Jeffrey Schoenberger is a senior consultant at Affinity Consulting Group LLC.

The Supreme Court of Missouri entered an order Dec. 16, 2025, that, in part, simplified redaction instructions and enhanced the process for correcting redaction. As you review your redaction process, remember Adobe Acrobat Pro has a built-in redaction tool you can use to help protect your clients’ sensitive information. 

Whether you’ve used Acrobat for a while or are just getting started, here is the six-step process to most effectively use its tools to remove not only text, but AI metadata.

1. Open the PDF you want to redact in Adobe Acrobat Pro 
 

2. Activate the redaction tool 

a. Go to the “All tools” pane on the left (or select “All tools” from the top menu bar). 

b. Scroll down and locate the “Redact a PDF” tool, then click it. If you don’t see “Redact a PDF,” you may need to click the blue “View more” link at the bottom to see the option. Alternatively, you can click the magnifying glass on the top right of the toolbar and search for “Redact,” then click “Redact text and images.” 

c. A new “Redact a PDF” pane will open on the left-hand side.

3. Mark content for redaction

Acrobat lets you redact text and images in three ways. You can select text or images piecemeal, you can redact entire pages, or you can have Acrobat search your document for words or phrases (e.g., social security numbers, account numbers, children’s names) and mark those for redaction. Note that the third option, called “Find text and redact,” only works in PDFs with optical character recognition, meaning you can search and copy and paste text in the PDFs. 

For this example, we’ll do “Redact text and images.”

a. Click the “Redact text and images” button in the “Redact a PDF” pane. 

b. Use your mouse to select text or images you want to redact. For text, click and drag to highlight what you want to redact. For images, click directly on the image or area. Your selection should be surrounded by a red border. Hovering over it should turn the text or image solid black.

4. Preview and apply the redactions 

a. Once you’ve marked all areas, click “Apply” at the bottom right of the “Redact a PDF” pane. 

b. A prompt will ask if you’re certain you want to permanently redact the content. You also will have a toggle switch to “Sanitize and remove hidden information.” It’s generally recommended to enable “Sanitize and remove hidden information,” since it now removes embedded AI-generated metadata that may not be visible but could contain sensitive prompts or summaries. By toggling this switch on, in addition to performing your redactions, Acrobat will search your document for metadata (e.g., comments, bookmarks, attachments, form fields, and AI content) and remove it. 

c. Click “Continue.”

5. Save the redacted PDF

Acrobat will prompt you to save a copy of the document with a file suffix of “Redacted.” Navigate to your preferred saving location and click “Save.” 

Acrobat will also ask you to save a second copy, because redactions are permanent and irreversible. You now have two PDF documents: the original with all sensitive information intact; and the redacted one, with sensitive information removed, suitable for filing or distribution.

6. Review the document to ensure all sensitive content is correctly redacted 

Properly redacting private information protects your clients, complies with confidentiality rules, and guards against sanctions or malpractice claims. Many firms now add redaction checks to their internal audit trail. Schedule in time to double-check your work — and Acrobat’s.

Conclusion 

With these steps in Adobe Acrobat Pro, you can securely remove confidential content and protect your clients’ information. If you have questions, Adobe provides a redaction guide on its website. 
To help you even better serve your clients, access no-cost comparison charts, white papers, checklists, and more at MoBar.org/LPM.

Ask the average person how lawyers differ from their neighbors and one answer you’re likely to hear is, “They speak a different language — legalese.” Sadly, that perception is not wrong. 

In contrast to other professions, lawyers tend to cling to the language of the past with a seemingly unshakeable tenacity. This includes contracts that announce themselves with “WITNESSETH,” references to “the said minor child,” and the dreaded “here” family (herein, hereinabove, heretofore, hereby, etc.). There are dozens of examples of archaic, outdated words and phrases that lawyers use, erecting barriers to comprehension and unnecessarily requiring clients to ask what documents mean. 

How is it that these words from the distant past persist, and what can lawyers do to break the mold and give clients separation agreements, sales contracts, leases, trusts, pleadings, and a host of other documents written in language they can readily understand? 

How and why 

First — the how and why. My own theory, based on personal experience and nods of recognition when I’ve outlined it to other lawyers, has to do with our first experiences as “baby lawyers.” 

Law school graduates possess lots of knowledge about the law of contracts, torts, trusts and estates, property, and other substantive areas. They have learned how to read cases and statutes and how to find the law. Frequently, however, they have little knowledge about how our profession is practiced in the real world. 

When my first employer asked me to draft a PDL motion (a motion pendente lite for temporary orders in a family law case), I had no clue where to begin. Recognizing my confused look, he quickly found an example and handed it to me. “COMES NOW, THE PETITIONER,” it began, so I duly inserted the relevant information from the case I was assigned into the old motion. That document became my template for future motions. And since the motion closed with, “WHEREFORE, Petitioner prays,” that phrase appeared at the end of every pleading I drafted. “That’s the way it’s done,” I thought to myself. 

It doesn’t take a great deal of imagination to visualize the same scene occurring when my boss began his life as a lawyer and his first employer similarly handed him examples to rely upon for drafting pleadings, contracts, and other legal documents. 

Another likely contributor to outdated writing style is a lawyer’s fear of risking a bad outcome from using untested language. Some lawyers may think, “If it was good enough for other lawyers, it’s good enough for me,” or, “It’s what the judge expects.” 

So, if a lawyer in 1940 wrote a contract stating, “NOW, THEREFORE, in consideration of the mutual promises and other good and valuable consideration herein expressed, the sufficiency of which is hereby acknowledged, the parties hereto agree as follows,” modern lawyers may fear that changing that lingo will jeopardize the contract’s effectiveness.

Write how you speak 

In “Legal Writing in Plain English,” Bryan Garner, editor of “Black’s Law Dictionary,” offers lawyers a simple suggestion: “If you wouldn’t say it, don’t write it.” 

Consider giving those outdated templates a much-needed refresh. Read them carefully and consider whether the average person would understand the language. If you, a highly trained professional, are struggling with any of the words or the convoluted syntax, your clients may have trouble making sense of the document. 

Constantly ask, “What does this word or phrase add to the document?” If the only answer is “Because it’s always been there,” take it out. Once you’ve decided you need to make changes, where should you begin? Here are a few suggestions for streamlining your documents so clients can understand them: 

Assume document will be attacked by that lawyer 

You know the one — the lawyer who twists words in a sufficiently plausible way that you will have to respond, and your client will have to pay you while you try to convince a judge that your words meant what you intended them to mean. If you start with simple, modern language and sentences, you are setting yourself (and your client) up for success from the beginning. 

Jettison the jargon 

No statute or rule requires pleadings to open with “Comes now…” Get rid of the formulaic language and replace it with the simplest possible version. Instead of, “Petitioner, by and through counsel, for her Petition for Dissolution of Marriage, states and avers as follows,” change it to, “Petitioner, for her petition for dissolution of marriage, states:,” for example. 

One easy change that will immediately make documents clearer is to give “herein” the heave-ho. Every time a contract refers to a proposition “stated herein,” I ask the question, “In what?” Does that mean in this paragraph? In this section? In this document? In the pending action? While in most instances, the answer will be clear from context, lawyers can eliminate all possibility of misinterpretation with a few clarifying words like, “as stated in this [paragraph/agreement/section].” 

Once you get rolling, you will discover other ancient hangers-on that can be thrown in the trash forever. “Wherefore, Plaintiff prays” becomes, “Plaintiff therefore requests.” “In witness whereof the parties hereunto have set their hands to these presents as a deed on the day month and year hereinbefore mentioned,” becomes simply a blank preceded by the word “Date.” You get the idea. 

Say it once 

“Null and void.” “Cease and desist.” “Indemnify and hold harmless.” 

Some lawyers believe the notion that saying something twice is the legal equivalent of double bagging at the grocery store. Remember the basic contract principle that each word in a contract is to be given meaning. By saying something twice, a lawyer may give another lawyer the opportunity to insist to a judge that the two terms have distinct meanings.¹ Pick one. 

Also, eliminate “belt-and-suspenders” numbers. Perhaps when lawyers handwrote contracts, they needed to spell the number out and then put the numerals in parentheses: “three hundred twenty-seven (327).” In a typed document, though, there is nothing ambiguous about “327.” You will, however, create unnecessary ambiguity by saying “twenty-four (6).” That kind of error disappears if you settle on one version — words or numbers.

Additionally, have the parties agree once at the beginning of the contract, rather than reminding readers throughout the document that, “the Parties further agree…” If the contract began with, “The Parties agree:” then you’ve fulfilled that contract requirement. All there is left to say is what they’ve agreed to. And there’s no reason to say, “The Parties agree as follows” or “to wit.” 

Define terms

Since my practice focuses on family law, I’m accustomed to pleadings and agreements that refer to the petitioner and the respondent, usually capitalized (superfluous capitalization, in my opinion). By page three of a separation agreement, however, it’s very easy to lose track of which party is which. Due to the confusion, a lawyer may accidentally award the Lamborghini to the husband instead of the wife, for example. 

The simple fix: Define the parties by their first names at the top of the document — “Petitioner, Morgan Miserable (‘Morgan’).” Notice it didn’t say “(hereinafter sometimes referred to in this Agreement as ‘Morgan,’)” and yet you understood exactly what it meant. Once the court approves the separation agreement, they are no longer husband and wife, but they will most likely retain their first names. 

Lawyers can define the separation agreement as “the Agreement.” The date of entry of a judgment of dissolution of marriage in this example, is defined as “the Entry Date.” The anticipated judgment becomes “the Judgment.” More complicated terms, such as a definition of “net income,” lawyers can explain once, with subsequent references using the name of the defined term. Lawyers can use capital letters to clarify which terms are defined so there is no confusion between, say, “a party” and “a Party,” with the latter meaning a party to the action. 

Simplify, simplify, simplify 

After drafting a document, reread it, both to make sure there aren’t any errors and to see how it could be more concise. Some formulas may jump out immediately. “In the event that” can almost always be replaced with “If.” Try it out. You’ll be amazed at how quickly you’ll begin to remove that overworked phrase. 

Eliminate unnecessary modifiers. When a document states, “The Parties currently hold title to…” in a separation agreement, ask, “When other than ‘currently’ could it be talking about?” When the boilerplate says, “as provided for in any law now or hereinafter effective of this state or any other state or territory of the United States or any foreign country,” it can be shortened to, “as provided for in any law in effect now or in the future in any state or country.” 

And don’t forget the boilerplate, the most neglected section of most contracts. Lawyers focus closely on the terms of the contract, but they often forget that the boilerplate contains other terms the parties must agree upon. “That’s what we always put in contracts,” is not a good enough answer to a client’s questions about these “standard” paragraphs. Every sentence needs to be clear, not to mention grammatical. 

Have another person read your document

Both for ensuring clarity and avoiding legal and factual mistakes, it makes sense to have another lawyer in the office review the document. Sometimes lawyers get so involved in the drafting they miss something crucial. If you are a solo practitioner, ask a paralegal or a legal assistant to review the document for clarity. 

Conclusion 

I always tell clients that if they don’t understand every term in a contract I’m asking them to sign or approve, I haven’t finished my job. 

Begin by eliminating every word people don’t use in normal speech and replacing each with the modern equivalent. Go through a second time to make certain you haven’t repeated yourself unnecessarily. Have a non-lawyer read the document and give feedback. If an administrative assistant doesn’t understand, there’s a good chance a client won’t either. 

Take pride in your writing. Even the densest contract can be made understandable with a little extra effort. The more time you spend on a document, the shorter it may get as you eliminate unnecessary repetition and replace the ancient with the modern.

Endnotes 
1 “There has been a welter of needless litigation over the doublet [indemnify and hold harmless], as litigants have wasted countless dollars fighting over imaginary differences between the words – differences that have no historical justification.” Bryan Garner, Garner’s Dictionary of Legal Usage (2011).

If an unforeseen emergency – like another pandemic – occurred, would you already have contingency plans in place? If you retired, would the law firm continue operating smoothly? Strategic succession and contingency planning can help you prepare for the future so you can even better serve your clients without disruption.

Contingency planning prepares you for the unknown, the unplanned. Succession planning, on the other hand, is the preparation for a planned exit from the firm (most often retirement). The two go hand-in-hand.

When considering what the future might hold, you must think about the people who will carry the torch in your absence, the core processes that keep business running smoothly, and how to transition work and clients seamlessly.

