A week or so ago, LawyerSmack had its inaugural Q&A/AMA with a leading figure in the legal industry – Ross Guberman. Ross is the president of Legal Writing Pro, a training and consulting firm. From Alaska and Hawaii to Paris and Hong Kong, he has conducted close to two thousand programs on three continents for prominent law firms, for judges and courts, and for dozens of agencies, corporations, and associations. His workshops are among the highest rated in the world of professional legal education.

An edited transcript of the live conversation is below.

Punctuation, Spacing, & Commas

Ross Guberman
Hi everyone! Great to be with you all on a 75 degree day in DC!

keithrl
Ok, first and most important questions per a member are: Oxford Comma, Period Spacing, and Justified Type

Ross Guberman 
It took a millisecond before I got an Oxford comma question.

keithrl
I do want to lead off with this question since it was the topic of heated discussion earlier: *Spacing after a period* 1 or 2?

Ross Guberman 
1 space or 2? That’s closely linked with the age of the attorney or judge. Anyone who learned how to type on a typewriter will gravitate toward two spaces. But…..one space is the way of the future! And what Typography for Lawyers recommends. So there.

Note that almost everything on the web has one space after a period.

Ross Guberman 
I see there’s a question about Oxford commas. The recent case about the Maine dairy delivery truck drivers was overhyped. The real question is consistency. The legislation had inconsistent use of commas. 84-85 percent of American commercial agreements do NOT use the Oxford comma.

Emoji & Hyperlinks

brian
1) Do emojis have a place in legal writing?

2) How do I become an expert witness for what emojis mean? If I’m an attorney how do I qualify someone as an emoji expert? (if that’s in your wheelhouse)

keithrl
I also think brian’s question is something that points towards the future. *Emoji in legal writing?*

Ross Guberman 
Emojis for lawyers are best for supervisors who have a caustic style.

ryanlocke
Ross, what stuff have you seen in atty writing that seems ahead of its time

Ross Guberman 
Ahead of its time: Creative use of timelines rather than a list of dates.

Ross Guberman 
Also hyperlinks for all authorities. And corporate-style executive summaries.

Chadwick
I really like that idea – The timeline

keithrl
Yes please C-suite summaries.

Chadwick
I do PI at times, and doing a timeline of treatment would be just delightful

Ross Guberman 
So many judges tell me in my surveys that they hate full dates and prefer timelines or at least phrases like “a month later.”

Chezky
Should references to websites/email addresses in briefs be hyperlinked?

Ross Guberman 
Websites yes, but email address no. I think some applications automatically hyperlink websites in briefs.

ryanlocke
I’m waiting for the brief with a link to an explainer video

Ross Guberman 
Posner once said he’d be open to watching videos!

Chadwick
Before or after he went insane?

Ross Guberman 
There are trademark lawyers who never include a picture of the alleged infringement.
It was before he……retired from the 7th Circuit.

Footnotes & Formatting

Mark
Ross, my boss often tells me that “having to read footnotes is like being on your honeymoon and having the next door neighbor knocking on your front door.” He’s an appellate attorney and refuses to use footnotes in all but the most unique circumstances. What are your thoughts on footnotes?

Ross Guberman 
Mark, your boss did not make up that line. I’ve heard it 1,000 times! The real question with footnotes, for the anti-footnote crowd, is what they propose one does with material that’s normally in footnotes such as additional authorities for the same point, statutory language surrounding the disputed text, etc.

keithrl
Someone was asking earlier – other than writing to preference of the judge, *what is your take on justified / non-justified formatting?*

Ross Guberman
I defer to Matt Butterick, author of Typography for Lawyers. He says nonjustified. Justified text leads to inconsistent spacing from line to line.

Chezky
How quickly do you see “cleaned up” taking off?

Ross Guberman 
“Cleaned up” is hot right now! Though I just had lunch with two high-up appellate judges who were opposed.

Chezky
I never understood why some italicize citations and some underline. Any insight?

