Practice Technology

How to leverage technology to transform legal writing

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Ari Kaplan

Ari Kaplan. Photo by Lauren Hillary.

Ari Kaplan recently spoke with Ross Guberman, the founder of Legal Writing Pro, which helps attorneys and judges write more effectively, and the developer of BriefCatch, a legal editing software tool.

Ari Kaplan: Tell us about your background and the genesis of BriefCatch.

Ross Guberman: For about 16 years, I mainly had a workshop business, always involving legal writing in its various manifestations. I started with summer associates and new associates in BigLaw firms. Then I developed other types of programs on business development writing, contract drafting and programs for various specialty practices. I have also worked with various judges and courts, which has grown over the years. Around 2016-2017, many people in my workshops started asking about automating writing tips and techniques or having some sort of macro. That is when I began dipping my toes into the legal tech world.

Ari Kaplan: Was there a specific issue or event that inspired you to pursue the development of BriefCatch?

Ross Guberman: People of all experience levels, from law students up to senior partners and judges, wanted to address briefs, contracts or opinions efficiently and in their entirety. They were not really able to do so, which is a problem I wanted to solve. Also, around this time, there were a range of emerging legal tech products, which inspired me to give the development of BriefCatch a shot.

Ari Kaplan: How did you create the rules that BriefCatch relies on?

Ross Guberman headshotRoss Guberman is the founder of Legal Writing Pro, which helps attorneys and judges write more effectively, and the developer of BriefCatch, a legal editing software tool.

Ross Guberman: When you develop software, you have to decide early on what kind of platform you will use and the type of technology to leverage. I learned a natural language processing system to create the rules. At first, it was really impressionistic and random. For instance, I would see something in a brief or remember something from a workshop and then code the rule. Eventually, I had about 3,000 rules when I launched. In subsequent years, I became more systematic and created them in in bunches.

Ari Kaplan: What are the common ways that BriefCatch is helping legal writers?

Ross Guberman: Because the labor cost of writing has decreased, it is just so easy to copy and paste, type and summarize. As a result, people almost paradoxically need another tool, a countervailing tool to push them in the opposite direction. It is much easier to type three or four words that come into your mind than it is to combine them all into a precise, but harder to access, single word. As humans, we need some sort of push, whether manual or technological, to find the sweet spot of tight, well-chosen wording.

Ari Kaplan: How does a tool like BriefCatch reflect the broad application of technology in the legal profession today?

Ross Guberman: There has been this war of sorts between efficiency and quality because many lawyers operating under time pressure also need to produce the best possible work product. BriefCatch makes those two things work in tandem because the technology can scan an entire document and apply 12,000 rules to it in just a few seconds. This allows people to spend less time editing and yet have more control over quality. It is the kind of technology people appreciate these days since it makes time less of an enemy. In fact, you end up spending much less time while still creating a superior product.

Ari Kaplan: Have you seen a change in the quality of writing in legal?

Ross Guberman: Yes. You see a lot more of what I would call passive writing, not passive voice. There is a lot of copying, long quoting, adapting models and summarizing. They are very tempting when you’re facing pressure, but they rarely lead to the kind of product you really want to be producing. We need something to take us away from this work and prompt us to incorporate a little bit more thought and careful intent before the words get on the screen.

Ari Kaplan: Where should legal professionals focus their writing, ideas, structure, grammar and creativity?

Ross Guberman: One thing I have found that will really help a lot of people trying to improve their process and make it more enjoyable is to build in a moment early on after finishing their fact gathering or legal research to consider what you have learned and begin to type all of the things going on in your head and turn them into coherent points. You seldom want to jump from the research- or fact-gathering phase to a stream-of-consciousness writing effort. Instead, challenge yourself to begin with a content-based structure.

Ari Kaplan: How do you see legal drafting evolving?

Ross Guberman: It will be fascinating with the excitement around automation and AI in contracts. I would imagine it will become incredibly easy to gather high-quality building blocks in agreements, such as key provisions, or standard language for balancing tests in litigation, resulting in more consistency and higher quality. What will be a challenge will be tailoring language to a specific transaction or dispute. In an ideal world, technology will free legal professionals from the more tedious parts of writing in favor of more productive thinking and strategizing on content. There is a lot of excitement now about marrying different parts of a lawyer’s skill set that are currently seen as separate, such as a writing and editing product married to a legal research tool. Combined with a document automation product, all create an exciting workflow that allows you perform discrete steps simultaneously.

Listen to the complete interview at Reinventing Professionals.

Ari Kaplan regularly interviews leaders in the legal industry and in the broader professional services community to share perspective, highlight transformative change and introduce new technology at his blog and on iTunes.

This column reflects the opinions of the author and not necessarily the views of the ABA Journal—or the American Bar Association.

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