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Appellate Issues

Winter 2025

It’s Past Time for Real E-Briefing

Linda L Morkan

It’s Past Time for Real E-Briefing
Kseniya Ovchinnikova via Getty Images

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The tools and techniques for efficiently and effectively creating reader-friendly electronic briefs have been available for years, but often lawyers do not take full advantage.  Artificial Intelligence, of course, is a game changer, but there are a number other useful tools and techniques that attorneys fail to use on a regular basis, many of which have been available for decades now.  A four member panel, moderated by Brian Miller of Texas law firm Royston, Rayzor, Vickery & Williams, explained to attendees at the 2024 Appellate Judges Education Institute what technology practitioners and courts should be using on a regular basis.  The panelists were:  Justice Peter W. Sacks of the Massachusetts Appeals Court; Raffi Melkonian of  law firm Wright, Close & Barger LLP; Jennifer Shircliff, Staff Attorney at the Indiana Supreme Court; and Brian Knudsen of Thomson Reuters, Vice-President of Large Law Firms.

“It’s important to think about where we have been,” said Melkonian. “Our generation will straddle both sides of a major technological change in briefing.”  We are going from hard copy records to linking briefs to an electronic online record.  We have to use the available tools in the most beneficial manner.

The other panelists echoed Melkonian’s sentiments.  Justice[ML1]  Sacks says that when he arrived on the Massachusetts Appeals Court, the court was more advanced than the attorney general’s office.  He would carry hard copy briefs to read on the subway going to work.  Now the briefs are all on his iPad.  He has access to everything from every case he’s handled in the last six to seven years.  He can cite check on the iPad too.

Shircliff said the proper use of the technology is critical to keeping the record in order and for efficient administration of justice.  Knudsen adds that generative AI has been rapidly adopted, unlike other technologies.  But if used incorrectly, it can really hurt you.

What have we learned about reading on screens?

Miller points out that Robert Dubose, who authored a short paper, “Legal Writing for the Rewired Brain,” emphasized that studies of screen-reading eye movement have observed an F-shaped heat map pattern on screens.  Dubose gave talks about how this affects our briefing.  Things at the top are noticed, things on the left margin are noticed more, and things in the middle that have emphasis, tend to get noticed.  This realization drove Miller to consciously place emphasis on the starts of sections, the starts of pages, and the starts of middle paragraphs.  Don’t bury important points by putting them elsewhere.  Don’t assume the entire brief will be read.  Account for skimmers who only read first lines or sentences.  Tables and headings are more important than ever.  If the header is not informative and persuasive, it will take away from the accompanying text.

Melkonian observes that screen readers find it hard to read substantive footnotes.  They read side to side to digest the text, but footnotes force them to scroll down in the midst of that to catch what is being said there.  Because of this, he has dramatically decreased his use of footnotes in briefing.  Shircliff agrees that she does not see footnotes used much and tries to use them sparingly herself.  When she does, it is for inconsequential information.

Judge Sacks disagrees somewhat, as he likes footnotes.  They are important to his writing.  He likes to anticipate questions and put the answers in the footnote.  He typically has a little over one footnote a page in his opinions, though he is trying to reduce his usage to one every other page.  He notes that he reads all briefs on iPad in portrait format.  And he reads all the footnotes.  He dislikes footnotes in a smaller font, however, because they are harder to read.  Some judges, however, may skip the footnotes.  And in some jurisdictions, if an argument is presented in a footnote, it is not preserved.

Miller aligns with Melkonian on footnotes.  He wants to make it easy on the reader.  If it is substantive argument, he says it should be in the main text.  People sometimes zoom their briefs to the width of the reader, and then have to scroll up and down to see the footnotes.  Footnotes are good for citation strings, not for a core part of the argument.

How can the electronic brief format be used creatively?

Judge Sacks says he loves to see charts, photos, timelines, maps, and any other visual aid that helps the reader understand the case.  Of course, do not portray the imagery as evidence if it is not.  But pictures and drawings help the reader visualize the facts.  They provide a framework for remembering the case.  If you cannot put the imagery in the brief, be sure to provide a reference early on.  Charts and graphs help arrange the facts in the reader’s mind.  They can be easily inserted into the brief or an addendum.

Miller and Shircliff agree with Judge Sacks.  Imagery can be the best way to show the court you are right, the proverbial wisdom being that the most persuasive advocacy will “show, not tell.”  For example, in a challenge to annexation of property, Miller used an image of the Octopus shaped city boundaries to make his case.  In a construction defect case, he inserted the illustrative expert slides from trial into the brief.  This is better than forcing the reader to go to the appendix.  He was involved in a retaliation case once, where the county attorney took the position that the employees were saying horrible things about their boss and coworkers in text messages.  The county attorney just quoted the text messages in the brief but could have done so with greater effect if he had inserted text bubbles.  Be careful, though, not to overuse these sort of presentation techniques or it will diminish their effect.

