In every legal drama, it’s the oral arguments that get all the attention. But for most cases, what really wins is good legal writing. And today on the Filevine Fireside, we’re talking with one of this country’s most esteemed legal writers.

Ross Guberman has worked with thousands of attorneys and judges and dozens of state and federal agencies teaching the in’s and out’s of great legal writing. He’s the president of Legal Writing Pro (an advanced training and consulting firm), and he just released the editing tool BriefCatch.

Ross is also a professorial lecturer in Law at the George Washington University Law School and holds degrees from Yale, the Sorbonne, and the University of Chicago Law School. He’s here to talk about his work, and to give us a few tips to improve and polish our legal writing.

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Katie: This is The Filevine Fireside and I’m Katie Wolf. In every legal drama, it’s the oral arguments that get all of the attention. But for most cases, what really wins is good legal writing. Today on The Filevine Fireside, we’re talking with one of this country’s most esteemed legal writers. Ross Guberman has worked with thousands of attorneys, judges and dozens of state and federal agencies, teaching the ins and outs of great legal writing. He’s the president of Legal Writing Pro, an advanced training and consulting firm and he just released the editing tool, “Briefcatch” at Ross is also a professorial lecturer in law at the George Washington University Law School and holds degrees from Yale, the Sorbonne and The University of Chicago Law School. He’s here to talk about his work and give us a few tips to improve and polish our legal writing. Thank you so much for talking with us today Ross.

Ross: Thanks to you as well, Kate. I’m happy to be here.

Katie: You’ve done a lot of things in your life, Ross. How did you become the legal writing guy?

Ross: Yeah, I have done quite a few things and that was actually before I even went to law school. I went to law school a little bit later in life. I had kind of a graduate level of background in literature. I worked in publishing and translating a bit. I certainly focused a lot on writing while I was in law school and when I was a summer associate and in practice as well. I worked for a huge firm and did a lot of writing there. Then, I decided to go out on my own and I did a bunch of things at that point. I started teaching at GW Law School here in Washington, D.C., where I still live. I worked as an investigative reporter, focusing on business and financial and legal stories. Then I started writing briefs and editing briefs for some big firms with the D.C. offices. At one of those firms one of the partners just asked me sort of spontaneously if I wanted to put together a class for the associates on how to write a better brief and I wasn’t quite sure about what to do on that front, but I did agree and I did it and that’s sort of how it started. So, it started kind of with my own idea. Unfortunately, I can’t even take credit for it. It was really somebody else’s idea and then as with many businesses, it just sort of sputtered along for a little bit, a few months, and then it grew and grew and grew and now I have about 250 different clients.

Katie: So, you have a background in literature. When people think of good literature, they don’t usually think of legal briefs but what have you learned from that background that informs the work that you do now?

Ross: That’s actually a really interesting point because many people who are literary types have a lot of trouble with legal or judicial writing. The kind of literature that I was fascinated by, even in my doctoral program, tended to lean more towards the narrative non-fiction genre. I was always really really fascinated by clear controlled Hemingway-type writing, although my specialty was actually not in English literature. I was always very interested in journalism as well. When I got to law school, you would think I would have felt alienated in legal writing class but I actually loved my legal writing class from day one because various things I valued in English prose were at least in theory valued in legal writing as well. I also think just the close analysis of writing that you learn to do so well, if you studied literature at the graduate level, it’s really helped me a lot with my current job too.

Katie: Yes, that deep understanding of rhetoric. I’ve heard law students kind of bad mouth their legal writing classes. Do you have opinions about the way that legal writing is taught in schools?

Ross: Yeah, it’s interesting. It really does seem to be a little bit of a punching bag, the legal writing class. I actually taught it once, believe it or not. A long time ago I taught a class and then I did a seminar with a self-selecting crowd for many years as well, which was probably more enjoyable, quite frankly. A few thoughts on that. One is, new law students are a little bit nervous and the only feedback they get is often in the legal writing class, so I think there’s a little bit of insecurity sometimes and a little bit of hostility thrown at the legal writing class. I also think it’s an incredibly hard class to teach well and a lot of law schools do their best, and I think the full-time faculty generally put their heart and soul into the class. Some schools are sort of an adjunct program where you have people who are good at practicing but not necessarily skilled at teaching, so that’s a problem. Frankly, it’s really hard to teach writing.

