Recently the Consultwebs legal marketing podcast, LAWsome, met up with Ross Guberman, legal writing scholar and creator of the legal composition and editing software, BriefCatch, to discuss legal writing, legal tech, and a few tips lawyers can use right now to improve the clarity of their legal writing.

We hope you enjoy this sample of the interview and you can listen to the full episode on The LAWsome Podcast website.

Jake: So Legal Writing Pro, BriefCatch, explain what it is, why you made it, and what the response has been from the community of your users?

Ross: So Legal Writing Pro came first. BriefCatch was much later in the story and the Legal Writing Pro grew a little bit organically and a little slowly when I decided to venture out into the law firm in general, legal education world. So Legal Writing Pro is sort of a holding company, you might call it for workshops that I’ve done for various audiences, mainly lawyers, sometimes judges, sometimes business people.

And I also have some e-learning products, and coaching products, and assessment products, too, and books, and toolkits, and manuals, and some online tools. And then much more recently, I launched BriefCatch and got into the software and add-on world as you mentioned. And that’s been something that’s been…I’ve been passionate about for the last few years, but it launched just a year ago. So I’m doing a lot more of a software now and a little bit less with all the live workshops and other formal training modes.

Jake: Nice. And so, BriefCatch came out of your work on doing consulting because… Did you feel like you just wanted to be right over their shoulder, or what is that add-on kind of thought? Because I don’t think a lot of people consider it as an option, you know.

Ross: Yeah. I think that spontaneous laughter with right over their shoulder was apt. I don’t wanna be too controlling, right, or creepy, or trying micromanage people [inaudible 00:01:43]. It’s pretty much that, though, I’d say maybe a little bit the other way around, in the sense that a lot of people who have followed me, attended my workshops, read my books, or all three, had said to me in different forms in different venues that they really wish there was some way to have a lot of the things that I teach or talk about automated, both to save time but also to help make them sink in a little bit and make them, you know, part of the lawyer or judge’s workflow. So I can’t I can’t even really take credit for the idea. It was really more something from my followers.

Jake: That’s [inaudible 00:02:22]… Well, but that makes sense that you listen to your audience and created something that they were asking for, rather than coming up with, you know, an inflatable…what? I don’t know.

Ross: No, that’s right. It’s also, it’s intimidating to get started with software. It’s obviously much easier to throw together a live workshop and, you know, try it out at our firm. Software really, really has a long, long ramp before you can really feel like you’re even getting going.

Jake: Oh, of course. And so, you said it just launched this year. So what has the response been from people who are using BriefCatch?

Ross: You know, really, honestly, beyond anything that I could have hoped for. You know, so far it’s been out for just really a month, a month and a year. I guess this is month 13 here, February 2019. So obviously, I was nervous when it first launched, and I wasn’t quite sure what to expect. And I had to wait and see what the actual response to the substantive part of the product itself would be. But I have a lot of different types of users ranging from, you know, college students up to Supreme Court justices, and managing partners, or firms, and really everybody in between.

So that part has been really rewarding. And I have a lot of people who kind of communicate with each other about BriefCatch because it has a scoring system or post on social media about it, so that’s been enjoyable, too. And of course, I have a lot of goals for enhancing the product. So I’m not anywhere near being done, but really, so far, so good. I’m very grateful.

Jake: Explain to us this disconnect between legal education and legal experience when it comes to drafting and crafting these documents. How are schools getting it right and maybe how can they step up their game, and is there a place in there for BriefCatch to sort of work its magic?

Ross: Well, I can address the last part, by the away, because it’s timely. Because in the last couple of weeks, several law schools actually have bought BriefCatch for the entire student body and faculty. So, I mean, I think that’s a good idea, even though I’m obviously biased. But to go to your more, you know, in your core question, I’ve grown to have a lot of sympathy for the legal writing professors of America, and I actually did teach the class once. And I taught an upper level class many years after that.

