Matthew has spent more than 25 years advising high-net-worth individuals and families on complex estate and wealth transfer planning, as well as charitable giving, and he continues to serve as outside General Counsel to the St. Louis Community Foundation alongside his leadership role. Inside his own firm, Matthew carries a specific title: Harrison LLP's top power user of Legora. 

What follows is Matthew's account of the bet he made on AI, what being a power user actually requires, and how he's turned his own habits into a firm-wide strategy.

Making innovation the centerpiece of firm strategy

Innovation is a defining pillar of Harrison LLP’s direction, with AI emerging as one of its clearest expressions. “I remember when an associate told me about ChatGPT and I thought, 'This is going to change everything,'” Matthew says. 

Championing AI as managing partner meant owning the uncertainty it created. “An associate asked me, after hearing us talk about Legora, 'Is my job okay?'” Matthew recalls. His answer set the tone for how the firm would think about AI going forward: “If you're spending less time on routine work and more time in the meeting with the client, finding out why she's so passionate about how she wants to leave her legacy, that's more value for everybody.”

Getting the rest of the firm on board took care. It started small, a beta test group that met periodically to trade tips and figure out what was actually working. “That group has since become our broader Legora users group,” Matthew says, “so the knowledge-sharing culture that developed early carried over into how we operate now.”

The other piece is a nomination process: Legora users at the firm periodically identify a peer they think would genuinely benefit from the tool. “The thinking behind it is that seeing a colleague you respect use something effectively tends to move people more than any top-down push,” Matthew explains.

What makes a Legora power user

“I have great fun with Legora,” Matthew says. He explains how it isn't a tool he opens for a task and closes when it's done; it runs alongside everything he does. He uses it as an active thinking partner — for research, outlining, drafting, and testing arguments — not as a shortcut, but as a way to move faster toward stronger work.

“The moments where I've felt the biggest impact have been in document-heavy situations where volume itself is the enemy,” Matthew says. “When you're reviewing twenty years of trust administration records, or trying to understand how a complex business interest interacts with a long-standing estate plan, everything is findable, eventually. The question is how long it takes, and what that costs.”

“Getting there takes time no one can afford to waste,” he says. “Legora has surfaced things that I then confirmed were worth pursuing. In this work, that time doesn't disappear. It goes right back into the analysis that shapes the outcome.”

“It's also great for client meetings,” he says, where the real advantage isn't preparation but responsiveness. “It just creates a much better experience. With Legora, you can check in real time and you have the answer.”

Where judgment and Legora meet

Matthew is careful to draw a line between the technology and the judgment that directs it. He stresses how private client work carries a heavy psychological and behavioral component. It’s as much about figuring out what a client actually wants, and sometimes helping them work that out for themselves, as it is about the law itself. 

“What you have to know is human psychology, behavioral economics, and how to be a counselor,” he says. “You have to know how to think. You have to know how to be creative in solving problems. If you're not learning those things, you're going to struggle practicing law.”

The difficulty compounds with scale. “A single family might have business interests in three states, a foreign spouse, a charitable foundation, kids with very different relationships to money, and a trust drafted ten years before any of that existed,” Matthew says. “And ten years is forever. The amount of wealth changes. The types of assets change. The goals and values evolve. The humans these plans are built to protect and benefit evolve. The plan was right when it was written. The world just kept moving, and these families kept evolving with it.”

“Legora has been quite valuable to me in those situations. When I'm working through a dense file, what I need isn't just to surface basic structural issues for confirmation. I need to probe for the interconnected layers that may no longer match present circumstances, the current goals, the current values, the current asset mix. It helps me do that faster and more systematically. The entire review of that material is guided by my judgment and by what I've learned working with these families over many years. Legora just makes sure I'm covering the ground I need to cover.”

That judgment doesn't arrive on day one, which is why Matthew has taken a fairly unique approach to when AI is introduced to the firm’s lawyers. “We don't have associates using AI for the first three years. They do the work on their own first,” Matthew says. “Writing is thinking. The process of taking something complex and expressing it in a way a client can actually understand isn't a side skill you pick up later. It's central to how you develop as a lawyer, and it takes real repetition. Law school teaches you to write for professors and examiners, which is a different thing entirely. We worry that if you skip that early struggle, you lose something that's hard to get back.”

What comes next for the profession

“The thing I'm most interested in is what happens when AI is good enough to help us do the work we've always wanted to do but couldn't justify the hours for,” Matthew says. Private client lawyers, he argues, are often caught up in the details, too busy with the infrastructure. “Many of us turn down long-term trust administration roles, for example, not because we don't know how or shouldn't be in it, but because we're so busy with everything else,” he says.

“The constraint has never been expertise. It's hours,” he says. “AI gives us those hours back, and when it does, that's not a marginal improvement. That's a real expansion of what we can deliver for families. And I think that's going to be true for every law firm in America.”

Matthew has also noticed the shift on the client side of the table. “It used to be once or twice a year you'd hear 'AI said this,'” he says. “Now it's every single day. And you can tell when clients have put your own documents into their own AI: they're asking much more targeted, sophisticated questions. They got their basic questions answered before the meeting, and now we're having much more productive conversations. I always think: more value, less time,” he says. “How is that not a win for everybody?”

When asked about what’s next, Matthew says: “The older I get, and the more experience I accumulate, the more I find myself thinking there is just so much I still don't know. That's always been true in this work. But it's especially true with AI, which is moving faster than any of us can fully track. We're trying hard to stay humble about it and treat everything as iterative. We're learning as we go, same as everyone else.”

That combination, moving early and decisively, then staying honest about what's still unknown, is what's shaped Matthew's approach to AI at every stage: the early bet he made on it, the policy he built around it, and the discipline he brings as a power user.