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Microsoft's 13 worst missteps of all time

Woody Leonhard | Jan. 15, 2013
DOS 4.0, Zune, and Windows 8 are but a few of the landmarks among 25 years of failures Redmond-style

There's that branding thing again.

Microsoft misstep No. 6. Windows Live

Which brings me to Live. In November 2005, Microsoft announced Windows Live and Office Live, kicking off one of the most confusing branding exercises in the history of international commerce. Decades from now, B-schools will be using Windows Live as an example of branding gone insane.

At first, Windows Live drew on MSN-branded software -- MSN Messenger became Windows Live Messenger, for example; MSN Hotmail became Windows Live Hotmail -- and added an online security scanner, the OneCare antivirus package, and a method for sharing your Internet Explorer favorites across multiple machines. From the beginning, Windows Live was an odd hodgepodge of websites, Web-based applications, and PC-based applications, with a browser add-on tossed in for good measure.

Then it grew. And grew. In August 2006, Microsoft unveiled to testers a website called Windows Live Essentials. Microsoft pulled down the site shortly after, replacing it with a similar site called Windows Live Installer (yes, it was a website) that downloaded Windows Live Messenger, Mail, and Writer. In October 2008, Microsoft announced that Windows Live Installer (the website) would become Windows Live Essentials (the website and software package), and Windows 7 would not ship with Windows Mail, Photo Gallery, or Movie Maker. Instead, Windows 7 would give customers links and encouragement to download and run those applications and several others. At the time, it wasn't clear if Microsoft was yanking those applications out of Windows in order to get Win7 as a whole shipped on time or if the programs were removed over antitrust concerns -- possibly both.

Over the course of many years, Windows Live included about 50 different products, few of which talked to each other, with absolutely no discernible common objective. Basically, whenever the powers that be decided to publish a new program -- online, local, website, whatever -- they branded it "Live" and kicked it out the chute.

Earlier this year, Microsoft started dropping the "Live" moniker, setting off yet another round of branding confusion. Windows Live Essentials became Windows Essentials, and Windows Live SkyDrive became just plain SkyDrive. But Windows Live Mail, Messenger, and Writer still have "Live" in their names.

Microsoft misstep No. 5: Windows 8

Windows 8 is turning out to be a misstep of unprecedented proportions. The fundamental problem, as many of us at InfoWorld have described repeatedly, is the Jekyll-and-Hyde nature of the Frankenstein interface. Clearly, with Windows sales heading deeply down and the entire PC hardware industry going with it, Microsoft had to do something. Relegating the old-fashioned Windows desktop to a tile on a new mobile phone app hasn't done the trick.

 

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