Eyeing the Office

With its new iPhone release, Apple ups the ante in its battle against the BlackBerry.

The American Lawyer

By Alan Cohen

October 01, 2009



It used to be that the only thing lawyers tried to recruit was new clients. But these days, seemingly every firm has a group of attorneys pushing to bring aboard something else entirely: iPhones. And they want them badly. "I have probably 15 people who continue to e-mail me about it," says the IT director at an Am Law 100 firm who asked not to be identified. "This one attorney, he goes out and finds someone who says he can solve any iPhone problem for $175," he says. "These attorneys, they want this thing so much, they are off trying to solve my problems. God bless them, but they don't know what they're doing."

The issue isn't technical. It's relatively simple to hook an iPhone into a corporate network, since it can use the same Microsoft Exchange Server that most firms already use for their BlackBerrys. Instead, IT directors' reluctance boils down to this: The BlackBerry was designed from the ground up to do one thing: transmit e-mail securely. Other features have been tacked onto newer models, but robust, secure, immediate e-mail was--and is--at the BlackBerry's core. The iPhone, on the other hand, is more of a consumer device with e-mail tacked on. Law firms shied away from the iPhone because it couldn't match the BlackBerry on security. And security--well, that's at the core of a law firm IT director's job. "The original iPhone and the later 3G model had no local encryption, which meant that everything on the device was stored in clear text," says the IT director. "The simple passcodes many users had--if they used any passcode at all--could be hacked, and then everything would be viewable. We told our attorneys this was a deal-breaker."

But with the release of the latest iPhone, the 3GS, along with the new iPhone 3.0 operating system, the platform is looking more business-friendly. Forget about the consumer-oriented enhancements (like the upgraded camera on the 3GS, capable of shooting video). The real story, at least for law firms, is the vast array of enterprise-focused improvements. The 3GS phone now has local encryption along with more memory (up to 32 gigabytes) and a faster processor. And with the 3.0 OS, law firms running Exchange can require the use of strong passwords (the complicated ones, with numbers and letters, that no one except IT administrators want to take the time to create and use) and remotely wipe devices that have been lost or stolen. Users get a long-awaited cut-copy-paste feature (a glaring omission on the iPhone until now), a landscape keyboard option for easier typing, and the ability to search the "from," "to," and "subject" headers (but not, alas, the body) on their e-mail, as well as their iPhone contact list, calendar, and notes.

We've been using the new iPhone 3GS, running the 3.0 OS, and we like it a lot. It's zippier than previous iPhones (Web pages load faster, and there's less of a lag when switching between applications). The bigger keyboard space makes typing more manageable (but, like those minute BlackBerry keys, it's still not perfect). Extra memory is something we're always happy to get, and yes, the video camera is pretty nifty, as is the compass, which can pivot a Google Map so that it's pointing in the direction you need to go. Still, is the iPhone really ready for law firms?

We asked some law firm IT directors, and the answers were no big surprise: Tech directors who have already embraced the iPhone say it's ready, now more than ever. Those who haven't say that even with its enhancements, the platform still isn't quite there yet.

Our verdict: The pro-iPhone group is starting to make the better case. No one is advocating tossing out every BlackBerry and going all-iPhone. Even Chapman and Cutler, which is as Apple-friendly a law firm as you're going to find (all of its lawyers and staff are on Macs), has 11 BlackBerry users alongside its 190 iPhone lawyers, according to Todd Nugent, the firm's chief information officer. (The firm also has 40 users on Treos, since those devices can be plugged into, or "tethered" to, laptops, allowing lawyers to use the handheld's network connection to link their computers to the Internet--a handy feature that U.S. iPhones and older BlackBerry devices don't offer, although some non-U.S. iPhones do.) The firm lets users choose for themselves and supports each platform.

