Practical use of AI in law firms

A summary and review of AI tools for plaintiffs’ attorneys, from case intake to case management, legal research and brief writing

Robert Simon
2023 November

As a trial lawyer/law-firm owner/legal-tech owner I am thrown into many meetings where I am clearly the dumbest person. A lot. But after listening, paying attention, researching, and most importantly, practicing, I am here to share some lessons. And practical how-tos. This article will discuss various products that we have vetted over the last several years or months.

Ethics check

Your name is on the pleading. Your signature on the work product. Treat AI as if you are getting handed a product from a fresh law clerk, that you haven’t thought a whole lot about yet. The excuse, “The robot did my MSJ Opp” is just going to get you sanctioned. So, when in doubt, fact-check it throughout!

Basic AI

Everything is AI now. I was watching Vanderpump Rules and they had a commercial about skincare that had AI. Skincare! Look folks, don’t fall for it. Many companies are throwing up companies overnight, white labeling ChatGPT, and saying they have AI. It is a mirage. AI is artificial intelligence. It has to be intelligent on something. Something specific. Something with fantastic data. Something with a lot of reps on that fantastic data.

When you are using basic ChatGPT it is pulling information from all over the internet. It could be the 57th page of Reddit. It may be totally wrong. The data is wrong. It is learning on the wrong thing. Learning from the wrong person. Going back to the law-clerk analogy. If you get a law clerk, fresh out, and you task them with writing a brief, they will do an okay job with it. They will leverage Westlaw, use their resources and do the best they can. Then you have to fact-check it, edit it, quality-control it. But over time, imagine that law clerk learning really fast. And only using a specific data set that has all the right answers. They learn your way. Now we are onto something.

When using AI, see what it was taught from. Its data set. If it is built on legal research, it may not be so good at medical timelines. If it is taught how to read and analyze medical records, it may not be so good at writing you a poem in perfect iambic pentameter.

Below are products that we have vetted many times. These are our honest opinions, thoughts and use cases. I encourage all of you to find a mentor or someone to learn this with and bounce ideas off of.

Case-management systems

Everyone should be paperless and on a cloud-based case management system. It will make you all much more efficient, allow your firm to scale, save you a lot of money, and in the end, if used correctly, make you a lot of money. With that comes higher quality of life. Less overhead for your firm makes it a bigger recovery for your clients. It is a win-win. In my eyes there are seven big systems, and depending on your situation, one is right for you. For me, it is all about their integration, customer service, and ease of use. In no particular order, here they are, with my brief thoughts on each:


By the time this article is published Clio will have released its new PI Suite, which we have been able to test drive for the better part of a year. Clio likely has the most engineers and really treats its customers well. One of my favorite things about Clio is they integrate with so many other platforms and are heavily invested in the legal-tech industry. They find other products, on-board them, highlight them, and help them succeed. Clio also has a custom LSA portal in a Google partnership that makes them very appealing. Clio really has a partner platform for whatever you are looking for. It integrates with pretty much every AI product that I mention below. I am a big fan of Clio. Also, Clio just announced the launch of Clio Duo, an AI bot on their platform that can assist you with any task, knowing all of your data.Imagine just asking it to create a link to all depositions in a case and emailing it to whomever you like. Whew.

Casepeer/My Case

Casepeer was acquired by My Case, so I will treat them one and the same. Casepeer is still likely the best “out of the box solution” for anyone starting their firm. Their integrations team also rolls out the red carpet to make sure that you are on the correct path. They will make sure that you can easily push your case data and files wherever you need them to go: to an expert reviewing your case, or to another attorney for collaboration. They are a company born out of SoCal and know California and our firms very well. They also have some very exciting products on the horizon. I am a big fan of the founders and believe in them. This is no exception.


Filevine was created by a personal- injury lawyer and is likely the most customizable platform to suit your needs. I know some Filevine superusers who have really taken the time to automate pretty much everything from intake to settlement. This platform also has a few AI products built into it, like AI Fields, and AI Demands. It can pull data from your cases and give you quick summaries, review depositions, etc. Their product, Lead Docket, also has some really cool features coming up to help you qualify cases from intake based off your own criteria and metrics. Filevine also announced AI Leads, which will qualify the cases coming through your intake. It will hopefully tell you which ones are good, and which ones you may want to refer to Attorney Share or other platforms or people in your network.

Smart Advocate

This case-management platform very easily handles a large volume of cases. This type of platform, if you are generating a lot of cases and/or doing mass torts, is the perfect vehicle. They also have been building bridges for integrations to make it very easy to work with them. Their CTO is one of the smartest people in those smart rooms that I am in. If you are a firm getting a lot of cases, whether keeping them or referring them out, this is a good one for you.


This is built on Salesforce, unlike all the others. This is meant for larger firms, like 30-plus users. This is fantastic at analyzing your data. Figuring out case cost per acquisition. This is a great tool if you wish to generate and track large numbers of cases. They have a wonderful management team that is easy to work with and will help make sure it works for you.


This is a newer platform, maybe lesser known, but they have a dedicated CEO and team ready to help PI law firms grow quickly. They can get you up and running in a day. They are big on back-end operations. Since they are a young company, they are eager to please, and really can help you significantly with anything custom that you need. They also have some really cool financial analytics that will help your firm grow.

Law firm intake/marketing

Whippy AI

This company is, at its core, a front-end concierge service for client contact and communication. The platform can handle your clients’ Google reviews when the case is closed. It has dummy text numbers to text with your clients. It also acts as a mini-CRM to store all the data of anyone that engages on the platform.

