Microsoft’s Successes and Failures

When I read Kelly Sheridan’s article, “Microsoft at 40: 5 Successes, 5 Failures”, what struck me was how selective and shallow it was. Here are the “successes” she lists:

  • MS-DOS
  • Windows 95
  • Microsoft Office
  • Windows XP
  • Microsoft 10

and here are the “failures”

  • The mobile market
  • Microsoft Windows Vista
  • Bob
  • Microsoft Zune
  • Windows 8

Rather than critique each of those picks let me propose what I’d consider Microsoft’s greatest successes and failures of the last 40 years. Successes first.

Convincing people that buggy software was normal and acceptable

For the last three decades at least Microsoft has had a tremendous ability to convince people that software that was released prematurely should just be accepted. Burroughs was driven out of business by software that was no worse than some versions of MS-DOS or Microsoft Windows. IMO this is Microsoft’s primary gift and I really don’t understand how they do it.

Releasing new versions until they succeed

A related genius of Microsoft is its ability to just keep producing new versions of software until a product actually takes root, a process that describes practically every product that Microsoft has ever succeeded with. DOS had some versions that were total flops. The first actually usable version of Windows was 3.1. Before Microsoft Word and Microsoft Excel there were Multi-Tool Word and Multiplan. The list goes on.

I think it was Winston Churchill who said that success consists in failing repeatedly without losing heart. If any company embodies that, it must be Microsoft.

The ability to change course

Microsoft has engaged in an enormous number of major course corrections over the years: deciding to be an operating systems company rather than an applications and development tools company, embracing networking, embracing the Internet, and now embracing mobile computing. Frequently these course corrections have been undertaken with all the appearances of panic but somehow the company has managed to weather the storm. This ability of Microsoft’s is truly amazing.


One of the reasons Microsoft has been able to use the strategy outlined above is that it has bundled its products together. Microsoft Basic was bundled with DOS as was MS-Works. Internet Explorer was bundled with Microsoft Windows 95 (ultimately). Windows has a long list of programs bundled with it that we have come to expect but are actually add-on products that aren’t part of an operating system.

Convincing people they were technology leaders

Microsoft is not now and never has been a technology leader. Its foundation product was a not particularly good Basic interpreter. It didn’t develop DOS—somebody else did that. The Microsoft products that were developed by other companies include DOS, Works, Internet Explorer, and SQL Server, just to name a few. Other products, e.g. Windows, Zune, were “me, too” products. I believe that Word incorporated the codebase of an earlier Xerox word processing product but I don’t think I could ever prove that. It is known that several versions of Windows incorporated public domain networking software into the operating system kernel.

Microsoft operating systems have never been technology leaders. Microsoft didn’t invent the integrated applications suite but it capitalized the heck out of the idea.

Now I’ll list some failures.

Settling for the middle

Microsoft concentrated for so many years on the middle of the computer marketplace it lost the high ends and low ends, turning its products into niche products.

Losing the operating system wars

For decades Microsoft’s objective was to be the dominant operating system company. Today most computers use something other than a Microsoft operating system while Windows continues to dominate the desktop. Desktop (and desktop-replacement) sales have been flat for almost a decade. That marketplace isn’t dead but it isn’t a growth segment, either. Although the next failure in this list illustrates an attempt to change that, I don’t believe it will be successful.


For decades the preferred Microsoft user interface was based on something developed by IBM called the CUA/SAA architecture (Common User Access/System Application Architecture). That’s the familiar menu bar, files menu, etc. user interface so many people have learned (that they have learned it makes it “intuitive”). Windows 8 incorporated something called the Metro development architecture (or language). This is yet another example of Microsoft’s pushing something that’s flopped in the past (they’ve been promoting aspects of Metro for 20 years). I don’t think they’ll succeed this time.

I would be remiss in any discussion of Microsoft’s failures without mentioning the company’s early hostility to networking and the Internet. The latter resulted in the panicked release of a service pack for Windows 95 that included Internet Explorer and its bundling of IE into all successive versions of Windows both as an application and (I believe) at a deeper level. Microsoft turned those two early failures into successes in remarkably nimble turnarounds. Note that every “success” except the premature inclusion of Windows 10 in Ms. Sheridan’s list is 14 or more years old. We’ll see if Microsoft is still “the comeback kid”.


There are a couple of things I wanted to work into that post but neglected to that I’ll mentioned here. The first is one of Microsoft’s major successes: Wintel. For twenty-five years Microsoft and Intel were able to strategize their developments to mutual benefit. Not only that but major releases of Microsoft operating systems goosed sales for the entire computer industry. That relationship among Microsoft, Intel, and the computer industry as a whole seems to have broken down. I don’t know why.

Finally, there’s a phrase used to describe much of what Ms. Sheridan characterizes as Microsoft’s “failures”: “the Microsoft curse”. Every other major release of Windows is a flop. I think that epitomizes something more basic about the company which I’d speculate is that there’s a conflict between what Microsoft needs to do to keep its stock value up and what it is able to achieve realistically in its development cycle. In essence I think its schedule for issuing major releases is injuring the Microsoft brand.

5 comments… add one
  • ... Link

    Isn’t a lot lof their success based on luck? Lucky that the UNIX guys turned their backs on IBM, lucky that IBM considered them next, lucky that they knew where to buy an operating system on short order and that the guy sold it to them cheap? Basically they won the lottery with all those improbable bits.

