Author Archives: Wayne

About Wayne

Wayne Schiess teaches basic legal writing at the University of Texas School of Law and also focuses on legal drafting, persuasion, and plain English. He is a frequent CLE and seminar speaker on those subjects and has written dozens of articles on practical legal-writing skills, plus four books. He graduated from Cornell Law School, practiced law for three years at the Texas firm of Baker Botts, and in 1992 joined the faculty at Texas. In 2012 and 2015, he was named the law school's legal-writing teacher of the year. In 2011, the Texas Pattern Jury Charges Plain Language Project, for which he was the drafting consultant, was named a finalist for a ClearMark Award by the Center for Plain Language. In 2009, five of his short articles were featured in the Scribes Journal of Legal Writing "Best of" series. In 2007, this legal-writing blog (LEGIBLE) was selected for the ABA Journal Blawg 100: "The best Websites by lawyers for lawyers."

Grammar in Real Cases

Passives, apostrophes, and commas

Legal writers should always aim for grammatically correct prose. Why? To me, the key reason is to establish and maintain credibility: When readers see that you know how to write correctly, they are also likely to believe that you stated the facts and law correctly and presented accurate, valid arguments, explanations, or advice.

But occasionally, grammar itself becomes an issue in a case. Here are some grammatical matters that made it into caselaw, including one that made headlines. For the first three examples below, I thank Professor Diana Simon and her excellent book, The (Not Too Serious) Grammar, Punctuation, and Style Guide to Legal Writing published by Carolina Academic Press in 2022.

Although using the passive voice is not a grammar error, using it unwisely can have bad consequences. In one case, a due-process claim written in the passive voice failed to identify who did the “assuring” in the following statement from the complaint: “she was assured that she would continue on the job as long as she performed satisfactorily.” As a result, the judge dismissed that claim.[1]

In another case, a lawyer used apostrophes inconsistently in a settlement offer before trial—sometimes Plaintiffs and sometimes Plaintiff’s. The court said, “The offer was apostrophe-challenged, creating ambiguities ….” Thus, the offer failed to satisfy the particularity requirement, and the court reversed an award of attorney’s fees.[2]

One case involved a comma splice—joining independent clauses with only a comma when a period, semicolon, or conjunction is called for. A federal district judge, attempting to apply state law, noted, “The Supreme Court of South Dakota first recognized a cause of action for insurance bad faith in [Champion]. The published version of the Champion case unfortunately … employed a comma splice in a key passage, creating a confusing standard.”[3]

And then there’s a serial-comma case that made some headlines in 2018.[4] Under Maine law, overtime-wage laws do not apply to—

The canning, processing, preserving, freezing, drying, marketing, storing, packing for shipment or distribution of: [certain products].[5]

The question:

  • Is “packing for shipment” one activity, and “distribution” a separate activity?

That would be correct if there had been a serial comma after “shipment.”

  • Or is the activity, “packing for shipment or distribution”?

That would be correct if the drafter was a practitioner of the serial comma but had intentionally omitted it because “packing for shipment or distribution” was intended to be a single activity.

The specific question before the First Circuit was about truck drivers: if distribution is a separate activity, drivers are not entitled to overtime pay. But if the activity is “packing for shipment or distribution,” the drivers are entitled to overtime pay because drivers don’t pack; they distribute.

The court declined to apply Maine’s Legislative Drafting Manual, which calls for omitting the serial comma—a common approach, especially in journalism. That would have made “packing for shipment” a separate activity from “distribution,”  and the drivers would not be entitled to overtime pay.

Instead, the court relied on parallelism, pointing out that the listed activities were all gerunds (-ing) except for distribution, and as a result, distribution was not a separate activity, but a part of the “packing” activity.

Treating “packing for shipment or distribution” as a single activity means that the list lacked a conjunction. Thus, the “or” in “packing for shipment or distribution” was part of that single activity and could not serve as the conjunction for the larger list.

Can you have a list without a conjunction before the last item, even if you don’t use a comma?

Yes, you can, although doing so is a rhetorical technique called “asyndeton.” Asyndeton means creating a list but omitting the coordinating conjunction: The flag is red, white, blue (omitting “and”). So although the court expressed some distaste for the idea, it implicitly accepted asyndeton as a legitimate drafting practice.[6]


[1] Ponder v. Cnty. of Winnebago, 2021 WL 3269842, *7, *12 (N.D. Ill. Sept. 30, 2021).

