Headings I Win: Crafting Winning Headings

Learn how to craft winning headers and quickly improve the effectiveness of your headlines.
  • Joe Regalia
Authors often spend months agonizing to find the perfect title for their books. And it’s because titles matter. They change how readers see everything that comes after the cover is opened.
What would be lost if these books were named something less: “A Brave New World,” “A Hundred Years of Solitude,” or, of course “To Kill a Mockingbird”? And take a few modern titles that undeniably do some work: “The Particular Sadness of Lemon Cake,” “The God of Small Things,” and “No One Belongs Here More Than You.”
We use titles in legal writing, too. We just call them headings. And because our briefs often contain many stories (whether legal or factual), we use different headings to capture each distinct part. If anything, these headings are more important to lawyers than they are to novelists. Headings can be game changers—and crafting good ones is an art unto itself:

Pithy & Organized

If headings are pithy and well organized, they will convince your reader to read your document and keep reading;

Easy to Navigate

Outstanding features for highly customizable Courses, Units, Lessons, and Quizzes

Big Picture

Leveraging places of emphasis, sentence variety, dialogue, examples and hypotheticals, and more.


Simple techniques to bring storytelling skills into every aspect of your legal practice. 

Key Points

Well-crafted headings that capture your best points will persuade;


Finally, headings can do wonders for your storytelling skills: framing how your readers see good and bad facts.  
And at bottom, as Bryan Garner points out, until you’re ready to write excellent headings that capture the essence of each section—you probably don’t understand your points well enough to persuade.
Despite all this, many lawyers ignore headings. They copy and paste the same titles in every brief they churn out. There is a “Background” heading, an “Argument” heading, and one for the “Conclusion.” If the reader is lucky, there are a few (often generic and nondescript) headings dropped into the Argument section.
So how do you build the heading of your dreams? First, I have few basic heading musts. Then I offer some advanced tools if you’re ready to truly embrace the power of the heading.

The Basics

Let's review some basics about good headings. These should not be negotiable.

Use headings anytime they will help your reader

First, use headings anytime they will help your reader—which for most lawyers, means using them a lot more than they do. There is no reason to force a reader to skim pages of argument, paragraph by paragraph, to figure out what points are where. Nor is there any reason to drop a reader into a factual abyss with mountains of details and no headings to guide them. Remember to use headings in your fact sections and in your discussion. Not only can you use headings for each issue or sub issue—you can use them within a section to signal subparts. Take this example from an excellent brief:
There are two rules that emerge from this trio of cases.

FDCPA claims cannot be brought after the statutory period. Both Gracey and Park repeat that the statutory period still matters.


FDCPA claims cannot be brought by a third party. The Park court went to great lengths carving third parties out from the sorts of plaintiffs who can bring these claims.

Don't make headings too long

Second, don't make your headings too long. Even a few lines of clunky text can do more harm than good. A dense heading, aside from probably being skipped altogether, just signals that a verbose slog must be coming in the body. I don’t know about you, but I would find something else to do if I opened a brief and this (real) heading greeted me:
This Court Should Grant Certiorari Pursuant to Rule 39(a)(1)(D) Because the Court of Criminal Appeals’ Decision Affirming Summary Dismissal of Mr. Marin’s Claim that He Received Ineffective Assistance Of Appellate Counsel Due to Appellant Counsel’s Failure to Argue That Remand Was Necessary to Demonstrate That Mr. Marin Reasonably Relied on the State’s Action Is In Conflict With Moore v. Texas, Montgomery v. Louisiana, Brumfield v. Cain, Hall v. Florida, and Smith v. State”
Instead, consider aiming for a couple lines of tight text. It’s going to take some crafting, but the payoff is real:
Counsel was ineffective because he failed to explain to the lower court that, once free, Rene spent four years building a family and career—all in reliance on the state’s mistake.

Use consistent formatting

Next, make sure your headings are formatted consistently. That means the same ordinals, the same formatting, and the same spacing for each equivalent heading throughout your document.
Traditionally, headings in legal documents start with roman numerals at the top level (I, II, III); then to go to capitals (A, B, C); numerals (1, 2, 3); lower case letters (a, b,c); and then romanettes (i, ii, iii). For the more bold, some folks suggest that a numeral system is easier to read. So 1, then 1.1, and so on. 