First-rate players

You can’t plan for the future without planning for those who will succeed you or take over in the event of an unplanned absence. Early identification of star players provides you with time to mold them into stellar leaders and rainmakers. The sooner you start working with these key players, the more time you have available to help shape them into whom the firm needs them to be.

Fundamental processes

Numerous fundamental processes drive every firm. Strategic planning requires identifying those processes and documenting every step, from client intake to closing letters. Process documentation has immediate benefits. New hire onboarding is more efficient, and process documentation helps get everyone in the firm on the same page.

While documenting processes, look for areas of potential improvement and gaps in the firm’s coverage. Ensure that there is a back-up for each task. Should someone suddenly leave the firm, you don’t want to be left in the lurch.

Future transitions

Transitioning work and clients is never easy. The most successful transitions start before retirement is on the horizon and must begin before an emergency is upon the firm. Ensure that every client works with and trusts at least two lawyers in the firm. Clients must be comfortable with your replacement long before you decide to retire.

Train associates to handle every type of matter that comes in. Work side-by-side on the complicated matters and provide them guidance on how to handle the thorniest issues. Then, when you are ready to retire or an emergency arises, they will be prepared to handle the workload.

This type of planning isn’t easy. Keep succession and contingency planning in mind with every decision your firm makes so you – and your clients – don’t have to worry in the future.

For more resources on contingency and succession planning, visit The Missouri Bar’s Law Practice Management Resource Center.

Document management solutions are critical to the success of today’s law firm. Legal specific document management eliminates the wild, wild west approach to document storage and security and significantly improves the efficiency and productivity of legal professionals.

 Selecting a document management system (DMS) can be daunting, but here are four simple steps to get you started on the path to selecting the perfect DMS for your firm or legal department.

Identify core features of your DMS

Understand the real needs of your firm before looking at a document management system. Does your firm have issues capturing emails? Are your challenges with finding documents? Are there difficulties with saving documents consistently and naming conventions? Truly recognizing the needs of your firm or department is the first step to understanding and selecting the features needed in a DMS.

Rank feature importance

One document management solution will probably not provide you with EVERYTHING on your list. Ranking your requirements will help. Know what features are critical to your firm or department. Know which ones you’d like to have but could live without and which ones you definitely do not want or need. It may be necessary to trade off some features that mean little to your process in place of ones that cannot be compromised.

Evaluate on premise solutions versus hosted, cloud-based solutions

Understand your choices when selecting the DMS configuration that’s best for your firm. Keep in mind that the number of on-premises vendors diminishes each year. Most investment and development focus on hosted (AKA cloud-based) solutions.

With on-premises solutions, you’ll need to consider whether you have someone with the knowledge to set-up and maintain the system, plus hardware/software costs and specialized manpower for maintenance. You also want a clear sense of the vendor’s long-term strategy for its on-premises product. If you must have an on-premises DMS, perhaps for regulatory reasons, ensure you understand the vendor’s commitment to future support for and investment in their on-premises products.

For hosted solutions, consider recurring costs (usually monthly, quarterly, or annually) to maintain servers and warehouse your documents, understand your data will live elsewhere, and maintain a strong internet connection.

Identify the choice that best meets your needs and budget.

Explore solutions via demo

Document management solutions should enhance the work your firm is doing, not add more steps or additional challenges. By watching an actual demonstration and seeing how a document management system’s features are performed, you’ll see which system will make your teams more productive and efficient.

Also, if a DMS indicates it can perform a critical function, ask the demonstrator to show you how it’s done.

For more resources on opening, building, managing, protecting, and winding down a law practice, visit The Missouri Bar’s Law Practice Management Resource Center.

For lawyers – particularly solos and those responsible for making payroll each month – it seems there are only two states of the business. Either you are too busy to breathe, or you are scrounging around for billable work.

One of my colleagues refers to slow spells as time to “shake the trees” and work on those small tasks that need to be completed but you’ve forgotten about, or they were always less pressing than other matters. There are useful things you can do during slow periods that will eventually turn your “molasses time” into money:

Invest in training

You and your employees use core tools every day. I guarantee the computer programs you already own have features that would help you work faster and more accurately.

• If you draft documents, do you have templates with key language in one place that’s consistently editable with ease?
   
• Have you customized your email application with rules to filter incoming mail, separating client correspondence from newsletters and advertisements?
   
• How about setting up reusable task templates in your case management system?
   
• Have you developed a documented procedure for redacting PDFs for filing?

 Use your downtime to learn how to use your tools better.

If this interests you, Missouri Bar members get a 20% discount on Affinity’s legal-specific software manuals. Go here and use the coupon code MOBARMANUALS.

Catch up on CLE

Irrespective of business conditions, you will need CLE at the end of your reporting period, June 30, 2024. The Missouri Bar allows a portion of self-study CLEs to apply towards your MCLE hours. Here is a list of upcoming CLE programs.

Take inventory

Take inventory of your technology. Ask the following questions:

• Who has what? Make a list of each staffer and what they have as far as computers, monitors, scanners, printers, phones, and headsets. Also record what software each staffer has, the version of that software, and any associated licensing key. The software list says who has access to special software, like a child support calculator, and whose software should be upgraded.
   
• Where is it? After making the list, identify where that equipment is. Some equipment will likely at the office, but given hybrid-work policies, a fair portion might be in the homes of remote employees.
   
• How old is it? Record the purchase date and warranty status of each piece.

This inventory list will serve you well for two purposes: insurance claims, if necessary, and planning for replacement of equipment as it ages out of warranty.

Everything has a process

What you do in the firm has an “order of execution” or checklist of events/actions you take – from drafting a letter to a client to scheduling a meeting to creating, and executing documents. Even paying rent or restocking the coffee beans has a checklist.

Document how you do both administrative and substantive processes. Documenting processes will help you discover and eliminate bottlenecks. It also creates a “cookbook” should the person “in the know” be on vacation and the work still gets done.

Use the spreadsheet here to start your documentation process. Start with these two LPM whitepapers as your guides.

Centralize your knowledgebase

If you currently create client documents – whether it be a letter, estate plan, or operating agreement – by finding the most recent one you created for a client and modifying it for the current situation, you’re wasting time and relying on your memory to locate the starting point.

Take time to gather a representative set of recent documents – wills, for example – and assemble a single template, a starting document that contains the best versions of your provisions. Put those provisions into a single word processing document to use as your future starting point. See this LPM checklist as a guide on the subject.

Slow times in your business are stressful but remember there are useful things you can do during those times that will pay dividends down the road. And focusing your mind on something immediate and useful has benefits of its own.

For more practice management tips, visit MoBar.org/LPM for whitepages and checklists, as well as News.MoBar.org for articles covering a wide array of topics.

When was the last time you considered what font to use in a document? While document formatting is just one piece of the branding puzzle, anyone comfortable using a word processor can easily tackle it.

Font

Start the document branding journey by carefully considering the font. Generally speaking, legal documents should contain only one font, and all documents produced by a legal organization should use the same font (except as required by specific jurisdictions). Therefore, you should not take font choice lightly.

System fonts versus proprietary fonts

System fonts -- specifically those included with Windows -- are available on nearly every computer. If working from a Mac, be careful not to select fonts included only with macOS.

Proprietary fonts (those purchased from third parties) are expensive and won't display correctly on computers that don't have that font installed. For anyone frequently exchanging word processor documents with those outside the organization, proprietary fonts are not an option.

To give a system font a proprietary look, consider adjusting the spacing between letters and turning on kerning. In Microsoft Word, these settings are located on the "Advanced" tab of the font settings (right-click in the document and select "font" to open the font settings).

Serif versus sans serif

Once you have narrowed down the universe of potential fonts to the list of system fonts, select either a serif or sans serif font. Serif fonts have “feet” on the letters, such as Times New Roman and Courier New. Sans serif fonts do not have feet, like Arial and Calibri.

Traditionally, serif fonts are considered more readable because typographers design the “feet” to draw the reader’s eye rightward across a word, sentence, etc. In the same vein, sans serif fonts were used for titles, headings, and other short phrases because of their more “abrupt” design style. However, more recent studies have shown no differences in readability between serif and sans serif fonts.

Even though most lawyers use serif fonts, few courts require their use.

Whether a serif or sans serif font is the right choice depends on whether your organization's brand is more traditional or modern. Serif fonts give documents a traditional look. Sans serif fonts give a document a modern, clean look.

Monospaced versus proportionally spaced

Additionally, fonts are either monospaced or proportionally spaced. Monospaced fonts’ characters are given equal width. Proportional fonts’ characters are given the appropriate space based on the width of the character.

In Courier New (a monospaced font), for example, thin characters (such as an “i”) are given the same space as wider characters (such as an “m”). In Times New Roman (a proportionally spaced font), an “i” is given only as much space as it needs – considerably less space than an “m.”

As a result, proportional fonts are significantly easier to read. Unless required by your jurisdiction, avoid monospaced fonts.

Read the font across different mediums

Some fonts are designed with a target “platform” (i.e., paper, TV, LCD, etc.) in mind. For example, with the release of Office 2007 for Windows (and 2008 for Mac), Microsoft changed the default Word font from Times New Roman (a serif font commissioned by The Times in 1931 for use on newsprint) with Calibri (a sans serif font designed with digital reading in mind) because users are viewing documents online more than printing the document.¹

View the font on the screen and in print before deciding. When adjusting the spacing between letters, experiment with different spacing up close, far away, on the screen, and in print. When in doubt, consider whether the typical reader will print the document or read it on the screen.

Paragraphs

Once you select a font, the next step in branding is to determine how the paragraphs will look. Paragraph settings, such as line spacing, spacing between paragraphs, alignment, and indents, are all intertwined. One cannot select a single paragraph attribute in a vacuum.

Whether paragraphs are double-spaced, single-spaced, or somewhere in-between affects how the document looks and its readability. Double-spaced paragraphs are ideal for editing on paper, and single-spaced paragraphs are better for reading.

Frequently, courts require paragraphs to be double-spaced, so check with your jurisdiction on spacing requirements. On the other hand, for contracts, estate plans, and other documents not filed with the court, consider single-spacing to improve readability.

When working with double-spaced paragraphs, include a first-line indent to set each paragraph apart. Spacing between double-spaced paragraphs is unnecessary and will needlessly increase the page count.

Even when paragraphs are double-spaced, headings should be single-spaced. Very few courts, if any, require headings to be double-spaced.

Consider using 12 points of space between single-spaced paragraphs. Twelve points are the equivalent of a single blank line. This white space helps readers easily see where each paragraph begins and ends and provides a visual resting place. Especially in complex legal documents, a visual resting place is critical for improving readability. When using a blank line between each single-spaced paragraph, it is unnecessary to use a first-line indent.

Finally, consider alignment. Most legal documents are fully justified (the text spans from the left margin to the right margin). To line up the text along both margins, the word processor varies the width of the space between words from line to line. While full justification looks nice from a distance, it is more challenging to read than text that is left-aligned with even spacing between words. Carefully consider whether the appearance of the document or its readability is more important.

Cohesive formatting

No matter what formatting you choose, the most important part of branding through document formatting is creating a cohesive look for your organization. All lawyers must be on board with the decisions made for the documents to positively reflect the organization’s branding. Selecting one consistent set of formatting guidelines for the business is more important than getting the formatting just right.

Endnotes

1 In late 2023, Microsoft updated the default Word font to Apotos, also a sans serif font. www.nytimes.com/2024/02/28/technology/microsoft-word-font-aptos.

When was the last time you thought about what font to use in a document? Unfortunately, most legal document formatting occurs “the way it has always been done.” Further, many lawyers mistakenly believe they are required to use Times New Roman font. While some courts require or prefer Times New Roman, most do not.

While document formatting is just one piece of the branding puzzle, anyone comfortable using a word processor can easily tackle it. There is no need to hire a graphic designer or other professional to change document formatting. There is no time like the present to carry over consistent branding into documents your organization produces.

Font

Start the document branding journey by carefully considering the font. Generally speaking, legal documents should contain only one font, and all documents produced by a legal organization should use the same font (except as required by specific jurisdictions). Therefore, you should not take font choice lightly.

Select from system fonts – specifically those included with Windows and, therefore, available on nearly every computer. If working from a Mac, be careful not to select fonts included only with macOS. Proprietary fonts (those purchased from third parties) are expensive and will not display correctly on computers that do not have those fonts installed. For anyone frequently exchanging word processor documents with anyone outside the organization, proprietary fonts are not an option.