We think that this is the line firms should (and eventually will) take. Not every lawyer uses handhelds in the same way, and while the BlackBerry and the iPhone aim to do everything for everyone, they don't, and they probably won't for a long time, if ever. For instance, some users live and die on e-mail, and even the most ardent iPhone evangelists concede that those users are better off with a BlackBerry. "It's so e-mail–focused, and a bit faster with messages, that when an attorney tells me they'll just be doing e-mail, I tell them to get a BlackBerry," says Jeffrey Richardson, an attorney at Adams and Reese (where about 40 of 250 attorneys use iPhones) who also operates the iPhone J.D. blog (iphonejd.com). "But if they want to do a little bit more, especially if they want to take advantage of apps, then they might want to think about an iPhone."

Indeed, apps--those programs you can download to your iPhone, usually for $1-$10 apiece--may turn out to be Apple's most potent tool in breaking down law firm resistance. Each app lets an iPhone user perform a new task on the device, from finding local cab companies to editing Word documents. More than 65,000 apps are now available, including many designed for lawyers. "You can download statutes, the Federal Rules of Evidence and Federal Rules of Civil Procedure, Black's Law Dictionary , and programs like Documents to Go, which let you view and edit Word docs attached to e-mail," says Richardson. "You may not want to rewrite an entire document on an iPhone, but to look quickly at a memo and do some quick edits and e-mail it out, this is great stuff."

With some 1.5 billion apps downloaded since the App Store launched a year ago, Apple has been extraordinarily successful doing what so many content providers and wireless carriers have been lousy at—pushing add-on software to mobile devices. But what has some iPhone-ready law firms most excited is the prospect of apps they design themselves and integrate with their other software.

"With the 3.0 update, Apple has opened the door for us to do some cool stuff," says Andrew Jurczyk, chief information officer at Sonnenschein Nath & Rosenthal, where a couple hundred iPhones are in use. "Before, you couldn't pass information from one application to another; Apple had everything locked down. But the developer toolkit is now much more robust. We can [envision] building an app that tracks the time a lawyer spends on a client call and automatically sends that information to our accounting system."

As for security, the firms that have adopted iPhones say it's a nonissue, once you've put in a bit of work. Sonnenschein's IT department, for example, wrote its own security certificates--encrypted digital files installed on a mobile device that tells the server back home that this is a legitimate Sonnenschein device and it's okay to let it connect. These certificates don't just authenticate a device; they also manage its security, making sure that users use strong passwords. On the BlackBerry platform, there's no need to write these certificates. They're supplied by the BlackBerry Enterprise Server, or BES, running via Microsoft Exchange. "The iPhone does take more effort," Jurczyk acknowledges. "And the BlackBerry does have more from an administrative perspective, a whole back-end toolkit to micromanage the device. But the argument that the iPhone is not secure is not valid."

Security, however, isn't the only issue that's keeping some firms on the fence. From the start, the iPhone's battery life had been a key shortcoming. It still is. While some users say they are seeing somewhat better results with the 3GS, we found that we still needed to plug in the adapter each night to be guaranteed a useful life the next day. And for firms that are pushing e-mail out from their Exchange servers, it's an especially big problem. ActiveSync--the component of Exchange that routes e-mail from server to phone--"is device-and server-intense, a lot of push and pull that drains the battery," says Tony Cordeiro, the chief information officer at White & Case, which isn't using the iPhone but is keeping tabs on its evolution. "What if someone is working on a deal and they are pushing and pulling and the thing goes dead? Then you need a second device to go with your all-in-one device."

Cordeiro wants to see better message tracking features as well--an area where the BlackBerry scores big. "ActiveSync has been problematic," he says. "There's no trail, so if someone says they never got a message, it's difficult to trace where it went. With the BlackBerry you have far superior logging. You can tell whether a message was delivered, who received it, and so on."

In the end, two things are clear: The iPhone is a revolutionary device that's getting better and better, but it still has some flaws. The equation that firms need to work out--balancing the device's growing list of advantages against its dwindling list of shortcomings--may be leaning in the iPhone's favor. But it looks like it's going to take another revision, and maybe more, to push firms over the edge.




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