I am thrilled to post this insightful article from my good friend, Tara Cheever. Tara is a co-founder of LitSoftware. LitSoftware suite of products, including TrialPad and TranscriptPad, among others, revolutionized how litigators practice their cases. Thanks Tara!

A cultural clash has been brewing within law firms for years. On one side are midlevel associates who grew up immersed in the sleek, intuitive world of Apple products. On the other side, legacy IT teams prefer entrenched Microsoft-based infrastructure, and are often dismissive of Apple altogether. As this clash reaches a boiling point, law firms may soon face an existential choice: stick with what’s comfortable for their IT departments, or embrace the future of technology that a growing number of associates not only prefer but demand.

In a recent American Lawyer survey reported by Samson Amore in Law.com, midlevel associates voiced their frustrations over “lame laptops” and “batteries about to explode.” For these associates—many of whom are accustomed to the efficiency, stability, and cool factor of their personal Apple devices—the switch to firm-issued Windows laptops is more than just an inconvenience. It’s a workflow nightmare.

The Complaints

What’s the complaint? Many associates, fresh out of law school, have been using MacBooks and iPads since their high school and undergraduate days. Law school classrooms are dominated by Mac users, with reports from some schools indicating that up to 85% of students bring Macs to class. These students-turned-associates now find themselves tethered to outdated, clunky PCs, running Windows systems that don’t feel like an upgrade but rather a step back.

And it’s not just midlevel associates feeling this pain. Partners, too, often vent their frustration, especially those who use Apple products at home. They, like their associates, wonder why their firm-issued laptops can’t match the seamless experience they enjoy on their iPads and iPhones, especially when much of their software is cloud-based.

As firms focus on efficiency, the lack of investment in reliable, high-quality tech becomes more glaring

It’s not hard to sympathize with their frustration. As firms focus on efficiency, the lack of investment in reliable, high-quality tech becomes more glaring. As one story illustrates, co-counsel on a large insurance defense case were all issued outdated ThinkPads that were simply not fit for purpose. Locked-down laptops, restrictive email policies, and file size limitations made collaboration downright painful. Associates spent hours navigating tech barriers that should have taken minutes. The result? Lost productivity, mounting frustration, and time-based bills to the client were far larger than they needed to be.

For many associates, opening a creaky, underperforming laptop in a public setting can feel like a professional faux pas. In a world where image matters, they’re embarrassed by their firm-issued technology and infuriated when it fails to work properly. In contrast, Apple products function and they elevate the user’s professional presence.

Tom Vidal, a Partner in Pryor Cashman’s Litigation, Media + Entertainment, Intellectual Property, and Technology Groups, echoes that sentiment saying, “Law firms can no longer treat legal technology as simple commodity products. Computing devices and software are not office supplies but vital tools that can enhance or detract from the delivery of world-class legal services. Apple products promote delivering quality legal services in three ways. First, the user experience is more reliable and less prone to configuration problems. These tools famously “just work.”

Second, the hardware is high quality and suffers less downtime than PCs. Moreover, with services like AppleCare+, replacing non-working hardware is simple and convenient. Third, the app ecosystem is designed to solve very specific problems efficiently.” Tom prefers mobile devices and web or iPad apps to access data instead of the “thin clients” provided to establish a remote connection with firm servers. He believes that “If IT departments were more welcoming to Apple products, they could enable lawyers to bring more creative solutions to their clients’ legal problems. The good news is that firms are becoming much more open to incorporating iPads and iPhones into the firm’s tech infrastructure. My trial team, for example, runs almost entirely and almost exclusively on iPads.”

Why Apple?

Why this attachment to Apple? There’s the famously simple answer, echoed by Mr. Vidal above: Apple products just work.”

