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Leveraging Technology to Improve Legal Writing | Ross Guberman

Most legal writers know about Ross Guberman, author and founder of Legal Writing Pro. Ross was one of the first legal writing instructors to work with law firms and practitioners across the country. Ross also developed BriefCatch, a software solution that helps legal writers make their briefs and motions better. In this week’s episode, Ross talks with Todd Smith and Jody Sanders about his teaching, his books on legal and judicial opinion writing, and BriefCatch—all with the aim to improve written work product across the legal industry.

Listen to the podcast here:

Leveraging Technology to Improve Legal Writing | Ross Guberman

We have as our guest Ross Guberman of Legal Writing Pro, who’s also an author and entrepreneur. We are going to talk about all those facets of his career and life today. Thanks for joining us, Ross.

Thanks for having me on.

Thanks for being with us. We are looking forward to visiting with you. As we usually do on our show, we allow you to introduce yourself to our audience. We are the Texas Appellate Law Podcast but we have trial lawyers, judges and other people within and outside of Texas who read. For anyone who doesn’t know you, tell us a little bit about yourself, your background and what led you into law.

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I got into law in a somewhat strange way. I was doing graduate work in Comparative Literature and got burned out quickly at the start of the Ph.D. program. I was going to school at Yale and I ended up hanging out with a lot of Yale law students. I didn’t know any lawyers. There aren’t too many in my family, but they were so animated all the time. They were flying off to Haiti. I remember – I’m dating myself – but there was a crisis with Aristide and a couple of them said, “You don’t seem to like grad school too much. Why don’t you go to law school?” I did. That was in the 1990s. I started law school in ‘95. I continued the same pattern of being a little impulsive. I did practice, enjoyed it, but I then stopped. I did a bunch of different things, including editing briefs and I taught at the first online university. I started teaching at a law school in DC here at GW. One of the firms I wrote briefs for asked me to put together a class for their associates and that’s how the whole thing got started. That was about 20 years ago.

You have made a name for yourself as a legal writing expert. You have authored a couple of books and started a company called Legal Writing Pro. Was that the genesis of Legal Writing Pro, your early career in doing writing and instructing for law firms?

In hindsight, it seems like a smooth path, but I had no idea when I got started whether it was going to work. I didn’t know exactly how I was going to structure things. It was a little bit happenstance-like. One good thing with law firms is they tend to follow each other in a pack. I did have a sense early on that you had to break through the AmLaw 100 barrier. Once you got through that barrier everything would be easier. I did that first workshop that was casual. I started pounding the pavement. Back then there was email but it wasn’t too efficient. You get a critical mass of clients but it takes a while. As Malcolm Gladwell says, “I hit the tipping point,” and then it was easier but it’s not an easy business to get into.

Were you doing any ghostwriting advocacy work for firms like that or were you mostly instructing other lawyers on how to write?

I did ghostwrite different types of projects. They were stimulating. I was working from home before it was cool because at that time I didn’t have an official position at the firm. I had a variety of projects, writing and editing. I also worked as a journalist during that time too, so that was another element. I was doing a lot of different things and hoping they would all congeal into a viable career path and they did.

You were on the early end. I feel like legal writing is a subject of study that has taken off in the last couple of years and it seems like you are one of the early ones pushing that out there, which is cool.

In law school, I loved the class and that’s fairly uncommon. I hear a lot of complaining. I was exposed to your fellow Texan Bryan Garner in my 1st or 2nd year in law school. That got me excited. I read his books. It’s also true that I had this literary analysis background, but that might be more of a coincidence than anything else. Certainly, it was something that I gravitated towards. Starting on the first day of law school that was the one thing I did understand and feel comfortable with. Even when I was a summer associate that was always my strength.

From there were you able to grow Legal Writing Pro beyond yourself? We have talked about how you’ve got a couple of other things going on but I’m curious about what direction you wound up taking Legal Writing Pro in. I know that’s still out there and part of what you are doing. Tell us more about the company and what it has been up to.

Looking back, I probably took on too much. Certainly, when I was younger years ago, in 2009, I did 220 workshops and I had a week once with eleven workshops in six cities including Saturday. A lot of things are like this. When it’s your own business, you don’t feel you can say no and you don’t want to say no because it’s exciting. I’ve got a lot of satisfaction out of what I did and I still do it. What happened in addition to simply adding more clients all the time, which tended to be the same types of firms over again, they all copy each other. I also expanded into different types of writing like IP contracts and business development writing. I had so many different things going on. Although I was on the road all the time and busier than I should have been, it was always stimulating. I was always trying to find new fields or practices to explore and conquer.