Keep the tone civil

Finally, headings are no excuse to use a different tone than you would in the body. Lawyers often throw sensational advocacy into their headings—like personal attacks or over-the-top characterizations. Just because a heading is not followed by a cite does not mean that your credibility is any less at stake. So please none of this, from a real filing:
Plaintiffs lost this case and they know it, so they are desperately grasping for life on a new legal theory about statutory remedies that utterly fail out of the gate. 

Advanced Techniques

There are several heading techniques that the best advocates use. And for good reason: some of these are supported by cognitive science and research. If nothing else, many of the most winningest advocates use them. 

Style matters, so craft headings using vibrant, concrete words and sentence structure  

Headings are your readers’ first introduction to your section—so they should be inviting. By sprucing up the yard of your section, your readers will want to come in and read more. Your headings are your promise that clear, engaging prose will be inside. Take this engaging nugget from a motion for summary judgment:
Marx sidestepped the extra tax penalties by ballooning the fees he raked in from his own customers.
Other than using strong verbs and nouns—the pithier and smoother you make your headings, the better they will stick in your reader’s mind. So use tools like sentence balance, echo words, alliteration, and the array of sentence-level style tools at your disposal.
Try this heading out for size, and note the word balance, the placement of “buyout” at the end of the first clause to emphasize that key word, the repeated “b” words, and the trio of parallel phrases to tie things up:
Plaintiffs press for an interpretation where they can breach and buyout—but that has never been the parties’ intent, they said so under oath, and their actions confirm it. 
You aren’t going to craft gems like this without some thought, but the effort will pay off.

Pay attention to typography

The same typography science I’ve covered in other posts applies to headings: weird fonts or emphasis combinations are harder to read. A lot of people like all caps, but the only research on point I know of suggests that it’s harder to read. Many counsel against underlining for the same reasons, and I tend to agree. But what I know can’t be good is a mashup of emphasis like this:
This Court Should Grant Certiorari Pursuant to Rule 39(a)(1)(D) Because the Court of Criminal Appeals’ Decision Affirming Summary Dismissal of Mr. Hoffman’s Claim that He Received Ineffective Assistance Of Appellate Counsel Due . . .
And I don’t know why you’d use different fonts for headings than you use in the rest of the document—but lawyers do that al the time. Look at the difference in readability when you just bold the heading:
This Court should grant certiorari pursuant to Rule 39(a)(1)(D) because the Court of Criminal Appeals’ decision affirming summary dismissal of Mr. Hoffman’s claim . . .

Don't let headings come as a surprise

One of the most frustrating things for me as a reader is when a brief has a bunch of headings that are either so deep into the weeds or lack so little setup beforehand—I can’t actually get anything out of them until I read the whole section.
That strategy makes no sense. If your reader has no context to understand your headings, they are unlikely to remember them in the first place (all readers want to connect what they are learning to what came before). And how can your heading frame or persuade if your reader can’t even understand it? Not to mention that, as explained above, some of the magic of good headings is that they tell a mini-story about your entire brief right in the table of contents.
There are a few strategies to make sure that your headings will make sense to the new reader. First, keep your headings at a high enough level—and in a sensical order—so that your reader can understand the basics when they first read the table of contents. Indeed, that’s a good test. If a fresh reader would have no idea what your headings mean or how they fit together from reading them in isolation, you aren’t getting all that you can out of this tool.
Take this example from a transgender-bathroom-ban case penned by writing guru and federal judge Jennifer Dorsey. Notice how you need no extra explanation to follow these fact headings:
1. Brandilyn Netz becomes Bradley Roberts.

2. [The school district] officially bans Roberts from both the men's and women's bathrooms.

3. [The district] circulates an email informing Roberts's coworkers that they should refer to him as a man.

4. Roberts files administrative charges and [the district] lifts the bathroom ban.
Second, to make them hit even harder, setup your headings beforehand. In your introduction, you can preview the substance of all the headings that are coming. Then as you enter each section, you can further roadmap the coming headings and briefly explain why they matter. This allows you to add a little more nuance. See how easy it is to pick up on this heading with just a little setup: 
Because the plaintiff has alleged no injury caused by the cars, there is no standing here. But even if there were, the alleged harm was all suffered back before the statute of limitations ran.

A. Plaintiff alleges only that he was unable to use his car for an hour—that is not the sort of injury required to have standing.

. . .

