Recently I wrote about ten things Microsoft doesn’t get enough credit for. Today I want to point out ten opportunities that they missed, things I was there for. I’m avoiding anything that is not public knowledge, of course.
I’m not suggesting they should have jumped on all of these; it might not have been an economically sound decision to do so. However, I think it’s instructive, when folks examine that giant of a company, to think about why even a good company can’t see — or do — everything.
- Cloud-based Office apps such as Google Docs. As I noted in a post last year, Microsoft invented this in early 1999. I was part of that, but we couldn’t figure out any way that the Office team would be interested or see it as other than a distraction. In retrospect, I still don’t, and it’s an area they can still take the lead in if they really decide the time has come… but still, Microsoft thought of it first.
- BizTalk Server a decade ago was the best product no one had heard of. It was the Rosetta Stone for disparate data systems. Microsoft could have gotten into a whole lot of data centers translating between, say, IBM and Oracle, which would have positioned them for other sales. BizTalk was actually a pretty cool and descriptive name, but it didn’t fit with any of the other naming conventions. (On the other hand, BizTalk Orchestration — a/k/a workflow — wasn’t quite as succinct.) Eventually, those other products got sufficiently better to obviate the need for a separate product such as BizTalk, but there was a big window for Microsoft to improve their penetration into big data centers.
- Flash. I don’t know why the leaders of the Windows team didn’t see Flash as a threat ten years ago.
- The iPod. Microsoft had all the pieces in place a year before the iPod came out, but couldn’t figure out whether it wanted to sell hardware or try to get vendors to improve the quality and usability of their MP3 products. That said, I never heard even a whisper of something like the iTunes store, which was a big key to Apple’s success.
- The iPad. People I respect at Microsoft keep telling me that no one wants a phone large enough to also do computer-type work on. As I say, I respect them, many of whom are in the Mobile business, but I respectfully disagree with them. (So does Steve Jobs, apparently.) Context is all. I believe the desire for a single connected device outweighs the size issue. Look at netbooks. If you’re already carrying a laptop, why carry a phone too? Microsoft had the core idea a dozen years ago and a VP assigned to drive it (see the note on Dick Brass below).
- Firefox – a/k/a continued progress with Internet Explorer. Now this one gets very confused in the practical world by the pressure from the US Department of Justice and the European Union, but Microsoft pretty much put aside advancement of Internet Explorer once they had the majority market share — something they certainly didn’t do with Office or Project or Windows, for example. They had a great team working on IE4 and IE5 and then let it get away from them. I’m not sure this was a bad decision, by the way, since IE wasn’t bringing in revenue or advancing other corporate objectives at that point. Still, when Steve Ballmer chants “Developers, Developers, Developers,” a lot of those developers were turned off by Microsoft letting IE slide.
- Windows Mobile. Was it a consumer O/S? No. Was it a competitor to BlackBerry? No, at least not for many versions. It was never clear to me what it was supposed to be, but it missed both of those core markets. And early versions simply weren’t up to snuff as a phone. Also, they never promoted an Apps Store — except internally, on a site many employees loved. That site, by the way, was named better than many external products: WMStuff (Windows Mobile was always WM internally).
- The sense of mission. Google made big waves with Don’t Be Evil. Microsoft had a similar sense of mission, especially back when Bill Gates was CEO. It’s to Bill’s credit that he never used PR from his foundation’s work to directly bolster Microsoft. The company felt in the 90s like we were on a mission to make the world a better place through technology, and somehow we never communicated that. I also think this sense of mission has diminished this century, as I noted in a previous post.
- The IE “Wonderful World” ad. This was, I believe, the second-best industry ad (after Apple’s “1984“) until the I’m-a-Mac/I’m-a-PC ads — and amazingly I cannot locate a single copy of it on line. It ran, as I recall, in late 1994 or early 1995. Microsoft advertising had a chance to take a terrific new direction… but slowly reverted back to the old way. Of course, I can’t argue that Microsoft hasn’t been successful with the old way, despite the inroads Apple has made in a few areas. Still, more of these ads might have changed public perception of Microsoft significantly and for the better. And with better ads, maybe sleeker packaging would have followed.