How would you go about learning a new field in things like contract and business development? Was that something you had a background in or did you have to take what you already knew and apply it to a new arena?

I do have that professional student thing. Even now when I’m older, I do enjoy throwing myself into some new field, hobby or something that is sometimes obscure that I have never had a chance to put my arms around. With some of that I did have probably had most of what I needed like business development writing, how to mind the journalistic style when you are a lawyer and still be authoritative. But with things like patent prosecution or stock purchase agreements, you have to be much more rigorous. The one thing that has often separated me is I always have my ear to practitioners. There are a lot of pie-in-the-sky consultants out there in legal writing and otherwise. I’m also extroverted and I love meeting people, so I learned a lot from actual practicing lawyers when it came to what they wanted to learn or what they found challenging in these different practice areas. That helped me a lot too.

I love your reference to Gladwell’s “tipping point” because that’s an accurate description. You do reach a point where suddenly, the thing takes on a life that’s greater than you. Eventually, as an entrepreneur, even though it is tempting to take every assignment or client that comes in, you have to be a little more selective. Or else, you will be doing things that aren’t as productive or profitable and you wouldn’t get to spend as much time at home. I’m sure that the travel schedule you described was a bit grueling.

I’m always embarrassed to say this but I love business travel. I don’t know if I grew to love it or it’s something in me. For some reason, I’ve never gotten tired of the rat race of going from one airport or hotel to the next because I always found something enjoyable on a lot of these trips. I saw someone, did something or went to some restaurant I had heard about. There are moments where I was exhausted like anybody else and you have the usual nightmare flight cancellations in a blizzard. I found it all fun and I was also grateful. I’m going to wherever I’m going, LA or Cleveland on someone else’s dime.

I’m also the one who decided to accept the invitation. It isn’t like I have all these clients that are ordering me to show up to take a deposition. I always felt like I was lucky. Also, I didn’t have to work. What grinds people down who travel a lot is they have a tough workday, sometimes 6:00 PM to 7:00 PM. They run to the airport, stressed out and land at midnight. You don’t have a chance to have a normal meal and I didn’t have that. My actual work was not stressful and I didn’t have surprises over time. I always knew when I was supposed to start and stop.

I want to get into the book Point Made: How to Write Like the Nation’s Top Advocates and it’s now on the second edition, which made me feel old because I remember the first edition quite well, but this is a great resource for people who are wanting to learn how to improve their legal writing. Tell us about how you decided to write the book and what your approach was? What was going through your mind as you decided to do this?

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Legal Writing Technology: It takes a while to find something you could share and explain.

It’s a good story that will make me look passive because as with the other thing we discussed it was somebody else’s idea. What happened is I wrote an article about the chief justice. This was early on when I knew his reputation as a brief writer. This was right before the time he’s nominated for the Supreme Court and instantly, chief justice. The article is called Five Ways to Write like John Roberts. It was something that I spent a fair amount of time on but I can’t remember how I distributed it because there was no social media, but somehow it got a wide following.

In Oxford University Press, there’s an editor there who’s a smart and savvy guy. It was his idea for me to write Point Made. He contacted me and thought that this was incredible. They try and break these things down into steps and thought of writing a book so I did. I’m now finishing the third edition, supposedly. When you look at it, it doesn’t seem like it would be that hard but believe me it’s hard. Especially the first book. Point Made was my first book and I would have done some things differently but I also think it was an absolutely incredible experience to immerse myself in great advocacy and great brief writing. Also, try to figure out what the heck is going on, make it concrete and try to break it into 50 tips, 50 lawyers and the like. It was a big project.

What was your process for writing the book?

Messy. These things seem obvious not only in hindsight to me but it was also difficult back then to get briefs. You didn’t have all these online libraries. I had an absent-minded professor approach. I had stacks of briefs everywhere and I did have people working for me but at some point, I had settled on a set of techniques and tried to make them concrete. I also had to stop collecting briefs. I’m not ashamed to say I do love what I do so I did want to keep reading and staying in student mode but at some point, I felt I figured it out. Here are 50 techniques and 50 advocates.

