There is no doubt that Windows 7 has gotten much better feedback than Windows Vista. As such, many organizations are likely to be tempted to skip Vista, and move directly from XP to Windows 7. However, skipping a version of Windows comes with quite a few risks. I've just read a white paper from Gartner that includes some interesting arguments on why skipping Vista might not be such a good idea. The document was published in July but continues to be just as, if not more, relevant today. Because it is now clearer what improvements Windows 7 will bring, it is a good time for those who plan to skip Vista to re-evaluate that plan.
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I have summarized the main risks outlined in Gartner's paper.
Windows 7’s release date unsure ^
It is uncertain when Windows 7 RTM will be available. Most likely, it will be released in the first half of 2010. However, Microsoft might once again postpone the release of a new Windows version. Therefore, it is not really possible to plan when you will finally get rid of Windows XP.
Windows 7 stability uncertain ^
Even if Windows 7 is released at the beginning of 2010, it will take time to tell whether it is stable. Most organizations will deploy Windows 7 only by 2012. Can you wait this long?
ISVs will drop support for Windows XP ^
Independent software vendors (ISVs) will begin to drop support for Windows XP in early 2010, and, by 2012, most ISVs won't support XP anymore. As for OEM support for Windows XP, in 2009 only 80% of OEMs will fully support XP, and by 2010 this number will possibly have dropped to only 50 or 60%.
Pressure to deploy Windows 7 too early ^
If you skip Vista, you will be forced to deploy Windows 7 sooner or later, because ISVs and OEMs will not support XP anymore. Unfortunately, many ISVs will not yet support Windows 7. You will then run into the same problems as those organizations who adopted Windows Vista too early.
Budget problems ^
Deploying Windows 7 might require upgrading some of your applications, which will increase costs. The necessary budget for new hardware and software licenses might not be available at the time when migration to Windows 7 is unavoidable.
Additional Windows license costs ^
As soon as Windows 7 is available, you probably will have to buy Vista licenses to be able to install XP on new PCs. When you then upgrade to Windows 7 you will have to buy additional Windows 7 licenses. If, instead of XP, you deploy Vista on new PCs, you will be able to buy Windows 7 licenses, which will include downgrade rights to Vista, but probably not to XP.
Vista’s availability may end too early ^
If Vista licenses can't be bought anymore before you are ready to deploy Windows 7 it may be impossible to legally install XP on new PCs.
From my perspective, this all sounds very reasonable. The main argument of Vista detractors is that Windows XP works just fine. The problem is that this might change soon. You might feel that is unlikely that there will be software or hardware that won't work with XP anytime soon. However, "working with" and "being supported by" are two different things. What if you have a major problem with an important application, but your software vendor tells you that they can't help because you are running it on Windows XP? Skipping a Windows version has always caused problems. I doubt that it will be any different this time.
However, I also agree with Gartner that small organizations able to perform a forklift migration (replace all PCs at once) could save costs. For them, it will be a matter of not missing the right point in time.
I'd like to add two more arguments. First of all, I am convinced that it makes sense to migrate to Vista, simply because it is a great operating system. Windows 7 has a couple of interesting new features, but it is basically an evolutionary release. The important changes, especially the new security model, the improved user interface, and the new imaging capabilities, are all Vista developments.
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Secondly, if your organization skips Vista, you will be hopelessly left behind as an IT pro. This will not be good for you or for your organization. Once you do deploy Windows 7, you will have to learn all of the Vista stuff, plus the Windows 7 enhancements, in a very short time. This will mean stress and a higher risk of error. And, if you do skip Vista, and end up changing employers before 2012, you’d better make sure that you only apply to organizations who also didn't like Vista.