Better Legal Writing Starts with Confident Legal Writing

By Ivy B. Grey

When junior and mid-level associates aim to improve their legal writing, most try to be better, clearer, more concise, more persuasive, or more precise. I have yet to meet anyone who declares that they want to be a more confident legal writer. Yet if you lack confidence then increasing it is key. Confidence in your legal writing will help you meet your objectives. Training providers should take note because confidence also improves productivity and efficiency.

Confident junior and mid-level associates produce better work on time, with less stress. This is because a confident writer knows how to move on and allocate time appropriately to each part of the research and drafting process. An insecure writer will inevitably misuse time, which causes other parts of the process to be minimized—or skipped completely. It’s also one reason why otherwise promising lawyers miss deadlines.

So how can we develop confidence (and get help with judgment) before we reach veteran status?

Lawyers Hide Their Lack of Confidence

It may surprise you to think of lawyers lacking confidence. Many insecure lawyers don’t even think of themselves that way. But the truth is that the profession is self-selecting towards insecurity and then reinforces it.

As young lawyers, our insecurity and corresponding perfectionism is a large part of what drives us to work extraordinarily hard and deliver exceptional performance. In Empson’s terminology, we’re insecure over-achievers. And for many elite professional organizations like BigLaw or the Big Four, our insecurity was a feature not a flaw. In fact, people like us were recruited specifically for it. As insecure over-achievers we were ideal workers because we’re both self-motivating and self-disciplining.

At first, this is a boon for law firms. With low billing rates and high tolerance for write-downs, the crazed work habits of junior associates can be lucrative. But at some point, our perfectionism and tendency to overwork and second guess becomes a flaw rather than a feature.

When we should be taking on more responsibility and spreading our wings, we get weighed down by imposter syndrome. After years of doing unimportant low-risk work, we’ve come to believe that the important work is for other, more senior people. We don’t trust ourselves. Somewhere during the transition from junior to mid-level associate, incredible attention to detail becomes bad. Your reviews start to suffer.

Perfectionism and attention to detail are now the mark of a “slow” associate rather than a careful one. To make up for it, many associates find themselves at the other end of the spectrum. In an effort to be fast, they become “sloppy.” Partners lose trust. This judgment is equally damning.

This is when confidence takes a second hit—and the quality of work begins to rapidly deteriorate. Stopping this downward spiral is necessary. Simple writing techniques and technology can help.

How to Build Confidence

When you’re worried about your work, it’s hard to see what you should do next. Technology can help in three ways:

  1. Use timers to allocate your time properly.
  2. Use automated research assistants to confirm your research and keep you from going further down the rabbit trail.
  3. Use legal-specific proofreading and editing tools to make sure your writing is as polished and concise as possible.

1.      Use Timers to Manage Your Time

First, start with simple tech. Use your calendar to make sure that you start projects on time. Then use your timer to ensure that you allocate your time properly. Research has shown that high-quality writing is largely due to spending enough time proofreading and editing.

Here’s how you should allocate your time:

  • 40% of your time planning and outlining;
  • 25% of your time writing a first draft; and
  • 35% of your time revising, editing, and proofreading.

That said, it can be incredibly hard to get started. If that’s your issue, try the “Pomodoro Technique” to focus on a task for 25 minutes. (Here’s an online timer to help.)

2.      Use an Electronic Research Assistant

Many associates spend days on research, looking under every rock and chasing every idea. This leaves little time for reviewing cases and synthesizing the law. And you still wonder whether you’ve found everything! New research tools like CARA by CaseText  can help you analyze and understand the task at hand, focus your research, and know when to stop.

3.      Use Proofreading and Editing Tools

Finally, though you should spend 35% of your time revising, editing, and proofreading, it’s unlikely that you will do so. That means that you need to speed up the process without sacrificing quality, accuracy, or polish. Reliable legal writing tools like PerfectIt and WordRake are available to help.

a.       WordRake

Drafting and editing is a difficult part of any legal writing assignment. And it’s harder to write a shorter document. This is where WordRake helps. WordRake is an editing tool that helps make legal documents shorter and more readable. It improves legal writing style by simplifying and clarifying text, cutting legalese, and recommending plain English replacements.

b.      PerfectIt

Proofreading, polishing, checking for consistency, and following the leading legal writing style and citation guides is a required part of finalizing any written document. It’s time-consuming but necessary. Unfortunately, this part is usually left to the last minute and done poorly. You don’t have time to review over and over again. Still you can’t skip proofreading because these mistakes show inattentiveness and can really hurt your reputation. This is where PerfectIt helps.

PerfectIt is a proofreading tool that checks for legal-specific typos, enforces consistency, and conforms your writing to the guidance found in The Redbook: A Manual On Legal Style by Bryan Garner and Black’s Law Dictionary. It will also find formatting, spacing, spelling, and capitalization errors in Bluebook citations.


Working faster, producing clean work, and being confident in your written work is a challenge! And it’s in our nature to constantly question ourselves. But improving writing doesn’t have to be complicated. Use timers, research assistants and proofreading tools to help you improve your confidence. These simple steps will help you to stay sane and get past the rough transition from junior to mid-level associate. With a little help from technology, we can learn to be confident and quick without sacrificing quality. You’ll find that your writing is better, clearer, more concise, more persuasive, and more precise.


Ivy B. Grey is the author of American Legal Style for PerfectIt. It adds polish, reduces frustration, and saves non-billable time. Ms. Grey is also a Senior Attorney at Griffin Hamersky LLP. She's been named as a Rising Star in the New York Metro Area five years in a row, and her significant representations include In re AMR Corp. (American Airlines), In re Dewey & LeBoeuf LLP, In re Eastman Kodak Company, and In re Nortel Networks Inc.

Avoid errors. Protect your reputation.