How Imposter Syndrome Leads to Bad Legal Writing (and Seven Tips to Fix It)

By Ivy B. Grey


Every young lawyer knows imposter syndrome. It’s the feeling that you’re an incompetent fraud—and it’s just a matter of time before others discover. But do those feelings affect our legal writing?

I’ve been working with Gary Kinder, the founder of WordRake, for over 18 months now. He’s someone I’ve long admired, so I jump at every opportunity to get his advice on legal writing. Every time, it amazes me that Gary is so down-to-earth and that he doesn’t sound like a lawyer or professor. Because he uses plain language, conversations are accessible and the advice seems manageable. Some of my own imposter syndrome melts away. I feel released from the expectation to “sound like a lawyer.”

That has got me thinking: Maybe bad legal writing stems from feeling like we’re imposters?

According to Gary, we expect ourselves to be expert writers when we’re just starting practice. But we’ve had only a handful of opportunities to write legal documents. In our efforts to avoid growing pains, we want to “write like lawyers” straight away. So we try to signal we are smart lawyers—and that’s where we go wrong.

How Imposter Syndrome Leads to Bad Writing

Imposter syndrome is particularly prevalent at the beginning of your career. It causes us to lack confidence in work. Gary pointed out that, because we want people to take us seriously as lawyers and we don’t feel that we’ve earned it yet, we make mistakes. Those mistakes stem from lacking confidence that our words will be enough. So we give too much deference to what has been written before. And we don’t trust our judgment about which issues to focus on. This bogs down our writing and makes every document an exhausting slog. Luckily, we can be better legal writers when we stop trying to sound like TV lawyers and focus on clear, simple communication.

Seven Tips for Good Writing

Here’s the advice that Gary gave about legal writing. If one of the top legal writing experts in the world can approach writing with such simplicity, maybe we all can, too?

  1. Tell your client’s story, not your conclusions. Tell the story as it happened. Don’t use conclusory words, such as obviously, clearly, or surprisingly. Instead, emphasize facts you think are important. Use them to put your reader in the shoes of your client. By lining up the facts and creating empathy for our position, you make it difficult to disagree with your conclusion.
  2. Use fewer quotes. Over-reliance on quotes from cases takes away from your own writing. Your job is to interpret and apply rules, not repeat them.
  3. Use your own words. Great legal thinkers deserve deference for their concepts, but the words used are not sacred. Don’t be afraid to simplify writing and use your own words.
  4. Narrow your focus. A short document is generally better written and better received. It’s hard to do if you feel you must write about (and support) three points. So decide which point is the most important and focus on that one. When the reader receives your document and notices it is three or four pages under the limit, she will already have a better view of your argument.
  5. Defined terms are overvalued. You can write a clearer document that flows better if you minimize defined terms. But you must accept responsibility for your reader’s understanding. Focus on clear ideas and sentence structure. Some of your sentences may be longer, but a long sentence is acceptable if it is clear.
  6. Clarity trumps brevity. Do not fall prey to hard and fast rules about sentence length. In reality, those are artificial. There is nothing inherently wrong with a long sentence. You could write a 75-word sentence that is acceptable and beautiful. The key is that it must contain no unnecessary words.
  7. Polish your documents. Polished documents encourage a generous reading. So do two simple things: Proofread to correct mistakes and enforce consistency. And edit to include headings to give obvious structure to your document. Use tools like jEugene and American Legal Style for PerfectIt to ensure that your writing is error-free. These programs are inexpensive so you can afford to buy them for yourself. Your reputation is worth it.

A Mentor in Your Machine

The seven tips from Gary are doable if you try. Having a writing coach or a mentor would help you learn faster. But when you’re already struggling with feeling like you don’t belong, it's hard to accept help. Two programs can help:

WordRake helps make your documents shorter and more readable. It improves legal writing style by simplifying and clarifying text, cutting legalese, and recommending plain English replacements.

PerfectIt with American Legal Style adds polish to your documents. It checks for over 13,000 legal-specific typos, inconsistencies, and other mistakes. It will also find formatting, spacing, spelling, and capitalization errors in Bluebook citations. By fixing small details, it gives you more time to focus on substance and meaning.


Finding your footing in legal practice and developing your voice as a legal writer takes time. You will eventually feel like you belong and you will trust your own judgment. In the meantime, you can get past the feelings of shame that come with asking for help by using low-cost software to improve your writing. You’ll have more time to edit and improve text, and it will help build your confidence and learn faster too. Both programs come with a free trial, so try PerfectIt and WordRake today and see how much better the legal writing process can be.


About Ivy B. Grey, JD, LLM

Ivy B. Grey is the creator of American Legal Style and an advisor to PerfectIt. Her work on technology competence and ethics has made her a respected thought leader in legal tech. In 2018, Ivy was recognized as a FastCase 50 Honoree and a Women of Legal Tech, class of 2018 honoree by the ABA Law Technology Resource Center.

Ivy practiced in the field of corporate bankruptcy law for ten years before making her transition to full-time legal tech in November 2018. Ivy received her LL.M. from St. John’s University School of Law and J.D. from the University of Houston Law Center.

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