Katie: Your book is subtitled, How to Write Like the Nation’s Top Advocates. When you look at the very best attorneys, what makes their writing stand out?

Ross: Probably a couple of things. The first would be that If you read their writing out loud, it sounds very direct, natural, confident and conversational. That’s really rare and really hard to pull off so that’s one general unifying trait I’ve noticed. Then the other I’d say is most of the really great legal writers, the kinds who would be in my book, have a little bit more creativity than a lot of lawyers have so they come up with more interesting examples, analogies, metaphors or hypotheticals. You just feel like behind the scenes, they’re trying much harder than a lot of us do to take dry legal or factual concepts and bring them to life.

Katie: Now, a lot of your work, well, any good writing work involves putting yourself in the shoes of the audience and in this case the audience is often a judge. How have you been able to get a judge’s perspective on briefs?

Ross: I’m really lucky because I actually do a lot of work with judges and do a lot of training of judges, federal and state, so a little bit through osmosis I’ve actually gotten to learn a lot of things about what judges like, what they don’t like, what they see, what they wish they didn’t see but they don’t see that they wish they did see, and then I’ve also been in part because I’ve had these connections with the judiciary, I’ve been lucky to be able to do these nationwide surveys of judges so I make them anonymous and I try to go after a broad squaff of judges and I get lots and lots and lots of input on everything from fonts to use of case law.

Katie: What are things that attorneys do all the time that just really annoys judges?

Ross: One would be the snarky word phrase or opening introductory phrase. So, one of these “Clearly unable to unmask any evidence that would actually prove any element of a cause of action, plaintiff.” That kind of thing drives judges crazy. Also, when people use the words tellingly a lot or baselessly a lot or preposterously, those kinds of things also really make judges roll their eyes. So, that’s one general category. Another thing I hear a lot of complaints about is just sort of in the beating a dead horse category. So, having the summary judgment standard go on for ¾ of a page, or saying what the four elements of negligence are and having five different case sites and a block quote, so there’s a lot of complaining about that. And then, the other is probably just not being really honest about weaknesses in your own case, bad facts in your own client’s fact pattern or frankly weaknesses in some of the cases that you’d think generally support your position. So, just a general lack of honesty and a lack of candor mixed with sort of grandstanding obliviating that really takes what is by definition a complex dispute or it would have been settled and tried to make it just so one sided that you actually start to lose credibility.

Katie: How do you recommend sort of threading that needle where you are persuasive while still appearing and sounding objective, neutral and trustworthy?

Ross: That’s a great question. What seems to work the best, even if it isn’t as fun in the short term for a lot of lawyers, is to write a first draft that consists of nothing but pure logic facts and legal analysis. You make your argument tight, you make it organized, you get your headings in order, but it’s all loveless, right? No emotion, no rhetoric, no name calling, no fireworks. Then, after you’ve done that, it’s like a little bit of a reward. Then, you go back and you can add a little bit of the color, you can slam things a little bit, you can add a few modifiers here if you want. A couple of adjectives and a couple of adverbs aren’t going to kill anybody. You always do that last. And what I think a lot of people do these days because people always write in such a state of frenzy, is they sort of emote first and they type a lot of sentences and paragraphs that are mostly about how long they have recited and how stupid the other side’s points are and how misleading the other side’s cases are. And then they try to fill in the blanks with actual legal analysis but it’s probably better to do it the other way around.

Katie: That’s really good advice. That is good. More and more judges are reading briefs online. Does that make any difference in how you should write a brief? Does it matter if a judge is reading something on a screen or printed out in front of them?