Once you have narrowed down the list of system fonts, the next step is to select either a serif or sans serif font. Serif fonts have “feet” on the letters; Times New Roman and Courier New are examples of serif fonts. Sans serif fonts do not have feet; Arial and Calibri are examples of sans serif fonts. Traditionally, serif fonts are considered more readable because typographers design the “feet” to draw the reader’s eye rightward across a word, sentence, etc. In the same vein, sans serif fonts were used for titles, headings, and other short phrases because of their more “abrupt” design style. However, more recent studies have shown no differences in readability between serif and sans serif fonts. Even though most lawyers use serif fonts, very few courts require their use.

Whether a serif or sans serif font is the right choice for you depends on whether the brand is more traditional or modern. Serif fonts give documents a traditional look. Sans serif fonts give a document a modern, clean look. Consider the rest of the organization’s brand when deciding between serif and sans serif fonts.

Additionally, fonts are either monospaced or proportionally spaced. Monospaced fonts’ characters are given equal width. Proportional fonts’ characters are given the appropriate space based on the width of the character. In Courier New (a monospaced font), for example, thin characters (such as an “i”) are given the same space as wider characters (such as an “m”). In Times New Roman (a proportionally spaced font), an “i” is given only as much space as it needs – considerably less space than an “m.” As a result, proportional fonts are significantly easier to read. Unless required by your jurisdiction, avoid monospaced fonts.

Consider how each font looks when reading the document and how the fonts look when viewing the document from a distance. Further, some fonts look better on the screen than in print and vice versa. Indeed, some fonts are designed with a target “platform” (i.e., paper, TV, LCD, etc.) expressly in mind. For example, with the release of Office 2007 for Windows (and 2008 for Mac), Microsoft changed the default Word font from Times New Roman (a serif font commissioned by The Times of London in 1931 for use on newsprint) with Calibri (a sans serif font designed with digital reading in mind) because, as Word program manager Joe Friend explained, “We believed that more and more documents would never be printed but would solely be consumed on a digital device.”

Be sure to view the font on the screen and in print before deciding on a font. When in doubt, consider whether the typical reader will print the document or read it on the screen.

Paragraphs

Once you select a font, the next step in branding is to determine how the paragraphs will look. Paragraph settings, such as line spacing, spacing between paragraphs, alignment, and indents, are all intertwined. One cannot select a single paragraph attribute in a vacuum.

Whether paragraphs are double-spaced, single-spaced, or somewhere in-between affects how the document looks and its readability. Double-spaced paragraphs are ideal for editing on paper, and single-spaced paragraphs are better for reading. Frequently, courts require paragraphs to be double-spaced. Be sure to check with your jurisdiction on spacing requirements. On the other hand, for contracts, estate plans, and other documents not filed with the court, consider single-spacing to improve readability.

When working with double-spaced paragraphs, include a first-line indent to set each paragraph apart. Spacing between double-spaced paragraphs is unnecessary and will needlessly increase the page count. Even when paragraphs are double-spaced, headings should be single-spaced. Very few courts, if any, require headings to be double-spaced.

Consider using 12 points of space between single-spaced paragraphs. Twelve points are the equivalent of a single blank line (essentially, instead of indenting on the next line after you hit the “Enter” key once, hit “Enter” a second time so there is a line of space between the two paragraphs). This white space helps readers easily see where each paragraph begins and ends and provides a visual resting place. Especially in complex legal documents, a visual resting place is critical for improving readability. When using a blank line between each single-spaced paragraph, it is unnecessary to use a first-line indent. For example, see how this article’s paragraphs are formatted.

Finally, consider alignment. Most legal documents are fully justified (the text spans from the left margin to the right margin). To line up the text along both margins, the word processor varies the width of the space between words from line to line. While full justification looks nice from a distance, it is more challenging to read compared to text that is left-aligned with even spacing between words. Carefully consider whether the appearance of the document or its readability is more important.

Formatting must be cohesive

No matter what formatting you choose, the most important part of branding through document formatting is creating a cohesive look for your organization. All lawyers must be on board with the decisions made for the documents to positively reflect the organization’s branding. Selecting one consistent set of formatting guidelines for the business is more important than getting the formatting just right.

We’re here to help

The Missouri Bar has scores of document management resources on topics, including rules for template building and establishing file naming conventions in our Practice Management Center. If you have questions or want advice on managing your documents, reach out to mobarlpm@affinityconsulting.com or schedule a no-cost consult with the experts at Affinity Consulting.

Collaboration happens in two forms: asynchronous and real-time. We generally prefer asynchronous communication – text messages, emails, and voicemails – over real-time communication. How often do you text or email from your smartphone compared to making actual phone calls in a day?

Asynchronous

Asynchronous collaboration allows people to work from anywhere at a time convenient to them. Early birds can collaborate with night owls. New Yorkers can collaborate with counterparts in the Far East. Time zones don’t matter. Here are tips to make asynchronous collaboration better:

Share basic documents

1. If you’re not on the paperless bandwagon, start by getting a scanner to turn important papers into something that can be shared easily. After scanning the document, programs like Adobe Acrobat or ABBYY FineReader can convert a PDF to an editable Microsoft Word document.
2. To collaborate over the Internet, your document must be accessible to your collaborator. The easiest sharing platform is Dropbox, although there are plenty of competitors in this market. In fact, Apple (iCloud Drive), Google (G Drive), and Microsoft (OneDrive) all offer free space, but I think they’re just a bit more challenging to share from compared to Dropbox.
3. Apple’s Pages, Google’s Docs, and Microsoft Word offer free web-based versions of their respective word processors. If your collaborator doesn’t have the same word processor as you, they can access these free versions to edit the document you share, although they must create an account with the vendor if they don’t already have one.
4. Each person can now edit the document. Some word processors also allow several individuals track their suggested edits.

Share information rather than a document

1. Microsoft’s OneNote is the most cross-platform of the note-taking or “everything bucket” solutions. Create a notebook, share it with your collaborator, and either of you can put just about anything you can imagine in there: lists; checklists; images (whose in-image text, like a billboard or street sign, is searchable like typed text); other documents like Word, Excel, or PDF files; and even handwritten notes from an Apple Pencil (via the OneNote iPad app) or Surface Pen (via a Microsoft Surface device). OneNote is available on all the major platforms (Windows, Mac, iOS, and Android). There’s even a web-based version if you’re collaborating with someone who doesn’t want to download the free app.
2. All major web-based practice management platforms offer some version of a client portal, but don’t be limited by the word “client.” These portals are shared spaces where anyone you allow can see and interact with information you choose to make available from your practice management program. Vendors offer a wide array of features under the umbrella term of “client portal.” Clio, for example, lets you share just about anything through the portal. Clients can even upload documents and send you secure communications through it. Cosmolex offers a similarly rich portal experience. Actionstep’s portal, on the other hand, is restricted to document sharing. Visit our Practice Management Center to get an idea of features, comparisons, and considerations regarding client portal services. If you decide to buy, the bar’s Member Benefits page provides discounts for many top contenders.

Real-time collaboration

If you and your collaborator need to work on the same document simultaneously, I have two questions for you: 1) how tech-savvy is your collaborator, and 2) how complex is the shared document (e.g., complex formatting, lots of images, etc.)?

Technophobe collaborators
If the person you’re sharing the document with is not a technophile like you, then the easiest thing to do is a web meeting where one of you opens the document and shares your screen. You can even grant keyboard and mouse control to your fellow participant, so that person can edit and navigate the document while the document resides on your computer. All major web meeting platforms support screen and control sharing, though many require a paid account. If you’ve made it this far into the pandemic without a paid account at Zoom, WebEx, or similar, this comparison chart will help you choose one. And, once you’ve made that choice, read up on video conferencing professionally and get a pair of good headphones. Although you don’t need it for mere document collaboration, I recommend getting a high-quality webcam. The ones built into laptops are not good, a fact even the Wall Street Journal confirmed. I have and like Logitech’s Brio Ultra HD Pro Business, personally. Despite the alphabet-soup of a name, it works wonderfully, has 4K resolution, a built-in microphone, a privacy shutter (great if your office doubles as a bedroom), and supports Windows Hello. Plus, it’s actually in stock now.

Complex documents
Complex documents share best in their native formats. In the legal world, this usually means Microsoft Word, Excel, and PowerPoint. Luckily, sharing is easy for these programs, and your collaborator doesn’t have to own (or subscribe to) Microsoft Office. Here are the steps to share a Microsoft Office document via OneDrive (or OneDrive for Business or SharePoint) so that others can open and edit it at the same time as you, so that you see each other’s changes as they happen:

1. Save your document to OneDrive.
2. Open the document via the Office desktop app or the Office web app.
3. Click the “Share” button in the top right of the Office app.
4. Enter the email address of your collaborator. Type a message if you like. Then click “Send.”
5. As an alternative to the step above, you can choose “Copy link” if you’d prefer to send the person a web link via a text message or other means.
6. The collaborator receives a link he or she can click to access and edit the document.
7. When you both have the document open simultaneously, you will see a circle with initials of others in the document in the top right of the app or web app window. Clicking on a pair of initials reveals what page of the document that person is currently viewing or editing.

Mix and match

Depending on the information you’re sharing and the tech skills of your collaboration counterparts, one method may make more sense than another. In my experience, older clients prefer web meetings where you control everything as they comment or dictate text. Other folks prefer asynchronous document sharing because, like text messages or emails, they can review the documents at a time convenient to them.

The Manage a Practice page of the Practice Management Center contains scores of white papers, checklists, charts, and other articles relating to this topic. Missouri Bar members can also schedule a free consultation through the Ask an Expert page or by emailing MoBarLPM@affinityconsulting.com.

Many would argue video conferencing shone the brightest over the last year in terms of legal technologies, allowing lawyers to hold client meetings, make court appearances, and even attend grandma’s virtual birthday party. But just because video conferencing got the most attention doesn’t mean it was the true pandemic workhorse for law firms. Legal professionals are ultimately wordsmiths. The clients don’t need to see your smiling face, but they do need the settlement agreements, incorporation packages, or estate planning documents they hired you to draft. 

The COVID-19 pandemic was a trial by fire for most firms’ document creation, storage, and distribution methods, particularly for remote workers. Some firms  sailed through while others crashed on the rocky shoals of paper-first, no backups, conflicted copies, and the dreaded “Legal Document v4 final final I mean it this time.docx” naming convention. 

As people who spend lots of time talking about, deploying, and training on document management systems for law firms, we’re comfortable saying that not every lawyer needs a full-fledged document management system. If you’re a true solo practitioner or a solo with a single support staffer, a cloud-based document storage solution is probably a better fit. But, once you get beyond three or four firm employees, and indeed the more you scale up, the advantages of a full document management system become self-evident. 

Two ways to handle documents 

Storing your documents is passive. Document storage is a place to save documents for later retrieval and potentially sharing with others. It’s a virtual filing cabinet — nothing more, nothing less. Your computer’s hard drive, a shared server drive at your office, even cloud-based storage such as Dropbox and Google Drive: nothing happens to these documents while they’re in storage, and the users can’t do anything with the documents apart from viewing and editing them. This option might be adequate for the solo or very small firm. Click here to learn how you can get the best parts of document management for free 

Managing your documents is active. A document management system (DMS) provides the user with tools to manage, organize, and otherwise make the documents useful for the firm. A DMS will do what document storage cannot. You can see and recall each iteration of a document with view, restore, or compare capabilities. You can check documents in/out, keeping others from making changes simultaneously and creating conflicting versions of the same document. A robust DMS will index every document and email stored within it, making all content immediately searchable. A robust DMS can convert scanned documents or image-based PDF files to text-enabled documents.  

Why firms benefit from a full DMS 

Matter-centricity: A matter-centric DMS allows users to create a “matter” – a virtual file cabinet to store and manage documents, email, and notes that relate to that matter. Dropbox, OneDrive, and SharePoint do not natively understand or work with “matters” as a concept (unless you want to spend money to upgrade the services). The user is on his own in creating folders and storing files. 

Email management: In law, an email is a document like any other. A legal DMS can store, index, and manage email just as it does documents. It’s ideal to get a legal-centric DMS that integrates with MS Outlook so users can save emails directly to a matter. The holy grail of any electronic case file is its completeness. A DMS dramatically eases the process of getting an email from your inbox to the case file, where others can see it, and where it is forever bound to the case and client to which it applies. 

Document types and tagging: Law firms work with all kinds of documents: motions, orders, pleadings, complaints, contracts, and so on. By tagging documents, you can identify the exact type in your DMS. By categorizing in this way, users can quickly assess the type or nature of a document immediately. Fundamentally, these tools help people other than the document’s original author find and interact with the document. Maybe the author is on vacation and you need to print a copy of an opinion letter he sent to a client. With a DMS, you just search for documents of the type “opinion letter” drafted by the vacationing employee. 

