Writing to Win: The Legal Writer

Introduction to the New Edition

Good writing is timeless. Except, of course, when it’s not.

Periodically over the last ten years, I thought about revising my original book on legal and professional writing—Writing to Win: The Legal Writer. But as egocentric as it might seem, for a while I never found much I would change. Sure, some of the references marked the book as a product of a slightly earlier time—the references to the O. J. Simpson trial, Kenneth Starr, or vice-president Al Gore. But for the most part, the book seemed to illustrate the maxim that the principles of good writing don’t change all that much over time. A good brief in 1965—much less in the late 1990s when the book was written—is still a good brief today. Ditto for complaint writing, contracts, and even judicial opinions.

And yet: In a variety of ways, writing in many parts of the legal and business worlds has changed more since that book was written about a decade ago than in any comparable period over the last five centuries. We shape our tools and then our tools shape us, wrote the media theorist Marshall McLuhan a generation ago. Technological changes transform not only the methods of communication but their style as well. The invention of the printing press centuries ago not only altered the dissemination of information in Western cultures, it changed the way people spoke and the way they wrote—and there were constant complaints about it then, just like now.

In our time, of course, the recent development of computers, the Internet, and then smart phones (and all their manifestations, such as the iPad) has begun to do much the same thing. It’s undeniable that writing within the office and for clients is dramatically different than it was a decade ago. Whether we recognize it or not, that means that legal analysis and the ways we approach business problems have shifted as well.

These revolutionary changes are one of the subjects of this new edition of the book. In part, that makes this volume a primer on how to communicate successfully in this brave new world. Writing effective e-mails and shorter memos are skills very much at odds with the tools we acquire in school—where the goal is usually to be expansive and detailed as we display our knowledge in all its minutiae. These new forms of communication are also very different from the written and oral tools one needed to master to be a good lawyer or executive, circa 1990 and before.

Yet it’s not just these new forms one needs to master. Litigation and contract writing may not have begun to change much since the rise of e-culture. But they will, since it is inevitable that these documents will also be read differently as the years pass, as will even judicial opinions. Some courts now require e-filings. Justices Antonin Scalia and Elena Kagan read briefs on either an iPad or a Kindle, and they will soon be joined by many others.

It means, too, that a lawyer’s role and habits of mind will change as they have begun to do already. If the Internet, Twitter, and Facebook are altering the way we do our jobs and how well we do them, they’re changing the way we think as well. It was Professor Kingsfield in The Paper Chase who kept dwelling on the importance of thinking like a lawyer. How that’s changed at the beginning of the twenty-first century because of these technological shifts is the subject of this new edition too.

Perhaps unsurprisingly, this new focus reinforces many of the fundamental principles that writing teachers and books (including my previous volume) have been stressing for decades—use strong verbs or be concise—though the rationales for doing so have changed somewhat. Yet other suggestions are novel, as one might expect at the dawn of a new epoch.

This updated edition also has an increased spotlight on creative writing as it relates to the presentation of facts and argument, as well as a new section on how affidavits need to be better drafted so that they reflect the true voice of the person they are supposed to represent. And, throughout the text, there are new ideas and examples of both what to do and avoid.

There is an old Chinese curse: May you live in interesting times. Whether it’s a curse or not, we live in just such an era. So let’s begin to figure out how to adapt—the sooner the better.

Introduction

If you don’t need a weatherman to know which way the wind blows, you don’t need a literary critic to know how badly most lawyers write. You only need to turn to any page of most legal memos, briefs, judicial opinions, law review articles, and even e-mail to find convoluted sentences, tortuous phrasing, and boring passages filled with passive verbs. Charles Dickens was neither the first nor the last to complain about lawyers’ liking for the legal repetitions and prolixities. In fact, the term legal writing has become synonymous with poor writing: specifically, verbose and inflated prose that reads like … well, like it was written by a lawyer. Like the late Justice Potter Stewart on obscenity, we know it when we see it, and we see it all the time.

Here is an example. Several decades ago, Joel Henning, a legal consultant and writer, noted a little-publicized case. In David v. Heckler, 591 F. Supp. 1033 (E.D.N.Y. 1984), United States District Court Judge Jack Weinstein, one of the federal judiciary’s more distinguished judges and better writers, ruled that bad writing in government documents violates the due process clause of the Fourteenth Amendment of the Constitution. Judge Weinstein took the highly laudable step of ordering the Department of Health and Human Services to rewrite its review letters to Medicare claimants because they were incomprehensible and contained insufficient and misleading information.

One of the sentences in the letters that so upset Judge Weinstein read:

The amounts are based on statistics covering customary charges of an individual physician and prevailing rates by all physicians rendering similar services in a given locality.

