Live from Redmond, it's Windows and Office!

So inside the company, Windows Live has been known for sometime. There has been a lot of work that went into the announcement today, and on the whole this seems like a right step direction-wise, and really snaps into focus what MSN division and a lot of employees have known and felt for a long time. Is this a turn around of the giant tanker, of the same variety as the Internet remake of 1995? Only time will tell. But a lot of smart people are working on it, and I'm cautiously optimistic that a lot of positive things will come out of this.

Now that I've dispensed with the positive, constructive outlook of the "what" of this move, let me dive into something that's more critical, which is the "how." In particular, let's take a look at the branding of this initiatives: Office Live and Windows Live.

My guess is that it will work better for Office Live than it will be for Windows Live. Here's my reasoning: Office Live is targeted at the "Digital Workstyle" portion of the overall strategy, i.e. the enterprise, knowledge worker, etc. Office is a successful brand for the productivity market, and is probably quite extensible to what used to be called the "Back Office" suite of servers, such as SQL, Exchange, CRM, etc. I think Office Live has a reasonable chance of success as a brand. Although, for companies to trust Microsoft with a hosting service of the sort of Salesforce.com, there will be a hard sell in terms of security, reliability, confidentiality. The not-too-distant history of Hailstorm proves that this can be a hard sell, though it was also a very different climate back in 2000/2001. Doable, I think.

(BTW, who is the idiot that coined "Digital Workstyle"? Most companies don’t really see a mix of style and work. Workstyle is just dumb business speak, ala Why Business People Speak Like Idiots. Productivity, efficiency are much better themes to go on than "style" when it comes to work.)

Windows Live, though, I think is more problematic. Remember this is the Digital Lifestyle portion of the strategy, and so are targeted at the individuals, the consumers, the end users. Now, Windows is a widely recognized brand, but it's not always in the best light.

Monopoly, for one. Americans are known to be always rooting for the under dog, and Windows is Goliath if there ever was one. And the global citizen isn't so keen on the monopoly either; notice the EU and Korean investigation of the Windows franchise. It's generally perceived to be a bully rather than a friend.

Security, for another. Every one have heard about the security issues for Windows, virus infestation, and the patches galore in the last few years.

Old technology, for last. Windows is about your father's Oldsmobile. It's about the "poorly debugged set of device drivers", the file system, the tired GUI that's five years or older. It conveys a sense of the non-sexy side of technology, boring even. Nobody gets excited about it anymore. On the other hand, Google, Yahoo, and even MSN is the Pirius of today. It's about setting you free to do whatever, wherever. About reaching out to the world instead of compartmentalized at your machine. IMO leveraging Windows for the Live brand is like selling an Oldsmobile hybrid: it ain't going to sell well.

If you agree with me, then what explains the Windows rebranding of MSN? I submit to you that it's pure stubbornness and nostalgia . We are proud of Windows, and god knows it's what make all our market and financial successes possible. Thus we have a certain affinity to the name, particularly at the very highest level of the company. Their personal career and fortune, along with those of the company, all originated from Windows. Without Windows there's no Office, no MSN, no SQL server. It's Microsoft's Iwo Jimma, our Berlin Wall. Unfortunately, WWII and the cold war is over, and we are in a New World Order, and the game is different, but unless there's a dramatic jolt to Microsoft, it will be a long while before we can get pass Windows. Think about what it took for IBM to move on from the mainframe and mini computers to Linux: almost financial ruin.

I think Windows Live illustrate why this is still a fast Clipper ship, instead of a steam ship. The paradigm has shifted, and we are still trying to make it work in the old context. I hope I'm wrong about this.