Throat-clearing phrases are empty openers that delay the presentation of your argument. They slow down sentences, waste space, and frustrate readers. These phrases make the reader dig for the point, and some readers will give up before they find it.

The Illusion and Appeal of LLM Reasoning

Words like reasoning, thinking, and writing are the working tools of the legal profession. But with the rise of large language models, like OpenAI’s GPT, Anthropic’s Claude, and Google’s Gemini, these words are now used in a different way. If we don’t confront their false familiarity, we risk misunderstanding the capabilities of these tools and misplacing our trust in them.

Using Generative AI to Discover What You Don’t Want

Writers often discuss the zero draft—a rough document where they begin shaping their ideas. Anne Lamott calls it the “shitty first draft.” But what if getting to that point feels impossible? Before reaching the zero draft, writers can try something new: the negative draft.

Every generation of senior lawyers complains that junior lawyers can’t write. But becoming a lawyer takes years of post-secondary education and apprenticeship, so it’s not reasonable to interpret this complaint to mean young lawyers are illiterate. So what’s the source of this perennial complaint and how can we address it?

Introduction to the New(ish) Technology Competence

Technology competence is not new, but in the age of generative artificial intelligence (GenAI), it applies in new, more complex ways. Under ABA Model Rule 1.1 and its Comment 8, competent representation includes understanding the benefits and risks associated with relevant technology. When it issued ABA Formal Opinion 512, the ABA reaffirmed that the duty of technology competence applies to GenAI, along with all other ethical duties, including:

I am a fan. An unabashed fan. I admire people openly and I tell them—and everyone within earshot. So if you want my advice on networking, that’s it: Be a fan.

Since generative AI can produce polished text in seconds, it’s tempting to ask: Why write at all? If the end result, like a report, an email, a memo, or a presentation, looks the same whether written by a human or GenAI, why not just let the technology do the work? Because writing isn’t just about producing text. Writing is thinking.

Legal writing often feels formulaic. It follows established patterns and uses predictable structures. But those formulas exist for good reason. Predictable structures help legal readers—judges, lawyers, clerks, and other professionals—quickly understand the argument, locate key facts, and process information. Legal readers rely on them for cognitive shortcuts to handle their caseloads.

To write effectively, you must know your message before you start. Planning your pitch is the first step to writing for your audience. Everything before this stage serves you, not the reader.

Writing isn’t a linear process with a specific set of tools that a writer must use to succeed. It’s more like the messy, disjointed process of putting together a puzzle, where you don’t find the missing pieces until the end. Only after it has taken shape do you see it more clearly. But just because the act of writing is non-linear, doesn’t mean that the process has to be unstructured.

At the end of the school year, we’re thinking about gifts for soon-to-be graduates. The ideal gift will set a graduate up for success and provide lasting value.

Regardless of practice area, document creation consumes a significant portion of every lawyer’s time. According to Thomson Reuters, up to 60% of lawyer time is spent on writing, editing, and proofreading. Even after the first draft is complete, editing and proofreading can drag on for hours—and sometimes errors still slip through the cracks.

Dialog boxes often feel disruptive, but sometimes we’re so quick to dismiss dialog boxes that we miss key information. Some hidden gems are tucked away in WordRake’s dialog boxes.

WordRake’s complex algorithms are contextual—that’s what makes its editing suggestions so powerful and accurate. The algorithms operate using signals and triggers. So when you Rake a document and accept changes or otherwise edit the document, the available signals and triggers change. When you Rake a second time, WordRake might make additional editing suggestions your new wording revealed.

Our users rely on WordRake for quick and reliable editing for clarity and brevity. Every feature and function was designed to work within that streamlined user experience, focused solely on delivering accurate editing suggestions to improve your work. But the simplicity of the track-changes style and sleek interface means some WordRake features go unnoticed. Here are five hidden features you should check out.

When asked to edit an author’s work, how quickly can you turn around a document? If you’re an editor getting paid a flat or per-word fee, every second you save adds to your bottom line. And if you’re simply doing a favor for a colleague, you want to help them and get back to your own work quickly.

The most vocal and dedicated software users are powerhouses. To work more efficiently, power users tweak their apps and seek out hidden features. You hear about Microsoft power users, but did you know you can be a WordRake power user, too? Here’s how to use Microsoft’s customization options to customize your WordRake experience. Check out these three power user tricks.