So I also understand a little bit what kinds of pressures they’re on. So they become sort of punching bags for this, you know, this alleged gap between graduating law students skills and what lawyers need in practice. And I don’t think much… A lot of the criticism is fair because they can’t be held responsible for every single thing that one might not have going into law school and everything from writing rhetoric to oral communication, interviewing skills, and the like. So it’s easy, it is tempting to try to blame them, but again, for some reason, nobody blames the doctrinal professors, or even the clinics, or the deans, or anybody else. They seem to take it all out on the legal writing teachers.

So that’s sort of my sympathy, and it’s very genuine, and I feel it very strongly. On the other hand, I’ve noticed, especially in the last seven or eight years, that the legal writing courses have started becoming a little bit more nebulous in their focus. And they are seeking to not just teach writing, or maybe not even teach writing primarily, but become vehicles for discussing theories of rhetoric and client communication skills. And all that is great, but the truth is I can tell you for sure, with certainty, and a lot of experience, that law students today need a lot more writing training, not less.

And the idea that writing would just be sort of a part or maybe even a major part of one class, I think is really not that sensible given what employers are demanding and frankly very often complaining about. So obviously, there are ways to address this in upper level classes, having more creative or innovative writing base classes, maybe doing more with clinics. But really there’s only so much law schools can be expected to do especially when it comes to core writing skills that frankly don’t have that much to do with legal writing or legal documents themselves.

Jake: It’s interesting because you must have this deep admiration and respect for words. I mean, the way you are on Twitter is so amazing, whereas I think a lot of lawyers hate word. They’re hating the little dangling modifiers and the isms, and the Santa Clauses. Can you kind of riff on how you keep your relationship fresh with words? Because I think a lot of lawyers are, like, “Ah, I have to read. I have to write. It sucks.” But if you really love words, you love reading and writing. And, you know, I just kinda, you have a passion. And I just kinda want you to translate a little bit of that, how you keep it fresh because just riff on that, could you?

Ross: Yeah. That’s a fascinating line of inquiry. So, you know, I live in Washington DC, or in the suburbs. So I’m obviously surrounded by lawyers, and I noticed that sometimes you ask a lawyer, “Hey, what do you, you know, what you do? What’s your practice?” And they’ll say something like, “ERISA,” or, “Tax.” And they’ll immediately apologize for it, and they’ll say, “But, you know, it’s steady work,” or, “I’ve grown to sort of enjoy the tax code.”

And then you meet somebody else who does ERISA or tax and their eyes light up, and they’re actually proud. And I noticed the same thing with writing and legal writing. And even a lot of the legal writing teachers who will say things publicly, like, “Well, we really don’t just teach the passive voice or style. What we really do is teach there is a rhetoric,” as if they’re apologizing for the very thing that they’re supposed to be sharing. So that’s sort of how I see it.

I’m excited about it because I’m excited about it. And I’m excited about it because I went to law school, excited about language and words, and that was my background. But again, I think there probably is a parallel to lawyers who end up embracing, you know, the tax code or securities regulations. As you dive in and give it your all and don’t apologize or feel like you need to apologize, you end up finding your own energy and then that, I hope, is infectious.

And I think maybe that’s what you might be seeing on my Twitter feed is that I’m talking about things that out of context seem geeky or nerdy, or maybe even a little pretentious in some ways. But we have a lot of banter going, and I try to relate it to, you know, the writer as a human, or politics, or current events, or other different types of strategies or goals. And then it all starts to come alive as opposed to people feeling as you were saying before that writing is just about avoiding grammar mistakes or avoiding corrections. Of course, you’d be depressed if that’s how you saw words. You wanna look at all these as a way to add tools to your arsenal so you’re a better advocate for your clients, but also, I hope, have more fun writing in the first place.

Jake: Yeah. That’s so great.

Ross: Are you gonna start reading grammar books now?

Paul: You know what? Jake and I love pulling things apart, taxonomy, stuff like that, and looking, you know, because we do so much stuff with advertising. And it’s just amazing to us how sometimes things go unnoticed or become common place because I think people don’t always pay attention to that stuff. But, you know, I was… A couple of months ago I was looking for a house and we noticed that, like, the kitchens were described as stunning, like, “Really?” Like, “That’s dangerous, man.” I mean, like, “Think about what you’re writing.” You know, or the bedroom was enchanting.

