Ross Guberman, Founder and CEO of BriefCatch – Interview Series

Ross Guberman, Founder and CEO of BriefCatch, is a leading authority on legal writing with more than two decades of experience training lawyers, judges, government agencies, corporations, and professional organizations. A former practicing attorney, he has conducted thousands of legal-writing workshops across three continents and has spent nearly a decade training new federal judges on opinion writing. Guberman holds degrees from Yale University, the Sorbonne, and the University of Chicago Law School and is the author of Point Made: How to Write Like the Nation’s Top Advocates and Point Taken: How to Write Like the World’s Best Judges, as well as co-author of Deal Struck. His contributions to legal writing and innovation have earned him recognition including the Legal Writing Institute’s Golden Pen Award and a place on the Fastcase 50.

BriefCatch is a legal writing and editing platform designed to help lawyers produce clearer, more precise, and more persuasive documents. Built on Guberman’s decades of research into effective legal writing, the platform works within Microsoft Word and uses AI and natural language processing to provide real-time editing suggestions, writing analytics, and guidance tailored specifically to legal professionals. BriefCatch is used by law firms, judges, courts, and government agencies and is designed to improve documents such as briefs, motions, opinions, memos, and contracts while also serving as an ongoing writing-development tool for attorneys.

You founded BriefCatch in 2018 after years of teaching legal writing to lawyers, judges, and law firms. What problems did you repeatedly see in legal writing that convinced you software could help, and how has that original vision evolved as AI has entered the profession?

I kept seeing the same problems: sentences that pile on multiple introductory phrases, repetitive verbs and sentence patterns, and long quotations treated as self-explanatory. These habits are common in the work product of experienced lawyers, too. Under client and deadline pressure, even the best writers crave specific suggestions, not more mantras about being “clear and concise.”

In the one-off workshops that were my bread and butter, I shared tips, tricks, and techniques drawn from the work of the greatest legal writers. The lawyers and judges who attended seemed enthusiastic and even inspired, but then real life intervened. With the right software, I thought, I could offer similar help at any moment, day or night. The next thing I knew, I was an accidental founder of a start-up that turned thousands of patterns in legal writing into explainable (and codable) edits and examples.

GenAI has been an earthquake for my life’s work. It can generate seductively polished first drafts. More ominously, it can make a weak argument sound airtight before anyone has tested whether it holds up, fooling even the most astute readers. But harnessed in the right tools and workflows, GenAI can be a godsend for enhancing legal prose, verifying accuracy and integrity, and poking holes in arguments and analyses, whether a person or a machine wrote them.

BriefCatch is now being reintroduced as a unified legal writing suite rather than primarily an editing tool. What drove this evolution, and how much of it was a response to the rapid adoption of generative AI in legal workflows?

Generative AI sped things up, but these tools belonged together all along, no matter who, or what, writes the first draft.

Lawyers need to ask three related questions: Have I made my points well? Do the authorities support the argument? What can I learn from this draft for the next one? BriefCatch, CiteCheck, RealityCheck, and the Learning Hub are built to answer them. A sentence can carry a good argument but make the reader work too hard. Or it can sing off the page but lack support.

Access matters, too. Although much of my career has been spent serving the world’s biggest firms, I would love for solo practitioners to benefit from the same writing guidance and verification tools that Am Law 200 firms do. The idea is to make scrutiny and learning part of a lawyer’s everyday work instead of something you get once a year at a training workshop.

Generative AI can dramatically accelerate the first draft of a legal document, but BriefCatch is increasingly focused on what happens after that draft is created. Do you believe verification and quality control will ultimately become more important than generation itself in legal AI?

Yes. I expect the lion’s share of legal AI’s value to come from refining, verifying, and deepening existing drafts. Writing faster is appealing, but it doesn’t help you discern which arguments will resonate, which authorities support them, or which sentences make logical leaps.

The hard part remains: how do you tell when a polished paragraph laden with citations is a house of cards?

RealityCheck goes beyond determining whether a case or citation exists by assessing whether the authority actually s