When do you know it’s time to “graduate” to a DMS? 

Below are some questions to guide you in determining whether your firm would benefit from a DMS. 

• Do you need matter-centric organization of your firm’s documents? 

• Does your firm struggle to keep document organization consistent? 

• Do you need the ability to manage versions of documents as they evolve? 

• Do you need a process to check documents out (like library books), keeping them from being edited or forcing you to reconcile conflicted copies later? 

• Would you like scanned images to automatically become text-searchable PDFs rather than hoping individual employees remember to do this? 

• Do you need to streamline workflow by having scanners (or faxes) imported directly to your filing system? 

• Is your firm outgrowing your local hard drives or the simple cloud storage of a Dropbox or Google Drive? 

• Does your law firm want to decrease the amount and reduce the mass of paper and paper files? 

Welcoming a new DMS 

If you decide that moving to a full DMS is right for you, welcoming a new, core piece of software into your firm’s technology “stack” raises further questions: 

• What tools does the DMS integrate with? If you already have a practice management program, for example, you will want the two to play nice together. 

• What security features does the platform provide? Will it meet compliance standards for your area of practice or those imposed by your clients? 

• How much mobility will this product provide? What is the app situation like concerning iOS and Android? 

• How well does the platform organize and search files? 

• Does the platform support collaboration with internal and external stakeholders? Can you share files with the client or co-counsel directly from the DMS? 

We know we’ve given you a bunch to think about and probably raised some questions. The Manage a Practice page of the Practice Management Center contains dozens of white papers, checklists, and charts relating to this topic. If you have any questions, schedule a no-cost consultations through the Ask an Expert page or email mobarlpm@affinityconsulting.com. 

For solo lawyers or solo law firms with small support staffs, the “big boys” of legal document management systems, like NetDocuments, Worldox, or iManage, are overkill for your needs and possibly cost-prohibitive. Full-fledged document management systems (DMS) possess undeniable benefits, particularly user compliance, security, and searching. However, solo or small-firm legal professionals need not jealously eye their larger firm counterparts regarding core DMS benefits. 

Below are four core DMS features and some tips on reproducing those features with tools you already own or could acquire at a low cost. 

1. Saving 

Every full DMS possesses the ability to force user compliance. This means that the end-user is required to save files into the DMS; the system prevents saving to your desktop or a network drive. Traditional Windows or macOS open/save dialog boxes are replaced by ones directly and exclusively connected to the DMS. The obvious advantage is that every firm document resides in the DMS. 

There’s no forced compliance on where to save documents for the solo and small-firm professional without a DMS. However, human nature can take software’s place with what security researcher and host of the Security Now podcast, Steve Gibson, called “the tyranny of the default”: 

“‘[T]he tyranny of the default’…[is]…the expression I like to use for that we know most users don’t go in and change things. They just assume that someone smarter than them chose the settings that are best for them, and so they say ‘yes’ a lot when they’re asked questions…[W]hat that means is that if it’s enabled by default, it’ll tend to stay on…” (emphasis added). 

Once you set a default storage location, whether for yourself or another user at your firm, that person is unlikely to change it. A quick internet search can turn up how to change the default save location in Word for Windows (File > Options > Save), Word for Mac (if you use OneDrive/SharePoint), and Adobe Acrobat. Many other programs offer this “set and forget” save setting. Making this change means when you hit CRTL+S to save a document, you’ll start in the folder you selected as the default. Visit our whitepaper on Managing Your Documents without a DMS for tips on client/matter folder structure. For example, if you set the default location to “Clients,” you can drill down into the client and matter, saving you several save dialog clicks. And, if you forget to change the folder to the right client, at least the document is in the “Clients” folder so you can find it later, which brings us to… 

2. Searching 

Complete DMS offerings provide searching capabilities every bit as good as you see in Westlaw, Lexis, or Fastcase. You can search by document date, author, document type, document tags, and even “word X” within a certain number of words of “word Y.” 

The native system searches in Windows and macOS are good. However, with some search criteria – particularly when combining criteria, such as date plus document type plus keywords –  the free search utilities built into the operating systems fall. 

Fortunately, there are great affordable options available to enhance your document searches. For Windows users, I suggest X1 Desktop Search ($80 per year). For Mac-using lawyers, I recommend HoudaSpot ($34). Indeed, as a Mac-using lawyer, I use HoudahSpot all the time and am pleased with it. Affinity partners Paul Unger and Barron Henley would say the same about X1 as Windows users. 

With either program, you can start with a simple search, easily add or combine additional criteria, pick the folders you want to search, add and remove columns from a list of search results, and preview documents before opening them. They get you close to the quality of a DMS-based search without the added overhead and cost. 

3. Sharing 

Many DMS programs let you share files directly from their interface. Depending on the program, you can share an individual document or an entire folder. You can set an expiration date for access and permit those with access to upload files to the system or merely download them. A savvy user can replicate many of these features, though not all, via services like ShareFile, Dropbox, OneDrive/OneDrive for Business, or Google Drive. 

4. Safekeeping 

The common sync storage services listed above excel at ease of use but fall short on security. They will all serve as a form of backup for your data, which is no small thing, but they all have a weakness. Dropbox, Microsoft, Google, et al. encrypt data that you store with them both in transit and on their servers. However, the services hold the encryption keys. If they are served with a subpoena or lawful warrant, they can turn over readable data. Whether they inform you beforehand is spelled out in their terms of service. 

If you are storing client information where this possibility is untenable, look at either Boxcryptor or Sookasa. Both are affordable tools that ride on top of Dropbox, for example, and encrypt your files with a password that only you know. 

Alternatively, I recommend skipping the “normal” sync services and investigating Tresorit instead. It’s a sync service that requires you to define your own data password from the outset. They never have the opportunity to know what’s in your files. 

Keep two things in mind if you go the “trust no one” route by defining your own data password for added security. First, with any of Boxcryptor, Sooksa, and Tresorit, adding your own layer of encryption hinders the sharing features, unless you share the password with those to whom you give file or folder access. Second, if you lose or forget your encryption password, no one can save you. Your data is locked forever. 

Hopefully the above suggestions gave you ideas on getting some of the best benefits of a DMS for a solo or small firm without spending a lot of money or adding complexity to your technology setup. 

We know we’ve given you a bunch to think about, and you probably have some questions. The Manage a Practice page of the Practice Management Center contains dozens of white papers, checklists, and charts relating to this topic. If you have any questions, you can schedule a no-cost consultation through the Ask an Expert page or email mobarlpm@affinityconsulting.com. 

The COVID-19 pandemic highlighted the importance of mobility and the ability to work from anywhere. Before the pandemic, when we presented on "mobile lawyering" topics, we would spend 20% of the presentation preaching the virtues of being able to access matter information wherever you were (that doesn’t mean being “always available”). Examples included looking up facts or phone numbers at court or feeling comfortable leaving work early to attend a child's sporting event. The COVID-19 pandemic added a new spin on the importance of being able to "pick up and go."

Depending on the sophistication of your pre-pandemic setup, you may have felt some acute pains or noticed technology gaps. Below are ideas to address potential gaps.

It's not all or nothing

Don't think of going paperless, or "paper less" to start, as akin to extreme dieting. You don't have to throw out all your legal pads as though they were Halloween candy, just sitting there tempting you. If you are a fan of handwritten notes, and many studies extol handwritten over typed notes for recollection or "stickiness" in memory, then a good start would be to scan handwritten notes and file them on your computer with the other electronic documents for that matter.

If you don't have a high-quality, easy-to-use desktop scanner, we recommend the Fujitsu ScanSnap line. Their latest model, the ScanSnap iX1600, can usually be found on Amazon for about $400 and works with Windows PCs and Apple Macs. For those with mobile scanning needs, we recommend the ScanSnap S1300i and the ScanSnap iX100. Another portable option is the camera on your smartphone. Both Apple and Android app stores have several mobile apps that make it easy to scan multipage documents, use optical character recognition, and upload them to cloud storage services. SwiftScan is an excellent app for this purpose. It works on iOS and Android. An annual subscription to unlock all features costs $35.

Start with what you already have

Although full-featured document management systems ("DMS") like NetDocuments, iManage, and Worldox have wonderful, valuable features, the first step to paperless doesn't have to be opening your wallet.

If you are a solo or small firm, starting with a sync storage service places you on the right path for having the most recent version of files accessible everywhere. If you subscribe to Microsoft 365, you already have a terabyte of OneDrive space per person included in your plan. If you subscribe to Google Workspace, formerly G Suite, you have two terabytes of space per person already. If you subscribe to neither and just need cloud sync space, Dropbox's business plans start at three terabytes for $200 per year.

These offerings act as giant hard drives that save data from your computer to their servers while ensuring that any computers you connect to the service have access to the most recent versions of every saved file. The Missouri Bar's Practice Management site has an article with guidelines for managing your documents without a DMS, so the storage space has an understandable organization.

If you go this route, we recommend investing in a high-quality search program to help you locate documents. For Windows users, we suggest Copernic Professional Edition for $25 per year. For macOS, HoudahSpot is the way to go, for $35.

Meet PDF, your new pal

Going "paper less" means spending more time working with PDFs. Most legal professionals are comfortable downloading and reading PDFs, but less so with creating and customizing PDFs. Both Windows 10 and macOS can create PDFs as easily as printing to paper. You don't have to print a document and scan it back into the computer. Use the free functionality to create a PDF. Click here to learn what free PDF software can do for you.

More elaborate things with PDFs, like creating bookmarks to different pages or restricting how someone might edit the PDF you make, require spending some money to get a PDF editing program.

Everyone has heard of Adobe Acrobat, the granddaddy of PDF software. Adobe Acrobat Pro is available only as a subscription for $15 per user per month. That $15 per month subscription also includes access to Adobe Sign, Adobe's legally binding e-signature platform. If $15 per month is too much, or you dislike having more subscriptions, many PDF programs are available with the same features as Acrobat Pro (other than Adobe Sign) that you can buy on a traditional "pay once" model. Visit the PDF Programs Comparison Chart for more information.

Besides a good PDF program with editing features to replace your red markup pen, some legal professionals have found it helpful to rotate one of their computer monitors from landscape (wide) to portrait (tall). Rotating a monitor better reflects looking at a real piece of paper. Doing so is a two-step process. First, you must rotate the monitor physically. Most monitors support this out-of-the-box, but not all do. If your monitors do not rotate but do support VESA mounting, like a flat-screen TV, then a $40 stand from Vivo gets you over that hump. Second, you must tell the computer that you flipped the monitor; otherwise, everything will be sideways. Both Windows and macOS make this easy.

A potpourri of paperless practice pointers

• Audit History: For paper documents, you can't easily know who touched them last or perhaps who lost them entirely. Electronic documents stored in a cloud-sync service can keep a trail of who made what changes when. Dropbox's file recovery feature, for example, lets you look back and undo file changes for up to 180 days. Full DMS programs like NetDocuments take auditing, recovering, and restoring files to a whole other level of capability and security.
• iPractice on iPad: Once you become comfortable with digital files, if you want to set the legal pad and fountain pen aside, we recommend an iPad and Apple Pencil as your new notebook and pen. The Apple Pencil is key. No other stylus comes close. A base iPad Air ($600) with a second-generation Apple Pencil ($129) combined with either GoodNotes ($8) or Notability ($9) is a game-changer for handwriting fans. GoodNotes and Notability even search your chicken-scratch handwriting as if it were typed text and do a shockingly good job of it.
• PDF Bonus: Many full-featured PDF programs offer integration with Outlook on Windows, giving you the ability to save an email and its attachments to a "PDF-like" container where the email text is a PDF but the attachments remain in their native formats (e.g., Word, Excel, JPEG, etc.). You can save the email and its attachments as a single bundle.

Have questions? At no cost, members can ask an expert their legal technology or practice management questions via email or by scheduling a one-on-one, remote consultation.

Douglas E. Abrams

Douglas E. Abrams, a University of Missouri law professor, has written or co-written six books, which have appeared in a total of 22 editions. Four U.S. Supreme Court decisions have cited his law review articles. His writings have been downloaded worldwide more than 35,000 times. His latest book is Effective Legal Writing: A Guide for Students and Practitioners (West Academic, 2nd ed. 2021).

