Legal Writing Like an Entrepreneur

"Tomorrow becomes never. No matter how small the task, take the first step now!"

--Tim Ferriss 

Elon Musk's work style embodies what every entrepreneur wants to be: ridiculously efficient, meticulously organized, and so productive that everyone around him wonders how he manages it all. He runs multiple mega companies, dozens of projects, and spends several days a week with his five children. And he does it all by taking the same sort of productivity and organizational principles that startups use to build good businesses--and applying them to his own life. 

This very silicon valley trend of maximizing personal efficiency works. Musk reportedly schedules his day in five-minute increments, making it impossible for him to waste time. "From the second [Musk's] head lifts off his bedroom pillow at 7 a.m., his day has already been pre-planned in advance." And Musk is not an outlier: the best entrepreneurs are famous for bringing efficiency and productivity not just to their businesses, but to their personal habits, too. 

Then you have lawyers. We may be the most inefficient, unproductive gang. We seem to take about twice as long to do everything. People literally talk about hiring a lawyer just to delay things.

It's not just what others think about us: lawyers and law students really struggle with efficiency and productivity. And a lot of it comes down to our 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 something, edit, scrap things (and maybe 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. 

But entrepreneurs seem to be able to handle multitasking and deadlines just fine. So what can they teach us here?

There are two sets of tools that might help: (1) some silicon valley productivity principles that you can apply to your legal writing, and (2) some technology tools that can help you organize, draft, and manage your writing process. The latter includes everything from cutting-edge legal drafting software (like the amazing Brief Catch and the brainstorming tool Coggle) to teamwork apps that will automate your editing checklists. 

But one thing you need to know before we dive in: improving your productivity requires upfront investment. All of these tools require you to invest time, and sometimes, money. You must learn the tools, set them up, and work with them. And this truth is why most of us remain stuck in the same productivity ruts. So be ready to invest, and you will see results. 

1.    What entrepreneurs can teach us legal writers 

There are tons of productivity systems out there, and I've seen lawyers and law students thrive on many of them. For example, check out: Getting Things Done; the 2-minute rule; Kanban; Eating Live Frogs; Do the Worst Thing First; Must, Should, Want; Pomedero; and To-Done list.

But for this article, I want to get to the tech tools. And before we can do that, we need a couple first principles: Automation and processes. They sound boring, but both pack a punch if you use them right. 

Automation

Automation has you do three things: Take stock, dissect, and optimize. 

1. Take stock. List out all the writing tasks you do on a regular basis (daily, weekly, monthly, multiple times a year). 
2. Dissect. Cut up each task to expose its inner workings and identify each small step you take to complete it. 
3. 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?) and make sure you ferret out every part of the 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, and we'll look at some exciting technology in the next section. But the automation frame of mind is what matters here; the mindset that you are searching for ways to optimize what you do. You will be surprised at how even the smallest things help. For example, I always take some time to look up alternative words to replace the boring ones in my writing. That used to require me to open up a separate browser tab and paste words into an online thesaurus. But by spending some time automating, I now use a Grammarly plugin that automatically searches for alternative words just by highlighting them. The same task now takes me seconds: 

Again, there is no perfect way to optimize. But 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! 

Processes

Mark Twain had it right: “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.” He could have been talking about processes. Processes are different than automation. With automation, you optimize tasks. With processes, you plot out what tasks are helping or hurting and what order you should tackle them in. 

The value of planning out the step-by-step process you use for writing is manifold (Thanks Grammarly!). Perhaps most important, processes suck the anxiety out of overwhelming writing projects. Instead of worrying about the many things you have left to do, you can focus on the tiny next step, which is always more manageable. Building good processes is how I've helped countless students and lawyers get over writing and test anxiety. And it works for all of us. 

Another benefit of processes is that they ensure you don't miss important steps (say, during the editing or research process), while at the same time, allow you to cut any steps that aren't giving you enough bang. Like the famous Toyota Production System, you are designing a foolproof process for creating excellent writing.

I've talked about writing processes before. It's going to take some trial and error, but once you have a good process down, you will feel the anxiety and stress melt away. For an example, maybe your writing process starts with: 

1. Take a 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.
2. 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.
3. Get a high-level understanding of the law and write out some bullets 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 (say, 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 legal big picture. Otherwise, you're liable to scurry down rabbit holes with little payoff.
4. And so on...

2.    Tech tools to organize, draft, and manage your writing

First, check out my recent article looking at some of the latest grammar and style bots. These can eliminate a lot of stress from your editing tasks, at least. And if you're among the few lawyers or law students who haven't yet tried Ross Guberman's Brief Catch, you must. It's the first writing bot built exclusively for lawyers. And it works wonders. A couple of weeks ago I introduced Brief Catch to my second-semester law students, and their minds were blown. I've seen similar reactions from lawyers and judges. 

Second, I've collected some of the hottest tech tools that entrepreneurs use to get ahead--and that I've used with lawyers, law students, and judges to improve their writing process. Exploring them all (and the many others out there) could fill a book. So I've tried to stick to the most exciting and useful for now.  

Stop wasting time surfing and stay up to date

Many of us waste hours surfing for new articles about emerging caselaw, new practice developments, and everything else we care about. But there are tools that will run down these resources and deliver them to you on a platter. 

Westlaw, Lexis, Bloomberg, and Law 360 all offer sophisticated legal-alert tools. And they are easy to use. You simply type in some searches that will pull relevant articles and cases. Google Alerts takes about five seconds to setup: 

Then there are some tools that go deeper. Say you want to be alerted every time there is an update on a website--perhaps when a new opinion is released from a court and uploaded. Programs like Wachete let you do just that: simply select the areas of a website that you want to receive alerts about and the tool does the rest:

Automate your writing 

Several magical tools will help you keep track of your past writing, information, or resources 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 easy to use and beautiful. You can create tags and fields like an excel savant, but without any expertise or training. I encourage lawyers to use tools like this to manage all their past documents, cases, resources, or any other information they use a lot. Here is a sample I created for a court recently, which keeps track of past opinions with embedded links to the full documents: 

 

Create a writing and editing process 

This is where technology really shines. One of the most exciting tools for legal writers is 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. For example, I create editing checklists for attorneys and attach example images or documents illustrating the writing concept that I'm telling them to check for: 

 

Break through blocks and draft better

Several tools will 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 out 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: 

 

Organize with others 

Writing with others is tough. And some of that difficulty comes from simply coordinating who is doing what--and when. 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: 

 

Organize your writing tasks 

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 calendaring system. If there is anything that lawyers and law students get hooked on when I run them through these technologies, it's ToDoist: 

 

Other tech tools to try

Technology can make writing fun again. But you can't just rely on the tools built for lawyers. And you will need to start investing time in finding and learning new programs. Before we end, here are a couple other ideas to get you excited:

• Google searches: Google has all sorts of special search terms that few folks know about. Check some out here. 
• Hotkeys: Learning hotkeys can cut down little bites of time from each project--which adds up. Find some common ones here. 
• Programs that cut distractions: Freedom and Inbox Pause allow you to filter out annoying internet, email, or social media distraction.
• There are tons of other tools that can help with your writing productivity. For example, the OneTab extension will clear all of your browser tabs and save the links in a file. No more feeling pressured to save all your open browser tabs! 

A more productive you awaits! 

Joe Regalia is a law professor at the University of Nevada, Las Vegas, William S. Boyd School of Law and regularly leads workshops training legal writing and technology. The views he expresses here are solely his own and not intended to be legal advice. Check out his other articles and writing tips here.