Ross: Yeah. And [crosstalk 00:10:36] with the old…it has a lot of potential. I mean, [inaudible 00:10:40]. It’s probably just good for people with imagination.

Paul: But see, you’re doing it right there, like, it’s funny that there’s, you know, you have all these arrows in your quiver that you can use instead of being, like, “It’s got a bedroom.” You know, like, there’s something to it.

And it’s a human element. I think the more you get into it, the more you start to pay attention to these things, and I think it’s fascinating. But the other side of that is the machines and so, like, automated review, artificial intelligence, you know, we talked about Lola versus Skadden, you know. So, like, if a bot can do it at law.

So what are your thoughts about, you know, that sort of thing? Is there room in the future for human editing and drafting, or are we just gonna be feeding it into the machines and they’re gonna spit it out with corrections?

Ross: Well, I wouldn’t tell, you know, I wouldn’t give up hope quite yet, or write the profession off. Although, I do notice in my travels, not just in the United States, but abroad, there’s a lot of angst in the profession for all the reasons that you suggested. So if you think about what most lawyers would really rather be paid to do, strategy, counseling, thinking through legal issues, you know, maybe learning about the latest substantive trends, and then of course, translating all that to the written word content-wise, that is always going to be a need.

That’s always going to be something that only trained people with judgment and experience can do. And then if you think of the concept things that most lawyers frankly really don’t wanna do, even if it helps them churn hours, like, look for extra spaces or citation errors, or, you know, overly overused words, or, you know, repetitive patterns and sentence structure, or transitions, even basic line edits. I mean, I love that sort of thing. But I have to be honest, most lawyers really don’t. Well, those are all things that obviously these tools if they’re well-constructed and used, you know, with some discretion can help with.

So I do notice, even at kind of the fancy firms that I frequent, that a lot of documents that are being filed are substantively weak. In part because the deadline force people to just clean up all the details and not really have time to apply their vast, you know, legal knowledge and experience. And I think that would be a better allocation of time. So I am optimistic that in the long run this might actually be a great development because it will free most lawyers up from having to do things that they’re, A, not really interested in doing and, B, often not particularly good at, or not any better at than normal people would be.

Jake: So talking about those lawyers, just the JDs on the street, coming from different levels of rhetoric communication backgrounds, this is little tangent, before I ask the second to the last question. But what about the youngsters using words? Do you see any new forms of communications like GIFs, memes, emoticons, just kinda alternative forms of communication? What’s Ross Guberman’s future riffs on that kind of stuff? You think it’s got a place for it? Are we always gonna be using Victorian English? I mean, like, Edgar Allan Poe had to write like that because he got paid by the words, you know.

Ross: Sure. Yeah. I mean, I’m still in awe that a federal district court judge in Alabama in an antitrust case put a GIF with Tom Hanks saying, “Really,” when he got irritated with lawyers and that was, you know, a federal district court judge. So obviously, people are toying around with these different forms of communication. I don’t know if it’s to look hip or young, or what have you. But I really honestly, you know, they always say, and I have high school kids myself, they always say that it’s texting that’s destroying the writing of the youth today. I don’t believe that’s true, but that’s not our topic today, by the way. I have my own theories about high school kids and why they have writing problems.

Jake: You’ll come back.

Ross: When you talk about lawyers, I haven’t seen any evidence that memes, GIFs, texting, and emoticons have had any negative impact on the way people actually draft their legal product. And I don’t even really honestly notice that even motions and briefs, let alone contracts, are becoming more conversational or informal. If anything, I might even say I’ve noticed the opposite.

So, yeah, I think the problems are not connected in either sense positively or negatively to, you know, broader trends in the culture of texting, emoticons, and the like.

Jake: Interesting. Wow. Yeah. So, and it sort of outlines the problems in between the insular thoughts of legal versus, you know, real world. I wish you could just tell me, you know, tell it to me straight, you know. And it’s, like, we have this form over here in the way in which we communicate that you’re saying is trending towards more buttoned up language, which is just fascinating because, you know, someone just sending me a poop emoji and you’re, like, “Well, I guess I know what that means,” you know.

