An Interview with WordRake Founder and Legal Writing Expert Gary Kinder

Gary Kinder

After years of teaching legal writing courses, Gary Kinder noticed a pattern in the mistakes people were making. Once he noticed, he knew there had to be a way to make editing for clarity and brevity quicker and easier, freeing writers up to do more detail oriented editing. We asked him about how he came to create WordRake, and he shared the story with us.

What is your role and how did you get to where you are today?

After law school, I did not want to practice just yet. I passed the Florida bar, briefly taught Legal Writing at the University of Florida, then headed West to see snow. I worked as a bellman in the Sun Valley Lodge, tried cases one day a week as the county’s assistant prosecutor, and sold my first article to a national magazine. One cold January night, while working the front door of the Lodge, I met the wife of a famous novelist, who introduced me to her husband, who introduced me to a New York agent, who turned me over to his son, who was just beginning his career representing authors. He sold my first book to a New York publisher, and he is still my literary agent.

Eventually, I moved to Seattle, where I wanted to be an in-house editor for a big law firm, to help partners improve the important briefs and still give myself time to write. I have always enjoyed teaching—while in law school, I taught at the university’s College of Journalism. But I did not intend to teach lawyers how to improve their writing, until a Seattle firm asked me to teach a writing program, and that started a 30-year career teaching writing programs to lawyers around the country.

How do you define good legal writing?

All writing is the same, whether or not “legal.” The only difference between good writing and good legal writing is that good legal writing requires us to support an argument with citations. We don’t have to do that in a novel or a report. And litigators have to meet page and word limits, while other writers do not.

When we write a brief, “writing like a lawyer” can be the problem. Good legal writing is not combative, not recalcitrant, not unyielding. We sometimes forget we are officers of the court, there to help the judge do their job. The most effective way we can do that is to write like warm, logical, compassionate, intelligent, fair-minded humans.

We start by getting out of the office and gathering the best facts we can, like a good investigative reporter. No technology can help us do that, not even Artificial Intelligence. We use those facts to tell the judge a story. After reading our Facts, a judge often has already decided the case.

The key to all good writing is removing every word that does not convey meaning. Otherwise, judges and clients have to search through our words to find those with meaning and try to understand what we hope to communicate. We connect with judges and clients much faster if we use fewer words. I tell litigators that one of the most effective messages they can send to a judge is the number at the bottom of the last page of a brief. Rarely is that number below the page limit. If it is, that signals to the judge we have a good case and we know it well.

Why is good writing important to being a good lawyer?

In 1989, I met with a new federal judge who for decades had been on the Seattle trial scene as a consummate trial lawyer, ethical, and not afraid of the big or unpopular case. I still remember, word for word, two sentences he told me: “If you really do write well, you win more cases. It’s that simple.”

How do you use storytelling in legal writing?

Stories engage a judge and his clerk, and they interest clients. But few lawyers understand the concept of story; many think of story as “fairy tale” and therefore “frivolous.” Although we’re constantly told to “tell the judge a story,” ironically, no one ever teaches us how. In the Litigator Series, I teach lawyers first the meaning of story, then how to tell a story in their Facts, which helps to capture the judge’s imagination.

As the founder of WordRake, what made you think of automating the editing process?

To describe how WordRake came to be, I have to use the word organic: It just evolved out of my teaching. I would be in front of a roomful of lawyers editing a sentence on a screen to remove the unnecessary words, and I would see patterns. As time passed, I saw more patterns, and these patterns consistently exposed words not needed to convey the message. After a few years—and this is key—I realized I had seen no new patterns, so I had a finite set of signs that could help anyone spot needless words.

One day, I was teaching a writing program for the lawyers at a large patent firm. During a break a partner approached me and asked if I’d ever thought about trying to patent these patterns. Twenty years and twelve patents later, that lawyer has retired and the firm remains our patent counsel. Those patents form the basis of the WordRake editing software.

I still see dull and needless words in memoranda, contracts, and briefs; in magazines, novels, and books of narrative nonfiction—which means that even the best writers and their professional editors fail to see these unnecessary words. WordRake will highlight them. It even highlights the unnecessary words generated by Artificial Intelligence. For people who care about their writing—no matter what profession—the ability to spot unnecessary words quickly is indispensable.

Where do you hope WordRake will go from here?

Not long after we launched WordRake in 2012, the head of purchasing for a major city predicted that WordRake would become “as ubiquitous as spellcheck.” It hasn’t quite achieved that stature, but it is used by many thousands of people, from lawyers to business managers to novelists, who have to write and need their writing to be crisp and succinct. The software frequently surprises even me with some of its sophisticated edits.

What do you say to lawyers who fear tech because they don’t want to seek “outside” help for their work?

I’ve heard this statement mostly from law professors and partners, who don’t want students or new associates to rely on technology to help them; they forget that the same statement was once leveled at engineers—before they were allowed to use calculators. Just as few people can instantaneously multiply pi times any number greater than one, no one will ever be able to instantaneously discern every word with no meaning. The hard and creative work comes in solving that mathematical problem, or picking the right words and arranging them for maximum effect.

How can folks take advantage of your new legal writing classes?

Everything I’ve taught over the past thirty years, and a lot more, is now available in online courses at garykinder.com and writingforlawyers.com. I introduce, narrate, and wrap each course, which is filled with original animated graphics to illustrate the points. We have courses for litigators, associates, and legal professionals—how to gather the best facts, how to tell the judge a story, how to capture the judge’s imagination, how to build a bulletproof argument, how to get it down quickly, how to meet page limits, how to write a memorandum, how to spot unnecessary words. I find the video courses more effective than a live presentation because I can cover more material, and the lawyers and legal professionals can watch the videos as often as they like within a generous time frame. Also, a trainer or partner can facilitate them with no preparation—just hit the “ON” button. Here are links to four mini-lessons at our website:

What is the biggest misconception the general public has about legal writing?

