Tom Holm Teaches Advanced Persuasive Writing Techniques at Winston & Strawn LLP

Winston & Strawn LLP

I recently demonstrated persuasive writing techniques to litigation and business attorneys in the Los Angeles office of Winston & Strawn LLP. My workshop addressed three related topics:

  • Writing short, clear sentences;
  • Employing advanced persuasive writing and editing techniques; and
  • Structuring and writing persuasive rules, discussions of authority, and factually explicit arguments.

Writing short, clear sentences

Writing should enhance advocacy, not detract from it. So write short, clear sentences to ensure lucid arguments. Judges have heavy caseloads and—to put it gently—may at times lack sufficient time, support, and interest to methodically work through impenetrable arguments.

Don’t confuse opaque, convoluted writing with sophisticated thinking. Use short, clear sentences to compose complex arguments. Any mediocre mind can make arguments complicated. There’s no genius in analyzing a difficult issue and making it equally, if not more, difficult to understand than the analysis in your cited authority. Deep thought goes into clear expression. Smart advocates take difficult issues and distill them into transparent, accessible arguments. Make your judge’s life easier, not harder.

We discussed several techniques for writing short, clear sentences. Write short sentences for at least the following reasons:

  • Short sentences are easier to remember;
  • Short sentences are easier to understand; and
  • Short sentences give readers “resting places” that allow them to internalize your analysis. Periods provide resting places.
  • Reading even well-written legal analysis is hard: give judges ample opportunities to rest.

And we discussed two guidelines for writing short sentences:

  • Limiting each sentence to one idea; and
  • Keeping your typical sentence length to approximately 20 words.

But don’t rigidly apply these guidelines in every sentence. Some sentences will contain two ideas because you will vary the length and structure of your sentences to maintain your judge’s attention. And some ideas can’t be expressed in 20 words. But have principled reasons for writing longer sentences: don’t default to them. And don’t write several long sentences in a row.

We further discussed several techniques for writing short sentences, including the following:

  • Using active voice;
  • Avoiding nominalizations;
  • Changing complex phrases to simple words; and
  • Reducing glue words.

Reducing glue words is one of my favorite topics to discuss, in part because I learned about glue words from the late Professor Richard Wydick. Sentences contain two types of words: working words and glue words. Working words add meaning to sentences; glue words hold sentences together. Glue words are often words like the following:
“of,” “the,” “a,” “an,” “in,” “into,” “so,” “for,” “that,” “than,” “at,” “on,” “was,” “were.”

While glue words are necessary, they should comprise no more than 40% of your sentences, preferably less. Consider the following examples. The glue words are italicized.

  • Bad: “Julian offers only one declaration in support of his motion, the inadequate declaration of Astrid Rollo. The declaration of Ms. Rollo utterly fails to explain the reasons for Julian’s untimely motion.”
    • Two sentences, 31 words.
    • 11 glue words ÷ 31 words = 35.5% glue words.
  • Good: “Julian offers Astrid Rollo’s declaration to support his motion, but Ms. Rollo’s declaration demonstrates that Julian’s motion is untimely.”
    • One sentence, 20 words.
    • 4 glue words ÷ 20 words = 20% glue words.
  • Bad: “In light of the fact that I worked so hard on the structure of my writing, I feel I have a better chance of getting a judicial clerkship.”
    • 15 glue words ÷ 28 words = 53.6% glue words.
  • Good: “I improved my chances of getting a judicial clerkship because I toiled on my legal writing.”
    • 4 glue words ÷ 16 words = 25% glue words.

We also discussed several techniques for writing clear sentences, including the following:

  • Punctuating intelligently;
  • Avoiding subject-verb-object gaps;
  • Avoiding complex words where simple words provide the same meaning; and
  • Tabulating complex information.

Your job is to communicate—simply and directly. Unnecessarily complex verbiage interferes with your analysis; it doesn’t advance it. While you should find the best words for your arguments, use simple words wherever possible.

I have a fond memory—now that much time has passed—from a former student’s memorandum. He wrote the following: “Any further argument would be bootless.” I wasn’t aware that arguments needed boots, but I was horrified to learn that an argument might be unshorn. Yet upon my review of my dictionary, I learned that “bootless” simply meant “useless.” Don’t send your readers to the dictionary: use simple words.

Consider the following short list of complex versus simple words.

Complex Word

  • acquire
  • adjacent
  • ascertain
  • commence
  • endeavor
  • facilitate
  • initiate
  • intimate
  • numerous
  • originate
  • procure
  • residence
  • subsequently
  • terminate
  • transpire

Simple Word

  • get
  • next, near
  • learn, confirm, check
  • begin, start
  • try
  • help
  • begin
  • hint, imply, suggest
  • many
  • begin, start
  • get, buy, take
  • home, house, apartment
  • later, then, after
  • end, finish
  • happen, occur

Advanced persuasive writing techniques

It’s easy when teaching persuasive writing to simply suggest sentence-level techniques and provide sentence-level examples illustrating those techniques. But that narrow focus doesn’t help attorneys apply those techniques in their briefs because they aren’t shown how those techniques can be applied in the context of a complete argument. My program demonstrated how to incorporate and combine persuasive writing techniques in detailed, integrated writing samples.

We discussed several persuasive writing techniques, including the following:

  • Using active verbs;
  • Using proper syntax to highlight key points, rather than italicized and bolded text;
  • Using dashes to highlight phrases and clauses;
  • Using semi-colons to compare and contrast;
  • Using substantive transitions to highlight key facts and ideas; and
  • Using parallel construction.

