Planning a Pilot Windows 8 Deployment

Brien Posey, Freelance Writer and Former CIO | 11/13/2012 | 8 comments

Brien Posey
A pilot deployment is critical to the overall success of your organization's transition to Windows 8.

The pilot deployment involves more than just deploying Windows 8 to some of your organization's production desktops. It is a full on dress rehearsal for the organization-wide migration. Your pilot deployment needs to be carefully planned. Here are some of the most important aspects of pilot deployment testing.

Pilot deployment testing is something that you should not rush into. Prior to beginning a pilot deployment, you should have already completed all of your preliminary testing for Windows 8. At a minimum this means verifying that all of your applications will work with the new operating system and making sure that all of your desktops (or virtual desktops) have the hardware necessary for running Windows 8 efficiently. The pilot deployment phase is not the time to be ironing out upgrade glitches that occur due to hardware or software incompatibilities. Those glitches should have already been addressed prior to beginning the pilot deployment.

Of course, anyone who has worked in IT for any length of time knows that sometimes the unexpected happens even after thorough preparation. That being the case, you need to have an exit strategy in place for your pilot deployment. In theory, the operating systems that you deploy through your pilot deployment program should be permanent. However, because you are doing a test on production desktops, you will need a way of rolling back the deployment in the event that something goes wrong. After all, pilot deployments typically impact about 10 percent of the total organization, which means that if a problem did occur it would affect a large number of people.

By far the biggest mistake that IT pros tend to make when planning a pilot deployment is thinking of the pilot deployment as a test to verify the functionality of the new operating system in a production environment. Although this is certainly a part of the pilot deployment process, operating system testing should have already occurred long before the pilot deployment ever took place.

Pilot deployments are less about testing the compatibility and functionality of the new operating system than they are about verifying that the support infrastructure is working properly.

One way of testing your support infrastructure is to perform the pilot deployment in the same way that you will be eventually performing the organization wide transition. Typically, this will mean building deployment images and application packages and using a deployment mechanism such as the Windows Deployment Service to perform the actual installation. Doing so will help test your ability to create a functional image, that can be used to set up the Windows 8 desktops. The deployment process will also verify that your answer file is working properly, as are any customizations that you made within the deployment image.

Keep in mind however, that deploying a new operating system is only the first step in the operating system's life cycle. That being the case, you must use the pilot deployment as a way of verifying that your organization is prepared to handle the day-to-day maintenance of the new operating system.

One of the things that you should be testing is patch management. Microsoft has already announced the first security patch for Windows 8, and it is important to verify that your patch management solution is able to download and deploy Windows 8 patches.

Another aspect of the management process that needs to be tested is desktop activation. Most larger organizations use volume licensing and have server set up to manage the activation process. You must verify that these servers are equipped to handle Windows 8 activations.

Finally, you must ensure that your desktop management software works properly with Windows 8. Ideally, this is something that should have been tested prior to the pilot deployment. Even so, things sometimes work a little bit differently in a production environment than in a lab environment, so it is worth making sure that your desktop management software fully supports Windows 8.

The actual functionality tests that need to be performed will vary from one organization to the next. Generally speaking however, you should make sure that your desktop management software is able to perform hardware and software inventories of Windows 8 desktops, and that those inventories are accurate. Some organizations have reported the inability of their inventory software to recognize Metro apps. Likewise, you should also make sure that your helpdesk is able to offer remote assistance to users who are running Windows 8, and that your antivirus software works properly with the new operating system.

There is much more to a pilot deployment program than simply making sure that the new operating system works with the existing desktop apps. The pilot deployment should serve as a proof of concept illustrating your ability to effectively deploy and maintain the Windows 8 operating system.

View Comments: Newest First | Oldest First | Threaded View
batye   Planning a Pilot Windows 8 Deployment   12/3/2012 11:44:08 AM
Re: exit strategy
very good question, as proper planing is a must...
SaneIT   Planning a Pilot Windows 8 Deployment   11/19/2012 8:33:01 AM
Re: exit strategy
I'm looking at a different type of pilot with Win 8 that will have a very easy back out plan.  I'm putting together a plan to hand out a few tablets to key individuals so I can get some feedback concerning how training is going to have to be done and how intrusive the new UI will be when it comes to their work flow.  If the tablets go over well then I'll migrate just those few desktops as a second phase.  This will give them some time to become comfortable with the UI before migrating their desktops and hopefully make the transition easier, but even if everything falls apart it won't be difficult to roll back the desktops.
sohaibmasood   Planning a Pilot Windows 8 Deployment   11/14/2012 2:23:45 PM
Re: pre-piloting
Sara, usually there are test cases defined for all kinds of scenarios. Then weightage is assigned to the these test cases based on their criticality. During the testing phase they are checked thoroughly on metrics identified earlier. If they fulfill the requirements the tests are said to hold true if not they fail and a exit strategy needs to be defined (if it is not there). 
David Wagner   Planning a Pilot Windows 8 Deployment   11/14/2012 12:56:17 PM
Re: exit strategy
It is a good question, Sara. Hopefully the answer is "get ready to deploy to the rest of the team." But obviousy things go wrong, and when they do that's when the plan is really important.
Sara Peters   Planning a Pilot Windows 8 Deployment   11/14/2012 11:19:20 AM
Re: pre-piloting
@stotheco  My guess is that you just need a reeeeally good, thorough, test/dev environment that can replicate nearly every configuration you've got operating in your organization. But I'm sure Brien knows better than I!
stotheco   Planning a Pilot Windows 8 Deployment   11/14/2012 6:46:49 AM
Re: pre-piloting
Good Q, Sara, and I am wondering the same thing. What alternatives are there to pilot deployment and how effective are they, when pitted against the former?
Sara Peters   Planning a Pilot Windows 8 Deployment   11/13/2012 5:18:03 PM
exit strategy
Brien you mention that we should have a "pilot deployment exit strategy." Any advice on what that strategy should look like?
Sara Peters   Planning a Pilot Windows 8 Deployment   11/13/2012 5:16:26 PM
pre-piloting
Great point, Brien. "By far the biggest mistake that IT pros tend to make when planning a pilot deployment is thinking of the pilot deployment as a test to verify the functionality of the new operating system in a production environment...Pilot deployments are less about testing the compatibility and functionality of the new operating system than they are about verifying that the support infrastructure is working properly." I guess my question then is, what's the best way to test the compatability and functionality of the OS without doing a pilot deployment?


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