[2] Bradshaw v. Boynton-JCP Assocs., 125 So. 2d 289, 289, 290 (Fla. Dist. Ct. App. 2013).

[3] Anderson v. W. Nat. Mut. Ins. Co., 857 F. Supp. 2d 896, 903 (D.S.D. 2012).

[4] An Expensive Dispute About Serial Commas, ABA Journal (May-June 2018)​real_property_trust_estate/publications/probate-property-magazine/2018/may-june-2018/an-expensive-dispute-about-serial-commas/

[5] Me. Stat. tit. 26 § 664(3)(F).

[6] O’Connor v. Oakhurst Dairy, 851 F.3d 69, 71, 73, 76, 80-81 (1st Cir. 2017).

Use Word’s Navigation Pane to Improve Organization

I like to use the Navigation Pane in Microsoft Word to help me with large-scale organization. Here’s a step-by-step guide and then an example.

First, you need to be using Styles in Word. Here’s my brief guide to using Styles. Now, open a document in which you’ve used Styles to create headings. Then—

1. Click the View tab

2. Look for the option that includes Ruler, Gridlines, and Navigations Pane:

3. Check the box for Navigation Pane, so your screen should look like this:

4. Focus on the left-side Navigation Pane, which shows all the headings you’ve created in your document. It’s clickable and collapsible.

5. Read through all your headings, subheadings, and sub-subheadings—or do what I did: take a screenshot of it, print it out, and read it on paper.

You’re looking for anything related to the organization:

  • Are my main topic headings in the right order? A good order?
  • Are my headings parallel? That is, are all the headings or subheadings that are at the same outline level structured the same way? All complete sentences, for example.
  • Does the entire set of headings form a coherent outline?

Here’s a picture of the screencaptured Navigation Pane from one of my writing projects. You can see that I made notes on it, and I then made those edits to the headings in the document.

Writing in Threes

The power, the magic, and the charm of three

Anecdotal evidence suggests that when trying to persuade, presenting three concepts is better than presenting two. Or four. Or more. We see examples of memorable, powerful threes in advertising, in literature, and even in the Declaration of Independence:

  • snap, crackle, and pop
  • I came; I saw; I conquered
  • life, liberty, and the pursuit of happiness

Yes, I just gave three examples.

Do you have a sense of the importance of three in writing? Did you ever learn to write a “five-paragraph essay”? You present an introduction and a conclusion, but in between you write the first point, the second point, and the third point. The power of three.

When creating lists, when presenting claims, or when organizing arguments, writing in threes is common advice from legal-writing experts. Patrick Barry says, “Judges use the Rule of Three. Practitioners use the Rule of Three. And so do all manner of legal academics.”[1] Diana Simon advises that when possible, “distill your arguments down to three main points … and, if possible, eliminate arguments after that point .…”[2] And Bryan Garner reports that “A mathematician once told me that there are really only four numbers in the world: one, two, three, and many.[3]

But is the persuasive power of three anything more than good advice? Yes. Empirical studies validate the “magic of three,” as Diana Simon summarized in a recent article.”[4]

In one study, subjects learning a new word were better able to understand and apply the word’s meaning after being given three examples.[5] Similar research suggests that we consider evidence and examples to establish a pattern or a “streak” once they hit three.[6]

In another study, subjects described getting back together with an ex-partner, and the descriptions had from one to six reasons that the renewed relationship was good. In one scenario, the person described the ex-partner with four words: “intelligent, kind, funny, and cute.” Researchers noticed that the fourth word provoked skepticism in listeners, and overall, those who heard three positive traits were more likely to approve of the relationship than those who heard four.[7] The authors of that and other studies concluded that “the optimal number of claims is three ….”[8]

In the real world, you can’t always force legal standards into threes. After all, premises liability in Texas has four elements. But if one element is beyond dispute or if one has been waived or stipulated, your memo, motion, or brief can present the three remaining elements. Or maybe for the fourth element is supported by three arguments or three key pieces of evidence.

Would using some examples help you present your position? If so, consider using one or three, but not two—and definitely not four: remember the power of three. And when constructing sentences, if you have the opportunity to present parallel ideas, phrases, or clauses, see if you can reasonably present them in threes. So this:

  • The employer’s responses were hasty, terse, superficial, and disrespectful.

Is likely not as powerful as this:

  • The employer’s responses were hasty, terse, and superficial.

When you can, take advantage of the power of three.