Ross: I can, you know, not exactly break some news today, but I can tell you probably something you might find interesting. I’m about to… I’ve done a very extensive machine-learning AI study of legal work product over the last six months, and I just have two categories. I have famous writers like Elena Kagan and Paul Clement, and then I have everybody else. And one of the things that’s gonna come out when I publish this is that contrary to what everybody thinks, the prominent lawyers and judges of our profession do not at in any way, shape, or form have shorter sentences on average than random lawyers or judges. But they do have, and I’m very happy about this frankly, because it’s something I’ve noticed anecdotally, they do have shorter words.

And that’s what’s interesting is what I’ve noticed is is people have gotten weaker and weaker with grammar coming out of college and law school. They actually hide behind more and more legalistic pretentious, or just as you were saying before, generally quote big, unquote words, whereas the really top performers actually use a lot of very short pappy and punchy words. So there’s that too. So you have that sort of bifurcation that is probably not what a lot of people would expect.

Jake: That’s so dope. Okay. So what’s one thing that our listeners can do right now to make their legal writing experience betterer at their firm? I used betterer.

Ross: [crosstalk 00:17:45], Jake, You had to have the law firm at the end of the sentence. So, well, I’ll give you a couple of things. So one is, and this would be especially for associates or their counterparts and other types of employers, from the very first day of work, you have to make in your mind two different lists. And the first list is, or should consist of changes or edits that you see or have made that you know are reasonable that many people are gonna make or agree with and that you wanna commit to memory and internalize.

And then you need to have a completely separate list, you know, literally or figuratively of little quirks and idiosyncrasies that your supervisors have because one of the things I’ve noticed is people who are brilliant, they run into trouble. The job at fancy law firms or anywhere else often cannot distinguish between the two and they just become really, really flustered, and confused, and bitter.

So that’s kind of a process bit of advice. And you never wanna, by the way, think that everything is in that second category, that it’s all about idiosyncratic crazy supervisor preferences, because that lets you off the hook and doesn’t make you improve your own skills. So just plain writing wise, the part that you can control yourself, it doesn’t necessarily involve the food chain in law firms.

I would say, end of every draft, you have two minutes. In the first minute you do nothing but cut phrases down to a single word. And then the second minute, you do nothing but take long words and shorten them. So every time you see regarding or concerning, you change it to on or about. Every time you have demonstrate, illuminates, illustrates, you change it to something like show. And if you just do those two things in two minutes, you’ll probably have much better product. And a lot of people will do well who will spend an hour just aimlessly having angst in editing their product with no particular goal.

Ross: I know I gave a long two-part answer like a politician. I’m [crosstalk 00:19:59].

Jake: No, no, no, no. You can’t imagine how wonderfully tight that was. Because there is that idea is that do you just like it this way, or is this the way it should be? And I think you do have that pecking order no matter where you are.

Ross: So true.

Jake: And that’s a really interesting idea for that process.

Ross: The sad thing is the supervisors of the world are to blame, too, because, of course, they don’t like to admit that anything is just around idiosyncratic preference, right? They always say, like, “Are you crazy?” How could you think otherwise when it really is just their own issue?

Jake: Well, to get back, to counter that, what do you think someone who’s a shareholder or a partner could do to work on helping develop stronger writing skills downwards? Do you think you should be a little bit more open to somebody putting a GIF card poop emoji in the memo?

Ross: I think you should be really, really careful about shooting people down when they’re trying to do something creative or innovative, or even a little bit, you know, unconventional. If it seems generally in the client’s interest, and I think a lot of supervisors are too quick to immediately be negative and that ends up sending messages to the younger person that, you know, it’s just not even really worth trying. Anything I try to do is gonna be questioned. So I think that is part of it because it all, you know, that all spills into morale in the working relationship beyond writing and editing as far as just being a better supervisor, which is actually interestingly a topic of a workshop I ended up having developed because firms wanted it.

My general advice…and, you know, some people listen and agree but don’t do it and some people don’t care about being better supervisors because they are huge rainmakers. But my general advice is when people do a project, you know, someone does a project, to give them things that they can do or not do the next time to either replicate or avoid whatever it is you saw in the original project.