Given the dismal level of a lot of legal writing, that hardly seems so bad. It looks especially good in comparison to this sentence, which comes from Judge Weinstein’s own opinion in the matter:

Doubt as to whether this type of claim should be construed as barred by section 205(h), 42 U.S.C. §405(h), should be resolved in favor of finding jurisdiction since the availability of judicial review for constitutional questions is generally presumed.

The point isn’t simply that we might find Judge Weinstein himself in violation of the Constitution. Whenever I read something and I can’t understand it, Will Rogers said in a line that never failed to draw a laugh, I know it was written by a lawyer. Robert D. White, in his book Trials and Tribulations: Appealing Legal Humor, identified these ten unfortunate characteristics of legal writing:

1. Never use one word where ten will do.

2. Never use a small word where a big one will suffice.

3. Never use a simple statement where it appears that one of substantially greater complexity will achieve comparable goals.

4. Never use English where Latin, mutatis mutandis, will do.

5. Qualify virtually everything.

6. Do not be embarrassed about repeating yourself. Do not be embarrassed about repeating yourself.

7. Worry about the difference between which and that.

8. In pleadings and briefs, that which is defensible should be stated. That which is indefensible but you wish were true should merely be suggested.

9. Never refer to your opponent’s argument; he only makes assertions, and his assertions are always bald.

10. If a layperson can read a document from beginning to end without falling asleep, it needs work.

Yet legal writing doesn’t have to be this way, and this revised edition is my small attempt to continue to try to turn things around. It’s based on an advanced legal writing seminar I taught to third-year students at Harvard Law School for twelve years and continue to give in various versions to practicing lawyers, judges, and paralegals all around the country, and the world.

Numerous eminent books and blogs on legal writing are already out there, so I’ve tried to make this different. First, as an attorney and former litigator myself, I’ve tried to focus on the writing of lawyers, not judges. Most writers, after all, learn by emulation. Budding poets read Yeats, Eliot, and Stevens; young novelists immerse themselves in the works of Fitzgerald, Faulkner, and Austen. Law students and lawyers are the great exception; they train for a lifetime of advocacy or corporate practice by reading thousands of opinions of the sort they will never write, but few briefs or memos of the sort they will. Attorneys who can write like Cardozo or Holmes may become brilliant judges, but unfortunately, they are utterly unprepared for their work as practicing lawyers.

This book seeks to remedy that, first by providing dozens of good examples that lawyers can follow, written by other lawyers. Many of the rules I provide also come from interviews with judges and lawyers. When I practiced as a litigator and had to write a brief in, say, an administrative case, the first thing I wanted to see was a selection from a comparable brief by a David Boies or a Kathleen Sullivan. Yet there was nowhere to find such examples easily. Not all such selections here, I should add, are from winning briefs—a reminder, perhaps, that even the best advocates can play only the hand they’ve been dealt.

Second, as in my courses, I’ve tried to include examples and maxims from the worlds of journalism, advertising, and fiction writing. Anyone who can write a good ad can probably write a good legal argument, just as any good journalist probably knows how to compose a good statement of facts in an appellate brief. My view is that good writing tends to be pretty much the same everywhere. Sure, there are things that make legal writing different from other types of writing—especially if you have to do a lot of drafting of contracts and legislation or you are a judge crafting rules and decisions. Yet the differences tend to be exaggerated by lawyers and legal educators. Almost everything students learn in law school convinces them that legal prose is a domain unto itself. They hear their professors laud judicial opinions that often seem closer to a foreign language than to English. And unlike most other professionals, who entrust their written products to competent editors, legal academics give their articles to third-year students serving on law reviews, with the predictable consequence that no one but other legal academics will read them.

The key to good writing in school—and even on the bar exam—is often very much at odds with what makes good writing as a lawyer. That’s why, if I were designing a law school curriculum, I’d teach intensive legal writing in the last year—the bridge between academic and work life—and I’d focus far more than schools currently do on the essentials of argument and narrative writing. In firms and legal offices, I’d also insist that legal writing and argument be taught by someone who has actively practiced and litigated. Writing is not an academic exercise that can be cleverly taught through a series of PowerPoint slides. It’s a labor-intensive craft.

The discerning reader will notice dozens of writing rules scattered throughout the text. Of course, the best writers know that writing is not a dogmatic enterprise and the rules are made to be broken. The problem for those of us who have yet to achieve greatness, however, is that it’s hard to break the rules effectively without knowing them. Picasso couldn’t have become Picasso without learning to sketch a simple still life first.