Ever see the little chat bot that pops up on webpages? Go to mine, When you see my face pop up, you are talking to Whippy’s AI. It wants to learn everything about you and your case. It knows intake and what you want. It is trying to qualify the lead. What is happening on the backend, is Whippy is pushing that data into your case management system (it integrates with some of them). From there you can decide to keep it within your firm, call that client, sign that case, or push it into another product to refer the case and maintain a tracked referral fee.

What I love about this company is they offer white glove service to their customers. The AI chat bot has to know what you need to qualify your cases. Their CEO once won the World Series of Poker and their CTO is Irish and writes code with his team in Ireland eight hours before we even wake up! In the tech world it is important to believe in founders. They are a very important part of the products you are investing your time, money and energy into.


This product is not live yet, but intel suggests it will have the ability to use a mix of phone, chat, SMS and AI to do your intake for you. This is a product I am excited to see and test drive.

Munch AI

This is a content tool for social media. It is subscription based, only about $40-50 a month, and you can bang out quality content in minutes. You can take any recorded content that you did. Whether a self-recorded video on your iPhone; a podcast you were on; or a talk that you did; and it will cut up the most engaging posts for you; suggest which platform to post it on; with the verbiage to post, I can record five podcasts in a day, drop them into Munch, and have enough content for four months to be posted onto LinkedIn, Instagram, Facebook, YouTube shorts, etc., all directly from their platform. What used to take humans hours and weeks to do, is now seconds. Fantastic marketing tool.



Want to answer discovery in minutes when the defense sends it over? Or auto-propound discovery as soon as they file an answer? All using AI? This is a product for you. You can get the discovery from the defense and just drop it into the EsquireTek platform. It will create the Word document shells, with the correct captions, then auto-format the answers to the questions, and suggest objections to drop in.

You can then push the discovery questions, in a very easy-to-read format, directly to your client for them to fill out and send back to you. Discovery can be answered in minutes. A must for any firm. And now with us shifting to initial disclosures in discovery, starting January 1, 2024, to mirror the federal rules, their product is an absolute must. You should have your initial disclosures done and ready to go before you file your lawsuit. And your inquiries ready to go to the defense, too! All possible with this product.

Medical records/timelines


Likely the AI product of the year. This one or Casetext’s CoCounsel. But both have different use cases. This one is built on knowing medical records very well. It automates your demand letters. In what is a revolving door position at most firms, demand-writing, this product is only a couple hundred bucks a run. And it gets smarter. And never leaves. The product synchs with many case management platforms now. It can pull all your medical records and bills and auto-generate the demand letter. It will even tell you what records and bills you are missing. It will even suggest injuries you forget to work up.

But what it is really doing is creating a repository of settlement value – like the data the insurance companies already have — to even the playing fields for plaintiffs’ lawyers. Real data. We can now be armed with settlements and verdicts for similar fact patterns and injuries in seconds. The company is also working on other very cool products that I hope are out by the time this article is published. Because one is a game changer. Full disclosure – one of the founders is now a good friend. We talk binary code all day to each other and geek out about this stuff. This company even trains its staff with AI Avatars! I digress…


This is another company built on medical records and injuries. The company was founded by a researcher and biomechanical expert and knows the personal-injury game. They partnered with Amazon on this project, so you know it is good! You can drop in PDFs of a case given to you, or one from intake. You can drop it in, and in a few minutes it will put everything organized into folders. Medical records/bills; discovery; photographs; depositions. Under medical records it will have a timeline, with hyperlinks to the actual records. This is a new company and will evolve with even more cool features.

Legal research/briefs

Casetext’s CoCounsel

This product started as a legal-research company. It knows it very well. The cites are on point. The cases are all there and Shepardized. This is your “law clerk in a box.” And after it has a few weeks of learning time, and you learn how to ask it the right questions, it becomes your “senior partner who is the smartest at legal research and writing,” all in a box. You can prepare for expert depositions; have it give you outlines; write your legal briefs. I drop in studies from defense experts and ask it to critique and give me information. You can also drop in ten thousand pages of records and ask for a summary. Truly one of the products of the year. If you do any litigation, this is a must. Their AI is truly marvelous. They were recently acquired by Westlaw, so now the sky is the limit. I would get your subscriptions before they change pricing!

ClearBrief AI

This product gets used every day at our firm as well. Huge fan. If you get any motion or brief from the defense, you can drop it into their AI to fact check, show you how and why it is wrong. I know many judges who are now using it. We should be, too. Whatever I write here cannot do this product justice. So many use cases. This is monthly subscription- based, rather than some platforms that you pay per page analyzed.

When we get brought in late for a case to try, we drop all the documents into this platform and it will analyze everything for us. Like give you a great 90%-of-the-way-there read. Drop in depositions and ask it questions. The big misnomer is that this product is just for legal writing. It is not. It has many applications.

Start evolving now

Law is changing at a rapid pace. Listen to podcasts, read articles, and test-drive these products. Just 30 minutes a week will help you immensely to keep up. We are in a real position to automate the mundane and be free as lawyers to do the things we are really passionate about — and that is not indexing medical records and doing discovery shells! Start by getting a mentor in the tech space. Then vet the right case management tool for you. Start playing with products that can solve the negative time sucks in your practice. Let’s evolve and just meet in the metaverse for some virtual pickle ball or something.

Robert Simon Robert Simon

Bio as of June 2019:

Robert T. Simon is co-founder of the Simon Law Group and acts as the primary trial attorney. He is a proud member of ABOTA, CAALA, CAOC, CASD and OCTLA, is a past president and active board member of Los Angeles Trial Lawyers’ Charities.

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