Legal dramas are full of hot-headed lawyers overflowing with righteous indignation, ready to steamroll injustice by the force of their convictions. The courtroom scenes play out with biting repartee and shouts of “objection!” until at last the verdict is revealed, and the “good guys” walk away with their hard-earned, well-deserved victory. Opposing counsel glares as our heroic lawyer marches triumphantly to a waiting crowd of excited reporters and shares the good news.

Email has become the primary method of business communication—72% of people prefer email as their main source of business communication. But are we truly communicating? Sixty-four percent of businesspeople report having either sent or received an email that resulted in unintended anger or confusion. Research shows it’s because we’re not communicating effectively: Email senders overestimate their clarity and persuasiveness and email receivers only determine tone correctly 56% of the time.

Nominalizations—verbs or adjectives that have been converted into nouns—are common sources of obscurity, wordiness, and needless complexity in professional writing. While nominalizations may seem more formal when they appear in phrases like “reach a decision” or “make an assumption,” that requires equating formality with stodginess.

Effective business communication relies on clear, concise, specific, and meaningful writing. Clichés fail all four requirements. In your first draft, a cliché may feel so easy and familiar to write that it seems irreplaceable. But, upon revision, you’ll see that clichés are unoriginal, broad generalizations—and often redundant. Delete them. Replace them. Your readers will reward you with their attention.

A major advantage of eliminating clichés from your business writing is the clarity and precision it brings. Without the clutter of overused phrases, your writing will be more persuasive and impactful, and you’ll be seen as more authentic, authoritative, and trustworthy.

Legal writing requires the ability to present clear and persuasive arguments, which is why legal briefs need effective organization and structure. Two tools for enhancing the persuasive power of a brief are the Table of Contents (ToC) and point headings. By leveraging technology and honing organizational skills, lawyers can improve the clarity, coherence, and impact of their writing. Technology can simplify creating, organizing, and editing legal briefs so you can focus on finding the most persuasive arguments. In this article, we’ll discuss the importance of large- and small-scale organization and how to achieve it, as well as technology tools to help you construct a better legal brief.

Effective legal writing involves connecting compelling arguments with cited support from relevant legal authorities. A clear understanding of these authorities’ hierarchy amplifies the persuasive strength of your assertions. Mastering tools like the Table of Authorities (TOA) in Microsoft Word can improve your productivity. Combining legal writing skills with technological assistance elevates the quality of your work, ensures adherence to court timelines, and helps you concentrate on your argumentation.

Legal and business writing require a blend of precision, clarity, persuasion, and organization. With so many necessary elements, most legal and business documents are long and require more structure—for writers and readers—than a typical document. For writers, structure helps you maintain focus while crafting document content; for readers, structure guides them through the document and helps them see logical connections. Structure supports understanding, so finding ways to easily implement and adhere to structure will help you improve substance.

Business and legal documents must be precise, clear, and carefully structured because they serve as legal records, define relationships, and document important decisions. But writing in these fields is rarely done alone. A combination of authors, resources, and tools contribute to the final document. Subtle adjustments can change meaning or transform a good piece into an exceptional one. Tracking the evolution of a document and the source of changes is important to understand how and why the document changed so you can make sure it doesn’t drift from its goals.

Who must comply with plain language laws? Nearly everyone in business. According to Professor Michael Blasie, the leading expert on plain language laws, in addition to the federal government’s plain language laws, every state in the United States and Washington DC have plain language laws too. In an earlier article, we discussed federal plain language requirements; this article focuses on state laws that determine how private actors must write.

Writing in plain language helps you communicate with your audience. If that’s not enough incentive to write clearly and organize information logically, then consider this: Professionals throughout the United States and around the world are required to write in plain language.

If your organization cuts cost but doesn’t increase value, then you’re doing transformation wrong. This is a sign you’re adding complexity and processes that clients don’t want to pay for and your lawyers hate. But don’t give up. It is possible to ease burdens, elevate work, and satisfy clients simultaneously. The key is implementing improvements that increase value from the client’s perspective. To do so, it's time to move our focus from process to value. Take a holistic approach to workflow improvement by using the value stream framework.

If you confuse the words affect and effect, you’re not alone. These two words are some of the most commonly confused words in the English language! Because they sound alike, it can be even harder to keep them straight.

When we start out as lawyers, we’re so afraid of being caught unprepared that we try to memorize every fact, every detail, and every statute. It seems like the smart thing to do. After all, doesn’t every job posting require “attention to detail”? The problem is that details become our security blanket. When a partner, a judge, or a potential client asks a question, we regurgitate the facts we memorized the night before and rattle off code sections—surely, our knowledge will impress our audience.

