10 Mistakes Microsoft Made Over the Past Decade

By Don Reisinger  |  Posted 2009-12-30

10 Mistakes Microsoft Made Over the Past Decade

As the end of the decade nears, quite a few things have changed. Ten years ago, Bing, Chrome, Facebook and Twitter didn't exist. Windows 7 didn't exist. Not even the iPhone, the iPod Touch or the netbook were around. It was an exciting decade. But one thing that has remained relatively constant over that period is Microsoft's position in the marketplace.

The software giant that entered the 2000s is still a software giant. But over the past decade, its grip on the industry has slipped somewhat. It's no longer the invincible leader that some users expected it to be going into the 2010s. Today, Microsoft is less powerful than it once was.

That's mainly due to the mistakes the company has made over the past 10 years. Unfortunately, Microsoft believed that it could coast, easily dominating any market that it competed in. The company also failed to see the future, forcing it to play "catch up." Worst of all, Windows Vista severely affected brand loyalty. Suffice it to say that it has been a tough 10 years for Microsoft.

Let's take a look at the mistakes Microsoft has made to cause those problems.

1. Corporate lethargy

Microsoft walked into the new millennium on top of the tech world. The company had enjoyed unbridled success with Windows. Internet Explorer reigned supreme. It was a great time for the company. But over the course of the past 10 years, it quickly became clear that Microsoft believed that it could perform just as well without much worry of the competition or regulators. In fact, Microsoft engaged in the same strategies. In the meantime, the competition was innovating. It quickly put Microsoft back on its heels. But the damage was done. Microsoft believed the 2000s would be just like the 1990s. How wrong it was.

2. Windows Vista

Arguably one of Microsoft's biggest blunders, Windows Vista was everything a Windows operating system shouldn't have been. It was overrun with compatibility issues. Security was a major concern. And worst of all, companies thought better of deploying it in their operations. It was no small problem. With Windows XP, Microsoft was solidifying its presence as the dominant force in the operating-system market. But Windows Vista made vendors, consumers, and the enterprise think twice about the software giant. It has yet to repair the relationships with those stakeholders.

3. Follow the leader

When Apple released the iPod, Microsoft released the Zune. Once Google dominated the market with Search, Microsoft released Live Search and, more recently, Bing. As Google cornered the online-advertising market, Microsoft shot back with its own advertising platform. And that's just the tip of a very big iceberg. Microsoft did very little innovating over the past decade. For the most part, the competition did special things, while Redmond came up with a less-successful alternative. It can't make those same mistakes going forward.

4. Windows Mobile

Windows Mobile is another source of regret for Microsoft. The platform that once appealed quite well to the enterprise is now an afterthought. Both RIM's BlackBerry and the iPhone have made Windows Mobile devices obsolete. Worst of all, Microsoft's arch nemesis, Google, developed the Android mobile platform, which also stands above Microsoft's platform.

Microsoft Fighting Battles on Multiple Fronts


5. Web-based OS

As the top software maker in the OS space, just about anyone would expect Microsoft to be first to the online-OS market, right? Think again. Google beat Microsoft to the Web. And in the process, it firmly cemented itself as a major competitor going forward. Microsoft had the opportunity to lead the way to the next decade. Instead, it's forced to follow Google. It can still turn things around in the 2010s, but it better hurry up.

6. Google's online dominance

The Web is Google's domain. But with a little more foresight, it could have been Microsoft's. Over the past decade, Google has consistently innovated. The company realized what people really wanted out of Search. They knew what online services users were asking for. Google even understood how to turn Web advertising into a multi-billion dollar business. Microsoft didn't. And now, the company is trying desperately to catch up. If Microsoft started sooner in the decade, it wouldn't be in this position today.

7. Regulator scuffles

Microsoft shouldn't have fought government regulators nearly as much as it did over the past 10 years. The company spent a large portion of its time battling it out with regulators, all the while making it a bigger target for those same governing bodies going forward. And in the end, the government won several of those battles. Microsoft's tangles with regulators turned out to be more trouble than they were worth.

8. Internet Explorer

When Microsoft entered the past decade, the company's Internet Explorer easily ruled all others. Today, it still does, but to a much lesser extent. Firefox, Chrome, Safari, and Opera are viable alternatives that have attracted customer attention through neat ideas that Internet Explorer was slow to adopt. Granted, Microsoft's browser is still the market leader. But as it continues to lose market share with each passing year, it might only be a matter of time before Internet Explorer loses its standing in the market.

9. Security missteps

Windows security has been the subject of much debate over the past decade. Some have said that it has improved. Others have said that it has only gotten worse. In either case, one thing is certain: Windows security continues to be a thorn in Microsoft's side. There are more malicious hackers than ever. There are more threats to data security than ever. It's a bad time for OS security. And so far, Microsoft has done little to turn the tide.

10. The battle against open source

For the past 10 years, Microsoft has engaged in a battle with the open-source community that has only further divided the two camps. It should be noted that in recent months, Microsoft has made strides to reach out to the open-source community, but for now, that group is still skeptical of the software giant's intentions. By turning its back on open source for so long, Microsoft has found itself on an island as the market, led by Google, moves to open source and others, led by Microsoft, attempt to keep software closed. 

Once again, Microsoft was on the wrong side of history.

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