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  • Writer's pictureHarshal

Grammarly, ChatGPT, & Hemingway Versus Legal Contracts: Taming A Beast

Navigating Contract Complexity And Analyzing Readability: Using Tech to Decipher Legal Text


I improve my writing every day. Tools like Grammarly and Hemingway help me get immediate feedback on my writing. I use the feedback to make my writing more readable while reducing typos or grammatical mistakes.


But, some professionals work toward the opposite goal.


I am thinking of the legal profession when I write this! Contracts contracts contracts.


I hired a lawyer to write an internship contract for some hires. I wrote about the experience here. I’ll share my editing lowlights in this article.


Grammarly personified as a green person reviewing legal contracts marked with red throughout.
Grammarly personified as a green person reviewing legal contracts marked with red throughout.

Why And How Did I Hire A Legal Expert

I wrote more about this here.


Grammarly On The Legal Contract

Once I got a draft of the legal contract from the law expert, I reviewed it in MS Word. I had Grammarly plugin on my desktop. Grammarly found a large number of corrections. So many corrections that it overheated my PC.


It gave me 151 suggestions. It underlined every line in red, blue, green, or purple.

 legal contract highlighted from top to bottom by Grammarly for lack of clarity and conciseness.
legal contract highlighted from top to bottom by Grammarly for lack of clarity and conciseness.

Hemingway Editor On The Legal Contract

I tested the Hemingway editor on the legal contract. I assumed a grade 15 readability score. I was surprised the App rated the contract’s readability as grade 9 (better). The app found 142 issues with the text.

Hemingway app found 100s of issues with the legal contract’s readability.
Hemingway app found 100s of issues with the legal contract’s readability.

Unleashing ChatGPT On The Contract

I selected one part of the contract that had the most amount of red highlights in the Hemingway App. These were consecutive “very hard to read” sentences. The readability of this excerpt was grade-15. I asked ChatGPT to use simple language and bring the readability to a grade-6 level. Then I asked it to further simplify the readability to grade-4.

GIF of simplifying the legal language from grade 15 to grade 4.
GIF of simplifying the legal language from grade 15 to grade 4.

Confusing Contractual Culture That Conveys CYA

My takeaway from this experience was that experts write legal contracts in a complex style. It has jargon. It has flowery medieval Shakesperean language - like this sentence. It tired me out to read and edit it.


Contracts convey the philosophy of CYA. Risk reduction. Insurance against liability. Disaster mitigation. Regulation.


Instead of “let’s work together in good faith”, contracts convey “we need the threat of negative consequences to make us work together.”


Would I Use A Contract Again?

Yes. I want a risk mitigation plan in place. But I won’t refer to it daily when working with interns, freelancers, or clients. I want it to be the safety net that prevents us from falling into the chasm. Whereas I will continue to build trust through relationships. Build trust and show credibility to persuade or influence. I continue to influence my contributors and clients towards a shared vision.


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