Over Gotham’s objection, he then granted Sigma’s emergency application for permission to file a second amended complaint because Sigma believed the original amendment proposed the wrong new defendant.³

Judge Guilford’s opinion accented the second grant by citing and paraphrasing from British playwright William Shakespeare’s tragedy, “Romeo and Juliet.” “In love,” wrote the judge, “a rose by any other name may smell just as sweet, but in lawsuits, naming precisely the right party can mean everything.”⁴

Finding that Gotham’s objection did not identify any prejudice that the second grant would cause, the court cited and paraphrased from Shakespeare’s tragedy, “Hamlet”: “perhaps Gotham doth protest too much.”⁵

Judge Guilford thus joined the ranks of federal and state judges who, in recent years, have cited and quoted from Shakespeare’s plays to spice their written opinions’ substantive or procedural rulings.⁶ Judicial invocation of Shakespeare dates back to 1873, when the Supreme Court of Texas quoted from “As You Like It” in a decision that upheld the defendant’s indictment for theft of one head of cattle worth $12.⁷ Soon Shakespeare was invoked by other state supreme courts,⁸ including the Supreme Court of Missouri in 1890 and 1894.⁹ The U.S. Supreme Court invoked Shakespeare in 1893.¹⁰

A Common Theme
This article continues the theme of recent “Writing It Right” articles in the Journal of the Missouri Bar. These articles describe how federal and state judges today frequently accent their opinions’ substantive or procedural rulings with references to cultural markers that can resonate with the advocates, parties, and judges who comprise the opinions’ readership.

The courts’ broad array of cultural references demonstrates versatility. Some of my early articles in the Journal profiled judicial opinions that referenced terminologies, rules, and traditions of baseball,¹¹ football,¹² and other sports.¹³ Together these sports’ mass audiences help define American culture.¹⁴

Later my Journal articles profiled judicial references to classic television shows and movies that have held Americans’ attention for decades.¹⁵ Most recently, I turned along a literary path by profiling judicial references to well-known children’s stories, fairy tales, and Aesop’s Fables.¹⁶

This article continues along the literary path by turning to recent federal and state judicial opinions that reference plays of Shakespeare (1564-1614). Nearly 40 plays carry his authorship, and they still command attention in the United States and around the world centuries after their appearance.¹⁷ Many of the plays’ most famous quotes or phrases (such as the ones invoked in Sigma) remain familiar to many Americans, including advocates, parties, and judges.

“More Vivid, More Lively, and . . . More Memorable”
As a collection, my Journal articles (including this one) chronicle a practice by judges who, like Judge Guilford in Sigma, invoke popular culture in their opinions. This frequent judicial practice invites advocates also to invoke, where relevant and appropriate, references to cultural markers in their briefs and other written submissions. As I have written before, “advocates should feel comfortable following the courts’ lead by carefully referencing [cultural markers] to help sharpen substantive and procedural arguments in the filings they submit.”¹⁸

I have also written before that an advocate’s invocation of popular culture remains consistent with advice delivered by some of today’s leading judges. “Think of the poor judge who is reading . . . hundreds and hundreds of these briefs,” says Chief Justice John G. Roberts, Jr. “Liven up their life just a bit . . . with something interesting.”¹⁹

Justice Antonin Scalia similarly urged brief writers to “[m]ake it interesting.”²⁰ “I don’t think the law has to be dull . . . Legal briefs are necessarily filled with abstract concepts that are difficult to explain,” Justice Scalia continued.²¹ “Nothing clarifies their meaning as well as examples” that “cause the serious legal points you’re making to be more vivid, more lively, and hence more memorable.”²²

Cultural markers that help define the American experience can offer excellent “examples” that “liven up” written advocacy and “make it interesting” and “more memorable.” Advocates can serve the client’s cause by instilling vitality that carefully relates law to national culture beyond the printed legal page.

A Shakespeare Sampler
In addition to Sigma Financial Corp., here are two of the several recent decisions²³ whose opinions spiced up substantive or procedural rulings by citing and quoting Shakespeare.

LaFondfx, Inc. v. Kopelman²⁴
In the breach of contract action, the federal district court denied each party’s motion for sanctions against the other. The defendant alleged that the plaintiff had abused the litigation process by fabricating a document, and the plaintiff countered that the defendant had abused the process by filing its motion.²⁵

The court found that “both parties’ complaints about ‘vexatious’ litigation conduct by the other are not only weak but entirely hypocritical given that both parties, apparently fueled predominantly by animus towards the other, have turned a simple contract dispute into the next Marbury v. Madison.”²⁶

The court’s order that denied the parties’ dueling motions concluded by citing and quoting from “Romeo and Juliet”: “a plague o’ both your houses.”²⁷

United States v. Bary²⁸
Adel Abdel Bary, a member of a terrorist organization affiliated with al Qaeda, was incarcerated in federal prison on his guilty pleas for conspiracy crimes arising from his dissemination of propaganda leading up to the 1998 bombings of the American embassies in Kenya and Tanzania. In 2020, shortly before his scheduled release date, he moved for compassionate release on the ground that continued confinement put him at high risk of contracting COVID-19. (He was 60 years old and suffered from asthma and obesity, two aggravating conditions identified as attracting the virus.) When released, he would be removed to the United Kingdom on an immigration detainer.²⁹

The federal district court granted the motion about two weeks before Bary’s scheduled release date. On one hand, the court recognized that Bary committed “terrible” crimes as part of the conspiracy that led to the embassy attacks.³⁰ “But his participation is better characterized as spreading propaganda in coordination with the individuals who authorized the attacks. That too was a serious crime, but it was not as serious as the crimes of his co-conspirators.”³¹

On the other hand, the court concluded, “the benefit to society of requiring defendant to serve the final few weeks of his sentence does not outweigh the serious health risks he faces. . . . [T]he sooner defendant’s remaining days of imprisonment end, the greater the chance – in the event he contracts the virus and the virus proves fatal to him – that he could spend his last days or hours with his family rather in a jail cell.”³²

The Bary court quoted at length from Portia’s speech in Shakespeare’s “The Merchant of Venice”:

“The quality of mercy is not strained. It droppeth as the gentle rain from heaven Upon the place beneath. It is twice blest: It blesseth him that gives and him that takes. ‘Tis mightiest in the mightiest; it becomes The throned monarch better than his crown. His scepter shows the force of temporal power. The attribute to awe and majesty Wherein doth sit the dread and fear of kings; But mercy is above this sceptered sway. It is enthroned in the heart of kings; It is an attribute to God himself; And earthly power doth then show like God’s When mercy seasons justice.”³³

The court determined that in the Bary case, “the earthly power of the United States should allow mercy to season justice.”³⁴

Conclusion: “A Bit of Life”
This Shakespeare survey illustrates yet again that recitation of cultural markers can accent judicial opinions and written advocacy. The potential reward for advocates and their clients? More than 75 years ago, Judge Wiley B. Rutledge delivered this: “It helps to break the monotony of the printed legal page to add a bit of life now and then. . . . A dull brief may be good law. An interesting one will make the judge aware of this.”³⁵

Endnotes
1  Douglas E. Abrams, a University of Missouri law professor, has written or co-written six books, which have appeared in a total of 22 editions. Four U.S. Supreme Court decisions have cited his law review articles. His writings have been downloaded worldwide more than 35,000 times. His latest book is Effective Legal Writing: A Guide for Students and Practitioners (West Academic 2d ed. 2021).

Thank you to Sarah Walters (University of Missouri School of Law, Class of 2022) for her excellent research on this article.         

2  2016 WL 7508172 (C.D. Cal. Sept. 22, 2016).

3  Id. at *1.

4  Id.; William Shakespeare,Romeo and Juliet, act 2, sc. 2. 

5  Id. at *2; William Shakespeare, Hamlet, act 3, sc. 2.

6  See also, e.g., American Lung Ass’n v. Environmental Prot. Agency, 985 F.3d 914, 1011 n.107 (D.C. Cir. 2021) (Walker,  J., concurring in part and dissenting in part) (citing The Tragedy of Macbeth); United States v. Clancy, 979 F.3d 1135, 1136 (6th Cir. 2020) (citing and quoting from Othello); Hewitt v. Helix Energy Solutions Group, 983 F.3d 789, 809 n.39 (5th Cir. 2020) (Wiener, Jr., J., dissenting) (citing and quoting from The Tragedy of Macbeth); United States v. Mayendia-Blanco, 905 F.3d 26 (1st Cir. 2018) (quoting Hamlet, The Merchant of Venice, The Merry Wives of Windsor, Henry IV,and Much Ado About Nothing); Reed-Union Corp. v. Turtle Wax, Inc., 77 F.3d 909, 914 (7th Cir. 1996) (citing Romeo and Juliet); United States v. Bolton, 2021 WL 131445, *5 n.5 (D.D.C. Jan. 14, 2021); United States v. Madison, 2020 WL 7768460 *6 (M.D. Fla. Dec. 30, 2020) (citing and quoting from Hamlet); Oakwood Univ., Inc. v. Oakwood Univ. Alumni Ass’n, 2020 WL 4732074 *2 n.6 (N.D. Ala. Aug. 14, 2020) (citing and quoting from Romeo and Juliet); Gross v. Chapman, 2020 WL 4336062 *1 (N.D. Ill. July 28, 2020) (magistrate judge’s opinion) (citing and quoting from Romeo and Juliet); Rodgers v. Guyoungtech USA, Inc., CA 07-0837-WS-C *3 (S.D. Ala. Sept. 2, 2008) (citing and quoting from Henry IV); North Jackson Pharmacy, Inc. v. Caremark RX, Inc., 385 F.Supp.2d 740, *1 (N.D. Ill. Nov. 3, 2004) (citing and quoting from King John); H.V. Collins Co. v. Williams, 990 A.2d 845, 846 n.1 (R.I. 2010) (citing and quoting from The Merry Wives of Windsor); Nassa v. Hook-SupeRx, Inc., 790 A.2d 368 (R.I. 2002) (quoting citing and quoting from  Othello and King Richard II); Facey v. Facey, 249 Md.App.584, *115 n.13 (Md. Ct. Spec. App, Feb. 26, 2021) (citing and quoting from All’s Well That Ends Well); In re Altschul, 2020 WL 7867282, *1 (Tex. Ct. App. Dec. 30, 2020) (citing and quoting from Hamlet); R & R Capital, LLC v. Buck & Doe Run Valley Farms, LLC, 2008 WL 3846318 *1 n.1, *8  n. 55 (Del. Ct. Chancery Aug. 19, 2008) (citing and quoting from Hamlet and All’s Well That Ends Well); Safford v. Pitney Bowes, Inc., 1995 WL 263516 *1 (Conn. Super. Ct. Apr. 24, 1995) (citing and quoting from Romeo and Juliet).

7  State v. Murphy, 39 Tex. 46, 46 (1873).

8  See, e.g., Walton v. Bristol, 34 S.E. 544, 547 (N.C. 1899) (Clark, J., dissenting) (quoting from The Taming of the Shrew); State v. Snover, 63 N.J.L. 382, 384 (N.J. 1899) (citing and quoting from The Merry Wives of Windsor); State v. Langford, 33 S.E. 370, 371 (S.C. 1899) (quoting from Julius Caesar); Sims v. State, 36 S.W. 256 (Tex. Ct. Crim. App. 1896) (quoting from King John); Matts v. Borba, 37 P. 159, 160 (Cal. 1894) (quoting from The Merry Wives of Windsor); State v. Richards, 27 A. 122, 123 (1893) (quoting from Hamlet); Holyoke v. Holyoke, 6 A. 827, 828 (Me. 1886) (quoting from Hamlet); Wood v. State, 18 Fla. 967, 969 (1882) (quoting from Henry IV).                               

9  State v. Wisdom, 24 S.W. 1047, 1051 (Mo. 1894) (citing and quoting from Richard III); State v. Strattman, 13 S.W. 814, 817 (Mo. 1890) (quoting from The Passionate Pilgrim).

10  Magone v. Heller, 150 U.S.70, 74 (1893) (quoting from Timon of Athens).

11  Douglas E. Abrams, References to Baseball In Judicial Opinions and Written Advocacy, 72 J. Mo. Bar 268 (Sept.-Oct. 2016).

12  Douglas E. Abrams, References to Football In Judicial Opinions and Written Advocacy, 73 J. Mo. Bar 34 (Jan.-Feb. 2017).

13  Douglas E. Abrams, References to Spring’s Championship Sports In Judicial Opinions and Written Advocacy, 73 J. Mo. Bar 168 (May-June 2017).

14  See, e.g., Butts v. National Collegiate Athletic Ass’n, 751 F.2d 609, 612 (3d Cir. 1984) (discussing America’s “sports dominated culture”).