Ross: That is so true. I actually have the evidence that it’s true again from my survey so online and then it’s actually interesting how many judges, at least anonymously, say they read briefs on iPads or actually on their phones, which seems to me pretty hard to pull off to read a brief on an iPhone or a droid but they do so some of the things that would change would be number one, now more than ever you really need a lot of attention to white space, spacing in general, having some subheadings and having short paragraphs because people are just so much more demanding when they read things on screens than they might be if they’re curling up in front of the fireplace with something in print, so that’s one thing to think about. But, you’d be surprised. The main thing that I hear from judges when it comes to reading things on devices is actually a little bit more specific and that is that it drives judges crazy when they read things on devices if there’s anything in the footnotes at all; citations, extra authority or what have you, because what happens is depending on the device, sometimes the footnotes and end notes are moved to the wrong place and it just makes it really really hard, given that you don’t remember what page you were on because you weren’t looking at a whole page the way you would in print, it makes it really really hard for a judge to find their spot. So, I would say those two things, pay a lot more attention to formatting and generally having more white space and then just being really really cautious about footnotes.

Katie: Now, you don’t only advise people on how to write great briefs but you are also working with contracts and emails and the opinions that judges write. Do you want to talk a little bit about what the main pitfalls and problems are in those forms of writing?

Ross: Sure! Contract and contract drafting are two of the most stimulating but also frustrating parts of the legal writing empire so you have these competing forces in contract drafting. So, you have all sorts of efforts to make English language contracts, especially in the United States, more modern known as just plain English. There a lot of people who have other really great ideas about reforming contracts as well. They’ve thought through the language. They’ve tried to make things streamlined and consistent and clear. So, you have all of these things going on. But then you also have the reality and a lot of people don’t want to admit the reality is the reality but it is. So, the way things work and the way things have worked for decades, if not centuries, contract drafting is really heavy on inertia and it’s very very risk of verse and very little change. It’s really interesting. Unless you’re in the tech world and you’re looking at a contract on a licensing agreement that really is by definition, new. If you look at a financing agreement or a stock purchase agreement in 2018, it’s not that much different from what you might have seen 30 or 40 years ago. So, what I personally try to do in contract drafting because I do respect the pressures that corporate lawyers are under is this: I don’t try to completely reform the way people draw up contracts. I don’t tell them they need to burn everything and blow it up and start from scratch but what I do do is focus on words and phrases that have a history of being litigated and I try to give suggestions on how to avoid those same pitfalls. So, I talk about things like and and or, and and/or and the word material and different clauses and different problems with shall, may and must and I just try to get people to avoid the risk of litigation because I know it’s just not realistic to get people to throw out the entire way they draft agreements. I have a lot to say about emails too.

Katie: Yeah, what do you have to say about that?

Ross: Well, I never thought when I went into this business that I’d be spending so much time studying lawyer emails as I have. It’s actually pretty fascinating because the lawyers, like most professionals, write two types of emails. You have sort of the daily emails managing cases and transactions, setting up meetings, setting up calls and delivering basic information and then of course a lot of lawyers deliver substance information by email as well. So, what I’ve learned just to make a long story short is that in daily emails I compared with other professionals, a lot of lawyers are actually a little too short and sweet and curt and could stand being a little bit friendlier in trying to make a better connection with the audience. But, in the other kind of email the lawyer writes where he’s delivering legal advice or legal analysis, the problems and the complaints are exactly the opposite. So, some of that is part of our profession. The law is complicated and you need a lot of information so we should be given a little bit of a break. But, I have noticed over and over again, especially when I train in-house groups who complain a lot about law firm lawyers is a lot of lawyers spend too much time at the beginning of the substance of the email talking about what they’re going to talk about but really what we should be doing is giving the two or three main points if we’re going to spend the rest of the email threshing out. There you go. A little bit more warmth and friendliness in the beginning of the emails and a little bit more brevity but especially more front-loaded information in substance of emails.

Katie: Ross, also part of the work that you do is to train attorneys in the ways that they can talk with other attorneys and members of their staff about improving their legal writing because that can be a little bit of a touchy subject sometimes. What are suggestions that you have about how to talk to other members of your legal team about making your legal writing better?

