Microsoft's 13 Worst Missteps of All Time

DOS 4.0, Zune, and Windows 8 are but a few of the landmarks among 25 years of failures Redmond-style

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In the halcyon days of Windows 95, 98, and 2000, anyone installing Windows had to provide a serial number. The serial numbers weren't checked against a master database, so the same serial number could be used to install multiple copies of Windows.

With the consumer version of Windows XP, Microsoft added a validation step, where a specific serial number was matched against a key constructed from serial numbers from PC components. The resulting combination is checked against a central database. Changing your motherboard or network card, or in some cases other combinations of hardware, triggered a revalidation. Fail the validation, and Windows wouldn't work -- you had to call Microsoft to beg for forgiveness.

Hardware manufacturers had a different process for activating machines before they shipped. Volume licensees were given serial numbers that worked in bulk.

Windows XP SP1 cut customers some slack: It added a three-day grace period, so you could continue to use your Windows PC for three days while trying to get it reactivated.

Then the offal hit the fan. Over the course of several years, in many confusing steps, Microsoft rolled out its Genuine Advantage program to all Windows XP and later versions.

The earliest versions of WGA included a program called WGA Notifications that runs whenever you log on and validates your Windows license. They also included an ActiveX control that validated your license every time you tried to download specific Microsoft products, including Internet Explorer 7 and Microsoft Security Essentials. You were also prohibited from using Windows Update to get security patches (although you could download Critical patches manually). WGA reached its nadir in Windows Vista, where failing the WGA check meant your machine was put into "reduced-functionality mode," where you could go onto the Web for an hour at a stretch, before Windows locks up.

Predictably, the validation servers borked; false positives came to light. Microsoft got caught shipping data from unsuspecting PC users to the Microsoft servers once a day. Windows Genuine Spyware became the nom de guerre.

Howls, lawsuits, threats, cracks, and generally furious customers eventually drove Microsoft to backtrack. Reduced-functionality mode evolved into a paper tiger, with harmless balloon notifications about ungeniune wayward ways, and an irritating tendency to turn the desktop wallpaper black.

In Windows 7, WGA became Windows Activation Technology, no doubt to avoid the venom aimed at its predecessor. The newly renamed copy protection scheme retains its toothless nature, even in Windows 8. Microsoft can learn from its mistakes.

Microsoft misstep No. 7. BrandingI don't understand why Microsoft has such a terrible time with branding.

Some of the customer-confusing moves are just silly. In 1991, Microsoft jumped Word for Windows from Version 2 to Version 6, with no intervening version numbers. Word 2.0 was part of Office 3.0, but Word 6.0 was part of Office 4.0. When Microsoft released Office 95, it increased the version numbers of all of its components to 7.0: Word 7.0, Excel 7.0 (also called Excel 95; there was no Excel 6), PowerPoint 7.0 (there were no Versions 5 or 6), and Schedule+ 7.0, which morphed into Outlook.

Some of the branding is worse than silly. Stupid changes made years ago continue to confuse Microsoft users today. Consider how many email clients Microsoft supports at this moment. I can think of seven:

I could rant about most of those branding missteps, but allow me to concentrate on the last one. Can you believe that Microsoft intentionally threw away the name "Hotmail" -- one of the most widely recognized brand names in the world, right up there with Coca-Cola and McDonald's and Toyota and, yes, Microsoft -- turning it into something absolutely nobody understands?

That's worse than crazy. It's self-destructive.

Case in point: Microsoft's attempt to create a database of user IDs and associated data, including individuals' financial information. It all started with Hotmail: sign up for a account, and Microsoft stored the information you provided.

Then your Hotmail account suddenly became a Microsoft Passport, a fancy name for a single-login authentication service that Microsoft hoped would take over the Internet: Everywhere you go, the marketing material touted, you could log on with your Hotmail account, er, Microsoft Passport.  And if you put your credit card info into Microsoft Wallet (earlier called Passport Express Purchase), buying items anywhere on the Web would only take a couple of clicks.

The privacy groups went ballistic -- like the Joker, only less civilized.

Microsoft bobbed and weaved. To its credit, Microsoft hired one of its most vocal critics, to put reasonable limits on privacy incursion. The name of the service changed -- branding and rebranding as Microsoft Passport Network, MSN Passport, .Net Passport, Windows Live ID. Now we know it as a Microsoft account, and it's baked into Windows 8. The personal financial information came and went, and the terminology/branding seems to have stabilized: If Apple can have one Apple ID or Google a single Google account, you can certainly have a single Microsoft account -- if you can figure out how to get your old Zune, ZunePass, Xbox, and Windows Phone accounts switched over to a Microsoft account.

There's that branding thing again.

Microsoft misstep No. 6. Windows LiveWhich 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 8Windows 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.

Or maybe we're all wrong and Windows 8 will breathe new life into the PC industry. In another six months, we should know for sure.

