Three Tips for Finding the Joy in Legal Writing

Like most law firms, mine spends an extraordinary amount of time training its litigators on legal writing. We receive gobs of resources—continuing legal education notices, books on persuasive briefing, boot camp invitations, editing assistance, and so on. They’re helpful, of course. Learning how to communicate effectively with the client or the court or the jury is part of Lawyering 101.

I’ve noticed, though, that most of these resources try to mechanize the writing process. We are told to outline our arguments before starting to draft in earnest. We are reminded of the importance of signposts and topic sentences. We no longer start our sentences with “However” or “Therefore.” We learn that Century Schoolbook is a winning font and that two spaces after a period is gauche. Etc.

These instructions appeal to us. We lawyers are an inherently risk-averse bunch. We like processes and procedures; we prefer rules, not standards. A checklist approach to writing generally produces decent and fileable, if not especially inspired, writing.

But something tends to get left out of all this training—fun. Litigators are, at bottom, storytellers. It should be fun to work through framing and narrative arc and word selection and all of the other elements that go into quality writing. It should be fun to wrestle complicated facts and law into a simple, compelling argument. It should be fun to draft a relentlessly readable brief.

Most litigators like writing when they enter the profession. But then reality hits. Quick-turn deadlines and billable hour pressures all too often shrink the writing process into a brute-force exercise. Multiple rounds of editing often erase an author’s carefully crafted phrases. After a year or two of practice, writing can easily become a job, not a joy.

And that’s a shame. Having fun with the writing process makes litigation sustainable, if not downright enjoyable. It also makes a difference in the final product. I can tell when a colleague has had a great time drafting a brief. The brief takes creative risks. It contains pictures or an unusual narrative structure, or it is more conversational than the norm. It sparkles. These sorts of briefs are fun to read and easy to follow. They also tend to win.

So how can litigators inject more fun into the writing process? I’ve tried lots of different strategies, based on lots of different recommendations from lots of different people. Some have worked out; many have not. As it turns out, fun is personal. What follows are the three tips that have worked best for me. I hope at least one works for you, too.

Write a Story, Not a Brief

It’s fun to tell (and to read) a story. Stories have protagonists and antagonists. They have plots and tension and dénouements. Good stories, and all of the literary devices they use, keep the reader engaged from the first sentence to the last.

What does it mean to tell a story as a litigator? It’s all about framing. Unlike novelists, lawyers don’t have the luxury of starting from a blank slate. By the time we’re retained, there is usually a set of baseline facts and laws we are stuck with. We might interview witnesses and review documents to home in on the details, and we read statutes and cases carefully to see how much room we have to maneuver in our arguments. But any character and plot development is generally a matter of shading, not creation.

For a litigator, then, the framing is the story. A lawyer must be able to pinpoint the single best reason—whether legal or non-legal—why the client should win before starting to write. With the right framing, the brief should flow naturally and become a joy to draft. The right framing also lets the author emphasize helpful information and precedent, and contextualize the rest. I know my framing is good when the writing takes care of itself.

Some lawyers save the framing for last, if they even bother to frame at all. One fairly common practice is to start by drafting the argument section, then move to the facts, then finally throw in an introduction. It’s certainly possible to treat a brief like a set of legal Lincoln Logs that just need to be arranged in the right order before filing. But that approach misses the forest—the story—for the trees. And I strongly suspect that it’s not a great deal of fun to write that way.

That’s not to say framing is easy. It requires the author to have total mastery of the facts and the law before starting to write. It also requires an intuition about which potential arguments are most likely to appeal to the decision-maker. This is state-of-nature, best-judgment, Wild West stuff; there are no rules for the litigator in framing land.

Compare the wildly different framings in the petitioners’ briefs in two recent Supreme Court cases, Maslenjak v. United States, 582 U.S. 335 (2017), and Kennedy v. Bremerton School District, 142 S. Ct. 2407 (2022). Maslenjak involved an ethnic Serb from Bosnia who entered the United States as a refugee in 2000. A few years later, she applied for and received U.S. citizenship. Officials then learned Maslenjak had lied about her husband’s participation in the Bosnian Serb Army when she applied for refugee status. This was a problem because, as part of the naturalization process, Maslenjak attested that she had never lied to a government official to gain entry into the United States. Maslenjak was charged with illegally obtaining naturalization by “knowingly making a false statement under oath in a naturalization proceeding.” 582 U.S. at 340. The jury entered a guilty verdict, and the district court stripped Maslenjak of her citizenship. The appeal centered on whether the denaturalization statute should be read to include a materiality requirement.

