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Holland & Knight Partner Manfred Gabriel on Making a Fortress Dance

Liz Roegner

Getting change-averse legal teams to embrace new tech with enthusiasm is, according to AI Visionary Manfred Gabriel, like “asking a fortress to dance.” But it can be done—and he would know. Read on for his insights on how to help your firm see the opportunities and benefits presented by tech-forward solutions to modern challenges in the practice of law.

The legal sector has a reputation for being slow to embrace new technologies, but you stand out as an early explorer of AI. What are some of the structural barriers that keep law firms from adopting new technologies? How and why did you take an interest in AI?

The fundamental structural challenge is the legal profession itself, which is designed to produce stability and predictability in how society is organized. Asking lawyers to innovate rapidly is like asking a fortress to dance.

On the other hand, the best lawyers respond to client needs, and those evolve rapidly as the world changes. The most significant change in our lifetimes is the digital revolution and proliferation of electronically stored information. This has created a dynamic wherein the legal profession looks backward but moves forward, pulled by their clients’ needs.

There has been much exploration into the structure of the legal profession (which limits competition among lawyers), the role of the billable hour and the partnership model, and the traditional approach to how we train lawyers. Ultimately, though, all these conditions mean that innovation in the legal profession tends to be slow until there is a significant financial difference to clients, who then drive the process forward.

As a result, innovation happens in the fringe cases. In fact, that is how I got started leveraging AI (or machine learning, to be more precise): in extremely large, rushed antitrust matters where both the financial pressure and time pressure were enormous.

Can you share any lessons on how legal leaders can drive the adoption of new technologies, such as AI, inside law firms?

The only way to innovate inside the law firm is to find the pain and address it—no pain, no change. Law firms who are more financially sophisticated have an advantage because they are more likely to resist the temptation to hide the pain by leveraging cross-subsidies within the firm.

The only way to innovate inside the law firm is to find the pain and address it—no pain, no change.

Technical innovators should become financially literate enough to have this conversation with firm leadership. Speaking to long-term economic benefits can certainly help have an impact.

Over the course of your career, what are your wins that you are most proud of, and why?

I am proudest of having worked with amazing and talented people. That’s really all the job satisfaction I need. I am next proudest of the role I played in building a machine-learning driven document review business, including the conceptual framework I developed for managing and understanding large volumes of unstructured data. We translated that down to specific workflow design and business models.

What were your interests early on and what drew you to the practice of law?

I have always been fascinated by the nature of the law and its connection to language; I see the law as an attempt to organize and manage human society and behavior through the use of language (rather than violence).

As lawyers, we often focus on how specific rules break down or how behavior deviates from norms, and lose sight of the fundamental role law plays in organizing a society as free, open, and innovative (or unfortunately, the opposite). My interest in technology came later.

What do you do when you are not working? How do you decompress?

I love to bake bread (and was baking long before the pandemic), spend time outdoors, and play board games. But my interests change over time; I used to spend all my free time playing music, for example. I look forward to finding and exploring new interests over time. There is so much to see and learn in the world.

Which person (living or deceased) do you most admire?

There are many people who inspire and guide me. At the top of the list is my spouse, Christina: I have learned more from her than anyone, and I am delighted to be her partner. On the legal side, I most admire Anselm v. Feuerbach, Ruth Bader Ginsberg, and Bryan Garner.

Which historical figure do you most identify with?

I don’t identify with a historical figure in the sense that I want to be like them or compare myself to them. The historical figure I have been most fascinated by is Gaius Julius Caesar—who, among other things, was a brilliant lawyer and reformer.

What do you consider the most underrated quality or skill?

Synthesis—in the sense of analyzing the world around us at a higher level of abstraction that permits us bring in different concepts and experiences. I admire people who can see through the ripples of the immediate problem to discern the currents underneath, and thereby help me understand the world.


Liz Roegner is an account executive at Relativity. Before joining Relativity, she was a practicing attorney with Choate Hall & Stewart LLP in Boston, where she focused on commercial litigation, government investigations, and insurance/reinsurance arbitration.

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