Addressing your reader and potential client’s problems entails lending a listening ear and showing genuine empathy. Every problem you encounter has a human and emotional aspect that requires a proper and sensitive approach. Whether it’s a contract dispute over the interpretation of a cessation of business clause, an excused performance under a force majeure clause, or responsibility for undelivered goods, each case is a legal question to you—but never forget that it’s an emotional issue for your client. These situations call for empathy. And that means you must connect with your clients on a more personal level to address their pain points.

What difference can one minute make? It may surprise you to learn that one minute can be the difference between successfully completing two tasks—or fumbling them both. Let’s explore how this theory can help us with the documents we create at work.

Though we may be hired to interpret and apply the law, our clients rely on our writing skills to accurately capture their intent. It’s irresponsible to discount punctuation rules as pedantic and useless. Lawyers must get three comma rules right:

Even when we’re working in the same building, we rarely interact the people we work with in person and in real time. Now that we’re working from home, we’re relying on email more and more. Aside from a few Zoom conversations, your email writing style and etiquette may be the only thing a senior partner knows of you.

Writing short, simple, clear prose isn’t merely good practice. Science tells us it ensures that overwhelmed readers understand your message quickly and easily.

In middle school, we memorized vocabulary lists to learn new words and build our reading comprehension. In high school, we memorized vocabulary lists to prepare for college entrance exams. In law school, we memorized legal terms for cold calls and final exams. Success at these tedious memorization exercises led to academic accolades and bragging rights. After years of indoctrination, it’s no surprise that we would believe that a large vocabulary would impress readers. But if you believe that, you’d be wrong.

Though we continue to write legal memos as though they will be read on printed paper, that expectation no longer holds. Even before the recent shift to working remotely, email had become the primary method of business communication and email memos the vehicle to share legal analysis. Now the screen of the electronic device on which we read provides our structure, context, and limitations—we no longer rely on the printed page for this information.

When you run a business, demonstrating credibility and persuading others are your primary goals. You can’t do that without great business writing. But strong writing is easier discussed than accomplished. And it takes more than Strunk and White’s Elements of Style. From universal writing rules to advice that will change your process and your results, here are eight books (in no particular order) to make your writing better.

Your legal writing reference library should include more than the five standards: the Bluebook, the Redbook: A Manual on Legal Style, A Manual of Style for Contract Drafting, Garner’s Dictionary of Legal Usage, and Black’s Law Dictionary. There’s more to writing than mechanics and accurate definitions, and these books prove it. From universal rules and styles to advice that will change your process and your results, here are seven books (in no particular order) to make your writing better.

As Gary Kinder wrote in The Perfect Brief Part 11 - Polishing Your Brief, you should never use tricks to squeeze a brief into a word or page limit. It’s unethical and judges will notice—they’ve seen every trick we can imagine.

For most lawyers and law firms, their business strategy is three words long: “Do good work.” The assumption is that individual effort and intelligence are all that it takes to succeed. If it were ever true, it isn’t anymore. Today there’s a breakdown in trust and an uptick in blame that’s getting in the way of “good work.”

Innovation is now becoming an annoying buzzword. Even for people inclined to embrace legal innovation, the word is now eliciting groans. And for people afraid of change, innovation is such a loaded word that even thinking about it is overwhelming.

There’s only one certainty: The legal industry is continuing to change. Everything else is uncertain. The question is whether lawyers will adjust enough to remain a valuable and well-compensated part of it.

The legal industry is overrun with counterintuitive and counterproductive expectations about innovation. The demands for radical innovation seem to grow louder every day. The more frustrated we are with the lack of progress, the more extreme we are with our demands. But here’s a simple question: is the purpose of innovation to show our CEOs and clients that we are exploring the latest fashionable technology? Or is the purpose of innovation to increase revenue, value, and client satisfaction?

What does it take to thrive in today’s knowledge economy? If you read commentary from the legal industry, the answer is clear: innovation. This buzzword is alluring because it’s amorphous, ambiguous, ill-defined, and unmeasured. We can reward ourselves for “doing something,” while doing nothing at all.  If we can’t agree on a definition or direction, we can continue talking without taking any action.

It may feel good to encourage spontaneity and creativity, but random acts of innovation don’t work on a large scale. To be successful, innovation must be strategically executed and aligned to business strategies.  However, most companies fail to unite innovation and strategic initiatives.  PwC surveyed 1,200 executives about managing innovation and found that 54% struggled to connect innovation and business strategy.