And that’s not what really happens. What really happens nowadays is there’s no interaction at all other than by email and there’s just a markup, and maybe the younger person accepts the changes or maybe hands those off to somebody else. And there’s no real sense of what overall you could do next time to do the good thing well again or to avoid the thing that bothered the supervisor. So it’s really focusing on things that people can do or not do as opposed to just categorize in their writing as, like, ”This is pretty good, but it could have been better,” or, you know, ”You need to be clearer,” or, “You need to be less wordy,” or anything that just sounds more like a cheap judgment.

Jake: So we could keep going, but we can’t because we have stuff to do. So, Ross, if people wanna learn more about Legal Writing Pro like these seminars, those consulting…those lesson plans, and also BriefCatch, how can they find out more about you?

Ross: So BriefCatch, obviously, it has its own site,, and that’s original. Anybody can get a two-week free trial of the product. So that would be a good place to start when it comes to BriefCatch. My seminars, if you’re interested, you can learn more about them on my regular site But I also have, I have lots and lots and lots of free resources, all sorts of articles.

You know, I’m quoted in a lot of articles. I have my own articles. The ABA just published an article of mine after I surveyed about a thousand judges across the country anonymously and what they wanted in briefs. So you’ll see some of those linked on my site, or you can just google me. And I do really try to provide a lot of free resources, especially for the many lawyers in America who don’t work for the kinds of firms that can hire an outside consultant.

Jake: There’s one thing that I failed to talk to you about, and it just came up to me again, is that writing is creating. And I think that people think it’s so formulaic and formal that they forget that when a supervisor, like, shoots them down, it’s like you just told your kid that they’re painting looks like [inaudible 00:24:21].

Ross: Of course.

Jake: But it’s crazy because I think people say, ”Is it business or is it pleasure?” And, you know, you wanna be creative. Go and express yourself in the corner and that’s what creative stuff. We’re doing business here. But when I use the word “show” versus “demonstrated,” and you want me to use “demonstrated,” but I feel “show” is better, but then you shoot me down, it’s not just, like, business. There’s actually a heart that you’ve kinda stabbed, and I think there’s something about your energy that I think gets to that point. And I don’t think lawyers think they’re creators. Do you have any thought on that?

Ross: No, I do. And, you know, it’s interesting. I think for lawyers, even the many who don’t really immerse themselves in the finer points of syntax and grammar, I think for a lawyer to be criticized or shot down over writing is, and I’m not exaggerating, often devastating. And sometimes…I mean, that hurts their ego and morale for years or decades, but because it feels very, very personal. So one, you know, one anecdote, of course, would be to not think of creativity in terms of doing things like having cartoons or, you know, strange images…

Jake: Post-its everywhere is what it is. You’re right.

Ross: …but really creativity in the sense of having vivid verbs, creativity in the sense of maybe varying your sentence structure. I mean, we, you know, we’re a creative profession, but we have a lot of constraints. And if you try to push the envelope into the world of art or advertising, you’re really only gonna end up disappointed. So I think there’s a way to harness creativity and channel it into words and sentences where you get a lot of the benefits without some of the, you know, push back.

But most important thing is, as I think you’re getting at, is just to remember that for most lawyers and, frankly, law students, criticism over writing really is like criticizing them as professionals, if not people, and needs to be handled really tactfully, you know. And I probably need to do a better job with that myself. We all do.

Jake: But you know what? But that’s one of the things that me and Paul love is that we’re savage with each other on the editing, editing floor because we know that you gotta get rid…cut the fat. You know, people…Pixar, I bet they just crush people’s dreams, you know, because they’re, like, “That ain’t gonna fit. That ain’t gonna fly. I’m sorry, I have to tell you this.” Because there’s so much bad junk out there to really wanna get something good out there, it’s okay to be a little bit rough, but you have to have the tenacity to get roughed up. I like people going through my edits, blogs, and stuff, and being just savage with me because it makes me smarter. Because I’m, like, “Oh, oh.”

Ross: And then also because you probably see the light at the end of the tunnel, that whatever they’re doing is to help you be better at what you’re doing. But let’s be honest, a lot of times when lawyers criticize other lawyer’s writing, it’s really just to shoot them down or to make them feel bad. It isn’t to help them be better, and I think people do sense the difference.