I’ve attempted to make the organization of the book simple. Rather than provide dozens of pages of straight text, I’ve organized each chapter around a set of rules that, though lengthy at times, lawyers and students can apply easily. In Part I, I deal with the problems lawyers face as writers (organizing, strengthening prose, adapting to the new world of e-writing, and editing). In Part II, I address how lawyers can improve their written arguments, whether they are litigators or not. Part III treats litigation writing in all its manifold varieties (writing facts, arguments, complaints, affidavits, and in discovery). Part IV encompasses the everyday writing most lawyers must do (technical writing, memos, e-mails, letters, and the drafting of rules and contracts). In the conclusion, I discuss some of the philosophical reasons that lawyers have traditionally been poor writers. I’ve written the book so that one can read it straight through, or consult a specific chapter if one needs to write a specific type of legal document, such as a complaint. That means I’ve been repetitive at times. Every jurisdiction, of course, also has its own idiosyncrasies. So, while I’ve attempted to provide general principles for legal writing, always check your local rules before filing any document.

Many of my examples of both good and bad writing were given to me over the years by lawyers and judges who were assured they would remain anonymous. In many cases, I have identified the authors of my examples and the cases in which the examples appeared. In other instances, however, I cannot do so without disclosing too much about who sent me what, or unduly humiliating the author of a shabby document. In some examples, I have changed the names of the parties to avoid embarrassing them unnecessarily. In no case is the omitted information relevant; it is the writing, not the individual, that is important.

One final caveat: I have tried to inject a note of practicality where necessary, especially in reminding readers how judges read legal documents in the real world. At times my views may seem a little disrespectful. Yet after years of discussing the subject with dozens of lawyers, clerks, and members of the judiciary, I think it’s helpful to remind readers that judges were once lawyers, which means they suffer from all the occupational faults we have—if not more.

Like any writer, I stand on the tall shoulders of those who have addressed this subject previously. That’s particularly true when you write a book based on lecture notes compiled over several decades that seem to have suggestions from half the lawyers in America attached. Moreover, the blogs dealing with this topic have multiplied in recent years. I’ve tried to be accurate and credit everyone whose ideas crept into the text, and I have also provided an extensive bibliography. To those who have given me an idea or example somewhere along the line that remains unacknowledged—including my numerous research assistants at Harvard—I apologize, and thank you again.

But enough blabbering. The place to begin the process of improvement is with the basics that confront all legal writers: organization, the rules of the road, adapting to the new age, and editing. It is to these that we now turn.

PART I

The Fundamentals of

Legal Writing

CHAPTER 1 Organizing Your Material

CHAPTER 2 The Rules of the Road

CHAPTER 3 The Mechanics of Editing

CHAPTER 1

Organizing Your Material

I. The Overview: Getting Started by

Leading with Your Conclusion

II. Organizing Your Workplace Around Eight Rules

1. Remember that most writing difficulties are organizational difficulties.

2. Writing is something that most people do best alone.

3. Turn off the Internet.

4. Most writers need a regular time to compose.

5. The person who does the research should do the writing.

6. Don’t divide the drafting of a document among many writers.

7. Don’t stop when you’re stuck; instead stop when you don’t want to.

8. Keep a notebook and learn from other lawyers.

I. The Overview: Getting Started by Leading with Your Conclusion

For supposedly logical thinkers, lawyers often write surprisingly disorganized prose. Ask a lawyer what he or she intends to say, and you usually get a crisp, simple answer. Somehow, though, in the process of transferring that thought to writing, the clarity vanishes. Take this opening to a brief, filed in the U.S. Court of Appeals for the Fifth Circuit and cited in Tom Goldstein and Jethro Lieberman’s The Lawyer’s Guide to Writing Well:

Appellee initially filed a motion to strike appendices to brief for appellant.… Appellant filed a brief in response, which appellee replied to. Appellant has subsequently filed another brief on this motion, Appellant’s Reply to Appellant’s Brief in Response to Appellee’s Motion to Strike Appendices to Brief for Appellant (appellant’s most recent brief), to which the appellee herein responds.

A large part of the problem is the way lawyers organize and compose their material. Like everyone else, lawyers write in many ways. Some older lawyers still dictate off the top of their heads and then edit. Others ponder the matter and draw up a lengthy outline. Still others discuss the issue with a colleague and try several lead sentences before finally hitting the screen and dashing off a few paragraphs in a blaze of glory. Many just write in a kind of stream-of-consciousness style.

If a method works for you and you can’t conceive of doing things any other way, stick with your habit. Tradition has it that Ernest Hemingway used to sharpen close to twenty pencils and then go for a walk before writing. That said, however, one method of organization has tended to work well for legal writers in the past.

First, you must have a clear idea of what you’re going to say before you begin to write. Compare it to driving: If you’re going to travel from New York to Washington and you get into the car without having figured out what route you’re taking, you may still eventually arrive in Washington. The problem is that you may take your passengers to Albany or Providence before you finally get your bearings and head for Washington in the most direct fashion.

