The most successful lawyers today have a good dose of entrepreneur in them. They know that to do everything we need to do—and to do it well—you have to treat legal practice like a machine. You must optimize, configure, and organize. And that goes double for your legal writing.
I constantly get questions about how to deal with procrastination and the overwhelming feelings that come with putting together briefs and motions. When you step back, it’s easy to understand why. Legal writing is overwhelming. You have to figure out your goals, research tons, research some more, organize your points, write, edit, scrap things, and maybe even start over when it all doesn't turn out—and on and on. Then mix in some unreasonable deadlines. Little surprise that legal writing is where many of us have our meltdowns.
Create a Step-by-Step Drafting Process
The first way to maximize your legal writing potential is to work on building better processes. It turns out that Mark Twain was ahead of his time: “The secret of getting ahead is getting started. The secret of getting started is breaking your complex overwhelming tasks into small manageable tasks, and then starting on the first one.”
The simple act of following a step-by-step drafting process will smooth out many of your productivity problems. You’ll no longer waste time and energy deciding what to do next. You’ll stave off procrastination because the writing process will feel manageable. And you’ll focus better—and produce better results—by tackling one component of your draft at a time. With a good process in place, writing becomes like walking: One step after another.
Here’s a sample process many writers find helpful:
- Take half a sheet of paper and write down the main questions that your document must answer and your precise goals for the piece. This will anchor you in the next steps.
- Summarize the main facts that you think matter to the document—in bullet points. This list will change as you research and get drafting, but starting with a simple set of important facts will narrow the field when you start researching, which is often the trickiest step.
- Get a high-level understanding of the law and write out some bullet points for these, too. Keep them organized around the questions you wrote down earlier. You may already have a sense of the legal principles you care about (like if you are drafting a response to the legal points raised by the other side). But before getting into the weeds of legal research it always helps to orient, or reorient, to the big legal picture. Otherwise, you’re liable to scurry down rabbit holes with little payoff.
- With a better sense of what facts matter under the rules you’ve researched, return to your facts and see if there are any new ones to add to your list.
- With your updated list of key facts, exhaustively research the rules, one at a time. This step can be broken down into a few steps as well—like searching mandatory authority, then persuasive authority; writing down a list of key case citations that you will use on each point, etc.
- Then when you’ve got your research tackled, you probably want an outlining step of some sort, including steps to make sure that you consider all the counter-arguments to each of your points.
- Then you should add some actual drafting steps, like a rough first draft of each issue.
- Finally, you need several editing steps (see my post here for tips on those).
Maybe this is not the process for you. And I admit that 8 steps seems like a lot at first. But I challenge you to come up with a step-by-step writing process and give it a try on your next document. If you are like many others, you will instantly feel relief. Who knows, you might even start looking forward to that blank page.
Another powerful optimizer is automation. This simply means breaking down your writing workflow and finding ways to automate it (or make it more efficient).
To automate, do three things: Take stock, dissect, and optimize.
- Take Stock. List out all the writing tasks you do on a regular basis (daily, weekly, monthly, multiple times a year).
- Dissect. Cut up each task to expose its inner workings and identify each small step you take to complete it.
- Optimize. Take one discrete step at a time and ask: Is there a tool or system I can put in place to make this task faster, easier, or better? These tools can be practical or technological.
To apply automation to legal writing, take some document that you regularly put together. If you’re a litigator, maybe start with a motion to dismiss, a client letter, or whatever else you write with regularity. Like anything, it probably makes sense to prioritize the types of writing that you struggle with the most and work on those first.
Then sit down and brainstorm all the things you usually do to produce an excellent version of that document. Start at the beginning. Do you first sift through facts and mark them up? Look for similar documents you’ve written to steal ideas from? Talk through ideas with others? Make sure you ferret out every part of your process—right up to the polished masterpiece that you file or send off.
Be scrupulous. Even the smallest, most inconsequential tasks can matter. And achieving even small efficiencies or avoiding tiny headaches can build to big results.
With your long list of discrete tasks, now it’s time to optimize. There are tons of tools. But the automation mindset is what matters here—you are searching for ways to optimize what you do. You will be surprised at how even the smallest things help. To start you off, here are some ideas for optimizing:
- Find technology that will do it for you (more on that later).