Active verbs provide some of the best weapons in your writing arsenal. On a fundamental writing level, sentences written in active voice are shorter than those written in passive voice. And using active verbs helps you avoid nominalizations and excessive glue words. On a persuasive writing level, your sentences will have punch because your verbs will have punch. You will use less words and write more powerfully by choosing verbs that carry effective meaning. Verbs sound less strident than adverbs because verbs are the words that are supposed to carry the meaning in your sentences. So be creative in your verb choice, not your adverb choice. Find the right verb: you likely won’t need an adverb.

Consider my prior example regarding glue words: I eliminated unnecessary adverbs by choosing active, descriptive verbs.

  • Bad: “In light of the fact that I worked so hard on the structure of my writing, I feel I have a better chance of getting a judicial clerkship.”
  • Good: “I improved my chances of getting a judicial clerkship because I toiled on my legal writing.” (4 glue words ÷ 16 words = “25% glue words)
    • worked so hard” becomes “toiled.”
    • “I have a better chance” becomes "I improved my chances.”

And consider the following examples: active verbs lead to shorter, sharper sentences.

  • Bad: “The defendant unlawfully took money from the corporation.”
  • Good: “The defendant embezzled from the corporation.”
  • Bad: The defendant was spoken to in his customary residence.
  • Good: The police interrogated the defendant at his home.

Also, dashes are an underused persuasive writing tool: they help highlight facts or ideas in clauses. And dashes help vary your sentence length and structure, which keeps the court’s attention. So use dashes to highlight explanations and details in the middle of your sentences, and use dashes to augment points at the end of sentences.

Avoid using commas for this purpose. Commas are pedestrian and boring, unless they are serial commas—these are exciting and necessary, but are a topic for another post. And don’t use parentheses. Parentheses suggest tangential information. Highlight your points; don’t hide them.

    • Example: “Julian knew these facts when he filed his original complaint. Yet Julian failed to seek leave to amend until seven months later—after discovery is closed and only five weeks before trial.”

  • Example: “Forcing VGNB to invest more time and money in such large-scale discovery—much of which could have been done earlier and more efficiently had VGNB been aware of these allegations—would severely prejudice VGNB.”

Structuring and writing persuasive rules, discussions of authority, and factually explicit arguments

Here, we examined such issues as the following:

  • Articulating favorable overall rules;
  • Framing concise, factually detailed tests (aka sub-rules) that favorably frame issues and identify the facts that are sufficient to satisfy each component of an overall rule;
  • Using parallel construction in case discussions and arguments to reinforce tests;
  • Highlighting parallel and weaker facts in the cases to ensure discussions of authority—and parentheticals—provide as much support for arguments as possible;
  • Distinguishing contrary authority;
  • Organizing facts under factual propositions;
  • Organizing facts pursuant to the arguments they support; and
  • Weaving seamless arguments combining facts and law.

This segment ended with a discussion of several annotated writing samples. First, we discussed annotated sample sub-sections from two competing briefs. These writing samples illustrated how the same issue on summary judgment could be argued by each party and applied the writing techniques the attorneys were taught during the session.

Second, we reviewed annotated excerpts from an excellent ACLU brief relating to litigation arising from a segment on coal mining on the HBO Show Last Week Tonight with John Oliver. With this brief, we discussed framing compelling arguments using less traditional argument structures.


I appreciate the very positive evaluations I received for my workshop. Below are some representative comments, which were provided anonymously.

  • “I appreciated the broad overview, balanced with specific examples. I’ve attended other writing seminars where the examples were too basic or not realistic enough. Also, the written materials are concise and helpful—more helpful than being handed a book, as has happened in prior writing seminars.”
  • “It has been several years since I took a writing seminar, and I liked how much ground you covered, even topic/points that are basic. I have a short list of ‘takeaways’ to keep in mind as I draft and edit my next brief.”
  • “The parts of the presentation that helped me most was the early part on writing mechanics and the last part on the ACLU brief.”
  • “I liked the teaching materials very much and I plan to review more closely later on.”
  • “Discussion was helpful and amount of participation was right on.”
  • “Learned some very helpful writing tips. I liked the breakdown of specific examples.”
  • “The part that helped me the most was the explanation of test statements.”
  • “I especially appreciated going through the sample briefs.”
  • “The general overview and writing tips were very helpful. Passive language, sentence structure, brevity, word choice, etc. are so helpful for good legal writing.”
  • “The teaching materials were very helpful. I will study it.”
  • “While I thought the entire presentation was helpful, I actually found the reminders at the beginning of the presentation re short sentences, clarity, active voice, etc. to be very helpful. It’s been quite a few years since I learned these techniques and the reminders are necessary.”
  • “Fundamental and advanced writing techniques were very helpful.”
  • “I will use the teaching materials in the future.”
  • “The teaching materials will be handy in the future & I’ll be referring to them regularly.”

My mission

I help make attorneys better writers. My legal writing programs teach concrete strategies and techniques pertinent to all aspects of written analysis. All my programs include excellent teaching materials, writing samples, and handouts that attendees can rely on in their future work. And my teaching methods ensure that attendees will not only value and enjoy my programs, but will apply and retain what they’ve learned.

I also offer individual writing instruction to attorneys who wish to improve their written advocacy, including attorneys whose employers wish to give extra writing support. As part of my instruction, I critique attorneys’ actual memoranda to provide self-editing tools that allow them to approach their future work more effectively.

Join the attorneys whose writing has been enhanced by my instruction. Contact me to get started!

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