•  Stability and Security: Apple’s macOS is renowned for its stability and security, thanks to regular updates and a design that minimizes system vulnerabilities. iPad, for example, was designed to protect both data and privacy. Built-in security features help prevent anyone but the user from accessing the data on iPad and in iCloud, while built-in privacy features minimize how much user information is available to anyone but the user. And, users can adjust what information is shared and where it is shared. For law firms that handle sensitive, confidential client information, this should be a compelling factor. Apple’s closed ecosystem offers peace of mind that Windows often struggles to match.

•  Longer Lifespan: While the initial investment in Apple hardware may be higher, the longevity of Apple products more than makes up for it. A MacBook can last for years, often outpacing its Windows counterparts by several hardware cycles. When you factor in the cost of constantly replacing outdated PCs, the price argument starts to crumble.

•  Cloud Integration: Much of today’s legal software is cloud-based, making the need for Windows-based devices less relevant. Associates ask, “Why can’t I just use my Mac?” And they have a point. If the software is platform-agnostic, why force them onto clunky, outdated hardware?

There’s also an intangible quality that Apple products bring to the table—the cool factor. Associates want to be proud of the tools they use

•  Cool Factor: Let’s face it, there’s also an intangible quality that Apple products bring to the table—the cool factor. Associates want to be proud of the tools they use. Apple’s sleek design and user-friendly interfaces enhance the user experience, making long workdays just a little more bearable.

The Law Firm-Apple Disconnect

So why haven’t law firms embraced Apple products en masse? One big reason is that Apple challenges the comfort zone of entrenched IT departments. Many IT professionals have spent their careers immersed in the Windows environment, managing fleets of PCs and supporting Windows-based systems. Switching to Apple would require a shift in mindset and a willingness to learn and support a new system. For some, this presents a perceived threat to their job security. After all, Apple products require less maintenance and fewer troubleshooting calls.

This resistance to change comes at a cost. Firms that cling to outdated technology frustrate their workforce and risk falling behind in productivity, efficiency, and, perhaps most importantly, talent retention.

There is a middle ground many firms have claimed — requiring Windows PCs while at the same time supporting Apple devices like iPhone and iPad. This is the approach taken at Adams and Reese, a law firm with nearly 300 attorneys and advisors located in 21 offices and 10 states throughout the United States and Washington, D.C. As Jeff Richardson, the chair of the Technology Committee at Adams and Reese, explains: “Like other large law firms, we rely on important software for services such as our document management system that are designed to integrate with Outlook on a Windows PC. But almost all of our attorneys also use an iPhone, and a large number also use an iPad. Mobile Device Management software allows Apple products to be a secure part of our environment, and virtually all of the platforms that we use on our PCs can also be accessed using an app on an iPhone or iPad. Our attorneys love being able to use Apple’s intuitive and powerful mobile devices while providing legal services for our clients.”

Getting Ahead of the Curve

Some law firms are getting ahead of the curve, recognizing the long-term benefits of adopting Apple technology. These firms aim to see happier associates, smoother workflows, and enhanced security—all with less friction. By investing in Macs and iPads for their legal teams, they attempt to foster an environment where associates are more productive and engaged. And when a device does need support, Apple’s renowned customer service ensures that issues are resolved quickly, minimizing downtime.

Nathan Treanor, Executive Director of Dean Omar Branham Shirley, a tech-forward plaintiff’s firm with a national practice explained why the firm chose the Apple ecosystem instead of Windows PCs, “For us, choosing Apple over Windows came down to a few things: 1) the seamless integration between devices. 99% of our attorneys and staff have iPhones, and a large number of them use iPads. The ability to work across all devices helps with productivity and makes our lives easier. 2) Apple’s focus on security and privacy, especially when handling sensitive client information, gives us peace of mind that potential data breach or compromise risks are significantly reduced. And 3) despite the higher upfront cost, the reliability and longevity of Apple products leads to lower costs for replacing equipment in the long run.” He added, “I am sure there are other benefits… and, to be honest, Apple products just look better than most PC products. While I am sure most people wouldn’t admit that is a consideration, I am sure it plays a part.”

In today’s legal landscape, efficiency and security are paramount in the tools a firm chooses.