Ross: It’s interesting that you say that and I couldn’t agree more. It really is a touchy subject. I’ve actually been thinking about this for years. Why do lawyers get so sensitive when their writing is criticized? I think, in general, most professionals are similar in that respect. Writing is obviously seen as a court professional skill. It’s something that a lot of people pride themselves on. It’s obviously something that we’ve all been working on since Kindergarten or first grade but that doesn’t quite explain the reaction we get when we’re criticized so there must be something about our profession where we really just value writing even more and a criticism of our writing seems like a criticism of our entire competence so that’s sort of the backdrop of this challenge. I see this a lot in my daily work and even my one on one work from time to time. You have to be really sensitive to people’s self-image and ego, frankly, when you talk about writing so a couple of things that work. Again, not always what people want to do, people want to criticize, but here are a couple of things that work. One is to try to find some sort of third party authority for any point you make. So, in other words, you don’t want to be a supervisor who runs around saying, “I don’t like the phrase, ‘the fact that.’” You want to say, “I’m a big believer in the book Elements and Style by Strunk and White. I’ve always tried to cut ‘the fact that’ from my writings, Strunk and White said we should and I just want to pass that on to you.” So, I found that that goes over a thousand times better than just saying, “I,” that word I like or dislike something, so that’s number one. Then number two is people also seem to have a lot of trouble with is you don’t want to ever just criticize someone’s writing with an adjective. Like, “Hey this is unclear. This is unorganized.” You want to give them some practical or actionable step they can take to make their writing clearer or better organized for next time. It’s sort of a cheap shot as a supervisor to just declare that someone’s writing is a, b or c, in my view. It isn’t really doing them any service. It’s just going to make them feel bad. You really need to give them a little bit of an exit strategy and then they will react more favorably.

Katie: Your book Point Taken is about judicial writing. What are the special needs that you had to consider when you’re addressing judges writing?

Ross: You have to be really really careful when you address judges writing. So, litigators, even the most arrogant and confident litigators realize that at the end of the day they have to make judges and clerks happy. Judges don’t necessarily have something comparable in their lives so they don’t necessarily feel like somebody is going to process the opinion as an opinion as opposed to just the holding and judge the opinion as a piece of writing so that’s one thing I’ve learned is you have to be realistic about what judges can and cannot strive for daily in their writing because they have a different agenda than they might have had when they were in practice, so there’s that. Another challenge, although I’ve actually enjoyed this challenge, is very few people have really studied the writing of opinions. I know that because I wrote a book and there wasn’t much for me to read in preparation so it isn’t really clear to judges even what they’re supposed to be going for. It is actually pretty clear to most litigators what a brief is supposed to look like, so that’s different. We have those two challenges. But other than that, I’ve had some of the best professional experiences of my career working with judges so I don’t want to make it sound like it’s a tough road because there’s some of the best and grateful audiences I’ve ever worked with.

Katie: So, now in addition to the advising consulting and training that you do, you’ve created this editing tool called “Briefcatch.” Where’d you come up with the idea for this?

Ross: As I’ve toured around and done all of these workshops in different places, I have a really great system of editing for lawyers but what a lot of people would point out is it’s really really hard to remember all of these edits, especially when you’re under time pressure and exhausted and the like, so it actually wasn’t even really my idea. It was some of the younger attorneys, the hipper, younger attorneys that I train, would say to me, “Why don’t you create something, some kind of tact tool, that would actually flag a lot of these edits that would make suggestions” and you know I took their advice and I worked on it for over a year and I came up with this product that I launched just a few weeks ago called “Briefcatch.”

Katie: What makes it different from sort of a regular editing app?

Ross: So, it tackles 14 different features of lawyer’s writing. It actually works for other kinds of writing as well. It works for non-legal writing that lawyers do like articles and biographies. But it tackles everything from conciseness and preciseness to an effective use of case law, to citation errors to repetitive patterns with transitions, mistakes that spellcheck or grammar check just don’t know about. It flags cliché words that lawyer’s use. It really just gives you just sort of one step shopping for most of the things that any human editor, a top notch human editor, would look for.