Rather than focusing on her own denaturalization, Maslenjak’s merits brief framed the issue in terms of first principles—the near-inviolability of U.S. citizenship as a foundational part of our democracy:

[T]his case is not just about [Maslenjak’s] citizenship rights, but about the citizenship rights of all naturalized Americans. Precisely because those rights are so precious, there is no basis to conclude that Congress did (or constitutionally could) provide for them to be lost as the result of an immaterial false statement.

Brief for Petitioner at 4, Maslenjak, 582 U.S. 335 (No. 16-309).

The framing worked; the Court ruled unanimously in her favor.

Unlike the petitioner’s brief in Maslenjak, the petitioner’s brief in Kennedy focused squarely on the petitioner himself. (For an easy point of comparison, “Kennedy” appears 159 times in the Kennedy brief, while “Maslenjak” is used only 45 times in the Maslenjak brief.) Joseph Kennedy, a small-town high school football coach in Washington State, was suspended for praying on the field after games. He challenged the disciplinary action on First Amendment grounds. Kennedy’s brief focused on his own personal religious practice, not on generalized principles of religious liberty:

Joseph Kennedy is a high-school football coach. He is also a devout Christian who feels compelled to kneel and say a brief, quiet prayer of gratitude at the 50-yard line after each game. In a Nation founded on the preservation of freedom of religion and speech, those two things are not remotely incompatible. Yet, remarkably, the school district suspended Kennedy because he refused to move his personal religious observance behind closed doors.

Brief for Petitioner at 1, Kennedy, 142 S. Ct. 2407 (No. 21-418).

Once again, the framing worked; the Court ruled 6–3 for Kennedy.

There are fairly obvious reasons for the different framings in Maslenjak and Kennedy. Maslenjak was never going to be an especially sympathetic plaintiff, but Kennedy could plausibly be portrayed as the high school football coach who just wanted to pray quietly after games. The government had no real rejoinder to Maslenjak’s argument that citizenship is “precious” and should be stripped in only the rarest of circumstances. Kennedy’s appeal, though, raised conflicting First Amendment concerns that could only be given priority by reference to a sympathetic plaintiff. And, of course, the brief writers were addressing different Courts in 2017 and in 2022.

But despite their differences, both briefs told a single, clear, and consistent story. That is what winning briefs do—and it’s why they are fun to write.

Write the Introduction First

When I started practicing, I was, like most new attorneys, instructed to outline my briefs before writing them. This is what all of my outlines started with: “1. Introduction (TBD).”

I’d then dutifully follow up with two or three pages of bullets on the facts and the law, neatly organized under lines labeled “2. Background” and “3. Argument.” The outlines, if I can brag a bit, looked great. But they didn’t really work. Inevitably, as soon as I started writing, I would pick up on nuances and conflicts that I hadn’t noticed before. I’d learn that my outlines had overemphasized some facts and ignored others. I’d find that the legal arguments should be reordered. All of that work creating an outline, only to miss the essence of the case, was—to put it mildly—not fun.

After a year or so of this, I tried a different approach: I started to write a one- or two-page introduction before I outlined the brief. What a difference! The process gave me creative license to focus on the story, not just the facts and the law, from the very start. It forced me to distill everything I had learned during case development into the most compelling 500 words possible. It reminded me to align the background and argument sections with the framing, not the other way around. And it was a joy to feel like a writer again, not just a junior associate.

This practice, I think, pays off. Readers remember great introductions. Take the opening paragraphs from two opinions in Miller v. Jackson, [1977] 1 Q.B. 966 (C.A.), an English Court of Appeal judgment. Miller involved a dispute over a cricket pitch in a small English village. One of the openers, authored by Lord Justice Lane, is traditional—and boring. It recites the facts in chronological order and gives no clue about the author’s ultimate view of the case:

Since about 1905 cricket has been played on a field at the village of Lintz, County Durham. The village cricket ground is an important centre of village life in the summer months. It provides pleasure and relaxation for many, whether as spectators or players. We are told that the land is owned by the National Coal Board who let it to the club. The National Coal Board had also been the owners of an area of pasture-land to the north of the cricket ground. No difficulties arose from the use of the ground until 1972. The pasture-land had been sold by the National Coal Board to the Stanley Urban District Council in 1965, but in about 1972 it was bought from the J.D.C. by Messrs, Wimpey’s Ltd. Wimpey’s built a line of semi-detached houses there. One of those was bought by the plaintiffs. That is No. 20, Brackenridge—the name of the road.