[1] Patrick Barry, The Rule of Three, 15 Legal Comm. & Rhetoric 247, 247–48 (2018).

[2] Diana J. Simon, The Power of Connectivity: The Science and Art of Transitions, 18 Leg. Comm. & Rhetoric: JALWD 65, 80 (2021).

[3] Bryan A. Garner, Good Headings Show You’ve Thought Out Your Arguments Well in Advance, ABA J. (2015),​headings_​show_​youve_​thought_​out_​your_​arguments_​well_​in_​advance/

[4] Simon, The Power of Connectivity, at 76-77.

[5] Simon, The Power of Connectivity, at 77 citing Suzanne B. Shu & Kurt A. Carlson, When Three Charms but Four Alarms: Identifying the Optimal Number of Claims in Persuasion Settings, 78 J. Marketing 127, 137 (2014) citing J.B. Tenenbaum & F. Xu, Word Learning as Bayesian Inference, Psychol. Rev., 114(2), 245–72 (2000).

[6] Kurt A. Carlson & Suzanne B. Shu, The Rule of Three: How the Third Event Signals the Emergence of a Streak, 104(1) Org. Behav. & Hum. Decision Processes 113 (2007).

[7] Shu & Carlson, When Three Charms, as reported in Susannah Jacob, The Power of Three, N.Y. Times (Jan. 3, 2014),

[8] Id. at 138.

Connecting Legal Writing

Research and recommendations for transitions

In a recent article, Professor Diana J. Simon of the University of Arizona James E. Rogers College of Law gathered results from some empirical studies on the use of “connectives” (what I’d call “transitions”) in writing. Prof. Simon’s article is called, “The Power of Connectivity,”[1] and the advice is informative and valuable to legal writers who want to write readable, easily comprehensible prose.

Research by psycholinguists and cognitive psychologists shows that transitions in writing improve reader comprehension and even speed up reading and understanding.[2] Some of the research is basic and aligns with common sense: in one study, connecting two related sentences with the word “because” resulted in faster comprehension than the same two sentences without the connecting “because.”[3]

In another study, participants were given equal time to read multiple pairs of sentences. But one group read pairs connected with “because,” one group read pairs connected with “and,” and the third group read pairs with no connectives. When asked to write down what they remembered, recall was better for those who read the “because” pairs than for the other two groups.[4]

And one study asked participants to read four technical essays and then take a 10-question quiz about the content. Half the essays contained “logical connectives,” and half did not. The test scores were higher for those who read the connected essays, leading the researchers to conclude that “logical connectives appear to aid readers in understanding expository prose.”[5]

Professor Simon then describes transitions (connectives) as mainly linking or substantive. Understanding these two kinds of transitions can help us write connected prose.

Linking transitions are the most common type, and are well known to legal writers. They connect one idea or concept to another and show relationships. Here are some relationships with examples of linking transitions: addition (further, also), causation (therefore, thus), comparison (similarly, likewise), contrast (however, but), and sequence (first, second, third). Granted that these transitions are basic, nearly all legal writing could be improved by more and better use of linking transitions.

Substantive transitions show substantive links between ideas. Professor Simon focuses on three subcategories: repetition, restatement, and roadmapping.[6]

Repetition means literally repeating a key word or phrase from a previous sentence or paragraph, and when not overdone, creates connections in the reader’s mind. For example, when writing about a claim of premises liability, it would be unwise to refer to the claim as “premises liability” and then later “premises defect,” and later “owner liability.” That’s confusing. By repeating the key term, premises liability, the writing stays connected, easing the reader’s way.

Professor Simon notes that even the way we use cases employs repetition:

When the defendant is a governmental entity, a statutory prerequisite may be jurisdictional. Key v. ABC Co., 123 S.W.3d 456, 457 (Tex. 2000). In Key, the court used a three-step test to determine what is a jurisdictional prerequisite. Id.

The repeated case name, Key, creates the connection.

Restatement means recasting a concept for efficiency and reference:

The state argues that a statutory prerequisite is jurisdictional whenever the defendant is a governmental entity. This broad argument circumvents the court’s three-step test for determining what is a jurisdictional prerequisite.

Here, “broad argument” restates, in abbreviated form, the longer phrasing of the argument, creating a connection between the two sentences.

Finally, Professor Simon discusses roadmapping, which introduces a coming idea or ideas or can “alert the reader to a shift in thought ….”[7] For example:

  • The applicant’s request is supported by three key facts. First, …
  • Two valuable public policies underlie the statutory language. These policies are …
  • [From earlier in this column:] Professor Simon focuses on three subcategories: repetition, restatement, and roadmapping.

