Janelle at Microsoft had an interesting post asking if Microsoft was cool or not. She argues that since Microsoft launched Halo 3 and is rumored to be talking to Facebook that there should be some coolness points awarded. My personal take? Microsoft has cool people, that do cool things. But the two examples she gives are both things that Microsoft did not internally develop. Halo 3 is a Bungie product, and they're specifically talking about buying Facebook, not creating it. This tells me that Microsoft knows cool when they see it, but are they able to produce coolness themselves? Sure somethings they have are cool, Tafiti, CodeToLive is cool, alot of the stuff out of Microsoft Research is too. But is SharePoint cool? Is BizTalk? Do they need to be? Should they be? Coolness doesn't sell to CIOs, cool does play well with the people actually having to work with the products though. These are the people that will ask for or recommend things to the CIO. So by necessity I think Microsoft has to be Cool on the one side and Suit on the other. What do you think? Does Microsoft need to be cooler? Or is it hip to be square?