Katie: Ross, earlier you mentioned your Twitter account and I wanted to circle back around to that. I love your Twitter account. It made the ABA’s best law Twitter list. One thing that I notice is that you’re always asking questions. I would expect the grammar guy, the expert to be sort of pontificating from his Twitter feed but you are actually engaging and taking surveys of the people who follow you.

Ross: Yeah, you know, it’s embarrassing to say, but I actually really love my Twitter followers and I actually learn as much from them as they perhaps learn from me. I see Twitter, obviously people have different approaches to Twitter and I only know what works for me, but I like doing those polls, I like asking questions, I like sort of crowd sourcing and I don’t always agree with every single thing that everybody replies but I like having that interaction and the really amazing thing I’ve found is when I do these polls and I poll everything under the sun that can be polled that has to do with writing. I have something about the Stormy Daniels legal documents but I was going to say nine times out of ten, when I do these polls, and I’ve got thousands of followers, the answers I get from those votes is actually the answer that I think is right. Even when I ask incredibly difficult or obscure questions. it’s been really sort of encouraging in that way as well.

Katie: Wow. You mentioned Stormy Daniels. You do refer to a lot of hot button political issues in your Twitter but it’s almost to always ask about the grammar in which something has been presented which makes it playful.

Ross: Well, I hope so! I think it’s certainly a risk that I’m aware of. It’s tough though, because I’ve always tried to have fun examples and I’ve always tried to have provocative examples and I do like to follow things in the news and if you have those things as goals, you’re going to end up using a sentence that’s going to offend somebody based on the content, right? Or to be honest, sometimes based on the author. So, I hope I strike the right balance. I do try to be a little bit tongue in cheek. I think surely people know that if I have a sentence from President Trump or President Obama and I’m talking about a split infinitive, I’m not really taking a position on the terrorists or The Affordable Care Act. I think people generally get that but you know how people are. We’re in an era where people are quite often easily offended and I am very conscious of what you’re talking about and I try to strike the right balance.

Katie: I heard a rumor, Ross, that you’re working on a novel. Is that true?

Ross: Ha ha! Well, the rumor is true. But I’m always working on my novel and I never seem to make a lot of progress so I’m actually working on a legal thriller which is probably not a huge surprise given my background and given my law degree so if I ever find the time, and I’m not sure that’s going to happen, I will try to finish it. I’ll be sure you’re on my mailing list and you’ll be my only reader. It doesn’t come as easily to me as non-fiction writing. That much I can tell you. Fiction writing is harder for me.

Katie: Yeah, I wanted to ask if your legal writing background helps or hinders when it comes to writing a thriller?

Ross: To be honest, it probably hinders me because it’s impossible for me to do what people tell you to do when you’re writing a novel and just sort of blurt it all out on the screen. I’m not able to do that when I write. Not even if I write a grocery list. So, it probably hinders me a little bit, I’ve got to be honest.

Katie: I also have one final question, which is, are people often intimidated to talk to you? Because we know that we’re going to say something that is ungrammatical… are you a grammar stickler at all times or only when you’re dealing with formal legal writing?

Ross: So, my parting line on that is that I only notice grammar if I’m being paid to do so, which means I never notice anything in emails. I don’t notice anything in social life. We have all of these lawyers who are actually much more aggressive than I am about grammar. They seem to be lying in wait to catch someone making a mistake. This is all I do. You know, I’ve memorized every single rule under the sun so it doesn’t make me happy to find mistakes so I’m not going to lie. I’ve definitely had clients tell me they are intimidated to write me or email me but we just have to laugh about it together because honestly the last thing I’m going to do for fun is look for mistakes in anyone else’s writing unless I’m being paid to do so.

Katie: (Laughing) That is great to hear.

Ross: Don’t tell my kids that though. I want them to be afraid of me…(laughing).

Katie: Ross, it’s been such a joy to talk with you. Thank you so much for the information that you’ve given us.

Ross: Well, it’s great talking to you as well and I appreciate your thoughtful questions. Thanks for the opportunity.

Katie: I’m Katie Wolf and thanks for listening to The Filevine Fireside.