That it has to be dull. The two purest forms of story are athletic contests and legal cases, two sides pitted against each other with the outcome unknown. If lawyers remove unnecessary words and gather the best facts, their writing can be as engaging as any novel.

How would you like to see legal writing change in the next 10 years?

Writing is the most important thing, professionally, a lawyer does every day. The ability to write well crosses all courses we take in law school, many of which we will never use again. But we will write every day of a long career. Law schools should recognize this. I would like to see Legal Writing instructors become “professors” and earn tenure.

Do you think there is a difference between writing for litigation and writing for transactional work?

There is a distinct difference. I encourage new lawyers to remember:

  • Transactional lawyers look forward – how can we memorialize this transaction so neither party can deny the agreement without consequences?
  • Litigators look back – an event has occurred, and because of it, somebody claims to have been wronged and demands to be made whole.

What advice would you give to legal professionals who are just starting out in the legal world?

Volunteer for every assignment, and become indispensable.

What would you say to senior lawyers who don’t coach young writers to develop their skills?

I cannot tell you how many times I have heard partners talk about their good fortune in having a mentor back when they began their practice—the mentor who returned their writing looking like it was bleeding on the page. They’ve never forgotten that. Associates working with partners who tear apart their writing are the lucky ones.

At a minimum, senior lawyers must coach an associate’s inexperience, or that associate will continue to make the same mistakes, and the senior lawyer will have to edit the same problems over and over. I encourage associates to ask for feedback every time they work on a writing assignment. The more experienced lawyer must show the associate why that piece of writing does not work and how to make it better. I also advise assigning lawyers never to change an associate’s writing to make it different; only to make it better. Let them keep their own style. Assigning lawyers must remember they are developing not an associate but a colleague.

How can technology improve legal writing?

My editor began his publishing career at 22, editing Kurt Vonnegut. He is a bright Stanford graduate, and after 45 years he has edited many bestselling authors and winners of the Pulitzer Prize and National Book Award. He told me long ago that writing began to deteriorate when we went from the typewriter to the word processor: Instead of having to re-type a sentence, a paragraph, a page—tightening the writing each time with a better word or phrase here and there—we now could cut and paste whole sentences and paragraphs, even pages, after writing them only once.

Technology cannot improve writing. It can catch typos, disagreeing tenses, and the same word appearing twice. It can check citations and spot inconsistencies in contracts. But no technology can make our writing better. Nothing but writing and studying good writing will help us improve. To get better at writing briefs and memoranda, we need more time—rare in a law practice. But here’s how to create more time: focus on getting that first—messy, awful, embarrassing—draft down within minutes. Beginning to end. One page, maybe two. Nothing in front of us, all from memory. Then expand from there.

Getting the first draft down quickly is one of the many things I have taught over the years, too long to explain here, but I’ve included it in the course Meeting Page Limits.

How might technology competence connect to the legal writing process?

Understanding the technology available to help us avoid mistakes and hasten our writing process is crucial, even mandated in some states. It can relieve us of the tedious parts—outlining, checking citations, aligning words and phrases, editing, organizing evidence for trial—but we still have to do the hard part—the thinking and the writing. I encourage all lawyers not to rely on Artificial Intelligence, which requires the writer to double-check every sentence for authenticity, taking more time than it saves. AI has been with us only a short while and already the nightmares are legion: How many lawyers and law firms have been bit hard after relying on AI—which cites cases that don’t exist and holdings never written? Will that ever stop? Remember that when AI gets beyond “hallucinating,” it still can learn only from Whatever Is Out There, taught by Anyone Who Writes, homogenizing Everything Ever Written. This makes AI writing mediocre at best, and mediocrity does not please clients or convince judges. I predict that associates who do not rely on AI for their writing will consistently score higher in Associate Reviews, keep clients happy, convince judges, and please more partners.

About Gary Kinder

For the past 30 years, Gary has taught more than 1,000 writing programs for the American Bar Association and law firms like Jones Day, WilmerHale, and Latham & Watkins. He is also author of the New York Times bestseller Ship of Gold in the Deep Blue Sea. Adopted in thousands of law firms, companies, agencies, and universities, his editing software, WordRake, is available for Word, Outlook, and Mac. It is the first and only software in the world designed to help all professionals edit themselves inline for clarity, brevity, and, if desired, simplicity. Harvard Law School has called it “disruptive technology.”

About the Legal Writing Interview Series

WordRake founder Gary Kinder created the software to help legal writers edit for brevity and simplicity. In continued dedication to the most effective legal writing, this Series highlights the experience and advice of experts from professors to writing coaches to litigators. Looking to help boost your legal writing skills? Get a free 1-week trial of WordRake here.

Our Story

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WordRake founder Gary Kinder has taught over 1,000 writing programs for AMLAW 100 firms, Fortune 500 companies, and government agencies. He’s also a New York Times bestselling author. As a writing expert and coach, Gary was inspired to create WordRake when he noticed a pattern in writing errors that he thought he could address with technology.

In 2012, Gary and his team of engineers created WordRake editing software to help writers produce clear, concise, and effective prose. It runs in Microsoft Word and Outlook, and its suggested changes appear in the familiar track-changes style. It saves time and gives confidence. Writing and editing has never been easier.