Motorola’s Q phone weighs 4.1 ounces, fits easily in a shirt pocket, and is just 11.5 millimeters thick. It looks like a cross between Motorola’s successful Razr flip phone and Palm’s blockbuster Treo smart phone, and it’s tempting to compare the Q to the Treo 700p and Research in Motion’s BlackBerry 7290; all three devices are designed to let you check your e-mail, make telephone calls, save contacts in an address book, update your calendar, and browse the Web.

But Motorola isn’t positioning the Q as a Treo killer. Mike Booth, a senior director at Motorola who oversaw the product’s management, told me that it isn’t just another smart phone for business executives. Its relatively low price, thinness, stereo speakers, and 1.3-megapixel camera make it ideal for people who don’t have high-power jobs but would like to be more organized–people like artists, college students, and stay-at-home parents.

Most cell phones now have calendars and address books built in, but they also have interfaces that must have been designed by engineers who majored in torture–“Death by a thousand clicks!” In contrast, the Q’s Qwerty keyboard, jog dial, and five-way cursor control make its advanced features relatively straightforward to use–especially text messaging and the built-in Web browser.

The Q started as a project to make a stylish smart phone: think of an ultrathin Razr with a Qwerty keyboard. Motorola wanted something that execu­tives could use for both voice and data during the week and then take home for weekends with their fami­lies. But after trials that involved hundreds of ­people inside Motorola–many of whom were not technologists but receptionists, drivers, factory workers, and so on–the company realized that it had created something else altogether: an intelligent device that, says Booth, could be used by the “technologically illiterate.”

For just this reason, explains Booth, ­Motorola decided that the Q should run the Windows Mobile 5 operating system. After all, what could possibly be more familiar than Windows?

I disagree with that reasoning. In my tests I found Windows Mobile 5 on the Q to be slow, buggy, and cumbersome. Worst of all, the phone’s software generally fails to take into account the user’s current activities and goals–what you might think of as the “context.” Instead, Windows Mobile forces the user to understand what’s going on inside the phone–how data and functionality are divided among the phone’s various applications, how menus are structured, and even where files are stored.

In other words, the Q succeeds in bringing the experience of Windows to the mobile phone. This is its failing.

Hardware par Excellence

Despite its diminutive size and light weight, the Q is loaded with a combination of sweet components that isn’t found in any other phone today. There’s a jog wheel for fast scrolling through e-mail messages and Web pages–I wish my Treo had one! The stereo speakers are loud and have great fidelity. The camera, with a maxi­mum resolution of 1,280 by 1,024 pixels, takes remarkably good pictures when the light is bright. It also has a bright white LED for taking photographs in low light. Once you’ve taken a photo, you can send it off via Bluetooth or infrared, e-mail it to somebody as an attachment, attach it to an entry in your address book, or save it on a flash memory card. When you’re taking a picture, the jog wheel controls the camera’s zoom.

The hardware is awesome–and underexploited by the Windows Mobile software. For example, I found that you can also use the LED illuminator as a flashlight even when you aren’t taking a photo. This is so useful that you can now download a third-party program to turn on the illuminator at the press of a button.

I’ve owned more than a dozen PDAs and smart phones since I bought my first Palm back in the mid-1990s, and every one of them–including all my Treos–has required a special dock or proprie­tary cable for synching and charging. Not so with the Q: it has a socket for a standard “mini USB” cable that charges and syncs. And the Q’s headphone jack is on top–so you can use headphones with the Q in your pocket.

I have only two complaints about the Q’s hardware: the screen and the phone’s internal charger. The Q’s screen is strictly for inside use. Indoors, the color is saturated, and the text is easy to read. But go into the sunlight and it’s nearly impossible. Other phones, like my Sharp GX15, have a more expensive screen that becomes reflective in direct sunlight, which improves legibility. Worse, the Q’s screen is not a touch screen: Motorola’s designers told me they didn’t want the extra thickness and didn’t want a cell phone that required a stylus. Alas, while a touch screen might have required an extra millimeter or two, it would have made the phone much easier to use. And besides, a good touch screen doesn’t require a stylus: I do most of the clicking on my Treo with my finger.