I would pick up a stack and try to find good examples. The truth is, even if you read a brief by a luminary, it takes a while to find something that’s not only great but you could share and explain because out of context there are a lot of sentences that wouldn’t be meaningful. I traded excerpts and reconsidered some names. Once I got to that part it was easy. Putting this kind of book together was easy. It was figuring out how to break advocacy down to 50 techniques.

I can imagine the funneling process for that could easily get extensive if you weren’t willing to cut yourself off at a certain point.

Speaking of being old, I look at the 50 I had in the first edition. Someone passed away, some have been mired in scandal. You can’t freeze time. You want to say, “This is a negative profession. I’m trying to be positive. Here are 50 great people. They didn’t get the memo that they are supposed to behave and stick around to keep my list timely.”

I’m trying to imagine going through that process, before the age of readily electronically available briefs, either on Westlaw or Lexis. Pacer is still around but you still had to find them. There wasn’t some brief bank that you could go pick and choose from that would give you great examples of the points you are making in the book. That’s one of the things that is so helpful about the book is being able to flip to a specific point and seeing examples of the point being illustrated in the book by advocates that most of us have heard of. It also reminds me that Barack Obama has been a lawyer and advocate. You’ve got a few examples. It may be in the first edition and not the second. I can’t remember but it’s neat to see different examples from people who are in lawyer households anyway and maybe household names.

I tried to have a diverse set especially nowadays, people will criticize any selection but I did try to put some surprising names in there. I had some Texan and personal injury lawyers in there too. I try not to be too biased toward my own familiar zone of huge law firms. The third edition will be the same. I’ve got some people who are out and new people coming in.

I will identify one of the Texans that you are referencing and that’s Joe Jamail. There’s a phrase from him about hoodwinking Wall Street and cooking the books.

That’s the G-rated stuff. He got a little more powerful than that. These are family books. It must be suitable for kids. He had quite a personality from what I understand. I know I saw a video clip of this infamous deposition with him and he was not a wallflower.

Not a bit. His reputation definitely preceded him. In your approach between the additions are you looking to update the lessons much or is it more about refreshing the examples that you are giving in the book?

Does your advocacy change or does it seem like it is? For example, we wouldn’t want to draw a lot of conclusions right now when we are just getting out of COVID. People are thinking that some things have changed in trials even in logistical matters related to hearings and depositions and even brief writing. I don’t think advocacy changes that quickly but it’s possible that what makes somebody stick out changes and you have different priorities so I try to be sensitive to that.

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An example would be when I wrote the first edition, I know I have a thin chapter in there about tables, graphs or visual aids. Nowadays, that’s much more important, common and much less controversial. Some things did change. I try to look back even for another purpose. I was looking at Marshall’s Brown V Board of Education brief. Although the types of words changed and we did see some more formal style than we would see in the last couple of years, a lot of what made that brief great similarly would make briefs great nowadays. What people think of as a great advocate might be changing too because there is this push to have more diversity and not be maybe so elitist. I’m trying to be sensitive to that as well.

That’s an interesting point about visuals. I will look forward to seeing the third edition because we have had some guests on the show that talked about visuals and briefs, how important and useful they can be and illustrate complex concepts. This has been more than a 15 year project for you. Have you seen much change in the form of legal writing? We were taught in the age of Bryan Garner, “Let’s use active voice and avoid the passive.” Are you seeing shorter sentences and breaking them down into more simplistic terms? Are there any generalizations that you can even draw?

I try to be empirical about these things because of the BriefCatch, I do have a bunch of tools, analytical tools and statistical tools that measure whether things are changing. The truth is if you go back to Holmes and Jackson in their own ways had a direct personal style. It seems like we are getting better or further away from what people call old-fashioned or archaic writing. I’m not totally sure that’s the case. I don’t see that with law students for example. If anything, I feel they are more formalistic now and a little stiffer than even when I started.

At the same time, if you want to get attention now as an appellate advocate or frankly as a circuit court judge, although your sentences are not necessarily crisper and shorter, you are rewarded or at least you get in the news if you do things that are a little bit out there like pop culture references or some strange analogies. Overheated is a loaded term but let’s say fiery rhetoric. It’s interesting. I’m not sure if sentences are getting better. That’s probably more of a myth that people are writing more in plain English, whether they should or not.