Ross Guberman 
Underlining, like typing “–” for a dash and using two spaces after periods, stems from the typewriter era. Italicizing case names will give your work a more modern look.

How To Improve Your Legal Writing Skills

benler
My question for Ross
I really enjoy writing and want to hone my craft. How do I do that when I don’t have a skilled writer supervisor? Or anyone in my firm willing to spend that extra time to help me?

Ross Guberman 
Benler, that’s a common problem, and to same extent it’s not worth getting into power struggles. Get a free trial of my new editing software BriefCatch!

keithrl
Benler For me, it was a matter of getting my hands on as many legal writing books as I could. And then trying to read “good” commercial writing – the Economist, the Atlantic, etc.

Ross Guberman 
It’s good to read top-notch commercial writing, but even better to analyze it sentence-by-sentence and paragraph-by-paragraph.

Stedman
Any good examples we can run out and get?

Ross Guberman 
Good example of non-legal writing: Economist, Atlantic, New Yorker, and for corporate types, the WSJ. Here’s an article I wrote once called 5 Ways to Write Like The Economist 

keithrl
That’s actually a good question/thought – in Point Made you go out of your way to analyze briefs/opinions at a “tactical” level – how do you approach that? What was your methodology? Has it evolved over time?

Ross Guberman 
I tried to be somewhat empirical in Point Made. I looked at motions and briefs by widely renowned advocates and tried to look for choices they made (both big picture and little picture) that were different from the choices that the average litigator or appellate advocate makes.

Over time, I’ve expanded my reach to little-known advocates who are nevertheless stellar. And I’ve concluded that a few lawyers in this country are famous for being famous, at least when it comes to writing.

Use of Pictures and Modern Layout Styles

kirs
Use of pictures in briefs? I would much rather take a screenshot of an email or document and insert it into the body of the Answer/Motion rather than attach as an Exhibit. My older colleagues think I’m committing sacrilege…

Ross Guberman 
No, you are right. Over and over I hear judges (including old ones) clamor for visual aids. Are they concerned about authentication or something? Or do they just not like screenshots? Or do they object to anything visual in the body, period?

kirs
All of the above, depending on which old white guy I’m talking to at any given moment. I personally like that the doc is right there, in the body, no shuffling back and forth to find the exhibit.

Ross Guberman 
Ha! Well I’m a sort-of-old white guy, but I appreciate visual depictions, too.

kirs
Better odds the arbitrator (in my case) will actually read the damn thing

Ross Guberman 
With arbitration filings sometimes 200+ pages, you have your priorities straight.

keithrl
Along those lines: Is there a future for a contemporary style brief? We’re still formatting things like the printing press is the only tool available.

We all use desktop layout software. Could there be a “magazine” style brief? Columns, in-line pictures, etc.

Ross Guberman 
Multiple columns? Never underestimate the endurance of tradition in this profession. You would need an influential judge to suggest the practice, I think. Or maybe Californian litigators will lead the way.
Keep in mind that about 1/3 of briefs are still filed in Courier font in 2018.

keithrl
haha

kirs
With that mentioned: if you had your druthers, in what font would you submit all pleadings?

Ross Guberman 
Century Schoolbook? Garamond? Palatino Linotype? I use Palatino for my workshop materials.

ryanlocke
Have you seen any good examples of tables in briefs?

Ross Guberman 
Many good examples of tables. The best use is when there are competing interpretations or recollections of an event or language. I have even seen excellent use of tables in claim-construction briefs in patent litigation.

More On Emoji Use & Interpretation

keithrl
I want to come back to emoji. I know I’ve had a conversation with ryanlocke and he said he’s communicated with clients via emoji. It seems inevitable that emoji start showing up in discovery, etc. Eric Goldman released a law review article on emoji.They’re going to show up in legal writing – not for persuasion – but for explaining to the court what the hell they mean.

Have you seen any examples of this?

