How to Fix Microsoft: Get The Swagger Back
Recently I have started listening too Windows Weekly, hosted by Leo LePorte and Paul Thurrott. Right before Microsoft’s TechEd Paul posed a question on his Supersite for Windows on how to ‘Fix Microsoft’. He does not want product features, but more of a higher level answer. So today I thought I would take a stab.
The Problem
Before I offer (my opinion) how to fix Microsoft, I should explain what is wrong with Microsoft as I see it. Its an old company. I know, it’s only 35 but in today’s fast-paced Internet-driven world, it’s old.
Think about it like this: Microsoft has graduated college, gotten married, and now has a mortgage, a few kids and the minivan. When not working, any spare time is spent driving the kids to soccer, Little League, dance and birthday parties. At home it watches Two Kings, iCarly and various cartoons with the kids. Meanwhile, the priorities are paying the mortgage, the family healthcare, and building a retirement package. There is no energy left to really innovate.
I caught a small part of this week’s TechCrunch’s Disrupt, in particular an interview with a venture capitalist or angel investor. He was asked what it takes to create a successful company today. To summarize his response, he said you have to be young, creative and confident to succeed. Microsoft is not young anymore and it shows.
I feel fortunate to have come of age during the 80’s and 90’s. Things were happening in the technology space like never before. IBM was the big boring company with several other outliers like HP, Texas Instruments, etc. I cut my teeth on a TR-S 80 and my first computer was a Timex.
When I was in high school Microsoft really started to make its move from just providing software for IBM to being in the driver’s seat by defining the personal computer operating system with DOS and of course early versions of Windows.
In its early twenties, it got a big break by consumerizing the computer industry with Windows. This is when my friends first started to use computers for homework, like I had done in high school. No, I am not forgetting Apple; they were building a consumer base too.
Windows 3.1 started making waves around my campus in late ‘92 or ‘93. (It’s hard for me to remember exactly.) It was so cool! I made an NC State diamond logo for my wallpaper and amazed my friends, LOL. It empowered me to do some really cool stuff. Then I got Office, started writing, and creating charts and tables for my chemistry experiments.
As grad school approached so did Windows 95. I somehow found a way to get Beta version in late ‘94. It was cooler, and better than anything previously available. People were excited. I could play a Weezer video on my computer and of course DOOM.
On campus I was exposed to UNIX and the first versions of Linux. They never really appealed to me, because they the user experience was not intuitive. During my senior year, I actually wrote a book on how to be productive on our UNIX workstations, at the request of my classmates. Microsoft got the user experience problem and made things easy enough for the masses.
They also saw the need to make computers obtainable by the masses. Apple, while having a great approach on the UI too, wanted high margins. They still do. It took Apple another decade to figure out how to reach the masses at their large margins.
For the first 20 years Microsoft was gutsy and confident. They often succeeded and usually in a big way. They had their failures, like an early attempt at what would become Access. Over time those attempts at innovating have reduced the ratio of successes to failures. This has a psychological effect that is hard to overcome. It wears on you.
Today we see a Microsoft that still tries to innovate, but is scared. It’s scared to risk the retirement fund and the stability of the current good thing. It’s wife is reasonably satisfied, and the kids are growing up. In other words, Microsoft’s innovative energy is paralyzed by the secure comfortable family life; it’s scared to take real risks.
Sure Microsoft creates some really great stuff, just look at Kinect. I believe Windows Phone 7 and Zune are prime examples of great products lacking the consumer adoption they deserve. And don’t forget the whole tablet thing. I thought the Zune was just awesome from the day I heard about it. Mine has been an extra appendage for nearly 5 years now. I have shown and told friends about it the entire time. They all agree it’s a much better system than the iPod/iTunes world. Yet Microsoft never marketed it well. No one outside my Microsoft ecosystem has ever heard of it. Apple was gutsy enough with the iPod to make it a fad/fashion statement. They are doing the same with the iPhone/iPad today.
