Making Your Point: A Special Question & Answer Session About Effective Advocacy, with Ross Guberman

Several months ago, Ross Guberman dropped by the Thompson Hine Cleveland office of Jim Robenalt and introduced himself to Jim and me.   Ross knew that Jim and I do a Continuing Legal Education (CLE) program, and since he is in that business as well, he stopped to engage in some shop talk.  Soon, Jim had Ross on his speakerphone, talking with me as well, and I learned that Ross conducts CLEs  that are aimed at honing the writing skills of lawyers.  Ross later sent me a copy of his book Point Made, How to Write Like the Nation’s Top Advocates (Oxford 2011).

Jim and I are amateurs in the CLE business.  Jim has an active practice as one of his firm’s most seasoned trial partners, and I cannot find enough hours in the day for my book-writing projects.  As a person who does a lot of writing, I was not sure what to expect when I opened Ross’s book, but I was impressed by what I found.  Ross makes the business of writing legal documents—and I have drafted more words for briefs and motions than all the words in my eleven books combined—fascinating.   Better yet, he made several points that I am sure will find their way into my next book.

Because I know the work of a number of the “top advocates” Ross draws upon in his book, I found his approach particularly entertaining.  But I suspect that is true of everyone who read the book.  Ross’s book has been well-reviewed by all who have examined it, so I thought that I would call further attention to his work by conducting the following question-and-answer session with him, which occurred via email:

Getting Into the Teaching of Legal Writing

Q:  How did you find yourself working in this area of the law and develop your expertise?

A:  I drifted into law school on the later side, but that had its advantages.  I arrived armed with two humanities graduate degrees, a book under my belt, and a lot of experience in editing, translating, and publishing.  During law school, I focused on writing and advocacy, working as an articles editor and even writing briefs for a major firm during the school year.  After practicing for a few years, I also worked as an investigative journalist and taught advanced writing at GW law school.

Q:  Have you studied rhetoric, logic, dialectics—those classic areas of argumentation, because much of that work seems implicit in your approach, albeit in a much less esoteric and identifiable (and far more digestible) form?

A:  I was exposed to rhetoric and logic during my graduate work at the Sorbonne and then later at Yale.  I really enjoy translating difficult or dry writing concepts into an understandable form.  That’s probably why I so appreciate those lawyers who do the same thing with the law.

Q:  Any estimate of the number of students to whom you have given instruction?  How many classes do you typically hold each year?

A:  I conduct between 150 and 200 workshops a year around the world, with audiences ranging from a handful to several hundred.  I also speak at many retreats, conventions, and judicial conferences.  All told, I’ve probably worked with about 15,000 people, from law students to senior partners and federal judges.  About the same number have read (or at least bought) my book Point Made.  The variety in topics, venues, and audiences keeps me stimulated and motivated!

The Impact of Good Writing

Q:  Can a well-written brief or motion significantly assist an advocate with a weak case or position in influencing a judge?  Any examples of situations where well-crafted writing made the difference?

A:  Many lawyers win with lousy briefs or lose with great ones.  At a certain point, the law and the facts dominate.  And yet even Chief Justice Roberts has said that in close cases, the writing really matters.  At the trial level and at the state level, when judges are generally swamped and tend to shun oral argument, the writing may matter even more.

Q:  Do you have any way to determine if your instruction is working?  Any examples of your students’ work having been noticed or recognized for its writing cogency, prowess or professionalism?

A:   I’ve received a lot of appreciative notes and letters over the years. Some focus on process, thanking me for helping them enjoy writing or helping them write more efficiently.  Others focus on results, telling me that after using one of my techniques, they won praise from judges or clients.  The patterns can be interesting: My least appreciative audiences tend to be summer associates or new attorneys.  And some of my most enthusiastic followers are at the top of their game: say, federal judges or titans of the Supreme Court bar.

Book Versus Course

Q:  Did you develop your book, Point Made: How To Write Like The Nation’s Top Advocates, based on your experience in teaching?  What is the difference between attending one of your classes and reading your book?

A:  My workshops are practical: In a few short hours, I try to give participants as many concrete techniques as possible to improve their legal writing. I think that Point Made is practical, too, but it also had a quasi-scientific bent: I sought to tease out the differences in writing style between the average litigator and those at the very top of their game.

Q:  I found your fifty selected advocates intriguing—a real Who’s Who at the bar.  I know several of them well, and I could not agree more that their work is exemplary.  But how do you know they actually wrote the briefs you cite, rather than relying on, say a former Supreme Court law clerk working for their firm, if not one of your former students, for producing the final product?  Or does their name on the brief, and top quality work they’ve signed off on, qualify them?

