In enterprise IT circles, there is a well-known—and oft-debated—saying about Microsoft Corporation’s Windows operating systems: Skip every other version. Intentionally or not, law firms have generally followed that advice. Most embraced Windows XP, passed on the much-maligned Windows Vista, and upgraded to Windows 7, which gets high marks. It’s a pattern that would seem to doom Microsoft’s latest OS, Windows 8, which hit the market last October. In fact, The American Lawyer‘s 2012 survey of law firm technology departments, which was conducted before Windows 8 was released, found that just 7 percent of respondents said they planned to upgrade within a year ["Both Sides Now," November 2012].

Windows 8 ushers in a radically new user interface, featuring touch-activated tiles and eliminating the familiar Start button. That has sparked concerns. Will Windows 8 require too much training, too much adjustment in the way lawyers work? Will there be enough new benefits to make the switch worthwhile? There is the obvious question, too: If Windows 7 works so well, why rock the boat? Looking at the survey result, one might conclude that firms had already come up with their answer, and decided to sit this one out.

But that might not be the final answer. Law firms typically lag behind consumers and even other types of businesses when it comes to upgrading Windows. "New systems tend to be buggy, and we don’t want to expose ourselves unnecessarily," says Vic Peterson, the chief information officer at Stinson Morrison Hecker in Kansas City, Missouri. "For better or worse, we will let others learn before us, and we patch immediately." Law firms also use a lot of specialized software—everything from tax programs to add-ons that make documents easier to work with. Often these come from smaller vendors who aren’t quick to ensure compatibility with new versions of Windows. So that 7 percent adoption rate may not be a "no" to Windows 8 so much as a "not now."

But in the long run, Windows 8 may not be as easy to brush off as Windows ME (remember that one?) or Windows Vista (who can forget?). Touch-enabled tablets are making big inroads within firms, and as January’s Consumer Electronics Show made clear ["No Easy Decisions," March], touchscreen-equipped laptops and convertibles (a laptop that can be converted into a tablet) are coming en masse. So while a touch-optimized version of Windows will require time and training to master, it’s a chore that increasingly looks unavoidable—if not with Windows 8, then with future operating systems.

Like it or not, Microsoft’s latest upgrade signals the new realities and direction of enterprise technology. Firms that dismiss Windows 8 as "the version to skip" may, in the end, be doing themselves a disservice. We spoke with four law firms that are taking a serious look at Windows 8 to see how it fits with their technology strategy.

Undoubtedly, the biggest complaint about Windows 8 is the interface it presents at start- up: Instead of the conventional Windows desktop, users see a grid of tiles, each representing an application or a nugget of information (Microsoft calls this the Start screen). These tiles can be updated dynamically, so constantly changing data—like stock prices, flight status, and upcoming calendar appointments—can be rendered in real time. While this new Start screen can be navigated with a mouse, it clearly was designed with touch in mind: Tap a tile to go to an application or to see more information (such as your complete calendar for the day); swipe from the right of the screen to get the new ‘charms bar’ (with links to search and device management, among other functions); swipe from the left to switch among open applications. It’s an interface that is familiar—although not immediately intuitive—to anyone who has used a tablet. But for anyone who has not, it is a whole new world. And it’s a world that some lawyers don’t want to explore.

When Phillip Rightler, chief information officer at Thompson Coburn, polled his firm’s lawyers about Windows 8, one wrote back that "the new interface makes it much more challenging to use and throws out the baby with the bathwater [for] the sake of attacking a nonbusiness market." Another replied that "the interface is too strange." A third noted that he "intentionally purchased two new laptops the week before Windows 8 came out, both of which had a Windows 7 operating system, because I did not want it."

Thompson Coburn isn’t planning to deploy Windows 8 to its 300-plus attorneys anytime soon. But it is testing the new OS, Rightler says, "determining what, if any, role Windows 8 might have in the firm on touchscreen laptops and in conjunction with a planned hardware refresh in 2014." Rightler says the impact of the new interface may not be as dramatic as some lawyers think. Yes, it "takes a few days to adjust [to]," he says. "But those focused on productivity apps can bypass [it] if desired."