The kinds of things people talk about and the techniques they use are definitely getting more conversational. What I would like would be to preserve some of that. I understand our culture is also much more casual now. Some of that is good but sometimes people will take something a little hokey or corny, a little quip or a movie reference. That’s what makes you a great writer. It may or may not depending on the context. Even if it’s something that does work for the occasion, as you were suggesting before, what matters is not whether you have something from the latest Game of Thrones in your first paragraph, which is always what the legal media will cover.

What about when that fun part is over and you are analogizing a distinguishing case line doing textual analysis of statutes? Fewer people are good at writing about those things. It’s interesting. A lot of things are coming together. There’s more of a celebrity culture especially for judges but also for lawyers. We are getting more casual but it takes a lot of foundational writing skills to write crisply and clearly. It’s not like it’s a switch that you can turn on and say, “I’ve got it. I’m not going to write in convoluted prose. I’m not going to use these legalisms.” You have to have total control over what you are trying to get across and the links between the points, the most reader-friendly ways to articulate them. It’s a lot harder than people realize.

Have you seen changes in the approaches that good advocates are using from switching from paper to electronic briefing?

Hyperlinks, in cases and in general. I know a lot of judges appreciate that. Some courts are now requiring it. I know it makes a lot of people’s lives easier. They don’t have to have that mad rush to file but otherwise, at least, from my own vantage point, I don’t see that technology and the fact that you can file things electronically. I’m not necessarily sure that those are making people more efficient or more effective in themselves. It probably depends on what tools you are using and whether you are taking the time you now don’t have to spend driving to the courthouse or getting someone else and using that time and energy to up your game. Sometimes the mechanical part of writing is too easy that it can make us a little soft and there’s got to be a happy medium.

That book is a great reference for legal writers of all ilks but you took the time to write another book, geared specifically to judges that one is Point Taken: How to Write Like the World’s Greatest Judges. What strikes me about that title is, did you go outside the US?

I had to cut it off somewhere. There are a lot of countries out there. I needed to stick to English-speaking jurisdictions too. I have some Brits. I’ve got Lady Hale that I know in Assumption is now on the High Court. Australian Justice Kirby and some Canadians as well. That part was fun for me and I’ve gotten to go abroad and work with judges. What I know would be the American judiciary. If there’s one thing that, even now with global tensions, we are still the leader of it would be judicial opinion writing. Everywhere, I would go outside the country back when we could go outside the country easily, that is one thing I noticed. They all know Scalia, Kagan and Roberts.

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Legal Writing Technology: What people talk about and the techniques they use are more conversational.

They know their names, styles and have all these questions for me. I know there are issues with the judiciary but that the overall level of opinion writing in America is much higher than people realize because they haven’t had the chance to read opinions from these other countries, which are often almost impenetrable. The problem with judges is they don’t get any feedback. Everybody kisses their you know what all day long, 24 hours a day. This is also around the time I started being invited to train all the Federal judges. You have to think through what you are going to do, get up there and try to purport to tell judges how to write better opinions.

Do any of them ever say, “Mr. Guberman, how many opinions have you written?”

It’s funny because I still remember the first time I spoke at a Circuit Court Conference and it wasn’t the friendly Fifth Circuit. It was the Eighth Circuit though, which is nice. It’s midwestern. I was concerned about that to be honest, when I’ve gotten that reaction, it’s from summer associates, believe it or not. I never get it from law firm partners and I definitely never get it from judges. It’s because I’m careful and it’s also intuitive for me and natural because I wouldn’t even dream of thinking that I would come up with my own system of writing opinions.

What I have always done with judges is like what you are talking about with Point Made. Trying to look at judges who are widely renowned, universally respected and try to show other judges exactly what those judges are doing. For that reason, I have had 100% positive experiences with judges including the Supreme Court justices. Confident Circuit Court judges I have come in contact with are curious and much more open-minded than you might think.

I suspect that at least with the new judges, one of the tasks is to inform them that they don’t already know the real function of judicial writing, which is to convey the decisions in a way that the reader, the consumer of the American legal system can understand. If that’s true, I can see why judges would be open-minded to suggestions on how to present their opinions because you describe those dense opinions from other countries and it makes me think about reading a Texas case from many years ago and you can’t even figure out what the court is talking about.

