I've always thought of myself as someone who understands strategy, especially when it comes to technology strategy. There's only one company that really surprises me regularly, proving that I have lots to learn. It's Apple. They always seem to be doing something completely braindead and moronic, somehow get away with it and it almost always turns out to be an extremely smart and strategic move a year or two later. I wish I could work there and be involved in coming up with this stuff. It's just amazing smartness, and if there's a single thing I respect in life (and I think there is exactly a SINGLE one) then it's smartness.
Just take a look at Microsoft. I don't think they did ANYTHING that I'd consider really strategic or smart in the last decade. It's not that they make bad products, because in general they don't. (Although they have zero idea about cool factor and usability in some of their departments) They just didn't do anything smart or unexpected that turned out to be smart in a year.
They're bleeding all over the street on a very crucial shortcoming, for example. Their whole UI architecture, which is the underpinning of almost all the user experiences in their products, is getting very old. It all originates from the DOS times, and it was pretty neat back then. But a couple of decades later, it's archaic and limiting. Just take a look at the architecture of Cocoa, or Android's UI framework or anything, really, anything that happened in the last decade. And the worst thing is that they're so heavily invested in this stuff that they can't even change easily. Silverlight is coming along nicely, but nobody's using it. Ever. MFC and Managed bullshit and all this is just another abstraction layer on top of the same old engine.
I really hope they'll get their act together. They're too big and too important to be so stupid.
On the topic of strategy... I think what most people don't realize is that it's important to have a strategy, but it's a luxury to be able to execute one. You can have the brightest idea on how you could steer a market in a certain direction or how to create a new ecosystem, but without tools to execute, you're just daydreaming. And for those of us who don't have the resources that Google or Apple commands, our best chance is to have a strategy, and hope it executes itself through coincidence. What I mean is, if you have a private jet and you want to get to a party in Rome, you get on board and go there. If you're a hobo, you hitch a hike, or take a train that is going roughly in that direction and get closer and closer to it slowly. And most of the time by the time you arrive either's everyone already drunk, or they have already ran out of booze, or most likely the party's already over. I know that we're heading in the right direction. I know that we can party like hell. I just wish we'd have the money for a ticket.
On second thought.. It's easy to always say that I could have done it better if I had an army to command. But probably the road to having an army is also paved with strategy. And probably your own strategy should be based on your capabilities. And be just as smart and surprising as Apple's, only on a smaller scale.