15  Douglas E. Abrams, References to Television Shows In Judicial Opinions and Written Advocacy (Part 1), 75 J. Mo. Bar 25 (Jan.-Feb. 2019); Douglas E. Abrams, References to Television Shows In Judicial Opinions and Written Advocacy (Part 2), 75 J. Mo. Bar 85 (Mar.-Apr. 2019); Douglas E. Abrams, References to Movies In Judicial Opinions and Written Advocacy (Part 1), 75 J. Mo. Bar 222 (Sept.-Oct. 2019); Douglas E. Abrams, References to Movies In Judicial Opinions and Written Advocacy (Part 2), 75 J. Mo. Bar 297 (Nov.-Dec. 2019).

16  Douglas E. Abrams, References to Children’s Stories and Fairy Tales In Judicial Opinions and Written Advocacy, 76 J. Mo. Bar 212 (Sept.-Oct. 2020); Douglas E. Abrams, References to Aesop’s Fables In Judicial Opinions and Written Advocacy, 77 J. Mo. Bar 24 (Jan.-Feb. 2021).

17  See, e.g., The Complete Works of William Shakespeare (2004 ed.).

18  Douglas E. Abrams, References to Television Shows In Judicial Opinions and Written Advocacy (Part 1), 75 J. Mo. Bar 25, 25 (Jan.-Feb. 2019).

19  Bryan A. Garner, Interviews With Supreme Court Justices: Chief Justice John G. Roberts, Jr., 13 Scribes J. Legal Writing 5, 18 (2010).

20  Antonin Scalia & Bryan A. Garner, Making Your Case: The Art of Persuading Judges 112 (2018).

21  Id. at 111, 122.

22  Id.

23  See also cases cited in note 6 supra.          

24  2017 WL 2865505 (D. Colo. May 9, 2017).

25  Id. at *1.

26  Id.

27  Id. at n.1.; William Shakespeare, Romeo and Juliet, act 3, sc.1. 

28  2020 WL 5946985 (S.D.N.Y. Oct. 7, 2020).

29  Id. at *1.

30  Id.

31  Id. at *3.

32  Id. William Shakespeare, The Merchant of Venice, act 4, sc.1.

33  2020 WL 5946985 at *3.

34  Id. at *4.

35  Wiley B. Rutledge, The Appellate Brief, 28 A.B.A. J. 251, 254-55 (1942).

As a legal professional, you have encountered your fair share of PDF files and assumably created more than a few. Even in our personal lives, PDFs are ubiquitous: appliance instruction manuals, new car brochures, bank statements, etc. The PDF format’s great attraction is that it reproduces electronically exactly what a printed document looks like. And it does so across any device – smartphone, iPad, computer, TV, etc. 

The primary reason for PDF’s ubiquity in our lives comes from two business decisions Adobe, PDF’s creator, made 15-25 years ago. The first decision was made in the mid-to-late 1990s, at the start of the internet boom. Adobe decided to charge a bundle for the PDF creation software (Adobe Acrobat) and give away the software to read, but not edit, the files (Acrobat Reader). At the time, this was revolutionary. We’re accustomed now to opening Microsoft Word documents, for example, on devices that don’t have Word installed so you can read, but not edit, the file. That was hardly the case when Adobe took that innovative step. 

Similarly, Adobe had a version of Acrobat Reader for all platforms, not just Microsoft Windows, another major difference in the late 1990s when Apple macOS were a tiny, shrinking market and Linux was unheard of outside of nerd circles. Today, when we do so much computing through websites and phone applications, this move seems obvious. It was not at the time. 

Adobe’s second major strategic move came in 2008 when it took its PDF specifications and made them open source. With the specifications free to all, any developer could create software to create or read PDFs without running afoul of Adobe’s copyrights. And developers did. Now there are tons of PDF creation software packages at different price points. Adobe’s Acrobat Pro is still the gold standard and requires a subscription, but there are great alternative options, including free ones. 

What can free do for you? - Creating PDFs  

Ten or more years ago, if you wanted to create a PDF out of a document, you purchased software from Adobe or one of its newly minted competitors. If you’re running recent versions of macOS, Windows, or Microsoft Office, you don’t have to buy anything to create a PDF document of another electronic file. 

macOS users have had PDF creation ability since 2001. PDF creation is a system-level feature accessible through the print dialog box. Select “File” and “Print” (or “CMD” + “P” for keyboard fans), and “save as PDF” is located at the bottom center of the print dialog. Click here for details.  

Windows users have a similar capability in Windows 10. Select “File” and “Print” (or “CTRL” + “P” on your keyboard), select the “Microsoft Print to PDF” printer, and click “Print.” A dialog box will appear asking you to name the file and select a place to save it. Windows can also print multiple PDF files to a single combined PDF file. Just select the PDFs you want to combine in File Explorer, right-click, and select “Print.” The limitation here is the PDFs are combined in whatever order they appear in File Explorer; there’s no re-ordering. 

Microsoft Office, both for Windows and Mac, offers the ability to save most files as PDF, including Word files. 

For iOS users, you have the same ability, but it’s just more hidden. Tap the “Share Sheet” icon in the app and then tap “Print.” When the print preview for the document opens, do a “pinch and zoom” gesture to expand the document. The document will enlarge on the screen. It’s not obvious, but that enlarged document is a PDF. Tap the “Share Sheet” icon in the top right-hand corner and select the app or place you want to save or send the PDF. 

For Android users, the steps are similar to iOS, except instead of a “pinch and zoom” gesture there is a “Save to PDF” option to select from a dropdown menu. 

What can free do for you? - Editing for free 

Besides creating PDFs, you may want to edit, comment on, or otherwise mark them up. Free PDF software has you covered there, too. 

Acrobat Reader – Windows and Mac 

Acrobat Reader allows a user to comment on a document (such as sticky notes, annotations, highlights, etc.) and sign forms. You cannot do any editing for free, unlike Foxit Reader below. However, if you are willing to pay Adobe either $2/month ($24/year) or $10/month ($120/year), you can add either Adobe Export PDF or Adobe PDF Pack features to Reader. Export PDF adds the ability to turn PDF files into native Word, Excel, or RTF files. PDF Pack includes those features plus the ability to convert PDFs to PowerPoints or image files, create PDFs from files less than 100MB, and combine multiple PDFs into a single file. 

Foxit Reader – Windows and Mac 

Foxit Reader published a full manual on what their free Windows and Mac readers can do. With these free packages, you can get a PDF word count, sign and “stamp” documents, comment and annotate documents, fill out form documents, and even add bookmarks, links, and images to the PDF (assuming the PDF is not protected). 

Preview – Mac 

Mac users get a free, decently capable app with macOS. Its Preview app lets users annotate PDFs, fill out and sign forms, and add, delete, or move pages. This covers most of what you would generally want to do with PDFs. 

Generally speaking, you can generate a PDF and comment on it all without paying a dime. 

What costs money 

A couple of power features that legal professionals may need are not available for free anywhere. Those two features are redaction and Bates numbering. This may matter depending on your practice area. If you are not in litigation, neither may matter. But, particularly with redaction, do not tolerate shortcuts. Do not draw black boxes assuming that’s “good enough,” because nationally reported examples, such as the Broward County School Board case show us what happens when you redact improperly. 

Comment 6 to the Supreme Court of Missouri’s Rules of Professional Conduct 4-1.1 admonishes lawyers to “keep abreast of changes in the law and its practice.” This includes having the proper technology, knowing how to use it, and making sure supporting lawyers and non-lawyer staff have access and know how to use it. 

Fortunately, thanks to Adobe’s open sourcing of the PDF specifications, capable PDF software that redacts and Bates numbers doesn’t have to cost the $15/month (or $180/year) for Acrobat Pro DC (Acrobat Standard DC lacks redaction and Bates numbering). While Adobe’s offering includes access to its e-signature platform, which could be valuable during the pandemic, if you just need to redact and Bates number, $15/month could be considered high. Here are some lower-cost options: 

• Windows:  Foxit PhantomPDF Business (redaction and Bates numbering; $180 once or $132/year), Kofax Power PDF Advanced (redaction and Bates numbering; $180 once), and pdfDpcs Professional (redaction and Bates numbering; $107 once). Both Foxit and Kofax make a standard edition but, like Adobe’s, their standard editions lack redaction and Bates numbering. 

• Mac: Foxit PhantomPDF Mac (redaction only; $140 once or $99/year), Kofax Power PDF Standard for Mac (redaction and Bates numbering; $130 once); PDF Expert (redaction only; $50/year); and PDFpen for Mac or PDFpenPro for Mac (both have redaction and Bates numbering; $80 and $130 once, respectively). 

For more information, refer to the PDF software comparison chart in our practice management resources. If you have questions or want information from experts who have implemented these solutions for law practices and legal organizations, members can ask an expert their questions for free via email or during a virtual visit. 

Douglas E. Abrams

Douglas E. Abrams, a University of Missouri law professor, has written or co-written six books, which have appeared in a total of 22 editions. Four U.S. Supreme Court decisions have cited his law review articles. His writings have been downloaded worldwide more than 32,000 times. His latest book is Effective Legal Writing: A Guide for Students and Practitioners (West Academic, 2nd ed. 2021).

Judges typically write for audiences that differ from the audiences practitioners typically strive to reach. In judicial decision making as in advocacy or counseling, a legal writer communicates best by tailoring expression (1) to meet the writer’s own goals (which may be informative, persuasive, adversarial, cooperative, or some combination); (2) to meet the legal and factual context; and (3) to meet the likely audience’s circumstances.²

Regardless of individual goals, context, and circumstances, however, the eight strategies profiled below remain universal because the English language at its core knows only two types of writing – good and bad. Good legal writing is good writing about a legal subject.³ Justice Elena Kagan states the formula: “To be a good legal writer . . . is to know the law and be a good writer.”⁴

Now for the eight strategies. . . .    

1. Be Well-Read

Justice Felix Frankfurter had perceptive advice for young people who contemplate careers in the law: “The best way to prepare for the law is to [be] a well-read person.”⁵ Reading, he explained, enables lawyers to “acquire the capacity to use the English language on paper and in speech with the habits of clear thinking.”⁶

Justice Frankfurter did not mean to restrict the would-be lawyer’s reading list to law books and other sources of written legal expression. He meant to urge a diverse diet of fiction and non-fiction works whose styles and rhetorical competence can influence readers page by page.

Reading to improve one’s writing need not cease when a student receives the J.D., but can continue for years with both literary and legal works. A lawyer’s quest for improved writing skills remains a lifelong work in progress.

Writing styles and conventions have evolved over the years, but (as Justice Frankfurter suggested) fiction and non-fiction classics have generally stood the test of time. With so many print voices competing for attention today, more recent quality fiction and non-fiction works also tend to satisfy public scrutiny when the work emerges from significant effort and close editorial refinement.

Throughout a career, a lawyer reading law works for their legal doctrine can also weigh whether a particular book, treatise, law review article, or other source demonstrates a writing style worth emulating. One prominent contemporary nationwide law source stands out for meeting the test: U.S. Supreme Court opinions. The Court remains divided ideologically, but its opinions demonstrate quality writing, whether a particular decision seems liberal or conservative, and whether an opinion is a majority, concurrence, or dissent. The justices and their law clerks meet and surpass benchmarks for superior expression.

Paying attention to well-written literary or law works does not end the reader’s learning process. In their decision making and representational roles, judges and lawyers often must plod through writing that remains unpalatable to the eyes and ears. Even when a work of literature or law falls short on writing prowess, the work may nonetheless yield valuable lessons by demonstrating how not to write. As in many other areas of daily life, a person can learn from others’ failures as well as from their successes.

2. Treat Writing as a Full-Time Job

Judges and lawyers write when they compose at the keyboard, but that is not all. Without letting writing consume a well-rounded life, serious legal writers recognize that they are never “off duty” when a writing project beckons.

When I pursued a writing project early in my career, for example, I would keep a pen and paper in my pocket whenever I jogged or took a walk. I jotted down thoughts or phrases that came to me at the moment. Now I keep my phone in my pocket, ready to text, email, or dictate into my home or office. I even keep a pad and phone on the night table near the bed because words, phrases, or ideas that come at 2 a.m. may disappear from memory by morning. An idea here and an idea there can contribute to a quality final writing.

Inspiration can come when least expected. “Write down the thoughts of the moment,” advised Sir Francis Bacon (1561-1626), because thoughts that “come unsought are commonly the most valuable and should be secured, because they seldom return.”⁷

3. Strive to Overcome the “Hostile Audience”

When a person writes an inartfully expressed message to a friend, the friend may lend a helping hand. “I know what he really meant to say,” or “She could have said it better, but I get it.” The intended, but inartful, message can still resonate.