When it comes to efforts to improve legal service delivery, we tend to look outward. We consider how we should re-engineer processes; how we can better staff projects; and what technology we should use. We rarely stop to think about how we should improve ourselves.

Lawyers are struggling to embrace change and this is impeding innovation. Even for those who want to change, most efforts fail to deliver.  How can we put in so much effort for so little gain?  Maybe it’s because we’re not identifying the right problems to solve.

Our approach to technology and process improvement initiatives is often fueled by hope, driven by shame, and made urgent by fearful hype.

Despite the calls to innovate and excitement stemming from conferences, hack-a-thons, think-pieces, and podcasts, law firms aren’t actually innovating. As lawyers, we know that we need to change, but figuring out how and where to start is daunting. Frankly, we’re stuck. And we’re not helped by the hype and assertions that one single idea or one single piece of technology will be the panacea for our problems. The truth is that no one change or decision will be the right fit for every law firm or law department. Instead, what we need is a framework to determine the best direction for our individual circumstances. Workflow analysis can help.

Too many lawyers with great ideas that could improve legal practice are discouraged from even trying to innovate. As lawyers, we assume that innovation must mean invention, technology, and programming. By accepting that assumption, we are accepting the belief that innovation is something that other people do. But that’s not true. Innovation can be any new process or new way of thinking — and that can be game changing. Innovating is for lawyers, and lawyers already have the skills to be innovators. No coding necessary.

Technologists seem mystified that lawyers don’t embrace efficiency-enhancing innovations. Despite our reluctance to face it, as lawyers, we need look no further than our rewards structure to see why. Billable hours reward inefficiency. And that rewards structure has remained in place with the help of ethical fading. We think that we’re simply using the existing business model for our benefit. We use our history and familiarity with the billable hour framework to ignore that our goals and our clients’ goals are at cross-purposes.

One mistake, possibly more than any other, is the reason behind so many failed legal technology purchases. And law firm management and software vendors are equally to blame: they both treat the purchasing decision as the end goal. The result is a landscape littered with failed technology and innovation initiatives that is bad for management and vendors alike.

It’s been nearly fifteen years since the financial crisis of 2008, yet the legal industry is still reeling from it. Lawyers felt the shift from seller’s market to buyer’s market, but we weren’t sure that it would be permanent and didn’t know how to respond. For technology enthusiasts, the answer seemed obvious: use more legal technology. That may be part of the solution (and I genuinely believe it is). However, the way technologists promote their tools is self-defeating. Early adopters encourage them, and together they create an echo chamber that is unattractive and unappealing to the vast majority of our profession.

Legal writing can be a struggle because we’re expected to be fast and perfect. This creates a high-pressure situation where we’re sure to doubt ourselves. Fear, perfectionism, self-doubt, and external pressure are the main psychological ingredients for writer’s block. So how can we overcome writer’s block and get that first draft on paper?

While “legalese” may be the punchline for jokes about bad writing, the problem isn’t confined to the legal profession. Bad business writing is widespread and costs American companies an estimated $1.2 trillion per year. That may be a conservative estimate: a 2023 survey estimates that ineffective communication is costing American businesses $2 trillion each year. Let’s look at how unsatisfactory writing has affected businesses and why we should improve our writing skills.

Editing is a difficult task with many interconnected pieces. It requires that we know and apply writing, grammar, and style principles to complex topics. And some writing professors have found that even if you have vast knowledge of grammar, syntax, and style, you’ll still need help to apply that knowledge and thoroughly edit a piece of writing. Otherwise, you’ll either get overwhelmed with too much information or you won’t be able to remember enough to put the rules into practice while editing.

Because presenting our work in a clear and pleasing manner is so important, effective legal writers devote 35% of their time in any legal writing task to revising, editing, proofreading, and otherwise polishing the document.

Editing is the process of improving content, clarity, structure, and substance. It involves checking the content of the text to ensure that the ideas are expressed clearly and logically, and form a coherent and meaningful whole. It should be the first task you undertake after you have a fairly complete document. (Save the proofreading for later.) The purpose of editing is to make your document better. Here’s what to check:

We sat down with the newest member of the WordRake team, Ivy B. Grey, after completing her first month on the job. Ivy joined us in early November as our Director of Business Strategy. A legal tech entrepreneur and former lawyer, Ivy brings a wealth of knowledge to the WordRake team, and we’re excited to sit down with her and hear her progress and vision for the future.

Advice to improve your legal writing can sound flippant. How often have you heard “rules” like these?