three lawyers with significant practices, who are also very AI-forward, understand the technology and its potential, and have perspectives of where it goes — Adam in disputes, me as transactional, and Mark Opashinov with an advisory practice. What makes the Committee effective is that it's truly cross-functional: we have the leaders in the room who can shape strategy, understand how it lands in practice, and move ahead quickly to operationalize the concepts. That setup is the secret sauce of this committee.”

Adam explains how the connection to practice keeps the work focused on outcomes: “At the end of the day, we’re accountable to our clients. They’re the lifeblood of our business. We need to know that this is valuable for them.”

Access to the technology is equally important to their approach; the aim is to ensure Legora is available across the firm so that improvements in quality and efficiency are widely felt. “As the first national Canadian law firm to enter into a flagship partnership with Legora, we wanted to make sure the technology is available to all legal and business professionals at our firm,” Adam says. “We really want to give everybody the opportunity to deliver their best outputs to clients.”

How AI is reshaping how junior lawyers learn, reason, and contribute

Both Adam and Robert see AI as shaping how lawyers develop from the start of their careers; it influences how they learn, how they approach problems, and how quickly they build confidence.

“I wish that I had this technology when I was a junior,” Robert says. “They’re able to take a wealth of information from all the senior people around them. They can ask Legora about it. They can test ideas. They can guide themselves through their own learning pathways.”

This changes the level at which they engage with the law. “The juniors that are deploying it best are acting like a lawyer who’s been practicing for four years after only two,” Robert says. “Using AI, they can come to senior lawyers with questions that are already so far advanced.”

Adam expands on this, and touches on how access goes hand-in-hand with discernment. “I want our junior lawyers to have the courage to be critical of outputs that they get from all technology,” he says. “I want to see them developing the confidence to know the right questions to ask and the right answers to provide.

“The junior lawyer who would be glad to put a prompt into a chatbot and get an answer and forward that around isn’t going to have the same success as the one who’s thoughtful from the beginning, and then thoughtful about what comes back. I want them to apply their legal reasoning before they provide it to a client or before they provide it to me,” he says. “That’s where they add value.”

Robert points to a simple but powerful exercise to support this. After forming a view, he encourages his team to ask AI to take the opposite position and generate the strongest possible counterarguments, effectively using the technology “as a kind of sparring partner,” he says, “by asking it to question your assumptions, your arguments, and to iterate.” 

This process forces a deeper level of scrutiny, exposing weaknesses, sharpening reasoning, and strengthening the final output. It becomes a way of pressure-testing legal thinking before it reaches a client.

In that sense, AI becomes part of how lawyers develop their reasoning, not just how they produce work. “It’s like going to the gym for our minds,” Robert explains. “We now have the ability to do a mental workout in a way we’ve never been able to before.  Juniors can use AI to become better thinkers, to fortify their arguments, and make themselves sharper.”

Fostering a culture of flexibility, curiosity, and enthusiasm

Alongside this drive to sharpen thinking, adaptability becomes essential. “The tools that we’re offering today may not be the tools we’re offering a year from now,” Adam adds. “We need people who are not going to be rigid in their view of what skills are important. There’s a lot of opportunities to not only continue to improve McMillan’s practices but client practices too.”

Part of that is how AI is beginning to extend into shared client workflows. Legora’s Portal, for example, will allow lawyers and clients to work from the same environment, interacting with documents, data, and outputs in real time. 

Robert adds: “If you think broadly about it, there’s only opportunity for improving what we do for clients,” he says. “It’s so exciting to see the way the profession is going to evolve.” That shift is already showing up in practice, in the visibility he described earlier, in the way clients are kept informed, and in how transactions move. “It’s going to be a more comfortable process, more transparent,” he says. “And it’s going to lead to other possibilities that we haven’t even discovered yet.”

“We’re excited about improving our practice and supporting our clients,” Adam says. “Without enthusiasm, it all dies on a vine.”

Curiosity and open-mindedness at the center of AI’s future in law

From how they use AI in their own work to how they’ve structured it across the firm and introduced it to junior lawyers, the same theme runs through: a shift in how lawyers approach problems and develop their thinking.

Adam grounds this in what initially led him to law. Coming from a science background, he was drawn to work that offered more dynamic challenges. “Open-mindedness and curiosity are what led me to litigation in the first place,” he says. 

“It turned out that litigation offered the sort of problem solving and engagement that I was looking for,” Adam explains. “Every new case is a problem to be solved. It’s really interesting to be presented with a problem and to implement a strategic vision to help solve it.” 

That same mindset shapes how he engages with AI, using it as a tool to challenge and improve his work: “We can all use AI to get better every day. Robert and I can get better every day, and so can the people we work with, and the outcomes we provide to our clients.”

“Open-mindedness has always been the hallmark of the best lawyers I work with,” Robert agrees. “When you have an open mind, possibilities are endless.” 

“The mindset of using AI to challenge yourself and improve your work is part and parcel of being a curious and ever-improving professional,” Adam says. “AI helps you do that, if you want it to. If you’re open to it.”

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