Never afraid to speak his mind, Allard started pushing buttons way back in 1994, when, as an eager 25-year-old programmer only three years on Microsoft's payroll, he penned a sea-changing memo titled "Windows: The Next Killer Application on the Internet," which found its way to Gates. The note, now part of Microsoft lore, helped awaken Gates to the potential and threat of the Web. "I'm a pain-in-the-ass change agent," Allard says.

That's exactly what Microsoft needs if it hopes to again set the tech agenda. Windows and Office will deliver more revenues in coming years than the exports of many small nations. But Web spitfires such as Google Inc. and Salesforce.com have the wind at their backs. And while Microsoft continues to recruit top talent, it also continues to see key leaders move on: executives such as Vic Gundotra, a top evangelist in its developer division, who will soon join Google, and Brian Valentine, the longtime leader of the Windows server business, who now works for Amazon.com Inc.

Nowhere are Microsoft's missteps more apparent than in digital music. When that business first emerged five years ago, the company saw it through Windows-colored glasses. Using the same model that worked in PCs, Microsoft produced software to play music on computers and handheld devices, slapping the Windows brand on it and leaving the hardware design to partners. Microsoft figured Apple was making the same mistake it made with the iPod as it had made with its Macintosh PCs: By creating both the proprietary hardware and software, it would lock out partners and limit growth.

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But it turns out the silky experience of hardware married inextricably with software was crucial in coaxing non-techies into the world of digital music and downloading. Microsoft's market share pales in comparison with Apple's because its software never worked smoothly with devices that came from partners such as Creative Labs and with services from outfits like MTV. Apple seized 85% of the song download business and to date has sold 67 million devices and 1.5 billion songs.

When Allard's team hatched Zune, they unabashedly cribbed from Apple's playbook. Microsoft all but abandoned its music partners, built its own device, and offered its own music-selling service. Moreover, the player and service, which work exclusively with one another, operate far more smoothly than any previous iPod challenger.

Allard recognizes, though, that he can't beat Apple by merely mimicking its best features. So he wants to change the rules of the game. That's why he led the effort to include wireless fidelity, or Wi-Fi, inside Zune. Zunesters can use it to beam songs to friends' devices. Microsoft cut deals with record studios, persuading them to let consumers share music in a tolerable way; Zune includes technology that limits beamed songs to three plays or three days, whichever comes first. Labels bought into the idea of promotion. "My customer becomes your street team," Allard says.

Microsoft is betting that Zune will follow the path of Xbox: Like the game machine, Zune arrives as a flawed first version that screams for an update. And like a much criticized networking feature on Xbox that eventually gave it an edge when online gaming took off, Zune's Wi-Fi technology hints at a broader vision.

Sitting in the open, communal meeting space at the center of Zune headquarters -- a refurbished dance studio a few miles from the main Microsoft campus -- Allard wonders why every pundit is so focused on the device rather than the listening experience. He envisions a time (not soon, mind you) when all of your music will be "in the cloud" -- tech-speak for Net-connected servers that dish up content wherever you happen to be, beamed to any device. Hop on a plane, plug headphones into the armrest and poof!--there's your music. Set your hotel alarm clock to wake you to your favorite song. Zune may be a swell device, but for Allard it's a means to a much larger end.

The giant of Redmond is starting to take an Allard-like fresh look at many of its older product lines, as well. Webification can be seen seeping into all corners of Redmond, Wash. headquarters. Its leading proponent is Ozzie, who developed Lotus Notes in the 1980s, then joined Microsoft in 2005 when it acquired his Groove Networks. Ozzie quickly emerged as heir to Gates's role as technology sage. Under the year-old "Live" strategy, Microsoft is blending services it launches on the Web with programs consumers run on their PCs. That way, Netizens get a better experience using Web services when they harness Windows and the processing power of PCs. Take Windows Live Mail, a small software program that lets users view various e-mail accounts -- even Google's Gmail -- in the same window. Because it runs on a PC desktop, it's easy to include zippy features such as automatically completing an e-mail address after you type in a few keystrokes. Microsoft will give away services such as e-mail, limited Web hosting, and perhaps one day that portable jukebox in the sky Allard dreams of, making money from advertising and subscriptions.

Challenging Google on the Web and Apple in music are stretches for a company that critics say lacks a culture of innovation. But while nearly all the profits are from the old products, the growth opportunities are in the businesses Allard and Ozzie are igniting. Xbox, for example, should ring up $4.6 billion in sales in the fiscal year that ends next June, says Goldman Sachs & Co. analyst Rick Sherlund. That number should climb 67%, to $7.6 billion, in fiscal 2009. He estimates that Zune sales will climb from $250 million to $575 million over the same period. By that time he expects the Home & Entertainment unit, which includes Xbox and Zune, to kick in $1.2 billion in operating profits.

Lately, some outsiders who work with Microsoft detect signs that the culture is slowly shifting as well. "They're definitely in the middle of a strategy re-look," says Hewlett-Packard Co. chief strategy and technical officer Shane V. Robison, who chats with Microsoft brass. "It will be a fairly orderly evolution, but there's a lot of new discussion that I'm seeing."

There's hardly anything old school about Allard. On a drizzly fall night in the Seattle suburb of Issaquah, he sets out with some Microsoft mountain biking buddies for a ride through a pitch-black forest. Guided only by lights mounted to their helmets and handlebars, the group bumps over tree roots, splashes through puddles, and powers over trails, some no more than two feet wide. Allard hustles his bike up yet another hill, then stops to catch his breath and check his heart-rate monitor. It's racing high, at 197 beats per minute. A minute later he's back in the saddle, looking for the next hill to climb.

CONTINUED : A need for speed

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