In fact, Microsoft hasn’t abandoned the traditional Windows desktop in Windows 8 so much as hidden it. Users can access that interface, complete with the familiar task bar (but not the Start button), by pressing the "desktop" tile on the Start screen. One firm that is currently deploying Windows 8—Milwaukee’s von Briesen & Roper—is going one step further, using a third-party utility called Classic Shell, that gives Windows 8 a Windows 7 look and feel—complete with Start button and start menu. The new interface is bypassed on boot- up; users never see it.

This allowed von Briesen & Roper to upgrade to Windows 8 while avoiding (at least for now) a steep learning curve and push-back from users. "A lot of people were freaked out about the [new] interface with the tiles," says Bill Caraher, the firm’s CIO. "So we decided to run it in classic mode. Even though it looks like Windows 7, it is actually Windows 8." Not only did that simplify training and support, but it enabled von Briesen & Roper—which has about 110 attorneys and some 250 users—to deploy the new OS on more traditional hardware not equipped with touchscreens.

So rather than making Windows 8 look like Windows 7, why not just stick with Windows 7? For the effort to make sense, Windows 8 needs to offer sufficient productivity boosts. Not every CIO who has tested the new OS is convinced that it does. "In our overall analysis, from an efficiency point of view, [Windows 8] is not a net gain," says Sean Power, the CIO at Lathrop & Gage in Kansas City, Missouri. Von Briesen’s Caraher, on the other hand, said his firm’s Windows 8 tests "went very well, and we saw a huge boost in boot speeds, log-in times, Outlook performance, and multitasking." For his firm, these pluses tipped the balance.

This raises a crucial question: What advantages does Windows 8 bring to the table? Microsoft touts several enhancements, including a Windows Store for downloading software (think Apple’s App Store) and integration with Microsoft’s cloud-based file-hosting service, SkyDrive (think Dropbox). But in interviews with CIOs, only a subset of improvements were cited as providing particular benefits to law firms.

Chief among these were speed and security. "I give a lot of credit to Windows 8 and how it streamlines the start-up process," says Caraher. "We’ve gone from a couple of minutes to 4 seconds. And Outlook runs as soon as the splash screen disappears, no matter how large a user’s mailbox. It used to be that attorneys would turn on their machines, get coffee, and by the time they got back, Outlook might be ready. In just the waiting time we save, the upgrade pays off." The boot-up process is more secure, too, since Windows 8′s "secure boot" feature verifies that the OS has not been tampered with by malware. Performance is also enhanced by USB 3.0 support, which enables much faster transfers between the PC and peripherals like printers.

One new feature that combines both performance and security enhancements is the new Windows to Go option, which allows firms to put an imaged version of their Windows 8 desktop on a flash drive. This lets mobile users boot up the firm’s standard desktop from nonenterprise PCs, such as a machine at home or at a client’s site. "It improves home and remote computer management," says Rightler.

While software may get the immediate focus, Windows 8 may also cause firms to rethink their hardware setup, several CIOs say. For instance, firms that use dual monitors on the desktop—a common configuration—might want to replace one with a touchscreen. "You could use a [standard] monitor for productivity apps and the touchscreen for content consumption," says Rightler.

Meanwhile, Windows 8′s ability to run on both tablets and laptops presents the opportunity for a far more drastic hardware overhaul. "If tablets like the Surface Pro take off and users grow comfortable with the OS, then we have to consider whether it makes sense, in a hardware refresh, to issue a tablet instead of a laptop, and hook it up via a docking station when the user is at their desk," says Laurence Liss, chief technology officer at Blank Rome, which is in the early stages of testing Windows 8. "It won’t be a solution for every lawyer, but some may have that preference, the way that some today want a lightweight laptop and some want one with a bigger screen, so we offer both."

Windows 8 may present challenges, but it may also provide opportunities for delivering technology in new and flexible ways that let lawyers work the way that best suits them. For some firms, it may not warrant an upgrade, but for all firms it warrants a look.