    Oh, and lucky that the guys that ran Apple in the early days didn’t know what they were doing & were too arrogant to learn in time, lucky that Xerox didn’t know what to do with their own r&d, etc.

    M$ looks luckier than most to me. That’s not to say they haven’t worked hard, but many people had to ake mistakes to allow it to become the behemoth it is.

  • Ellipsis:

    My recollection of what happened is that IBM approached Digital Research, the developers of CP/M, first. Legend has it that the president of Digital Research was out flying his plane when IBM came to call and the rest, as they say, is history.

    The way I heard it is that the Microsoft-Unix relationship is a little different. Back in the day everybody who ran Unix purchased a source license. In those days the way you learned what Unix did was by reading the source code. I’ve got a copy sitting around here somewhere.

    Microsoft owned such a source license and hired a team of outside programmers to port Unix to the Intel 8086. They called the port Xenix.

    Microsoft did one of their major course corrections, decided Xenix was not in the company’s interests, and the team licensed Xenix from Microsoft and opened up shop as the Santa Cruz Operation. That company sold Xenix and then Unix ported to Intel for the next 15 years or so.

  • mike shupp Link

    Kind of an incomplete story. Let’s consider this “package” of MS products: MS Flight Simulator, Age of Empires, DirectX, X-Box. There have been a whole lot of games sold that riffed on Flight Simulator. And AoE sparked the Real Time Strategy genre, which is almost an industry in itself. DirectX has set rising standards for Windows-based games for many years. And the X-Box has had ups and downs, but has basically been a successful product. MS ought to get a plus for its impact on games.

    Secondly, Windows 2000 was basically a huge success, for successfully straddling the business-server market (i.e., the NT series) and the home-small office world of Win 9X users. Without Win2K, there’d likely never have been Win XP.

    Thirdly, MS’s server series, from NT 3.0 up to Windows Server 2014 has basically been successful. I don’t know that’s been as profitable as Redmond folks would like, and it’s not done much to reduce the influence of Linux and BSD Unix in the internet relay business, but MS would continue to be a major player in the telecommunications world even if completely dropped out of games and consumer operating systems. Can Apple say that?

    Another one-time product: SLATE. MS started the website and kept it going till it turned profitable, and the sold out. Arguably a whole lot of websites have coped Slate, and a whole lot of writers have earned their spurs working for the site.

    For failures … MS’s Bing search tool hasn’t really impressed me this past year — or the four or five years before in which I’ve used it either. (To be fair, I grumble at Google’s over-commercialism as well.)

    MS’s not been much of a power in virtual environments — the sort of place populated by VMware and Virtual Box and Qemu and so on. (They’ve got Virtual PC in several forms, and “hypervisors” in Win 8, MS doesn’t really push them on users.) This is short sighted from my vantage — what’s running in those hundreds of thousands of PCs in server farms but millions of copies of Windows-based PCs. But maybe MS’s attorneys told them to leave some business lines underdeveloped, so MS had competitors to point to.

    Embedded devices — from home security systems to factory machinery to office equipment. MS’s pretty much stayed out of this line of work as well.

    MS’s Home Server versions of Windows seem to have been a commercial failure. I’m unsurprised in retrospect, and if I’d thought about it beforehand I might have predicted it as well. But I wasn’t even aware the product line existed until today — which seems to make the point.

    MS Vista was a marketing failure, I’d say, rather than an actual bad product (I keep it on one partition on this machine and use it regularly). I think MS, having watched users leap without trepidation from one version of DOS to another to Win 3.1 to Win 95 to Win 98 and on to Win XP, took the adaptability of its users for granted. But what actually mattered is that, thanks to the growth in the market, most Windows users at the time had never used any OS other than Win XP — and the changed user interface in Vista was more than they would tolerate. True to form, MS made pretty much the same error with Win 8.

    About graphical UI’s in general, I’m ambivalent. I think it was a key in getting the general public to accept computers, not just at the office but for home and travel usage. That’s kind of good. But that’s also put computers in the hands of too many people who shouldn’t be trusted with high-tech toys or car keys or bright shiny sharp objects in general.

    I also sort of think if we had it to do all over again, we’d built an internet much more resistant to spammers and phishers and internet trolls and hackers and advertisers. More like CompuServe than the WWW, in other words. But we didn’t and much of the credit or blame goes to MS attempts to market computers and internet usage to people who lack any understanding of the technology. The internet SUCKS!!!! and it weren’t for Bill Gates and his rotten company … the internet’d likely suck some other way, which we will never know.

    Coming things. Near term, massive distributed processing networks look almost inevitable (“the cloud”). I don’t know if MS will do well or poorly here, and I don’t get a feeling that MS has it figured out either. They can’t ignore that environment, since Linux and BSD are sure to be important in it. But Google and Amazon are already established as purveyors of cloud services, so it’s not clear exactly what MS’s role ought to be.

    Looking further out… “the Internet of Things” is also coming along. This is going to be Very Very Big and MS would be insane to ignore it — but MS’s failure to do much with embedded devices suggests that this will not be a natural fit.

  • ... Link

    I thought of Wintel not long after my first comment. Glad you brought that up!

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