Apple Intelligence and Security: the Game Changer?

As law firms grapple with emerging technologies like AI, they will soon have another decision to make. How will AI be integrated into legal workflows, and which platforms will provide the safest, most confidential use of these tools?

Apple’s approach to on-device AI, with a focus on privacy and data security, positions it as a safe choice for firms dealing with sensitive legal matters. Meanwhile, Microsoft’s cloud-based AI solutions may introduce new concerns about data breaches and confidentiality risks. Law firms that want to remain competitive in the AI age must consider which platform offers the best blend of functionality and security.

In today’s legal landscape, efficiency and security are paramount in the tools a firm chooses. The burgeoning cultural divide between IT teams and a tech-savvy generation of attorneys is coming to a head, and firms that fail to embrace Apple technology risk alienating the very talent they rely on to thrive.

The question may not even be whether Apple is the better choice—it’s whether your IT team is holding you back from making it.

Photo Attribution: Photo by The Jopwell Collection on Unsplash


As many of you know, I regularly participate in Bob Ambrogi’s LegalTech Week journalist roundtable on Fridays. This past week, we actually did the roundtable live and in person at Relativity Fest. I raised two articles/developments during the roundtable. The first one had to do with the settlement by DoNotPay with the FTC, which Richard Tromans of Artificial Lawyer analyzed in a recent article. DoNotPay was fined for alleging offering legal services to consumers that they could not deliver. (Josh Browder,the owner of DoNotPay was not named as a defendant in the action).

The second was the announcement that Rocket Lawyer had been granted approval by the Arizona Supreme Court to operate as an alternative business structure. This approval paves the way for nonlawyer law firm ownership. Rocket Lawyer has previously secured similar permissions in Utah and the UK. I usually don’t post what I talk about during the roundtable since that would be a little redundant But the two articles raise some access to justice (A2J) issues that merit additional consideration and thought.

Continue Reading Access to Justice: Perfection Can’t Be the Enemy of Progress

I’m attending Relativity Fest this week in Chicago. Relativity Fest is put on by the e-discovery software provider Relativity. Relativity is one of the largest discovery software providers. Relativity Fest is its extravagant user conference. According to Relativity, there are a record 2000 attendees at this year’s show, the 15th annual one.

I attended a panel discussion early in the conference on the findings of an annual in-house counsel Survey conducted jointly by the consulting firm FTI and Relativity. On the panel were Ari Kaplan, the principal investigator for the Survey, Adam Weiss, Relativity’s Chief Legal Officer; Wendy King, Senior FTI Director; and Celia Perez, in-house counsel at FreightCar America.

This was the sixth such Survey. Kaplan talked to some 34 in-house counsel in 11 countries.

Continue Reading Relativity Fest 2024: E-Discovery Providers Like Relativity Pave The Way for Legal Embrace of GenAI

I recently chatted with Noah Waisberg, co-founder and CEO of Zuva, an M&A contract analysis firm. Noah was kind enough to give me a copy of the book he and Dr. Alexander Hudek recently authored AI For Lawyers, which is an excellent read.

In his book, Waisberg and Hudek talks about something called the Jevons Paradox. The Jevons Paradox is that generally speaking, when the price of a good or service comes down, consumption of it will typically go up. Waisberg and Hudek postulate that the same should be true for legal. As automation, AI, and Gen AI reduce the cost of legal services, there should be more cases brought. 

In my view, that means greater demand for legal services. More demand should mean more revenue and profit for the providers of legal services.

Continue Reading Unlocking Potential: Can AI and Gen AI Can Transform Insurance Defense and Carrier Relationships?

I recently attended LexSummit2024, the Filevine user conference. Filevine is a case management software provider. I also got a demo of vLex’s enhancement of its AI tool, Vincent from its Chief Strategy Officer, Ed Walters. VLex has historically been thought of as a legal research provider although now we its expansion, Walters describes vLex as a “legal intelligence company.” Lots of cool stuff, most of which is already out there in the marketplace. What struck me the most about these and other tools? Litigation is about to be completely disrupted across the board.