- Create templates with all the formatting worked out.
- Create quick-access buttons on Word and learn (or program) hotkeys for everything you do a lot.
- Create saved text that you commonly insert.
- Organize and tag documents or information you often use (we will talk about some tech tools to make this easy later).
- Have others help complete tasks who are experts.
- Use checklists to make the task quicker and more efficient.
- Keep track of tasks using project management software.
- Anything else you can think of!
Productivity hacks work for legal writers just like they work for everyone else.
Focus tools can do wonders. For example, once you have the gist of your document’s theme, try writing it on a post-it and sticking it next to your computer screen as you edit. Same for your document’s main goals. This will help keep you focused on what matters.
The Pomodoro Technique
Pomodoro is a much-acclaimed productivity hack. You work for 25-minute increments, broken up by short breaks. You don’t allow yourself to vary from your task during each 25-minute stint. You keep track of your breaks on paper. Tons of people—lawyers included—swear by Pomodoro. And you can always adjust the 25-minute increment up or down depending on what works for you.
By telling someone else when you plan to finish a writing project, perhaps a friend or, better yet, a boss—you can keep yourself to deadlines or risk shame. Even a Facebook post asking your friends to keep you accountable can help.
First Things First
Prioritize your most important tasks first. Pareto’s principle supports this productivity hack, which posits that 20% of our effort produces 80% of the results. This means that prioritizing tasks—perhaps for us writers, outlining let’s say—is more likely to produce results than wasting hours on less important tasks, like reading through stacks of similar cases.
This ranges from the simple, like putting away your smartphone while working, to the sophisticated, like installing site blockers that will keep your screens tuned to your work. Freedom is a great one.
Have two or three projects going at one time, so if you get sick of one, you can jump over to the other.
The Eisenhower Matrix
This classic approach has you create a matrix. In one box are the tasks that are urgent and important (tasks you will do immediately); then there is a box for important, but not urgent (tasks you will schedule to do later); then urgent, but not important (tasks you will delegate to someone else); and finally, neither urgent nor important (tasks that you will eliminate).
Wade Boggs, former baseball player for the Boston Red Sox, woke up at the same time each day, ate chicken before each game, took exactly 117 ground balls in practice, took batting practice at 5:17, and ran sprints at 7:17. As weird as it sounds, rituals are powerful cognitive tools. In multiple experiments, people following rituals performed better at cognitive tasks. So why not create your own writing rituals? Perhaps by writing in the same place each day. Or always outlining with a lucky pen!
Technology is another gamechanger for legal writers. The sky is the limit here, and we will talk a lot about the tools and skills to leverage technology in future posts. But some ideas include:
The latest grammar and style bots can instantly boost your writing style. BriefCatch is a favorite for legal writers.
Alerts and Updates
Want to stay up to date on a specific legal subject? Several tools will run down legal updates and deliver them to you on a platter, like Law360.
Several tools can help you keep track of your past writing (or anything else) so that it’s always at your fingertips. No more searching around for that last motion to dismiss you wrote. My favorite is Airtable. This tool is everything we love about spreadsheets but made into an easy to use and beautiful database.
Process programs are great for legal writers—like Process Street. This program automates all your checklists or processes. Not only can you create clean, printable checklists—but you can embed links and documents within individual items, allowing you to bring your checklists to a whole new level.
Outlining and Mind Mapping
Several tools can help you break through writer’s block and brainstorm or organize your legal writing. Two that I love right now are Workflowy and Coggle. Workflowy is a simple program that compartmentalizes your writing process, helping you focus on one section or topic at a time. The clean, simple interface transforms the drafting experience. And everything is easy to export to Word. Coggle is one of the many brainstorming apps out there that help you visualize ideas as you plan out your documents or arguments.
Technology programs like Monday and Trello make writing with others easy. These tools help you keep track of every aspect of a project with just a few clicks.
Keeping track of what you need to do next may be the most annoying part of writing. My favorite tech tool here is Todoist. So easy to use, and it syncs up with all your devices. It also has an intuitive and simple tagging and deadline system.
They let you do something instantly from your keyboard. Learning hotkeys can cut down little bites of time from each project—which adds up.
The possibilities to introduce processes and technology into your legal writing habits are nearly endless. I hope you'll try some of the above ideas for your next writing project.
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