Miller adds that electronic briefing has caused him to buck some conventions.  He was for a while locked into headers that were the same size as the rest of the text.  But legal writing seemed to be the only forum where writers were doing this.  In other publications, headers were not the same size, were not in all caps, and were easy to read.  He also varies the font in his headers from the body text.  Miller also now provides more space in the margins because it is easier to read a document when the columns are narrower.

What software tools should legal writers be using?

Today’s technology provides legal writers a number of useful tools for drafting well-written legal briefs and opinions.  The panelists encourage the use of five specific tools:  automatic formatting features in word processing applications; table of authorities applications; “read aloud” technology; a legal writing editor such as BriefCatch; and cite-checking tools such as Quick Check.

Automatic Formatting Features

Automatic Formatting Features

Automatic formatting features, such as the “styles” feature in Microsoft Word, can quickly conform the text in a brief to pre-selected formatting preferences allowing the drafter to format the brief quickly and consistently.  The “styles” feature in Word, for example, allows the writer to assign multiple formatting preferences (font, font size, line and paragraph spacing, indentations, etc.) to a single “style” and then apply that style to the text with a single button click, conforming the text to all of the pre-chosen formatting elements at one time.  For instance, one might cut and paste from a differently formatted pdf into the brief, apply the “block quote” style, and voila!  The text conforms to the pre-selected font, font size, linespacing, and indentations for block quotations with the click of one button.  Using the styles feature also facilitates the instant creation of a table of contents and bookmarks when the Word document is converted to pdf.

The styles feature in Word is one that Miller says should be taught in the first week of law school.  He is amazed at how many associates have to be trained how to use it.  It is easy to find in the main menu ribbon in Word.  It allows the creation of multiple different header styles for different levels of headers, automatically applies the pre-selected numbering, roman numerals, or lettering, sets the indentation according to the appropriate header level, and thereby ensures the section headers are uniform and properly numbered or lettered.  That outline carries into the table of contents, making it easy for the reader to see the structure of the argument at the start of the brief.

Table of Authorities Apps

Table of Authorities applications make the generation of a table of authorities much easier and, once the table is created, the page references can be automatically updated as revisions are made to the brief.  Miller demonstrated to the audience how this feature works in Microsoft Word.  Use the short key stroke Alt+shift+I to open a window for the tool.  The feature has some ability to find the citations itself, but sometimes needs help from the user.  After marking each of the citations, return to the references ribbon and insert table of authorities.  Once the table has been inserted, it can be updated with a right click when revisions are made to brief.

Table of Authorities Apps

Table of Authorities Apps

“Read Aloud” Technology

As the moniker suggests, read-aloud technology is software that converts text to speech.  Shircliff uses this tool a lot, finding it to be a real time-saver.  The staff attorneys often review one another’s memos.  If she is short on time, she will listen to a colleague’s memo instead of reading it.  Reviewing the writing this way helps minimize distractions and, in her view, shortens the time to review.

Melkonian also recommends the read aloud feature.  It is a great tool for ensuring the brief has no typos.  Of course, the client will not necessarily pay for four hours of aloud reading.  Sometimes it is better to just use Word’s own internal grammar checking tool, which is also good.

Miller adds that one of the benefits of hearing the writing read out loud by a computer is that the computer does not share the author’s implicit bias about how the writing should sound.  Listening to it read without human affect can reveal that the writing is too harsh and cold and rude; it is better to hear and correct this before the brief or opinion is published than to have the reader misunderstand the tone.

Legal Writing Editors

Legal writing editors help the drafter improve sentence and paragraph structure and word choice to improve the readability, comprehension, flow, and effectiveness of the written advocacy.  The panelists are particularly fond of BriefCatch, which comes from the mind of Ross Guberman, a renowned legal writing expert, and touts itself as the most advanced legal writing editor.  It not only improves the writing in a brief but also trains the author to become a better writer.

Shircliff has a subscription to BriefCatch.  The BriefCatch window pops up by clicking on a menu button in Word.  Any editing suggestions will be highlighted in the text with edits suggested in the reader to the right of the document.  It will compare your document with patterns that it has identified from top legal writers.  When it makes the editing suggestions it shows the source (Justice Kagan, Justice Roberts, etc.).  It will also score the writing and provide statistics, such as the length of words and sentences, use of passive voice usage, and so on, plus suggestions for improving those scores and statistics.  BriefCatch can also be used with email.

