Microsoft Is In Worse Shape Than You Think

In 1994, I wanted to get out of the Navy to start my own publishing company. One of my enablers was Microsoft.

To get my enterprise off the ground, I needed a couple of strong desktops and some software. So I wrote letters to about a dozen companies asking for freebies. I offered only my future loyalty in return.

The only company that responded at all was Microsoft. They sent me about $3,000 worth of software and a letter of encouragement from Bill Gates.

I tell that story only so you understand that I’ve been a loyal fan of Microsoft for a long time.


A few months ago, I panned Windows 8. Hard.  Here’s my damning prediction from September 1, 2012:

Windows 8 sucks.  I am sorry I upgraded to it.  I feel bad for people who make PCs and the many programmers who imagine, design, and code desktop application for Windows. Microsoft’s utter contempt for design has put all these people’s jobs in jeopardy. This OS is so awful that I expect computer makers will give customers the option of Windows 7 to prevent a complete sales disaster at Christmas.

My post was a quick, gut reaction to new operating system based on two weeks of daily use.

As soon as I posted that blog, I started to feel bad. I felt bad for many, many great friends who work for or have worked for Microsoft. I felt bad for the hundreds of programmers and system administrators I’ve worked with across my 15 year career as a technologist.

I felt bad for two reasons. First, I knew my words would hurt them, and I don’t like to hurt people’s feelings. Second, I knew my words were true and accurate. And I would not have written them if I didn’t think they needed to be written. (Microsoft will be better off if people don’t experience the ugliness of Windows 8.)

So what’s happened since my review of the RTM version of Windows 8? First, nothing has happened to change my mind about the OS.  Next, the market seems to agree with my assessment. 


  • Usability guru Jakob Nielsen eviscerated the OS saying “Hidden features, reduced discoverability, cognitive overhead from dual environments, and reduced power from a single-window UI and low information density. Too bad.”
  • NPD Group released a report this week concluding that Windows 8 has done nothing to help the PC market.
  • From the NPD report, we learned that Windows 8 market share of new sales is only 58 percent. By comparison, Windows 7’s market share was 83 percent in its first month after launch. That’s a huge let down.
  • Worse, Microsoft’s big gamble on the Surface tablet—supposedly an alternative to the iPad—has been a disaster. Windows-based tablet sales “have been almost nonexistent, with unit sales representing less than 1% of all Windows 8 device sales to date,” according to NPD Group.
  • Last year, Business Insider’ Jay Yarrow mapped out a “nightmare scenario” for Steve Ballmer, but concluded that the scenario would not play out. Friday, he changed his mind, writing “Microsoft's nightmare scenario is actually starting to take hold.”
  • Henry Blodget took a look at the situation and concluded that talk of a big Microsoft comeback is “delusional.”  Blodget points out an amazing statistic that I didn’t know: Apple’s iPhone business alone is bigger than all of Microsoft.

Yes, Microsoft is a behemoth in the enterprise. No, CIOs won’t walk into work tomorrow and send the deltree *.* command to their servers.

But Microsoft’s principal OEM buyers were already in trouble because of the shrinking PC market. Developers are still hooked on building apps for iOS. Consumers seem to hate Windows 8. The most desired Christmas gift is anything from Apple. Young people are being raised on iOS. Companies let employees bring their own devices (BYOD) to work, sometimes paying them a monthly technology grant to do so.

That’s a long string of problems to overcome for a company now smaller than one department at Apple.

At this point, I think Microsoft’s best hope is for Bill Gates to come out of retirement. But don’t hold your breath.