There are quite a few too. I don’t want to overhype equality in America. In Texas, I have read my own share of Texas cases that were not easy reads as well. Not by any of the ones reading because they all have really good taste. To your point, I’m always careful not to say anything that I learned from all these judges but the truth is I don’t think they know because the legal system and society don’t know. I’m not sure if they know what they are aiming for. You said something about making it understandable to the community and the thing is, are you supposed to make it understandable to high school students, which is what Justice Thomas said he strives for? Are you supposed to make it understandable for educated adults or to the parties but not necessarily anyone else, assuming that few people will ever read it?

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Are you supposed to make it good for law students? They are the main constituency of judicial opinions. You are supposed to make it understandable to lawyers. It’s certainly not clear to me either what exactly you are supposed to do. At least when people write briefs, even if they find it tedious, challenging or both, they at least understand what they are supposed to do. You are supposed to convince a judge or a panel of your client’s position, but opinion writing is not clear at all.

People say, “Don’t grandstand. Don’t do anything clever.” I’m not saying we should feel sorry for the judges but I can see why they get frustrated. They see all the ones that get all the praise and do what some would call grandstanding or drawing attention to themselves. They are trying to figure it out, “I did something. Look how accessible it is to cite Hamilton or the Bachelor.” The other judges hear that and they think, “What we are supposed to do is write for the masses.” Write an opinion that anybody can understand, but then they get criticized for that so then they try to be more formal and people complain that the opinions are too pretentious or pompous. It’s not easy.

That’s a great point about the different audiences that are susceptible to judicial legal opinion writing. I can appreciate how difficult it must be to go in, try and teach Federal judges how to write opinions. I have already expressed gratitude on behalf of the bar for your work in helping lawyers write better briefs. Another function of our show besides talking about nuts and bolts things like legal writing is to talk about legal technology. One of the things that I have seen coming from you is a lot of discussion of the product BriefCatch. We are interested in ways that technology can help lawyers, write better briefs, research better and we are also interested in educating lawyers on these tools. These are things that unless you happen to troll Ross Guberman on Twitter, you might not necessarily know about some of the things that are going on out there. We are privileged to be members of the Appellate Twitter so we are already fairly well educated. Tell us about BriefCatch, what it is and how you’ve got started with that?

No doubt that it’s an exciting time for legal tech. If the general press says that legal tech is the hottest tech sector, we are not usually at the vanguard of things so hats off to you, America’s lawyers. As I did all these workshops over the years and I still do them on Zoom, I would meet a lot of people who would say that they would take my classes or even follow me around and take them more than once but they found it hard to remember everything, let alone put it into practice. Early on, people would talk about macros like, “Could you make a Word macro?” You realize macros are not a solution if you are trying to take everything you want to help people with and make it widely available. I ended up looking into making my own software, which is a fairly intimidating thing. You have to figure out what you are going to do and find a developer. I did do all that. There was some trial and error. I certainly didn’t end up with the first developer that I hired. I can tell you that much. It launched a few years ago and it has been fantastic. I’m grateful for how it’s gone. I released or launched a new version and that’s a big deal.

I don’t want to make myself into some angel. I make money off of it. It’s for-profit but it’s also helped a lot of solo practitioners, people who live in other countries have to write legal documents in English much of the time or some of the time. A lot of law schools are buying it now. It also teaches a lot, which is not something people focus on as much. The main point is to let you instantly edit your legal work product or other types of writing too but it is designed for lawyers and judges. It’s going to take something like 10,200 different rules that will locate your Bluebooking and fix that. It will give you all sorts of powerful verb choices to replace 3, 4 or 5-word phrases and mix observations even while you are using case law. It does all sorts of things to your product if you want to polish it up. Especially in this new version, I have a lot of tips, tricks and explanations.

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Legal Writing Technology: The judges, legal systems, and society don’t know what to aim for in legal writing.

One reason I have been up so late is I have now added a couple of sentences for every example. If there is something about replacements for “accordingly,” instead of giving people options, I have something from Ginsburg, Chief Justice Roberts and Paul Clement. I will have different sentences now so people can have a little bit of inspiration too. It’s exciting. It was luck that I happened to do this when the legal tech was starting to take off. I’m certainly not done. I have other ideas and lots of the biggest law firms have now bought it. Some of the Supreme Court Justices use it. I have never shared any names. It has been fun.

Did you have any background in software development or was it you who took a chance on it?