- People. Microsoft has allowed some amazing people to get away because it couldn’t figure out how to use them effectively or give them appropriate challenges. Of course, Microsoft isn’t alone in this; many companies have the same problem. But for a company that believed people were its most important asset, those losses represent missed opportunities.
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Finally, I have to note Dick Brass’s much-talked-about piece in the NYTimes last week [free registration required].
First, this post and the two preceding posts about Microsoft were largely written before I read Dick’s OpEd; that said, I do think his observations are accurate at least in respect to the areas I was most aware of. I recommend you read the article itself rather than the various “takes” on it that have been floating about the Internet; it’s reasoned and specific, unlike most of what’s been said about it.
Second, my impression of Dick is that he’s very thoughtful and easy to work with; if he hit organizational barriers, it isn’t because he blundered into them with a bad attitude. I had a number of interesting conversations with him over the years, including one that I’ve written about in the past, where he showed me a wooden mockup of “the future of reading.” See my tenth bullet above; Dick Brass was certainly one of those folks.
Finally, what really matters will be Microsoft’s response to Dick’s challenge to be a better organization. Microsoft, like most companies, tends to get a bit defensive and insular when prodded from the outside, such as their awkward response to the iLoo, a supposed Internet-equipped portable toilet. Whatever face they show to the world here, it may or may not parallel the discussion now assuredly going on furiously within the Microsoft ranks. I hope Microsoft will respond positively internally, figuring out how their teams can be more supportive of each other. There are so many really good people there with so many good ideas, some of which — though we don’t know yet which ones — will change the industry and change the worlde.

Without reaching back too far into ancient history, there are others that have always confused me.
How about just consistent branding MSN Search -> Live Search -> Bing ?? Automap -> Streets and Trips -> Mappoint ??
Confusing packaging and feature matrices. Here’s a quiz, which versions of Windows 7 let you install IIS? Which version allow remote desktop access? How many consumers have the energy to actually figure this out? How is this list different than the packages of Vista or XP that included those features? Anyone who is not an employee or a VAR has no clue what is in which package.
One of my favorite technologies from Microsoft was the Windows Media music subscription model (and the whole Playsforsure ecosystem it brought forth to compete with iTunes). Years ago I subscribed to Yahoo! Music. I was thrilled. (I still think rental is a great model, but I realize I’m the oddball on this). I went to find a compatible MP3 player on the playsforsure site. The matrix of players and services that was presented was too confusing. Different services supported different player version. Some players required detailed firmware upgrades to work with different services, some playsforsure sites just would not work with playsforsure hardware. I muddled through and was still happy, but the simplicity of the iTunes ecosystem is quite a contrast.
Microsoft used to play a long strategic game. I don’t think they always have that patience now. I’ll go back to playsforsure as an example (but your biztalk example is likely a good one as well). To compete with the iTunes ecosystem Microsoft had a strategic alternative. They had partners. They had content. They had variety and competition. Because that ecosystem wasn’t catching on (for various reasons) they went forward with Zune and locked out their former partners from the new ecosystem. So, now I subscribe to Rhapsody and I am breathlessly waiting for the Rhapsody app for my Android phone.
Here’s a good one. InfoPath 1.0 deserves to be in a category by itself. Let’s see… The world at that time had adopted Html as the default UI for many data entry tasks. Infopath 1.0 comes out with a proprietary model that requires client licenses when everyone already has a free web browser on their desktop. Why couldn’t InfoPath generate ASP forms (or anything server side that wouldn’t require client software).
One more before I go. Attack the current big competitor instead of the next big winner. Go after Lotus Notes, but ignore Netscape. Go after Yahoo, but don’t notice Google. Go after Real Player Video, but miss Flash video. Go after Flash, but don’t notice Html 5. Silverlight is an amazing technology, but part of me thinks that both silverlight and flash as a category have seen their peek.
Thanks for letting me get that off my chest.
ML
Michael, I’m a music-rental guy too; I want to listen to a huge variety of songs each once in a while, rather than a set playlist repeatedly. And although I perhaps wasn’t explicit, I think this entire list goes to not necessarily “play[ing]a long strategic game” anymore.