Continue Reading A New Day For Litigation: AI Tools Are Redefining the Future

The Filevine user conference, LEXSummit2024 kicked off recently in Salt Lake City with a keynote presentation by its CEO, Ryan Anderson. Anderson offered up his view of where the company in specific, and perhaps legal tech, in general, should be going.

Anderson called to mind Steve Jobs and the iPhone introduction in 2007 as a map for the future. Anderson played a video of Job’s introduction of the iPhone. As most of you may remember, Jobs described iPhone as a device that combined three things—the iPod, a cell phone, and an internet communicator—into one. The genius of Jobs and the iPhone, said Anderson, was not that Apple created something entirely new. The genius was seeing the synergy of having a device do three things that three different devices previously did. This combination opened up the potential for innumerable new and different things because it gave customers something they needed and wanted. Given where we are today with the iPhone, the value of that insight seems pretty clear.

Continue Reading Ryan Anderson Lays Out Future of Filevine

I recently returned from the annual Conference of the International Legal Technology Association or, as it is usually referred to, ILTA. Over 4000 registrants from 32 countries. Over 200 exhibitors. Almost 350 speakers. To say this is a really big show would be an understatement. It’s certainly one of the biggest if not the biggest legal tech conferences. I have written about some particular observations from this year here and here.

So what did I learn about legal tech and the state of the “ecosystem”? Here are my top ten things:

Continue Reading The Top Ten Things I Learned at ILTACon This Year

Like it or not, we live in interesting times. They are times of danger and uncertainty; but they are also the most creative of any time in the history of mankind.

Robert Kennedy

The ILTA Conference I am attending this week is great for seeing where the legal tech industry is going. This is true especially for Big Law and large corporations. One trend is clear: we are witnessing the second wave of Gen AI in this legal market segment. In a word: its consolidation.

Continue Reading Gen AI’s Second Wave: The Rise of Consolidation in Legal Tech

The gargantuan ILTA (International Legal Technology Association) Conference kicked off today at Nashville’s sprawling Gaylord Opryland Hotel and Convention Center. (Well, sort of in Nashville. The Gaylord is in the Nashville suburbs, not downtown Nashville). Over 4000 registrants from 32 counties. Over 200 exhibitors many of whom hawking their AI and Gen AI wares. Almost 350 speakers (as in most shows these days, many of which are talking about Gen AI).

Indeed, one of the Ediscovery vendors wondered out loud to me whether there were still any Ediscovery issues left. All the conversations are dominated by Gen AI. The answer, of course, is that there are plenty of ongoing ediscovery problems. It’s just that, these days, it’s all Gen Ai, all the time.

You have to be careful with data and algorithms when making decisions

Continue Reading Beyond the Hype: Opening ILTA Keynote  Reminds Lawyers and Legal Professionals of Limits and Risks of Data Analytics and Gen AI

There are three kinds of lies: lies, damned lies, and statistics. Mark Twain 

I was told one time that there are firms that want to innovate, and there are firms that want to say they innovate. Meaning, of course, that some firms just want to get on the bandwagon and appear to follow trends for appearance’s sake. These firms either don’t know how to innovate or have no interest to begin with.

I thought about this idea when I was recently presenting with Dr. Maura Grossman. Dr. Grossman is a professor of Computer Science at the University of Waterloo in Canada, a consultant, and a lawyer. She has been a court-appointed special master on eDiscovery matters. She has represented Fortune 100 companies and financial institutions in dozens of civil actions. She invented one of the most widely used protocols for technology-assisted review. Oh, and in her spare time, she is an affiliate faculty member at the Vector Institute of Artificial Intelligence in Ontario, Canada.

Anecdotal Evidence Suggests Limited Use of Gen AI

Continue Reading Mind the Gap: the Disconnect Between Surveys and Anecdotal Evidence On Gen AI Use By Lawyers