I’m the one who can’t turn my iPhone off or on. Definitely no. Although I will say that I was not helpless. I have had to learn a natural language processing system for coding my rules. This is like coding. It’s because I’m a customer of software development, I hire people and learned more than I thought I would about how it all works. I’m a professional student so I have enjoyed that part too but I definitely stay away from the actual coding. I don’t want to cause all the electricity to go out or the computer to crash.

I was thinking something about this. The only thing available to us as legal writers was a spellchecker in our software and now there are different grammar checkers out there.

Good research tools now.

For certain, and many of them are either standalone products or Microsoft Word Add-ins. Is that the way that BriefCatch works? Is it a Word Add-in?

It doesn’t work as an add-in. I can’t say too much but we have something exciting coming out. It will not only be a Word Add-in soon. One thing with lawyer is, there are a lot of wariness about things being on the cloud. That’s why it was originally a Word add-in.

I love the cloud myself. It’s a beneficial thing. There is something to be said for being able to click a button in Microsoft Word and being able to have a piece of software run on your document right then and there. I have used a few of them. l track changes to the document, which I find helpful but it sounds like you are looking at the next big thing for BriefCatch and how to deliver that product out to your audience.

To make it effective, you need to give people choices and let them think. It’s the same as when you have a human editor. You don’t want to turn your brain off and sit back. What we are finding is, the more we give people prompts or examples, the more confident they feel and engaged they are so it’s the perfect marriage. You want to use the best parts of technology without letting it control you. You want to remain an active player at all times. That’s also some of these newer research projects that are taking off because you are still thinking through your client’s problem, it’s just the artificial intelligence engines help you find the cases you need much more efficiently.

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It seems like one of the overarching trends in legal tech is efficiency because the lawyers, clients and courts are seeing the benefits of it. The docket loads are what they are. It seems so many products are geared toward that end.

The flip side of that is there is a lot of consternation, especially in law firms because efficiency is not always the number one priority for lawyers when you are billing and there’s some fear that a lot of these tools will end up replacing core functions that lawyers now occupy. It’s a cynical way to think, number one. Number two, it doesn’t matter because the clients want efficiency. Nobody wants to pay $1,000 an hour for Bluebooking.

One thing I noticed on a lot of these Supreme Court briefs is there are sometimes two spaces between sentences when otherwise they are at one. There’s not one client out there who wants to pay these rates for that when BriefCatch and other products too can catch that in 100 millionths of a second. Ideally, as people look forward, there will be more time for strategy, client counseling, thinking things through and those are all high-value enterprises and functions that cannot be replaced by AI. We can resolve this leeriness that a lot of people now feel. They are worried about being made defunct.

The other thing that we have talked about a lot on this show that sometimes gets lost in this conversation is it opens a tremendous potential for access to justice for people that are underserved now.

It’s so true. Legal research products would be great for that. Editing products like mine and others are great but then there’s also this growing document automation sector if you want to call it a sector. Legal Zoom would be an example of something that already exists but it’s more static. This would be something that would be more adaptable and tailored but also easy enough to use that you don’t necessarily need to spend your life savings to get a simple will. If you have decided to get some investment property and you want to rent it out, you shouldn’t need to hire a real estate lawyer for a simple lease.

You can see that with contracts but it’s going to happen in litigation too. Casetext, which I have a marketing arrangement with that I should disclose. Casetext has this incredible product called Compose that takes things like motions to transfer venue, which is predictable. They follow the same factors and talk about the same facts. It turns out what I consider a good draft of the motion to transfer venue and I always think when I see it. How many lawyers now in America are sitting there frustrated? “What are the factors again? How do you know if it’s convenient for the witnesses?” Litigations behind contracts. There is a lot more legal tech now in the AI space for contracts but we are next, resubmissions are next.

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Legal Writing Technology: The general press says that legal tech is the hottest tech sector right now.

You mentioned some of the areas in which there’s clearly room for efficiency to be driven by technology. Side checking a brief, checking the style and spellcheck. This is spellcheck on steroids. It does a lot more than that. I have loved what you said about using examples. It sounds like your wedding Point Made to some degree with BriefCatch but by giving those examples from folks whose legal writing ought to be trusted and held up as an exemplar.