Ross Guberman 
In the recent kerfuffle over the VA Secretary’s European travel, there’s talk in the legal docs about the meaning of “XO” at the end of a message–whether it really means “kisses” or “kisses and hugs” or something else.

XO isn’t even an emoji, of course!

Chadwick
I thought that had an established meaning.

Ross Guberman 
The interesting thing about an emoji, as it would be manifested in discovery, is that an emoji is itself evidence that the preceding words don’t mean what they seem to mean. An emoji is a semi-conscious admission that a sentence might seem, say, rude, but the writer intends to show that it’s actually all in fun. But a smiley face could mean “I meant that to be nice” OR it could mean “I’m being passive-aggressive.”

keithrl
Right. There was this case last year and a Grand Jury said the emoji did not constitute a threat.

Ross Guberman
Like “I know where you live :-)” vs. “I know where you live.” My main professional experience with emojis is when BigLaw partners accused of being nasty to associates start putting smiley faces at the end of angry, critical emails to soften the blow.

Chadwick
What about the ambiguity cross platform of emoji? :man-man-girl-boy::gun: can mean widely different things across platforms

Ross Guberman 
I guess you retain an emoji expert in that case!

Using BriefCatch

keithrl
I had a question from someone earlier about BriefCatch – give us the elevator pitch.
And how does it work?

Ross Guberman 
The tool scans any draft instantly for thousands of possible editing suggestions. It also looks for patterns in your writing and will let you know which words or phrases you’re overusing along with strengths and weaknesses of a draft. And it has a scoring system that lets you compete with yourself and track improvement.

It’s been out for just a month, but so far so good!!!!

keithrl
I’ve seen lots of positive feedback on Twitter.

Ross Guberman 
Russian bots, no doubt!

ryanlocke
I know the problems with the macOS version of Word, but is there the possibility of a cloud version or stand-alone app in the future? Or do I need to dust off Parallels and come to terms with it.

keithrl
Oh yeah, I hear that complaint a lot. Where is the Mac version!

Ross Guberman 
For now we’re offering a no-obligation no-credit-card free trial: www.BriefCatch.com  We could do a cloud version, but there would be a trade-off with security.

keithrl
That’s fair. Security/privilege seems to concern people with it.

Ross Guberman 
I got a touching email today from someone willing to fork over $500 at Best Buy to get her first PC ever just to use BriefCatch. And she was a Mac-or-bust person before.

Mark
Is there any way you could put the analyzer to a web based platform? For example, I have the trial and I loved analyzing my brief to see the various scores. When my boss wants to check his brief, because he uses a Mac, he has to send it to me.

Ross Guberman 
We’re working on it! Web-based has some security issues, as do all web-based apps for lawyers, but it’s a tradeoff some are willing to make. And thanks so much for the kind words, Mark!

Wrapping Up & Bullet Points

keithrl
Okay, I have a final question cause we’ve already kept you for 40 minutes.

  • Bullet points are great for conveying a sequence of ideas.
  • They’re used all the time in business writing.
  • Why don’t more people use them in briefs?

Ross Guberman 
More and more people are using them in briefs. Even DOJ is! A few good opportunities for a bullet-pointed list: pivotal but complex facts, the three or four main reasons you should win, and, for the ambitious, reasons a case is analogous or distinguishable.

keithrl
Do you have a blog post or article that highlights a couple good examples?

Ross Guberman 
Also good for witness or expert qualifications. Yeah I have a book with a chapter of examples 🙂 (see there’s an emoji) 

keithrl
ha! And it’s a great book, I have both editions. Ross – Thank you so much for taking the time out of your day to answer some questions with us! When/if you make the cloud version available, let us know!

Everyone else – you can always access BriefCatch (& discount) via the membership discount page.

Ross Guberman 
It was a pleasure! Thanks, Keith, and thanks to all! Cloud version won’t be for a while, so steal a PC if need be and check it out. A good rest of the week to all!


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