Microsoft misstep No. 4: Windows 8 brandingThere's nothing inherently wrong with Windows 8 -- it's a noble (if flawed) attempt at bringing Windows into a more mobile future. There's plenty inherently wrong with Microsoft branding. When you bring the two together, the combination's absolutely lethal.

Please. I spent a whole day trying to come up with a worse name than "Windows RT." I couldn't do it. Microsoft could call the Metro-side-of-Windows-8-plus-Office-2013-RT just about anything, and it would be better than Windows RT.

So many people right now are so confused about the differences between Windows RT and Windows 8 that we won't hear the end of it for another decade -- or longer. Customers who buy a Windows RT tablet, thinking they were getting Windows, will be sorely upset. I bet the return rate for Windows RT tablets at the retail level goes well into double digits, simply because of the naming confusion.

Then there's Metro: immersive, Modern UI, Windows Store. I don't even know what to call it any more. I can imagine telling my Aunt Mildred that she needs to get a Modern UI Calculator from the Windows Store. I mean, Microsoft itself stopped using the term "UI" nearly a decade ago: It's always UX. You can call Metro apps "Windows Store apps," but not all apps in the Windows Store run on the Metro side (for example, Office 2013 is in the Windows Store). And not all Metro apps originate in the Windows Store -- the Metro Xbox Music app, for example, isn't really a Windows Store Xbox Music app because you don't download or install it from the Windows Store.

There's another Win8 branding inanity as predictable as tomorrow's sunrise. The next version of Windows will probably be called Windows 9 -- cool. Here's what I want to know: What will the next version of Windows RT be called? Windows 9 RT? Windows RT 2.0? Windows SU?

Microsoft misstep No. 3: Missed opportunities in the cloudIn the mid-1990s, Windows senior VP Jim Allchin and Internet Platform and Tools division senior VP Brad Silverberg crossed swords many times, with Silverberg pumping for faster expansion into the cloud and Allchin more intent on building on Windows' success. Allchin won, Silverberg left, and by 1999 the die had been cast.

In the mid-2000s, Windows president Steve Sinofsky and Microsoft Chief Software Architect Ray "of course we're in a post-PC world" Ozzie also had their differences of opinion, with Ozzie pushing hard to expand quickly in the cloud, and Sinofsky more intent on building on Windows' success. Sound familiar? Sinofsky won, Ozzie left, and by 2010, Microsoft had lost its second high-level visionary cloud advocate.

In the intervening 10 years, Microsoft embraced the cloud, but did so with one foot firmly entrenched in Windows and the other in Office. Innovative cloud designs, like Mesh, have been tossed aside, while me-too cloud products like SkyDrive garnered a big budget.

Microsoft's foray into the online advertising market, with the Bing search engine, hasn't gone particularly well in spite of Microsoft's successful attempt to stack the deck in Bing's favor on new Windows computers.

Perhaps the biggest cloud shortcoming for Microsoft, at least from a consumer point of view, is its inability to build an ecosystem that comes anywhere close to the Apple, Android, or even Amazon offerings. Apple's taken an enormous lead in the consumer cloud, with Android scurrying to catch up, and Microsoft not yet in the running.

Microsoft misstep No. 2: Management musical chairsI've talked about the Microsoft management musical chairs in a series of InfoWorld Tech Watch posts, most recently "Game of thrones: The men who would be Ballmer." Suffice it to say that all of the people capable of providing a steady transition from the reign of Ballmer have left the company.

Jim Allchin. Brad Silverberg. Paul Maritz. Nathan Myhrvold. Greg Maffei. Pete Higgins. Jeff Raikes. J Allard. Robbie Bach. Bill Veghte. Ray Ozzie. Bob Muglia. Steve Sinofsky. They're all legends, in their own way, and Microsoft had many more.

We still have some luminaries. Andy Lees survived the Sinofsky purge. Paul Maritz is still around, having spent years at VMware. Bill Veghte's at HP. There are others still at Microsoft, but most lack the experience to play in that league.

The lack of senior management depth may turn out to be Microsoft's biggest misstep in the early 2010s.

Microsoft misstep No. 1: Internet Explorer 6Microsoft's greatest misstep of all time? Internet Explorer 6. Consider:

Chances are good that more Windows computers have been infected via Internet Explorer 6 than by any other vector. Flash and Adobe Reader may come close, but IE6 is up there. ActiveX, IE6's evil toady, deserves its own ring in developer hell.

In the process of deploying IE6, Microsoft ran afoul of U.S. antitrust laws. The repercussions of the DoJ action resonated throughout Microsoft's product line for more than a decade, driving all sorts of design decisions that were at least partially influenced by antitrust concerns.

Microsoft lost an enormous amount of public goodwill over IE6. It's as if, suddenly, the average Windows user started to understand that their computer was at risk because of a bad piece of Microsoft software. Web developers did, and do, hate IE6, with its fussy quirks, outright bugs, and absolute disdain for anything reeking of a standard.

Microsoft took more than five years to ship an upgrade -- most likely the biggest misstep of all.

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