That’s a great point because I’m also trying to look ahead even when I’m dead or fully retired, I still care about students and the profession. Ideally, what we are heading to is a place where people will be constantly learning on the job through tools. I have made a fortune giving workshops and I’m not going to say anything bad about three-hour workshops. People seem to think they are helpful but given the realities of how I see young people changing with their attention spans and the like, this is almost for sure going to be the wave of the future.

I’m sure it’s going to even seep down to high school and junior high too. Everything isn’t going to be in 1 or 3-hour teaching or training blocks. I was thinking that now, basically, I have gotten most of Point Made into BriefCatch, the parts that people would remember because what they get on Point Made would be the examples. The way I explained them sometimes helps people too but that’s all in there now. You are onto something. You could start in law schools since there’s such concern about being prepared for practice. If they could, instead of saying, “Go write a memo for the first semester or write an appellate brief.” If they could be getting help in getting examples, seeing what’s out there, and understanding how actual lawyers write these things could be incredibly educational and more enjoyable too. I never saw any of these things in law school. I never saw a motion or a contract.

We have reached the point at which we thought we might let you get back to your regular daily schedule and maybe it sounds like get some sleep.

I can’t do naps though. I have never been able to take naps. Caffeine is my answer.

Supposedly, by this stage of an entrepreneur’s life, you are not supposed to have to pull the all-nighters anymore but you are clearly hands-on with your product and I appreciate that.

One thing we to do is invite our guests to the end of each show to offer a tip or a war story. We wanted to give you that chance to do that as well. Did you have anything you might want to share with our audience?

I will share something a little touchy-feely that may be appropriate for the times where everybody started coming out of their caverns and going back to the real world. The one thing I would say, especially to people on the younger side in the profession, the first 10 to 20 years is, there’s an enormous amount of negativity about the profession on social media. I have been thinking about this a lot. I would have never gone to law school if I had seen all the constant terrible, negative and nasty comments and I love Law Twitter. That’s a lot of my exposure.

What I would say is that you get praised a lot for being snarky and saying, “Everything sucks. The whole profession is corrupt.” I have seen over and over again for years that if you want to go and find something within the profession, whether it be a sign of a subset of a practice area or a group of lawyers that do things you find interesting or stimulating. Even though you don’t get nearly as much attention for being happy as a lawyer, everybody seems to want to hear tales of woe. There are a lot of happy lawyers out there but they are afraid to say they are happy. Somehow, it’s twisted into, “You don’t realize how miserable you are supposed to be.”

Writing is a good example by the way. You think, “Digital legal writing would be a nightmare.” Even if you can make a lot of money, people are defensive, know everything, plus the grammar is boring. I could have done all that and looked at it that way too but I try to be positive and excited. That would be my thought other than wondering why I stayed up 5:00 AM six nights in a row. Law Twitter is great but it’s toxic too. We all need to stop rewarding the critics all the time. They are all these great stories, people doing fantastic things and there’s not enough attention on that.

It’s worth remembering that a lot of people are very happy in their legal careers but they don’t go to Twitter to talk about it necessarily.

Two people sitting together having a discussion

Legal Writing Technology: The more we give people prompts, the more confident and engaged they are.

You would be mocked a lot of the time if you said something positive about the law. I said something positive about law school once and people acted like I was scandalous. I said something off the wall like, “I enjoyed law school,” and you are not allowed to say that.

There’s always going to be a hater.

Ross, we appreciate you giving us your time. This has a great conversation and it’s been fun to learn about this. Thank you so much.

Thanks to both of you and I hope you have a great weekend.

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About Ross Guberman

Ross GubermanRoss Guberman is the president of Legal Writing Pro LLC and the founder of BriefCatch LLC. From Alaska and Hawaii to Paris and Hong Kong, Ross has conducted thousands of workshops on three continents for prominent law firms, judges, agencies, corporations, and associations. His workshops are among the highest rated in the world of professional legal education. Ross holds degrees from Yale, the Sorbonne, and the University of Chicago Law School.

Ross’s Point Made: How to Write Like the Nation’s Top Advocates is an Amazon bestseller that reviewers have praised as a “tour de force” and “a must for the library of veteran litigators.” Ross also wrote Point Taken: How to Write Like the World’s Greatest Judges, which Court Review called “the best book . . . by far . . . about judicial writing.” He coauthored Deal Struck: The World’s Best Drafting Tips with Gary Karl and created the online contracts editor ContractCatch.

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