Should Microsoft Try to Be Cooler or Just Leave the Kids Alone?

Part of me wants Microsoft to make more consumer products for young people and invest more money in colorful and creative marketing campaigns. You know, be more like Apple. But another part wonders if it’s worth it for Microsoft to pursue something that it’s just not very good at.

I’m torn because Microsoft could be good at it; it could be cooler, and I think people want it to be a cooler company (that is, those that don’t loathe its very existence). But because it is a giant with its hand in just about everything technology nook and cranny, most of it for businesses, Microsoft sometimes stumbles as it tries to be all things to all people.

When trying to appeal to teens and twentysomethings, that stumble can turn into a freefall down a flight of stairs. They’re like the self-conscious 35-year-old who shows up overdressed at the party filled to the rafters with free-wheeling college kids. The music (coming from an iPod Touch naturally) stops. Everyone turns and looks at our Microsoft man. Somebody whispers: “Is that your uncle?” Poor guy doesn’t stand much of a chance.

Microsoft is often its own worst enemy when trying to snag the attention of young people. The most recent example is Softwear by Microsoft. These are ’80s retro t-shirts that say “DOS” or have a mug shot of a young Bill Gates. Huh? Is Microsoft really trying to market t-shirts with 25-year-old computer code on them to people who were sleeping in cribs in 1985?

Inexplicably, the rapper Common is involved in this. The t-shirts use his design. Microsoft and Common: NOT a collaboration I saw coming. I like Common’s music. He’s cool and talented and it’s a great idea for Microsoft to get someone like him involved in anything. But is printing the lyrics to one of his songs surrounded by MS-DOS code on a t-shirt good aesthetics or does it even make sense? It’s not even a popular song of his and it contains too many words for a t-shirt—printed in small green ’80s computer font no less. I’m no brand marketing whiz, but how does this t-shirt make me feel connected to Microsoft or want to buy its products? Isn’t that the point? What in the name of Pac Man and Alex P. Keaton is going on here?

The actual design of the t-shirts is pretty sweet if you like ’80s retro (I do), but Microsoft should have used this t-shirt opportunity to market the present and future, not try to stir up nostalgia for the early days of Windows, which young people who wear stylized t-shirts don’t even remember anyway. A better idea would have been t-shirts with a modern design plastering Windows, Windows Live, PCs, Hotmail, Internet Explorer, Zune and Xbox all over the place. Silverlight too. Maybe even Office. Vista? That would be ballsy.

The t-shirts aren’t even available (they will be Dec. 15) and Microsoft bloggers are already dropping the hammer on the whole concept. Microsoft Watch blogger Joe Wilcox goes to town in this post.

The Softwear t-shirts seem like another directionless Microsoft move, much like the short-lived Bill Gates/Jerry Seinfeld ad campaign, which by the way, was voted the No. 1 bad commercial while Apple’s “I’m a Mac, I’m a PC” ads were voted the No. 1 good commercial in Anderson Analytics’ 2008 survey of 1,000 college students.

Both the Softwear t-shirts and the Seinfeld/Gates ads are actually great ideas in my mind; they’re just poorly executed. And when you compare Microsoft’s amorphous marketing to the laser-beam brand focus of Apple’s ads, it’s hard not to see Microsoft as a rudderless boat floating around in circles.

I know that consumers are not where Microsoft gets its money, and it wouldn’t be financially sound of Microsoft to spend big money on consumer marketing, but the company does show enough potential from time to time that I can’t quite give up on them being cool.

For cool points, Xbox is a long-time staple in the gaming console market and The Zune is by many accounts an excellent MP3 player with a music subscription plan that is much more cost-effective than iTunes. I recently played around with the Zune for the first time and I love the large screen, the touch pad is easy to use and the sound is close to perfect.

It could be an iPod killer. Now if only Microsoft would market it more, and more importantly, market it well.

Have you given up on Microsoft being cool?