I would not like to be Steve Ballmer or Bill Gates right now. (Well, they are both billionaires, but still … )

Microsoft just simply cannot seem to execute lately. Release dates on everything are slipping, re-organizations of major divisions are coming every couple of months, the bad news is piling up, and they can’t even buy good press anymore.

Daniel Lyon’s recent article in Forbes is a case in point. He absolutely savages Microsoft. Not that he’s trying to be negative about the company or that he’s looking for bad news to report … it’s just that the facts are so bloody grim.

Let’s see … what’s going wrong?

1. Vista slipped (again!)
2. Ballmer and Co. did not reveal the slip to journalists at a press event just 2 days before the slip announcement came out. He must have known at that point that it would slip, but kept hyping the coming technology with never a hint of a problem. This does not help build your credibility with the chattering classes who write articles and file stories.
3. The new stuff in Vista and the Office 2007 is not (yet) plug & play for non-techies.
   

   The new programs are phenomenally complex, with scores of buttons and pull-down menus and myriad connections among various applications. A Microsoft VP zipped through a demo, moving information from Outlook to Powerpoint to Groove to some kind of social networking program that lets you see how your colleagues and your colleagues’ colleagues rate various Web sites.

   Well, what do you expect when the new features are primarily about relationships between applications. Anyone in development knows that when you build X, things are simple. When you build X and Y, you have not doubled your complexity, you’ve tripled it - at least if X and Y have to be able to play together. Well, Microsoft is integrating dozens of applications - the complexities (and therefore the difficulties) must be staggering.

4. The new features Microsoft is coming out with are inventive (great!) solutions for invented (uh oh) problems … using your a) cell phone to b) call your computer to c) access your email and d) have it read aloud to you is so laughably, stupidly complex and over-innovated and cumbersome a process that you wonder how on earth it got out of an new product ideas meeting. Must have been one of those “no-idea-is-bad” positive thinking sessions. They’re great, but at some point you have to apply the bullshit filter - you need a brutally honest Steve Jobs-ish person who will tell you you’re smoking something.
5. Microsoft is not connecting with tech buyers and tech journalists anymore. Can you imagine people just ignoring them and talking out loud as Steve Ballmer or Bill Gates addresses the room 5-6 years ago? Another way of putting it: would Microsoft have created such a useless “media event” 5-6 years ago with nothing really amazing, startling, new, or different to say or show?
6. Free alternatives to everything Microsoft are getting better and better every day.

I almost feel sorry for Microsoft. How can they be in such a rut, screwing up enormously month after month, year after year?

One thing to keep in mind, however. $50 billion in the bank buys you a lot of second chances. Maybe even a decade’s worth.

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BTW, Lyon’s article is an example of good things that are happening in “real” journalism. It’s a much more real, personal, and authentic article than your typical journalist would ever write - even in an opinion piece. I think blogs are having an impact on the way reporters write their stories, and I think it’s a great direction to be moving in.