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Interview with Ross Guberman – what does he teach lawyers about legal writing?

By November 29, 2011October 18th, 2019law practice

Awhile back I wrote a blog post that recommended Point Made, an excellent book on legal writing by Ross Guberman. As fortune would have it, I ran into Ross at a seminar we were both doing in Alaska for the Attorney Generals’ Office. We had a really nice dinner, and I learned a lot more about him as a result.

I thought it’d be interesting for some of the readers here to learn a bit more about him as well. Ross practiced law for awhile and then went on to become a full-time speaker. Legal writing is so important, and yet so many lawyers persist in using ineffective techniques (simply because they’ve noticed that most other lawyers use them as well).

I admire Ross for the passion and practical knowledge he brings to the legal profession. If I were in charge of planning my law firm’s retreat I’d book Ross as a speaker, without hesitation.

Below is a Q&A that we conducted via email. I hope you find it interesting. To learn more about Ross, you can also visit his company website.

–Your recent book, Point Made, uses an interesting method of teaching: you use examples from briefs that were actually filed to show effective techniques for persuading. How did you first get this idea?

So much of the advice you hear in this profession is about what NOT to do: “Never ask a question on cross-examination unless you know the answer.” “Avoid the passive voice.” “Don’t repeat yourself.”

I wanted to flip things around, focusing less on how to avoid mistakes and more on how to excel.

I also wanted to take an empirical approach. I chose 50 of the best advocates alive, and extracted 50 techniques that set their writing apart from the norm.

–Had you already collected most of the examples when you decided to write the book, or did you have to gather them once you decided to publish? Tell us about that process of gathering the examples.

Although hundreds of books address legal writing or advocacy in general, few include current examples from the top advocates.

So I embarked on my quest to find the best of the best. Long before Oxford asked me to write this book, I had dissected the Chief Justice John Roberts’s brief in Alaska v. EPA. I began there, and then I shifted to other advocates and, of course, to many other kinds of filings, including straightforward discovery motions and other trial motions.

As you can imagine, it’s a lot easier to find a stellar Supreme Court brief than to find a stellar motion for a protective order.

–What was it like to write your first book? What did you learn that you wish you’d known when you first started writing?

I had an academic book and some book translations published before law school, so I was somewhat familiar with the process. I felt a lot more pressure with this book, though, because I knew that people would actually read it!

I think I made the same mistake in putting this book together than many of us attorneys make in writing in general: I spent too long collecting information and waited too long to start pulling everything together. I wound up with too many examples from too many lawyers reflecting too many techniques. I should have cut myself off earlier.

I also underestimated the time you need to devote even after submitting the manuscript. Dealing with marketing, the copyeditors, even the designers—it all takes time, and when it’s your own book, it’s easy to obsess over these details.

On the positive side, you forget everything once you open the box with the early copies and see the book in stores and hear that people are reading it and enjoying it and even changing their approach to their work because of it.

–Have you talked to any of the (still practicing) attorneys that you used as examples in the book after it was written? What’s their take on the method of instruction that you used?

Yes, I have heard from quite a few of them.

The reaction has been positive. Some of them tell me that they hadn’t really known why they write the way they do, so they appreciate my explanations. Others say that they learned quite a bit from reading the excerpts from their colleagues and competitors. After all, they point out, even full-time Supreme Court advocates rarely have a chance to study the writing of other lawyers.

Still others suggest that I should have chosen different briefs or different examples; they sometimes point me to something they’ve written that’s dramatic or poetic but that to my mind doesn’t necessarily reflect a practical technique for practicing lawyers.

I should add that I’ve also heard from lawyers who think that I should have included them in the book instead!

–You chose Obama as an example of a good writer in your book. What effective techniques does he employ in his persuasive writing?

The briefs and cert petitions he signed feature unusually incisive examples and hypotheticals—the same techniques that made him such a well-regarded professor at The University of Chicago Law School, my alma mater. I also hear in those briefs some of the same fresh, direct language that he used on the campaign trail.

–Name 3 writing books, not focused on legal writing, that lawyers could use to significantly improve their writing.

I’m a big fan of the Joseph Williams Style series, so check out his Style: Lessons in Clarity and Grace or one of the earlier iterations.

I also love the recently published How to Write a Sentence: And How to Read One by Stanley Fish.

A little book called Edit Yourself by Bruce Ross-Larson is priceless as well.

I know you asked for books, but I would also recommend a word-by-word study of the writing in such publications as The New Yorker, The Economist, The Wall Street Journal, or the Atlantic.

–What were the challenges in starting and growing your speaking business?

On the substance side, writing is a notoriously tough topic to teach, so I struggled with how to break things down into manageable and memorable chunks. I also knew that most lawyers hated writing courses, so I wanted to find an appealing format that would put people at ease without pandering to them or resorting to cheap entertainment gimmicks.

On the business side, I faced the same challenge that everyone does: No one wants to hire you unless other people have hired you! I am eternally grateful to the law firms and bar associations that took a chance on me early on.

–Do you do all the administrative work yourself? If not, how do you handle the administrative issues that arise in your business?

I do no administrative work. No aptitude, no interest, and no time! I have 150 clients, constant travel, and constant inquiries, and it’s all I can do to keep up with those. So I am lucky to have several terrific part-time employees who work from home to keep the company and me in line.

–How has the Internet and computer technology affected your business?

I have often wondered how consultants used to manage without e-mail. I suppose that clients and consultants and colleagues alike “saved up” their questions and answers for longish telephone calls, so perhaps in the end things were simpler and saner. I know that on an average workday, I get close to 100 emails requiring some sort of response, not including all the emails I can delegate.

From another perspective—and people sometimes don’t like to hear me say this—typing all day on a computer can make legal writing worse, not better. Many lawyers spend a lot of time summarizing and copying authorities on their computer and not enough time distilling their points into clear thoughts falling in a linear progression.

Bottom line: in some ways, the Digital Age is good for business.

–What changes would you make to the typical law school curriculum to help graduates become better lawyers? To become better writers?

My answer may surprise you. I refuse to join the chorus of the many law-school critics today who want to turn law school into an apprenticeship-like trade school focusing solely on workaday lawyer skills. Law school should remain what it has always been: a professional school.

What I would suggest instead is integrating lawyer work product into the doctrinal classes. I know that when I took contracts, for example, I had one of the most brilliant legal scholars alive and enjoyed every minute of the course. But surely we could have reviewed some of the actual agreements in dispute or taken a stab at drafting or redrafting some of the provisions found to be ambiguous.

In upper-level courses on securities or tax or corporations, in addition to assigning the opinions, why not share the parties’ briefs, to get an idea of how lawyers shape arguments and how they could have done so more effectively?

One last thought: I recently came across a document on the history of the LSAT. Earlier versions, I learned, contained a writing component. How about bringing that back?

P.S. If you're a practicing lawyer, check out this Law Practice Assessment . After answering a few questions, you'll get detailed recommendations for improving five key areas of your practice.
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