No such helpful lifeline normally rescues judges and lawyers who write in an adversary system of civil and criminal justice. Judges and lawyers regularly face a “hostile audience,” readers who may try to make the words and ideas mean something the writer did not intend.⁸ For example, advocates and courts may seek to distinguish a judicial precedent or its analysis. Litigants and courts may parse a party’s briefs for apparent but unintended argument or concession. A meandering law review article may invite unintended interpretation, or else later application hurtful to the writer’s cause.⁹ In public and private forums alike, the legal writer may have little or no second chance to explain, clarify, or restate.

How can judges and practitioners help overcome the hostile audience? In a quite different context, French writer Guy de Maupassant advised writers to choose their words with especial care. “Whatever you want to say, there is only one word to express it, only one verb to give it movement, only one adjective to qualify it.”¹⁰ This advice seems too simple, however, because as Justice Frankfurter correctly observed in a legal context, words “seldom attain more than approximate precision.”¹¹

President and Chief Justice William Howard Taft offered judges and lawyers this more realistic strategy for carefully navigating hostile waters: “Don’t write so that you can be understood; write so that you can’t be misunderstood.”¹² In our adversary system, a legal writer may not be able to prevent “hostile” readers from attempting to refashion a precedent or written argument to suit the readers’ purposes, but a meticulous legal writer can make any attempts more difficult.  

4. Respect the Fundamentals. . .

As they do in many other lawyering pursuits, lawyers striving to write well should heed the fundamentals most of the time. Heeding the fundamentals of rhetoric makes sense because fundamentals earned their status by being generally applicable rather than inapplicable and generally helpful rather than unhelpful. The passage of time is their pedigree.

Basic rules of grammar, syntax, and spelling qualify as fundamentals. So too do the four characteristics of good legal writing advanced by professor Henry Weihofen: Good legal writing is concise, precise, simple, and clear.¹³

5. . . . But Follow a “Rule of Reason”

As they heed the fundamentals most of the time, legal writers should also remain masters of language, not its prisoners. Good writing sometimes summons a “rule of reason” that counsels prudent departures from expressive norms or conventions.

Purists sometimes frown on, for example, splitting infinitives, using contractions, writing sentence fragments, beginning sentences with conjunctions, or ending sentences with prepositions. But when “violating” a norm or convention seems to advance the message’s meaning, persuasion, or delivery, the legal writer should “violate.”

Consider the tart reply that Winston Churchill, a Nobel Laureate in Literature, reportedly delivered to criticism that his writing sometimes ended sentences with a preposition: “That is the sort of arrant pedantry up with which I shall not put.”¹⁴

6. Encourage Third-Person Editing

During a writing’s gestation, editing begins with the author because Justice Louis D. Brandeis was right: “There is no such thing as good writing. There is only good rewriting.”¹⁵ At some point before the final product emerges, however, self-editing may reach its outer limits. After living with the project for hours or days, the author may lose some capacity to bring a fresh perspective to the screen. Repetitive proofreading may dull the senses, and incomplete analysis, grammatical miscues, typos, or other shortcomings may escape detection.  

Enter third-person editing, the enlisting of fresh eyes and ears. My first professional exposure to the value of third-person editing came in the late 1970s, when I clerked for New York Court of Appeals Judge Hugh R. Jones.¹⁶ Judge Jones would draft an opinion longhand on a legal pad, and our administrative assistant would type it. Before the draft opinion left our chambers for circulation to the court’s other six members, the judge and his two law clerks — the third-person editors — would gather around the table to parse words, sentences, and paragraphs for content, style, grammar, spelling, and other elements that would help produce the best possible final writing.

Truth be told, Judge Jones’ drafts were exemplars even before the two law clerks contributed our input. The New York Timescalled him “an intellectual leader of the state’s highest court and one of its best writers,” accolades he richly deserved.¹⁷ He did not truly need the clerks’ input, but he made clear that he wanted it. “There is always room for improvement,” he would explain with genuine respect for our contributions. The final calls on suggested editorial changes were his as the author, but he also knew that few drafts left our editorial table as they had arrived because improvement is the essence of competent third-person editing.

Practicing lawyers also benefit from third-person editing of their drafts. Their editor can be a partner, associate, student intern, or someone else familiar with law and written expression. Practitioners often face tight time deadlines and lurking financial constraints, but allowing time for this law office give-and-take where possible can help produce more artful writing.  

In judicial chambers and law offices alike, a talented, conscientious third-person editor is the writer’s ally, not a troublesome meddler. Judges and lawyers should write with fierce pride of authorship, the inner spark that generates the impulse to produce a quality product. But these writers should temper this pride with humility that encourages and welcomes editorial input. A legal writer should reward skillful editors with the gratitude they deserve as essential, productive colleagues.

7. Avoid Textual Footnotes

“I hate footnotes and endnotes,” wrote President Barack Obama in his 2020 memoir.¹⁸

Footnotes (and their cousins, endnotes) come in two primary categories. The first category, “citation footnotes,” largely identify case law and other relevant sources to support factual, legal, or other points that the writer makes in the main text.

Critics such as the former president level most of their harshest criticism at the second category, “textual footnotes,” which consist of sentences or paragraphs that continue discussion that appears in the main text or that introduce new ideas or concepts.

Citation footnotes can serve essential purposes because, as professor John Kenneth Galbraith said, “everyone, professional and lay reader alike, needs to know on occasion the credential of a fact.”¹⁹ For judges and lawyers, these “credentials” usually mean case law or other precedent. Citation footnotes, professor Galbraith continued, can also “provide an exceedingly good index of the care with which a subject has been researched.”²⁰ A citation footnote may also suggest supportive further sources the reader may consult. Where the footnote is appended to a substantial quote or paraphrased source that appears in the main text, the citation may help avoid plagiarism or copyright concerns.

Textual footnotes, however, have been harshly criticized as annoying distractions that interrupt the flow with discussion that belongs either in the main text or else deleted altogether. Punctuating the criticism over the years have been such pejoratives as labeling textual footnotes as “an addiction . . .  which mangles all legal writing,” “an insidious plague,” and “a lazy form of writing.”²¹

U.S. Circuit Judge Abner J. Mikva attacked textual footnotes as “abominations” contrary to human physiology. “If God had intended the use of footnotes to be a norm, He would have put our eyes in vertically instead of horizontally.”²²

In a court submission, an advocate’s decision whether to use citation footnotes or textual footnotes must heed applicable court rules. These rules may prohibit footnotes, may discourage them, or may instruct advocates to place citations in the main text immediately following the sentence or passage they support.   

In judicial opinions, textual footnotes and citation footnotes laden with string cites can burden the administration of justice. On the one hand, the precedential effect of judicial footnotes remains a matter of controversy – are these footnotes merely extraneous, or is anything in an opinion “good law” potentially citable and relevant in future cases? When future advocates confront an arguably unnecessary footnote or an overwritten footnoted string cite, they may feel compelled to devote time (and the client’s resources) to deciphering each source for potential meaning and import.

On the other hand, some judges have identified a “rule of reason” that finds discrete useful purposes for textual footnotes in opinions, such as (1) to treat collateral issues controlled by binding precedent; (2) to identify issues not reached; (3) to present trial testimony that supports discussion in the main text; (4) to reply to concurring or dissenting opinions; or (5) to invite legislative or other law reform on one or more issues presented in the trial or appeal.²³

Prudence commends a default position for footnoting in judicial opinions, briefs, or other court submissions: Use citation footnotes for any of the worthwhile purposes discussed above. But avoid textual footnotes and use them only for sound reasons that appear consistent with the writer’s goals, the legal and factual context, and the likely audience’s circumstances.

8. Frontload

“Frontloading” has the legal writer enhance understanding and effect by opening a section, subsection, or other lengthy writing with a paragraph or two that orients readers with a summary and roadmap of what will follow. Frontloading recognizes that the writer’s familiarity with the facts and circumstances may initially exceed the reader’s, and it serves the writer’s communicative mission by focusing the reader’s attention at the outset.

A brief or other submission, for example, might begin with a preview such as this: “The plaintiff contends that ----------------------. This [section] first presents the facts that -------------------. The [section] then demonstrates that the plaintiff is entitled to ------------------------- under the applicable law.” The preview helps the writer convey the discussion that follows.

My presentation to Missouri’s appellate judges stressed the value of frontloading in judicial opinions. I used Judge Jones as an example because he frontloaded in many of his opinions. Here, for example, is the very first sentence of his majority opinion in Cohoes City School District v. Cohoes Teachers Association:²⁴

“We hold that a board of education cannot relinquish its ultimate responsibility with respect to tenure determinations and that a provision of a collective bargaining agreement which would have that effect is unenforceable as against public policy.”²⁵

Judge Jones then presented the facts, applied the facts to the law, and repeated the holding near the end of the opinion.

A frontloaded judicial opinion, beginning with “We hold that,” does more than orient and focus readers. By stating the holding up front, the court also makes it much more difficult for advocates to distinguish or refashion the holding to suit their positions in future cases.

Conclusion: Writing as an Opportunity

Law, wrote dean William L. Prosser, is “one of the principal literary professions” because “the average lawyer in the course of a lifetime does more writing than a novelist.”²⁶ Judges influence the law’s application and development through their written opinions and off-the-bench writings. Now that many courts have severely constricted and sometimes eliminated oral arguments, advocates must increasingly rely on written submissions to represent clients or causes.  For judges and advocates alike, quality writing remains central to the goals and aspirations that define professional responsibility.

Endnotes

1 Douglas E. Abrams, a University of Missouri law professor, has written or co-written six books, which have appeared in a total of 22 editions. Four U.S. Supreme Court decisions have cited his law review articles. His writings have been downloaded worldwide more than 33,000 times. His latest book is Effective Legal Writing: A Guide for Students and Practitioners (West Academic, 2nd ed. 2021). 

2 Douglas E. Abrams, Effective Legal Writing: A Guide For Students and Practitioners 14 (West Academic 2d ed. 2016).

3 Jay Wishingrad & Douglas E. Abrams, The Lawyer’s Bookshelf, N.Y.L.J., 2, (Dec. 12, 1980) (reviewing Richard C. Wydick’s Plain English For Lawyers (1st ed. 1979)).

4 LawProse, Hon. Elena Kagan, Associate Justice, Part 2 of 4, www.lawprose.org (July 15, 2015).

5 Larry Primeaux, Advice to a Young Person Interested in a Career in the Law, The Better Chancery Practice Blog (July 20, 2010), https://chancery12.wordpress.com/2010/07/20/advice-to-a-young-person-interested-in-a-career-in-the-law/.

6 Id.

7 David Young, Breakthrough Power for Leaders: A Daily Guide to an Extraordinary Life, 58 (2011) (quoting Bacon).

8 George D. Gopen, Writing from a Legal Perspective, 1 (1981).

9 Abrams, supra note 2, at 51; Jay Wishingrad & Douglas E. Abrams, Book Review, 1981 Duke L. J. 1061, 1063 (reviewing George D. Gopen’s Writing from a Legal Perspective 1 (1981)).

10 Guy de Maupassant, Selected Short Stories 10-11 (Roger Colet ed. 1971) (quoting French writer Gustave Flaubert).

11 Felix Frankfurter, Some Reflections on the Reading of Statutes, 47 Colum. L. Rev. 527, 528 (1947), reprinting Felix Frankfurter, Sixth Annual Benjamin N. Cardozo Lecture, 2 Rec. Bar Ass’n City of N.Y., No. 6 (1947).

12 Reporters’ Notebook: Bits and Pieces of News, Buffalo News, Sept. 15, 2008, at B2 (quoting Taft).

13 Henry Weihofen, Legal Writing Style 4, 8-104 (2d ed. (1980) (discussing the four fundamentals). See also Antonio Gidi & Henry Weihofen, Legal Writing Style (3d. ed. 2018).

14 Susan E. Rowe, Six to Nix: Grammar Rules to Leave Behind, 67 Or. St. Bar Bull. 37 (Nov. 2006) (quoting Churchill). See also Dominique Enright, The Wicked Wit of Winston Churchill 30 (Dominique Enright ed. 2001).  

15 Eugene C. Gerhart. Quote It II: A Dictionary of Memorable Legal Quotations 462 (1988) (quoting Justice Brandeis); Pride of Authorship, 37 A.B.A. J. 209 (1951) (editorial).