To get your direction straight, outlining can help. Yet not just any outline will do. Rather, before you sit down to write anything, whether it’s a four-line e-mail or a thirty-page brief, you should ask: If I had to condense my message to two or three sentences, what would those sentences be? If the judge or reader stopped me on the street and said, I only have about a half a minute, so who are you, what do you want, and why? Having figured out those two or three sentences, you’re ready to write and something more. Those first few sentences should be the first paragraph of any document. In legal writing, we should always lead with our conclusions or a summary.

Good lawyers do this all the time. Here’s how one advocate appealing a criminal conviction began her brief (the names have been changed):

The State’s entire case against Max Hugo turned on Trooper Dora Clayhorn’s testimony about her success in disguising herself as a college student, entering the enclosed porch of appellant’s home uninvited, proceeding into his living room, and there soliciting the sale of a quarter-gram of cocaine for only $25.00. That evidence was admitted only because the district court declined to suppress it as the fruit of an unlawful search, ruling that the New York police may target an individual and invite themselves to his residence for an undercover sting operation within the sanctity of his own home without a warrant and without any probable cause to believe either that appellant was selling drugs from his home or that he was even selling drugs at all.

Whether the government may roam at large in people’s homes as freely as it did in this case is an issue of first impression in this Court.

Or, take this introductory paragraph of the Statement in a Supreme Court brief filed by Andrew Frey and Evan Trager, among others, in Wachovia Bank, National Association v. Daniel Schmidt III, et al., 546 US 1001 (2005):

This case concerns the meaning of 28 U.S.C. §1348, which provides that, for purposes of diversity jurisdiction, national banks are treated as citizens of the states in which they are respectively located. At the time that Section 1348 and its predecessor statutes were enacted, all corporations, including state-chartered banks, were regarded as citizens of only a single state for diversity purposes. Here, however, the Fourth Circuit held that Section 1348 treats national banks as located in, and therefore as citizens of, all states in which they operate branches. Under its analysis, national banks may be citizens of multiple states across the country, and therefore have an access to the diversity jurisdiction of the federal courts that is uniquely limited as compared to their state-chartered competitors and other corporations. This holding is not dictated by the statutory language, was not intended by Congress, and is wholly illogical. It should be set aside.

Most lawyers find it terribly difficult to come up with an approximation of these initial sentences. After all, we’re taught from day one in law school that nothing is black or white—everything is a shade of gray. If you want to understand this, Your Honor, we seem to say, please sit down for four hours while I explain to you every nuance, detail, and comma. There’s no truth but the whole truth, or so we think. Moreover, the essence of an academic paper is to take a two-page idea and write about it for twenty-five pages. In law school, we are trained to write like law professors composing law review articles. That’s the genre, as the late Judge Harold Leventhal of the U.S. Court of Appeals for the D.C. Circuit once said, that spends thirty pages describing a problem you never knew existed and then spends fifty pages explaining why it will never be solved.

It’s not just law school that reinforces this tendency. Throughout our schooling, almost all of us are taught to compose using a version of what might be called the Western scientific method. Like a scientist, we see our job as sifting through all the evidence objectively, eventually delivering an impartial conclusion at the end.

Of course, the method makes sense in science, where we don’t want our prejudices to cloud our findings. But communication isn’t a science, even if economists and lawyers try to pretend their analysis is grounded in something equally pure. Moreover, in the real world, no one would think of presenting information that way. If you’re trying to tell me a book to read or movie to see, you begin by saying, "You should read Catcher in the Rye, explain why, and then go home. You don’t begin, The question is what book should you read?" then analyze the history of books, literary taste, and other topics before concluding with a recommendation on page 75—unless you’re writing an academic paper or exam, of course. Law school merely reinforces these tendencies.

The more highly educated and the older you are, the more you’ve been trained to write linearly—from beginning to middle to end. By and large, however, people don’t read that way anymore—at least on computers and at least in the legal-business world. In those worlds, the core of effective communication and argument, at least initially, is simplification. Unless readers know right up front where you’re heading and why, it’s very difficult for them to follow what you’re saying, much less be convinced by it.

I understand lawyers’ reluctance to commit themselves to those first few sentences. However, even though it seems difficult at first, anything can be condensed to such a summary. Take the U.S. Department of Justice antitrust action against Microsoft in the late 1990s. It was complicated by many issues, and there was probably enough discovery in the case to fill hundreds of boxes. Still, if you were arguing that case for the government, you could try to boil it down to this issue: Can Microsoft use its near monopoly on one product, Windows, to force consumers to take another, integrated product they may not want?

Or take Herman Melville’s Moby-Dick. Sure it’s long, but essentially it’s a novel about a group of sailors from Massachusetts who chase a giant white whale, eventually find it, and harpoon it while Captain Ahab gets chained to it. I know Melville would be terribly upset with such a condensation,