The techniques discussed here can help all legal writers increase and improve their use of transitions in legal writing. After all, science backs it up.


[1] Diana J. Simon, The Power of Connectivity: The Science and Art of Transitions, 18 Leg. Comm. & Rhetoric: JALWD 65 (2021).

[2] Id. at 66 n. 2, 3 and sources cited there.

[3] Id. (citations omitted).

[4] Id. at 67-68 (citations omitted).

[5] Id. at 78 (citations omitted).

[6] Id. at 74-75.

[7] Id. at 76.

Developing Editorial Judgment

It’s more than “read a lot” and “have a good ear.”

At a recent CLE talk, I said that implementing a certain technique would require “exercising editorial judgment.” A lawyer asked, “How do you develop editorial judgment?” In this column, I try to answer that question.

Note: This column is about words, sentences, paragraphs, and documents, not about substance and content, which are highly important in legal writing: Should I mention this fact? Should I include this topic [information, explanation, analysis, argument, counter-argument, policy, etc.]? Does my reader need more background—or less? And so on.

When you’re writing or editing a document for yourself or someone else, you end up making countless editorial decisions:

  • Should I use a semicolon or a dash here?
  • Should I use conversely, however, or but?
  • Is this sentence too long? If so, where should I break it?
  • Is this paragraph too long? If so, …
  • Should I use three levels of headings and subheadings—or only two?

And so on. We make most of these decisions instinctively, yet in doing so, we may not realize that we’re relying on editorial judgment: a storehouse of knowledge about the way writing works. Plus, factored into all these judgments are the context, the audience, the constraints, and the goals of the writing. That’s a whole lot of judgment to exercise.

I’ll focus on developing good editorial judgment as to the words, sentences, paragraphs, and documents you write. Here are my five key recommendations:

Look things up.

Whenever you have even a small or innocuous-seeming question or concern about words, syntax, sentences, grammar, punctuation, or style, consult a source. The internet works (I like “Grammar Girl” Mignon Fogarty[1]), but I recommend keeping at hand some good reference manuals—books—including references specific to legal writing. I’ve cited five good ones in the footnote.[2]

Read about writing.

I often see “read good writing” offered as advice for learning to write well. It’s good advice. But the reading most of us do is to learn content or to be entertained. The kind of reading you should do to improve your editorial judgment requires more effort, more focus, more planning. For me, it’s not reference manuals like those I mentioned above, but engaging, well-written books about writing well. These books inform and strengthen your editorial judgment. I’ve listed five in the footnote.[3]

Write a lot.

This idea is built-in for most legal writers. The more writing you do in a professional context, the more experience you gain, and experience contributes to editorial judgment. But if all you do is write a lot, without looking things up and without reading about writing, you tend to rest on plateaus; you write the same way you always have—particularly if you’re operating with harsh deadlines and heavy workloads. So write a lot, but improve and inform your writing judgment by looking things up and reading about writing.

Edit, edit, edit.

Subject every serious writing project to edits aimed at effectively and precisely conveying the content, clearly presenting that content in an organized fashion, and thoroughly improving the text for concision, clarity, and correctness. You could develop editing protocols and practice them consistently. You could create editing checklists and revise them over time. You could work at completing drafts early so you have more time to edit—and more time away from the document, which always improves editing.

Seek critique.

Open yourself up to suggestions, comments, and critiques of your writing offered by those you trust and whose writing you respect. One sure way to stymie your editorial judgment is to write the way you always have without seeking input from others.

Those are my best recommendations. Good luck.



[2] Deborah Bouchoux, Aspen Handbook for Legal Writers; Anne Enquist & Laurel Currie Oates, Just Writing: Grammar, Punctuation, and Style for the Legal Writer; Bryan A. Garner, Garner’s Dictionary of Legal Usage; Bryan A. Garner, The Redbook: A Manual on Legal Style; Texas Law Review, Manual on Usage & Style.

[3] Tom Goldstein & Jethro K. Lieberman, The Lawyer’s Guide to Writing Well; Ross Guberman, Point Made; Ross Guberman & Gary Karl, Deal Struck: The World’s Best Drafting Tips; Wayne Schiess, Legal Writing Nerd: Be One; Richard Wydick & Amy Sloan, Plain English for Lawyers.