Maybe that period 4-6 years ago for Microsoft was just a bad time. Longhorn was a big letdown, and like Paul Thurrott articulates probably the pinnacle event that changed things in Microsoft. They lost their confidence and swagger. As a former athlete I know confidence is very important part of success. You spend more time practicing techniques and building game plans than you do executing them. But the practice makes you confident in yourself. Winning games does too. Microsoft lost a lot of games earlier this decade.
The Swagger
Earlier this year my church did a 3 week series about swagger. It covered how people let things get you down, and on the contrary, let victories go to your head. Both of these extremes actually bring you down. But somewhere in the middle is a balance of confidence that helps you overcome defeats and humility in victory so you have a productive symmetry.

The defeats over the past decade have sent Microsoft too far into the fearful area. But again much of the 90s saw them expressing a bit too much hubris. Somewhere in the middle is a humble confidence where you can find great success.
So far Windows Phone has been less than amazing at the consumer level. Unfortunate for the Zune, no one knows about outside our tight inner circle of Microsoft fanboys. Evidently next week Microsoft will formally announce their modern tablet strategy. I firmly believe they have not lost the game yet in either of these markets. I firmly believe, despite the mass adoption of iOS and Droids (650k a day combined), they can solve some problems that exist with both those platforms. The enterprise story in particular.
First they need to start getting some wins, some small ones. And, as with all things Microsoft, that has to start with us, the developers. We need to create reliable, intuitive and exciting to use software. This is one of the reasons I am getting more and more into user experience. I am also a firm believer in the power HTML5 offers. Microsoft is seeing this and steering the ship the right direction, slowly, but they are.
In the mobile marketplace, I really like my Windows Phone. The UX person in me loves the Metro UI. I think it’s the far superior UI for mobile platforms. Sadly as I survey WP7 apps, I do not see the Metro UI implemented well or consistently. That’s on us as developers.
They rushed Windows Phone 7 for sure. Lots of features were shelved for later updates just to get the phone in the marketplace. I can live with that and be an early adopter. Mango is going to help them get closer to the competition. They still have some work to do, but I am seeing signs of innovation that will drive the competition. More importantly they need to be driving the mobile experience to a new level. Every company has to have their Unique Selling Positions to give them advantages. Windows Phone is succeeding in the UI right now, it just has to get some mass consumer adoption.
Here are my suggestions to promote the Windows Phone. Promote Microsoft Office on the phone. They need to push this feature in their commercials, just like the Netflix applications and other fun things. Don’t focus on satisfying small groups with minimal impact features, like Copy and Paste. Average users could really care less about this compared to having fun on their phone or being productive at work.
The mobile marketplace is just one part of what Microsoft has to offer. There are many other Microsoft products that are just not consumer sexy. Most are great products that are not marketed well. The consumer space gets all the attention from the press. But the press is only so intelligent. Consumer products like Windows Phone, Xbox, etc. may not drive large revenues but do drive the image of a company like Microsoft.
Conclusion
I think Microsoft has gone through a rough time in its life – a maturing process that beat it up. After losing some battles, it’s in the process of collecting itself and getting things back together. My hope is over the next 4-5 years we are going to see a more confident Microsoft. One that regains confidence to take chances and the swagger to fail and keep pushing.
It could completely fail. It could silently choose to become a large company with steady revenues and ride off in the sunset, much like IBM did. I seriously doubt it. Microsoft has a natural pride and drive to win. I know Microsoft; they want to win everything they try. I feed off that energy. I sense they feed off a similar spirit in us, the development community.
I will continue to write things like I did a few days ago criticizing the lack of touch in IE mobile. I have some more things in the pipeline. I will write about them, because I want a great platform to build awesome stuff, right now. Its selfish, I know. But I am smart enough to know, if we don’t ask for something, they won’t help us make it happen.
I get frustrated with things in the Microsoft world. But I am not counting them out. You should not either, not yet. Despite being a large corporation, it is still an organic entity with a life that parallels our own experiences. It’s time for Microsoft to enter the next phase of life confidently.
Edited By Beth Love