The second design flaw is that the phone won’t charge from a computer USB port if the battery is drained; from a cold start, you must use the charger that Motorola provides.

Icky Software

Despite all the jazzy hardware, it’s frustrating, not fun, to use the Q. This is a phone that should fit into the life of the user and the context of use, rather than forcing the user to understand its internal organization. Yet that kind of understanding is precisely what the Q demands. Geeks might gravitate to the Q for the challenge of figuring out how it works, but most average users will be exasperated.

Just consider the steps you need to go through to take an MP3 from your desktop computer and play it through the Q’s stereo sound system:

First you need to set up your desktop by installing Microsoft’s ActiveSync. This should be a one-click maneuver, but it’s complicated because ActiveSync also wants you to configure calendar and e-mail synchronization settings. If you use Microsoft Outlook, those settings are automatically imported. But if you use Microsoft’s free Outlook Express, ActiveSync recommends that you switch to Outlook! Once ActiveSync is installed, you need to reboot.

When ActiveSync is installed, a new “Mobile Device” icon will appear in your desktop’s “My Computer” window. I loaded my MP3s onto the Q by dragging the files onto this icon. Each MP3 needs to be resampled at 160 kilobits per second, a process that can be excruciatingly slow. While the songs are being resampled, Windows Explorer is frozen.

Once the MP3 is on the phone, you still can’t play it, because Microsoft’s Media Player doesn’t know it’s there. After all, Media Player is a separate application. So you need to follow these steps. First, run Media Player from the phone’s “Start” menu. Then click on the Q’s “Menu” button. Select “Library,” click “Menu” again, and select “Update Library.” This makes Media Player search through all the files on the Q, looking for new music. The phone tells you how many songs it found; you click “Done” to acknowledge its report, after which Media Player displays the “Library” screen again. But this screen doesn’t actually show you your music. Instead, it allows you to select “My Music,” “My Videos,” “My TV,” or “My Playlists.” Choose “My Music,” and you have a choice of viewing “All Music” or music grouped by “Artist,” “Album,” or “Genre.” Select “All Music,” and you will finally see the MP3 files that you transferred from your desktop. Select a song using the arrows, and then press the left button below the screen, which is now labeled “Play.”

This whole process is very logical. But I think that most people would rather just select their favorite songs, click a button that says “Put on My Q,” and have all these steps happen automatically in the background. To play music, most people would like to click a button and see a list of their songs; somebody who would rather see the list sorted by artist or album could click on another button to display some kind of menu.

Using the Q is so complicated because of Windows Mobile. All these convolutions result from Microsoft’s belief that the user should have lots of options and be made constantly aware of what is happening inside his or her computer.

It’s like driving a car with a manual transmission: control at the expense of convenience. Copy a new file onto the Q and you frequently need to click “Menu/Refresh” in the Windows File Manager to make the file appear. Try to send a message, and you’ll need to select whether you want to use SMS (the Short Message Service for sending text messages between cell phones), Outlook e-mail, mail from other e-mail providers, or MMS (for sending multimedia messages between cell phones). But a single program with multiple drill-down menus doesn’t reflect the way people use these different services. My Treo has one program for SMS, which works great for chat with a lot of quick back-and-forths, and a completely different application for e-mail. Each application is geared to the context in which a user is likely to use it.

It’s possible to build software that tries to understand the user’s context and act accordingly. Apple’s iTunes, for instance, copies music to your iPod in the background and lets you set up playlists even when your iPod is not connected. The software doesn’t have many options, but it’s an elegant, ­context-­aware interface.

A final way in which the Q duplicates the Windows experience is with cryptic error messages and frequent crashes. I tried to listen to my local public-radio station’s Windows Media stream and got the message “Alert: An unknown error 0X80070057 has occurred.” When I was evaluating the Q, I got many messages telling me that a program called gwes.exe had crashed. “Please tell Microsoft about this problem,” the phone requested.

Mike Booth was right: my 10-plus years of experience with Microsoft Windows on the desktop gave me the insight I needed to diagnose and repair the recurring problem with gwes.exe. I rebooted.

Simson Garfinkel researches computer forensics at the Harvard Center for Research on Computation and Society.

Motorola Q
$199.99, with a two-year contract for cellular-telephone service from Verizon Wireless