A:  I thought about this recently, after the New York Times published an op-ed about the supposed sin of having clerks write the first drafts of judicial opinions.  When my own book came out, I received a fair number of communications from people claiming that they had “proof” that they were the “true” authors of a certain sentence or two in my book.  I found myself scratching my head, as if I were being to ask to conduct some sort of CSI for brief-writers.  Of course, we all know that motions and briefs are written by teams.  After all, John Roberts probably wasn’t writing memos summarizing cases while drafting his brief in Alaska v. EPA as a top partner at Hogan. The bottom line, though, is that when you sign a brief, you are giving it your imprimatur. I’ve also learned that some of these big names do a lot more line editing than is commonly believed.

Q:  How do you analyze a brief or motion for its writing professionalism?  Do you have a checklist that you employ, say the fifty techniques you have developed for your instructions?

A:  I cannot tell you how many motions or briefs I skimmed in preparing this book!  Many times, I came out empty-handed.  Let’s face it: there aren’t a lot of beautifully written motions in limine out there.  Usually, I know if a brief is a winner after just a few lines.

Q:  What are the most common writing mistake lawyers make in drafting and presenting their arguments?

A: Let me give you three. First, not spending enough time on the introduction, challenging yourself to distill your dispute down to its essence and to enumerate for the court several specific reasons you should win.  Second, spending too much time on the obvious point that you think your opponent is generally wrong, wrong on the facts, wrong on the law, and wrong in its interpretations of individual cases.  Nothing is less surprising in litigation than your view that you are right and your opponent is wrong.  Cut to the chase.  Third, failing to include a short sentence on every page or so.  People have no idea how much readers appreciate the occasional crisp sentence or paragraph.

Q:  Do you have an audio or video version of your course?

A:  I’m no Luddite, but I have no plans to offer Webinars or to use other passive technologies.  I do, however, allow simultaneous videoconferencing or Webcasting of my live programs.

Q:  Is there any software that can (or, in fact, does) assist in improving legal writing?

A:  The best software is free: the readability statistics available in Grammar Options in Microsoft Word.  You can find out the average number of words per sentence, the average number of sentences per paragraph, the average number of syllables per word, and the percent of sentences written in the passive voice.  All of these are combined into an index ranging from 0-100 (try to top 30).

Not Just Advocates

Q:  I understand you’re working on a book about well-written judicial opinions.  I don’t want you to scoop yourself, but are you going to have fifty of the best judges in the business, just as you have fifty of the best advocates in Point Made?  And will they be all living, or will some be deceased?

A:   Some things will be different.  I’m looking for the best writers in the judiciary, not necessarily the best judges.  I’m going international this time.  And yes, I’m looking at deceased judges as well as living ones.

Q:  Do you conduct courses for judges as you do for advocates?  If you do, what are some of the key differences between a well-written brief or motion versus a well-written judicial decision or ruling?

A:   I do conduct workshops for judges, both here and abroad.  The main difference, it seems to me, is this: with a brief or motion, you know you’re writing for a judge.  With a judicial opinion, it’s an open question.  If I ask a room full of judges whom they think of when they write, I’ll get lots of different answers: the winning party, the losing party, counsel for the parties, other lawyers in the bar, casebook writers, academics, the press.  So it’s much easier for me to explain how to write a great preliminary statement than to explain how to write a great introduction to an opinion.  That aside, when it comes to sentence-level style and the fundamentals of structure, great brief writers have a lot in common with great opinion writers.

Q:  Finally, I have noticed in the reviews of Point Made that a number of non-lawyers have praise for your work, and found it helpful.  Any suggestions as to how a non-lawyer might best use your book?  Do you offer a course for non-lawyers?

A:  Part 4 of my book is chock full of 17 specific style techniques—I think that section is the most fun for non-lawyers.  Some non-lawyers also appreciate Part 2, on writing about facts.  I do present to non-lawyers regularly, both in-house and at conferences, and I get a lot of satisfaction out of teaching business writing.  In fact, one day I hope to write a book on that subject as well.

*  *  *

Jim and I have done a number of CLEs since meeting Ross.  He is not just “in the CLE business,” he is one of the stars of the CLE circuit.  We have encountered a number of managing partners and professional responsibility people who know Ross and his work well.  As good as they find his book, I’m told his class is even better.  So I look forward to attending one of his classes when the opportunity arises.  We all need to make our points better, and Ross Guberman has figured out how that can best be accomplished.