B. In any event, Plaintiff’s allegations are all about things that happened before 2012, so the 4-year statute of limitations has ran.

Avoid acronyms

Avoid acronyms (unless your reader is sure to know it, like CIA) or any other word, phrase, or concept that won’t make sense when reading the heading alone.

Use fact headings to tell a story

Headings may be at their most powerful when used in fact sections. Headings can help compartmentalize facts, you can use them to frame how your readers will see both the good and the bad, and they are just plain useful for trudging through the details that overflow most legal writing.
Consider also starting your fact section with a brief overview of your headings—I like to think of it as a movie trailer. You are offering a sneak peek of the big picture, and at the same time, setting up all of your fact headings.
Your fact headings should usually be chronological, and if not, at least in some easy-to-see logical order. Otherwise good luck putting together a story. Quotes can also help give a sense of narrative to your headings. And one final recommendation for fact headings: the present tense helps deliver a sense of time and narrative.
Check out this example, which brings all these techniques together: note the movie-trailer introduction, the use of quoted facts, the logical progression, and the present tense:
Park was in the fold from the start. She was told about EmGen diving, she then sold her stock, and then she lied and encouraged others to do so, too . . .

"Peter Bacanovic Thinks EmGen is Going to Start Trading Downward
Park Sells Her ImClone Stock

"Something is Going on With EmGen and Park Wants to Know What"

February 4, 2002: Park Lies to Investigators

February 13, 2002: Jamie Lies in Sworn Testimony

March 7, 2002: Sampson Lies to Investigators Again

April 10, 2002: Park Lies to Investigators Again

Park’s False Public Statements

Jamie Reveals the Truth

Make headings persuasive by highlighting key facts, themes, or phrases from the section

As I’ve said about introductions before: a lot of persuading is simply highlighting the right facts and points in the right way. And headings are another excellent place to do that highlighting. By sifting through your section to find those gems of key facts or law, you will be dishing your best work up on a platter for your reader.
Check out how this federal litigator flashes the key facts and legal points from his sections:
The defendant had no expectation of privacy in his bathroom because he “called police on the phone” and “asked them” to come inside.

This court has no jurisdiction because the deadline to file the complaint was June 2017 and plaintiff filed in September of that year.

The Supreme Court caselaw requires alleging the date, time, and means of carrying out the conspiracy.
Look at this clunker from a habeas brief. Not only is it long, but it doesn’t even capture any of the key persuasive points from the section:
This Court Should Grant Certiorari Pursuant to Rule 39(a)(1)(D) Because the Court of Criminal Appeals’ Decision Affirming Summary Dismissal of Mr. Hoffman’s Claim that He Received Ineffective Assistance Of Appellate Counsel Due to Appellant Counsel’s Failure to Argue That Remand Was Necessary to Demonstrate That Mr. Hoffman Is Intellectually Disabled.
Now check out how a rewrite—with even fewer words—can do more just by highlighting the right facts and points:
Cert is warranted because trial counsel never even mentioned that Mr. Hoffman was intellectually disabled—despite that he has an IQ of 50 and this court has held that an IQ of 65 warrants relief.
And for a more legal-centric example, take this beauty, again compliments of Judge Dorsey. And note the use of key points and phrases to highlight the essence of her analysis:   
1. The weight of authority suggests that Title VII's use of the word “sex” encompasses protections for discrimination against gender identity.

2. I join the weight of authority and hold that discrimination against a person based on transgender status is discrimination “because of sex” under Title VII.
And here’s some excellent examples shared by Bryan Garner:
The four-year statute of limitations bars this action because Mr. Smith waited six years to file this suit.

Two essential elements of fraud—intent to deceive and detrimental reliance— were not established.
Finally, I’ll leave you with a few observations from Bryan Garner about how the U.S. Solicitor General's office crafts headings. I think they are all great:
  • They use full, declarative sentences.
  • They use normal type (no all-caps or underlines) and single space.
  • Acronyms and initializations are disfavored.
  • No citations for cases mentioned in headings.
  • The headings all come together in the table of contents to tell a coherent story.
  • The headings move from major to minor supporting points—then to points refuting the other side.
So spend some more time on your headings. Your readers will thank you. 
Joe Regalia
Write.law co-founder Joe Regalia combines his experience as both practitioner and professor to create exciting new ways to teach legal skills.  Learn more about Joe

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