I started this series by discussing how Windows 7 is starting to feel like a major event much like Windows 95 was, and I suggested that this move is likely one you'll want to take at your leisure. But, if this is a Windows 95-like launch and Microsoft gets it right this time -- and with all of the automated tools developers now have that they didn't in 1995, they would have to be incredibly stupid not to get it right this time -- it is going to be a huge wave.
Windows 7: You Won't Be Ready
There clearly will be a number of aggressive early adopter sites for Windows 7, primarily because there will be a lot of companies in a great deal of Windows XP pain by 2010. Early adopters get substantial help from Microsoft to roll the product out, and I expect the line for that help will exceed the available resources. Most won't be ready for this product for at least a year after it launches, nor will they want to deploy a pre-SP1 offering.
This probably places the likely window for Windows 7 deployment in 2011 to 2012 t for those moving aggressively to the platform, and it may be better to wait for the maintenance release which would be due around 2012 or later. Recall, Windows 98 and Windows XP were both maintenance releases and far less disruptive than Windows 95 or Windows 2000 were for most shops.
This means the ideal time to deploy Windows 7 is likely when Windows 7.1 or 7.2 is ready, and that is a long time from now if you are still living off the nearly decade old Windows 2000/XP base.
Using Vista as a Hedge Against Windows 7
Now don't for a minute think I'm suggesting yanking out all of your XP machines and going to Vista immediately. But I am suggesting you look at bringing post SP1 Vista in under new hardware and get your users on more current generation technology so you aren't forced to move to Windows 7 prematurely.
Don't get me wrong, Windows 7 could be god's gift to the desktop, but I think it would be safe to say that, at least initially, most won't be ready to move to it right away. But it will be vastly better than Windows XP and we know that frustrated users, many of them executives, can force migrations and then hold you accountable if they don't go well. And early migrations seldom go well.
If you are on Vista when Windows 7 launches you'll have a stronger argument for waiting, when, and if, you move to Windows 7 (and you may be able to hold for the minor release of this product expected a year after Windows 7 SP1) you can then move at a more leisurely pace.
Also, generally, the migration from a platform to the following platform tends to go better than a skip migration.
I have to admit it would be nice to skip an OS, but as much as we'd like to avoid change, the reality is that the desktop, in terms of technology, continues evolving rapidly. And holding software stable, while hardware continues to evolve, traditionally results in breakage.
Your options are to try to hold on XP (and there is a major effort to do just that) and face an accelerated migration when Windows 7 shows up, or to move to Vista as you cycle in new hardware and buy time until you are ready for the big step. Neither path is without risk and it is always easier to sit back, but I'm afraid for many of you, if you sit back the decision may become forced.
In any case, it would be wise to stay up to speed on Windows 7 developments, revisit testing on Vista once SP1 ships, and stay flexible with regard to your desktop OS choice.
One thing is clear; Windows 7 is likely to be big. Whether it's Windows or Linux or a new Apple toy, it is generally better to not be out in front of the pack. Remember, prospectors get the arrows and the settlers get the land. If you can deploy Vista SP1, we are almost in the settler stage for that product.