BriefCatch Window

BriefCatch Window

BriefCatch Window

BriefCatch Window

Miller first used the free version of BriefCatch and immediately realized the value.  His favorite tool in BriefCatch is the scoring for concision and punchiness.  These measure the effect the words have on the reader; each word should have effect or it should not be there.  Concision quantitatively measures efficiency in the number of words, and punchiness measures the use of effective transitions, active verbs, and the like.

Cite-checking Tools

Cite checking can be done the old-fashioned way, or it can be done far more quickly and effectively with cite-checking software.  Cite checking software is used extensively by the judiciary (judge version).  According to Knudsen, the courts run reports 4,000 times per month on Westlaw’s cite-checking software called Quick Check.

Knudsen explains how Quick Check works.  First, the user loads a brief for analysis of the citations and quotations.  It can be the user’s own brief or an opponent’s brief.  After loading the briefs, Quick Check provides a summary that confirms the cases are good law and organizes the cases according to the arguments in the brief, showing the text in which the case is cited.  Quick Check will identify cases that are overruled or called into question by indirect authority and compare a quotation in the brief to the text of the actual opinion, highlighting any omissions or discrepancies.  It also finds related cases not cited in the brief, which helps the writer see research they may have missed or cases the other side has avoided.

Quick Check also provides an analysis called “potential mischaracterization.”  This feature will show whether the proposition relying on the citation appears to mischaracterize or misuse the holding or proposition in the case by taking the statements in the case out of context or paraphrasing them incorrectly.  While other software performs this function using AI classification or sequencing AI, Quick Check uses generative AI.  It provides a concise summary comparing what was cited in the brief to what was actually said in the authority cited so the user can be the ultimate judge of whether the citation is a mischaracterization.

Three out of five panelists were using Quick Check.  Judge Sacks does not use it to check the party’s briefs, but he does use it to check drafts of his own work.  It provides him helpful recommendations to look at other cases.

How will AI affect appellate briefing?

Artificial intelligence is advancing so quickly that it is hard to keep up, says Melkonian.  Advocates are already using AI to more quickly draft briefs and prepare for oral argument or even teach law students.  For instance, AI can be used to:

  1. Generate questions for a moot oral argument.
  2. Brainstorm ideas for briefs.
  3. Create a draft argument for why the court should want to hear the case.
  4. Find gaps or weaknesses in the arguments.
  5. Generate answers to proposed exam questions to find problems with the questions.

Melkonian is impressed with some of the answers AI has generated to rather difficult law school exam questions.  Amusingly, one time when he commented to AI on how good its response was, AI responded: “Thanks.  The answer basically wrote itself because it is just a basic trap scenario that makes appellate lawyers wake up in a sweat.”  Melkonian cautioned, however, that it can sometimes generate an incorrect argument.  Lawyers need to be careful when using AI.

Shircliff agrees.  Because AI is new and changing, it should be a supplement and not a replacement.  It can increase productivity as well as reduce the time to review and edit documents.  But it is there to help, not replace, the lawyer.

Judge Sacks forecasts that courts will be slow to adopt generative AI in case decision-making.  The ABA recently issued a formal opinion for practitioners and judges on the subject of using AI tools.  Lawyers must provide competent representation, which means lawyers need to be doing the thinking, not the computers.  Confidentiality is another problem; using AI sometimes means delivering the record or draft to a third party.  The information in the courts may be sealed, and we need to make sure it remains secure.  Courts also need to maintain the public’s confidence with assurance that courts are not allowing AI to make the decisions.  Otherwise, the legitimacy of the judicial system comes into question.  That said, Judge Sacks finds AI to be an amazing tool for stimulating thinking.

Unfortunately, lawyers will find inappropriate ways to use AI, says Miller.  But it can be used in a number of appropriate ways, such as testing theories, finding unexpected arguments, or anticipating an opponent’s arguments.

Knudsen agreed that generative AI is a fantastic tool for assisting in the generation of arguments but not for creating a finished, reliable product.  It is great for research or a first draft, but the attorney must still develop that research and the writing into a final draft.  Westlaw offers a document summarization and analysis tool that can be deployed to scan a large trial record for certain materials.  But the attorney must make sure the results rely on source material and check the cited sources.

Knudsen also noted that there is another powerful AI tool to consider for digesting the trial record: Westlaw’s timeline feature.  After you upload the record, Westlaw will generate a timeline, which can be used to create a first draft of a memorandum or brief.  He warns that lawyers need to be careful about the providers they are using, especially open-source models, which are not trained for legal-centric work.

In close, while it may take some investment of time to become familiar with the technology and software the panelists discussed, these tools promise to save the legal writer exponentially more time in the long run, not to mention improve the quality of the work product, when used properly.  It is high time for all to make good use of these tools.

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