Understanding the convoluted Windows path: How did it get so screwed up?

Windows XP is now officially obsolete. The OS is a malware magnet, yet Microsoft dropped support for it this month. A lot of folks are, or shortly will be, screwed.

Last week I spoke with a number of folks bringing out the latest Windows Update. 

I can attest to the fact they get it, so things will likely get better shortly. At the core of this belief are two big changes. Microsoft is focusing on the user once more and internal research no longer reports to the product managers. Taken together, this approach should avoid the kinds of difficulties that Windows Vista, 7 and 8 have had replacing Windows XP. Still, I thought it would be interesting to go back and review how we got into this mess in the first place.  

Let’s take a painful trip down memory lane and why we may be through the worst phase. Oh, and why it is likely a bad idea to adopt the strategy of companies that you beat the crap out of. Bad being an understatement.


Windows was positioned as a viable alternative to Mac OS because Apple wouldn’t license it. It was widely panned at the time as an unnecessary update to the then wildly popular command line interface. Seriously it was. It was initially just a shell that sat on top of DOS that kind of made it look like the MacOS. It is interesting to note that the most popular platform at the time wasn’t Apple’s or Microsoft’s, but rather, Commodore’s as it focused primarily on users while the others focused mostly on business.  

IBM and Microsoft jointly created OS/2 and then got into a tiff. They separated and Microsoft focused more on users, while IBM concetrated on the enterprise with OS/2. At the time, IBM was vastly bigger and more powerful than Microsoft. Commodore had pivoted to focus on business and by the early 90s was effectively gone. Microsoft doubled down on the user and with Windows 95, had an Apple like launch with lines around buildings and massive sales. Employees carried Windows 95 into their companies over the objections of their IT departments and Apple dropped into life support while OS/2 died.  

Microsoft then resurrected OS/2, calling it Windows NT and focused it on workstations and business. It wasn’t very popular. Windows reached 95% market share, yet Microsoft effectively killed off Windows 9x, replacing it with Windows NT and calling it Windows XP.   

Now let me stop here and point out how unusual this was. Had Microsoft been beaten by OS/2 it certainly would have made sense to copy the operating system and making this move like Samsung and Google did with iOS. But Microsoft stomped OS/2, then abandoned its winning platform for the losing one.  

They shifted most of their user based efforts to Zune, Media Servers, Portable Media Centers (all of which failed), and the Xbox which, thanks to Sony really screwing up with the PS3, eventually lead the market (Sony recently took that market back with the PS4).  

Apple, which had stopped falling at about 5% market share in the early part of last decade, brought out the iOS targeting users after Microsoft had shifted Windows to OS/2 and an enterprise focus from users and almost did to Microsoft what Microsoft had done to IBM. Meaning, Microsoft stumbled with Windows Vista, Windows 7, Windows Phone and finally Windows 8 – because the company had lost focus on its users. During this same period Google kicked Apple’s butt by repeating what Microsoft had done to Apple – creating an emulation of the iOS and giving it to Apple partner Samsung. (Apple is understandably upset). 

Netting this Out

So Microsoft kicks Apple’s butt, taking Apple’s concept broad market, kicking IBM’s butt by focusing on the user not business. Apple then kicks Microsoft’s butt using the same strategy Microsoft used on IBM and Google kicks Apple’s butt using the same strategy that Microsoft used on Apple. The reason we are in the Windows XP mess? Because Microsoft somehow became a blend of ‘90s Apple and IBM while Apple and Google channeled ‘90s Microsoft.  

Wrapping Up:  Things Getting Better and Lessons Learned

Part of the problem was market research, because it reported to product management and told product management what they wanted to know. In short, they told product management that Vista and Windows 8’s user interface were a really good ideas based on customer feedback and, in hindsight, they were full of crap particularly on that last part. The changes in reporting structure will prevent this happening again (or should).  

Satya Nadella has indicated he will be taking Microsoft back to basics, with the Windows team focused back on users for the next update and version of the OS. Thus far, the changes to Windows Phone have been capturing new users who are tiring of the iPhone’s limitations and Samsung’s tendency to deliver products rich in features that don’t work well.  

Now the very deep lesson that we should take away from this is that when you beat the crap out of someone in a battle it is unwise to switch strategies with them. Just saying…