Joe Regalia Profile picture
Mar 1, 2023 12 tweets 6 min read Read on X
We had #ChatGPT write a legal brief.

But instead of giving it a simple open-ended prompt, we taught it how to use some of the techniques used by the best legal writers in the world.

Check out what it came up with—if only more legal writers wrote this well. 1/x
To celebrate the upcoming launch of Write.law's new AI legal writing practice, we had our team work with GPT to write a motion from start to finish.

All we used was a simple list of factual details, some legal research notes, and our teams' prompts.

2/x
If you'd prefer an interactive version of the whole motion (complete with breakdowns of how we got GPT to craft each part of the motion) check it out here: write.law/writing-walkth…

Ok, let's break it down!

3/x
Use a deep introduction to do the work for readers.

☑️ GPT's intro paragraph orients you to the background of the case. Then it breaks down the key issues using specifics.

☑️ Judges love introductions that give them a cheat sheet of what matters like this.
Summarize the story with a quick movie trailer.

☑️ Consider beginning your fact sections with a quick movie trailer that gives readers the big-picture storyline at the outset—as GPT did.

☑️ This helps readers see the forest before the trees.
Craft factual headings that categorize each major group of details while also highlighting specifics.

☑️ Fact headings are a powerful way to highlight specific details from a section—as well as organize the factual details into a few manageable categories for readers.
Capture what matters from your fact paragraphs in the first sentence.

☑️ Distill the main takeaway from each paragraph at the outset. That way busy readers always know what matters, no matter how quickly they skim your document.

GPT agrees.
Surgically quote only what will help your readers.

☑️ If you find a good quote, use the smallest snippet that will serve your reader. Otherwise, let your better writing shine through.
Keep procedural standards short, to the point, and in plain language.

☑️ Most of your legal readers probably know the basic procedural standards (especially if it's a judge). So don't waste time with pages of legalese. Keep these sections short and easy to read.
Roadmap your points.

☑️ Readers love roadmaps. Number off your reasons or your sections or your categories, and it's almost impossible to get lost (so long as you stick to the map).
Stay tuned for the launch of the first AI-powered legal writing training, available only on Write.law!

#ChatGPT #appellatetwitter #legalwriting
I'll also give a shout-out to @BriefCatch and @legalwritingpro because a lot of the tuning we had to do were things I know for a fact BriefCatch would fix with a click. GPT + BriefCatch may constitute an entire top-notch lawyer!

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More from @writedotlaw

Apr 11
Most lawyers research in a straight line.

They find the statute. They find the leading cases. They pull a few quotations. Then they start explaining why their facts fit.

That works sometimes. It just does not take you very far. 🧵
The lawyers who do exceptional work use authority differently.

They do not treat it as a pile of answers.

They treat it as evidence. Something to test. Something to pressure. Something to compare, narrow, widen, flip, and question. (2/7)
That shift matters because the hard part of legal analysis usually is not finding some authority.

It is figuring out what that authority is really doing, what it leaves open, and how to explain that clearly enough that a judge sees it too.

A few moves make that possible: (3/7)
Read 7 tweets
Apr 4
We use commas throughout our writing, but many legal writers place them where they aren’t needed.

Others remove them from phrases or clauses even when they are necessary to avoid ambiguity.

Let’s break down the rules for when to use commas—and when to leave them out. 🧵
First, use commas to separate two independent clauses (full sentences) with a coordinating conjunction.

✅ Joe went to Saipan, and he loves reading. (2/8)
Do not use commas to join two full sentences without a conjunction (also called a comma splice).

❎ Joe went to Saipan, he likes to read. (3/8)
Read 8 tweets
Mar 4
Agents are changing the game for lawyers.

If you’re still thinking about “prompt engineering” as a spell-casting exercise, you’re already behind.

Let’s slow down and get clear on what’s actually happening. 🧵
An agent is a system that can break a task into sub-tasks, decide what to do next, evaluate intermediate outputs, and revise its own work.

Instead of one prompt and one answer, you get a loop.

Think less “question and answer” and more “junior associate with a workflow.” (2/7)
The new reality: workflow > wording.

When you’re using an agent, the real leverage is upstream and downstream:

What materials you feed it, how the task is staged, what checkpoints exist, who verifies what, what tools it can access, and what it is forbidden to do. (3/7) Image
Read 7 tweets
Feb 27
The Supreme Court just heard a major case: whether the President can use a 1977 emergency-powers statute to impose tariffs.

The private respondents—represented by Neal Katyal and a team of elite advocates—filed a merits brief that reads like a legal writing masterclass.

🧵
☑️ Open By Telling a Story, Not Stating a Rule

Most lawyers launch their briefs with procedural history or legal standards.

The best legal writers do something different—they tell a story first. Before readers can care about your rule, they need to care about the stakes. (2/6) Image
☑️ Turn Your Opponent’s Own Words Into Your Best Evidence

There’s no more devastating move in legal writing than using the other side’s own words against them.

When your opponent concedes a point, don’t let it slide by—put it center stage. (3/6) Image
Read 6 tweets
Jan 3
Most lawyers spend more time fighting Microsoft Word than using it.

That frustration usually gets chalked up to Word being “quirky.” It isn’t.

Here are the Word tools and skills that actually matter for lawyers and power users in 2026. 🧵
☑️ Start by Letting Styles Do the Heavy Lifting

If you format headings by changing font size and bolding text manually, Word treats every heading as unrelated.

That’s why numbering breaks, tables of contents fall apart, and cross-references stop updating. (2/7) Image
☑️ Fix Numbering the Way Word Expects You To

Legal numbering fails when people click the numbering button and hope for the best. Stable numbering comes from multilevel lists linked to heading styles.

The correct workflow looks like this: (3/7) Image
Read 7 tweets
Dec 5, 2025
Kirkland & Ellis’s brief in the blockbuster AI case, Thomson Reuters v. ROSS, lands like a masterclass.

It shows how advocates frame a narrative, marshal facts, and push the reader toward one inescapable conclusion.

Let’s unpack the writing techniques that make this one hum. 🧵
1️⃣ Choose a Frame That Carries the Whole Story

Kirkland doesn’t warm up. It opens with the entire case in a single hit. (2/8) Image
2️⃣ Distill the Point Before You Dive Into the Details

Great briefs announce the takeaway before the reader ever has to work for it. Kirkland does this over and over. (3/8) Image
Read 8 tweets

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