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Note to Microsoft: "Cool" can't be faked (nor should you try)

Microsoft wants to be cool, but what's cooler than cash?

Microsoft, for all its billions of dollars of profits each quarter, is not very cool. The company has become the cardigan-wearing frumpy uncle that dozes in an overstuffed leather armchair. He has nothing to prove. He's made it. probes Microsoft's latest attempt at coolness - a Softswear-created clothing campaign in partnership with rapper Common - and finds it wanting.

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?

Should Microsoft even bother? Let's face it: Microsoft is the IBM of our century. It's not Google, and never will be. Its DNA is wired differently.

This, by the way, is not a bad thing.

We actually discussed this at our Alfresco management meeting yesterday. I work with an executive team and engineering team that has a history of writing some of the world's best, most widely used enterprise code (Documentum, Business Objects, etc.). It's not a group that is likely to come up with the next Twitter (Fritter? Maybe it could be limited to only 80 characters and would have a clock to analyze how much time you're wasting ;-).

But it is the group that is writing web content management and Enterprise Content Management systems that power mission-critical applications for the world's biggest, most successful companies. Why change?

In Microsoft's case, it's true that by focusing on stodgy, boring enterprise software it risks making billions and billions of dollars but not having its 20-something CEO on the cover of Wired as "the coolest thing since the last 20-year old we featured in last month's edition," but should it care?

Microsoft's opportunity is exciting: it is lowering the bar, in terms of both cost and complexity, to a huge population of developers and enterprise buyers. Even with open source nipping at its heels, Microsoft is driving a lot of unnecessary expense out of enterprise software, enabling enterprises to save money while boosting productivity.

Wouldn't Microsoft rather do this than create the latest widget for the Web?