16 Douglas E. Abrams, supra note 2, at 83-84; Douglas E. Abrams, Judges and Their Editors, 3 Alb. Gov’t L. Rev. 392 (2010); Douglas E. Abrams, Hugh Richard Jones, in The Judges of the New York Court of Appeals: A Biographical History 725 (Albert M. Rosenblatt ed., 2007).

17 Laura Mansnerus, Hugh R. Jones, 86, Ex-Judge on the New York Court of Appeals, N.Y. Times, Mar. 6, 2001, at A19.

18 Barack Obama, A Promised Land xiv (2020).

19 John Kenneth Galbraith, The Great Crash 1929 xxiv (3d ed. 1972).

20 Id.

21 Douglas E. Abrams, supra note 2, at 109 (quoting W. Duane Benton, Arthur D. Austin, and Judge Richard A. Posner).

22 Abner J. Mikva, Law Reviews, Judicial Opinions, and Their Relationship to Writing, 30 Stetson L. Rev. 521, 524 (2000).

23 Douglas E. Abrams, supra note 2, at 114-15 (quoting Judges Ruggero J. Aldisert and Edward R. Becker).

24 Matter of Cohoes City School Dist. v Cohoes Teachers Assn., 40 N.Y.2d 774 (N.Y. 1976).

25 Id. at 775.

26 William L. Prosser, English as She Is Wrote, 7 J. Legal Educ. 155, 156 (1954-1955).

The lawyers I know like to read and write. The profession attracts folks who like researching and writing, hence the outsized number of humanities majors in our ranks. One of my favorite quotes is the apocryphal Mark Twain quote: “I didn’t have time to write you a short letter, so I wrote you a long one.” Were it a TV series, the quote would be described as “based on true events” rather than a genuine quotation. But the phrase and its sentiment go back much farther than Twain in 1871. Henry David Thoreau had a version in 1857: “Not that the story need be long, but it will take a long while to make it short.” Ben Franklin and John Locke also had their own versions. The oldest provable attribution comes from French mathematician and philosopher Blaise Pascal in 1657, who wrote, “I have made this longer than usual because I have not had time to make it shorter.” 

As harried legal professionals, we know that speed tends to produce errors and verbosity. Great minds throughout history felt this problem. There is no writer who would not benefit from an editor and no writing that would not benefit from tighter phrasing or the removal of redundant and duplicative words (see what I did there). 

Therefore, with all the humility I can muster as a writer, here are some suggestions to improve your legal writing. 

Be Concise: Active verbs are your friends here. 

Don’t write: “Defendant is guilty because of the fact that he stole the coat.” Instead write: “Defendant is guilty because he stole the coat.” 

Don’t write: “It is undisputed that defendant trespassed.” Instead write: “No one disputes that defendant trespassed.” 

Don’t write: “Tim was bitten by Sally’s dog.” Instead write: “Sally’s dog bit Tim.” 

Coupled Synonyms: The Norman Conquest is long past. 

Years ago, I took a CLE from Hamilton County Ohio Judge Mark Painter, who wrote two books on legal writing: “Write Well" and “The Legal Writer.” He walked attendees through the origin of coupled synonyms, phrases like “free and clear.” The historical reason for the coupling was one adjective was English and the other French. If you want to continue for history’s sake, that’s fine, but the coupled synonyms are unnecessary and have no unique legal effect. 

Don’t write: “Last Will and Testament.” Instead write: “Will.” 

Don’t write: “Ordered and decreed.” Instead write: “Ordered.” 

Lists: They deserve numbers or bullet points. 

Lawyers have a tendency to write lists in paragraph format. For example: “Recipient may dispose of the property by: 1) giving it to her descendants; 2) donating it to charity; or 3) selling it at auction.” Such paragraph-encased lists are not easy to spot when skimming documents. 

Instead write: “Recipient may dispose of the property by: 

1) giving it to her descendants; 

2) donating it to charity; or 

3) selling it at auction. 

Break long sentences into numbered, lettered, or bullet-pointed lists. Lists are easiest to read when each item is on its own line. When listing things, use parallel structure  — each item in the list should start with the same form of speech (such as a noun or verb). 

Use Names: Nouns are people too. 

Replace legal labels (Plaintiff, Defendant, Lessor, Lessee, etc.) with names. Good writing is about telling a story, and stories use names. 

Don’t write: “Defendant sold Plaintiff a defective toaster.” Instead write: “Big Box Co. sold Smith a defective toaster.” 

However, it is fine to use legal labels when discussing other cases or referring to classes of people. In this situation, generic legal labels reduce confusion by not introducing additional actors with “bit parts” in your story. 

Don’t write: “Big Box Co. sold Smith a defective toaster. Big Box Co.’s action violates §6 of the act. This court, in Thompson v. Giant Retailer, where Giant Retailer sold George Thompson three defective appliances, held that toasters are covered under §6.” 

Instead write: “Big Box Co. sold Smith a defective toaster. Big Box Co.’s action violates §6 of the act. This court previously held that §6 covers a retailer’s sale of a defective toaster.” Thompson v. Giant Retailer, 123 S.W.3d 456 (Mo. 2021). 

As an aside, I incline toward putting citations in footnotes rather than in line with paragraph text. I think paragraphs are more readable without the citations. Certain courts may dictate where citations appear. 

More Power: Add grammar tech to your writing arsenal. 

Microsoft Word's grammar checker has improved significantly. If you previously turned it off, turn it back on and see what it catches.  

To activate Microsoft Word’s grammar checker on Windows: click on Options under Word’s File menu. On the Proofing page, check the box to mark grammar errors as you type.  

On macOS: Click on Word menu, then Preferences, and then Spelling & Grammar. Under Grammar, check the box to mark grammar errors as you type. 

Microsoft also offers the Microsoft Editor, a writing assistant that works in Google’s Chrome and Microsoft’s Edge web browsers. While Word’s grammar checker is limited to one application, the Microsoft Editor helps improve your writing on any webpage. The free version checks just spelling and grammar. If you subscribe to a Microsoft 365 plan, the Editor also checks your browser-based writing for clarity, conciseness, formality, repetition, and punctuation. If you’re a Microsoft 365 customer, it’s free, so give it a try. 

A great non-Microsoft tool, with a devoted following, is Grammarly. It functions similarly to Editor but works not only in Word (via a plugin) and your browser, but also has iOS and Android keyboards (Grammar suggestions at your fingertips!). It also  has a full desktop app in case you write in a program other than Word. Grammarly has a free version with the same features and limitations as the free Editor. Paid versions of Grammarly start at $11.66/mo.  

Missouri Bar members also save 10% on any Wordrake subscription by using code MOBAR at checkout. Wordrake is an editing system for Microsoft Word and Outlook. 

Ready to Learn More 

See the new whitepaper, A Lawyer’s Guide to Writing Well, on the state bar’s practice management site for additional details. If a lawyer has questions or wants to do a deeper dive into writing and grammar software, schedule a free consultation with an expert or send an email to mobarlpm@affinityconsulting.com.  

Have you tried to compare products or services slightly off the beaten consumer path? Or well-known products for a non-marquee feature? Despite that product’s market being worth tens to hundreds of millions of dollars, the information is difficult to come by. 

If you’re in the market for a pillow or bedsheets, there are obvious sources of information such as the website Consumer Reports that rate pillows and bedsheets on relevant categories like softness, durability, and ease of cleaning, for example. Easy enough. But suppose you want to buy a pillow made in America or in a union shop? It’s harder to come by that information in part because most buyers are not including those features in their buying decisions. In that case, your best recourse is to look for manufacturers who brag about location or employees. You could also look to sites that promote “Made in America” products. 

The same information gap occurs with tech products too. To begin with, honest feature comparison sites that aren’t littered with ads are hard to come by for the general consumer. And once found, those sites target the broadly relevant features. Websites like PC Magazine or CNET will compare Dropbox, OneDrive, and G Drive, but they’re unlikely to do so with a legal professional in mind. General audience news sources will talk price, speed, and ease of use, all relevant to legal professionals as well as the general public, but they won’t address more esoteric things important to lawyers. A PC Magazine comparison won’t address data center locations, what the service does when served with a subpoena or warrant, or how you could use a “roll your own” encryption on top of the service. 

For legal-specific products, the problem is worse. While potential buyers can compare Dropbox, OneDrive, and G Drive, software and services targeted at legal professionals have websites and marketing materials that often offer vague descriptions of capabilities, lacking important caveats, and many times hide pricing behind a “Request a Consultation” form that results in a sales call. 

These problems are exacerbated because lawyers, particularly those new to the profession or unaccustomed to comparing and choosing software, may lack a good idea of what features they want in a practice management solution, for example. 

Using Your Resources to Make Good Legal Tech Decisions 

That’s where the Law Practice Management Resource Center come into play. We’ve collected and analyzed information in key law practice tech areas so you don’t have to. Let’s walk through an example: 

Suppose you find your case and matter organization lacking. You can’t access documents unless you’re in the office. You rely on one or more people to figure out what, if anything, a client owes you and how much, if anything, the client has in their trust account. A client calls, texts, or emails you inquiring about case statuses, and you spend time rifling through emails, handwritten notes, and your memory to give updates. You talked with clients all day but, at the end of the day, are hard-pressed to remember who you talked to for how long and what was discussed. The clients are happy, but poor recollection has cost you billable time. Not good! 

If we treat this like a law school exam, we can unpack it and get an idea of issues this law office should address when evaluating a new practice management system. 

• Document access: You want to be able to access documents from outside the office. Is it just documents or do you also want access to case information? How important is it that access works well on tablets or iPhones, or is good laptop access enough? 

• Accounting: You want to know what the client owes and what’s in his trust account irrespective of whether the bookkeeper or support staffer, if any, is reachable. Do you want to know other financial information as well, like upcoming rent or office supply bills in the same program? If not, what accounting program do you use now, and will it share data with your prospective practice management program? Should clients be able to see and pay bills over the internet? 

• Case status: Most practice management programs hold general case information, party contact information, calendar dates, and tasks. Most also have some form of document storage. All would be an improvement over the “rifling lawyer” in our hypothetical scenario, but there are wrinkles in the options. How important is mobile access and from what device? Many programs can capture email and sync calendars and contacts but are you a Microsoft 365 or Google Workspace firm? Many products, particularly the web-based ones, offer client portals where the client can see upcoming appointments, share documents, exchange secure messages with the lawyer, and see bills. Is this case status “self-help” a feature you want? Some programs integrate with voice over internet phone (VOIP) systems so phone call numbers and length become proposed time entries, so you don’t lose billable time as in our hypothetical situation. How valuable is that? 

As with a law school exam, our one paragraph hypothetical became three paragraphs of additional questions and considerations. You don’t want to do all the leg work yourself! 

Our Law Practice Management Resource Center offers checklists and whitepapers to spur these types of questions. Find the checklists (here and here) and whitepaper relevant to practice management software on our Law Practice Management website. Once you’ve picked your “must have” features and prioritized their importance, then head over to the Checklists and Charts resource, scroll down to the “Manage a Practice” heading, and you’ll find two relevant comparison charts. The “Practice Management Server-based” comparison chart compares vendors offering software that would install on a desktop or server that you maintain. This route is popular with lawyers who have more complex needs, want to integrate with other desktop software such as PCLaw or Microsoft Word, and those who don’t want client data stored with a cloud-based provider. The “Practice Management Cloud-based” comparison chart compares vendors whose offerings run in a web browser, requiring little to no software maintenance on the user’s side. This route is better for lawyers newer to practice, those who are more mobile, those who desire tablet or smartphone apps, and those who don’t want to make an upfront investment in software and hardware to run traditional software. 

The comparison chart organization makes feature analysis easy. For example, if you are committed to desktop/server software over a web-based solution but want the ability to email or text appointment reminders to clients, then Coyote Analytics is your answer. Or if you’re committed to a web-based offering but want offline access to case information because you have spotty internet, then Smokeball is your answer. Missouri Bar members receive discounts on many top practice management programs, including Smokeball, at the Member Benefits section of the bar’s website. 

Finally, once you’ve selected a practice management solution, be sure to clean up your data before moving case and billing information to the new system. 

Much More to Discover 

Practice management software is just one example of high-value, legal tech decisions that the comparison charts can help you make. Comparisons exist for everything from document management solutions (that can talk to your practice management solution) to document assembly tools (that can pull information from practice management software into documents) to voice over internet phone (VOIP) that can automatically create times from phone calls. Visit all the checklists and comparison charts available for bar members. 

If you have any questions or want information from experts who’ve implemented these solutions for law practices and legal organizations, visit LPM’s Ask an Expert to email questions or schedule a phone or video call.