The other paragraph, though, written by Lord Denning, is a zinger:

In summertime village cricket is the delight of everyone. Nearly every village has its own cricket field where the young men play and the old men watch. In the village of Lintz in County Durham they have their own ground, where they have played these last seventy years. They tend it well. The wicket area is well rolled and mown. The outfield is kept short. It has a good club-house for the players and seats for the onlookers. The village team play there on Saturdays and Sundays. They belong to a league, competing with the neighbouring villages. On other evenings after work they practice while the light lasts. Yet now after these 70 years a Judge of the High Court has ordered that they must not play there anymore, he has issued an injunction to stop them. He has done it at the instance of a newcomer who is no lover of cricket. This newcomer has built, or has had built for him, a house on the edge of the cricket ground which four years ago was a field where cattle grazed. The animals did not mind the cricket. But now this adjoining field has been turned into a housing estate. The newcomer bought one of the houses on the edge of the cricket ground. No doubt the open space was a selling point. Now he complains that, when a batsman hits a six, the ball has been known to land in his garden or on or near his house. His wife has got so upset about it that they always go out at weekends. They do not go into the garden when cricket is being played. They say that this is intolerable. So they asked the Judge to stop the cricket being played. And the Judge, I am sorry to say, feels that the cricket must be stopped: with the consequences, I suppose, that the Lintz cricket-club will disappear. The cricket ground will be turned to some other use. I expect for more houses or a factory. The young men will turn to other things instead of cricket. The whole village will be much the poorer. And all this because of a newcomer who has just bought a house there next to the cricket ground.

Now, I know next to nothing about cricket or the town of Lintz in County Durham. I would not otherwise be inclined to care about them. But Lord Denning used his introduction to vividly portray the tension between a seven-decade sporting tradition in an otherwise bucolic village and an interloper who wanted to shut it down. The introduction turned what could easily have been a dry, forgettable dispute about the law of nuisance into a narrative that should resonate with anyone who has ever had an irritating neighbor. Even though Lord Denning did not mention any specific legal principles or cases (which here I think is a feature, not a bug), he still let the reader know what was at stake and where his opinion was likely to go.

It’s fun to be a Lord Denning. It’s also generally quite effective. The introduction is the reader’s first view of the case, and it should be anything but an afterthought.

Write the First Draft for Yourself

A few years ago, a colleague told me that he often spends an hour or more crafting the perfect first sentence for a brief. At the time, I thought he was nuts. Everyone knows that briefs evolve. Reviewers edit, often liberally. The likelihood that any specific sentence—especially the first one in a brief—makes it through the editing process untouched can be vanishingly small. Supreme Court justices get to use phrases like “jiggery-pokery,” but those phrases are prime for the scalpel if they come from an associate’s desk. So why place so much pressure on a single sentence?

My initial reaction was, I think, a fairly common one among litigators. When you measure your writing in six-minute increments, and when you know that your phrasing will likely be changed, it can be hard to focus on perfecting the prose. After all, briefs that begin with crutches like “This case is about . . .” still get the point across well enough.

After I spent some time thinking about my colleague’s advice, though, I realized he was onto something—he writes the first draft for himself. I’ve adopted this approach now, too. During the initial drafting process, I am my own final judge. I organize and reorganize the brief until I think it is in the best possible order. I carefully select my words and phrases and play around with them until I am satisfied. The end product is a draft that I am proud to have written and happy to share. From there, the group editing phase turns into a separate, but welcome, project to finalize the brief.

Separating the drafting and editing phases helps me maintain the joy of each. It also creates a positive feedback loop: My standards sharpen with each round of external editing, which in turn improves the next brief I write. It’s difficult to satisfy an ever-more-demanding internal critic—but it’s also incredibly rewarding.

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Legal writing should be fun, not a slog. Exhausting? Potentially. Time-consuming? Probably. Challenging? Definitely. But it should never, ever, lack joy.

Laura Hill can be reached at [email protected].