The final support date for Windows XP is just 840 days away and while that might seem like a long time, you and I both know that April 8, 2014 will come all too soon for some companies who are still reluctant to make the move.

If you’re still on Windows XP and are planning to rollout Windows 7, here are 10 questions you’ll want to ask yourself while planning out your deployment:

1. Do we need to invest in test hardware, personnel and infrastructure? Notice it doesn’t say IF testing should be done. That’s a given. But can you set up a lab – either physical or virtual – where the deployment process and end configuration can be tried out? Who will do the testing? How will it be done?
2. What hardware do we need to replace? Make sure you know the minimum requirements are for Windows 7 and which of your computers will need to be upgraded or replaced. The Microsoft Assessment and Planning (MAP) Toolkit is a free tool that can help you collect detailed information on your current infrastructure for an analysis of your hardware and device compatibility and give recommendations.
3. Do we need to build and maintain a desktop image? If your organization tends to get a lot of new machines coming in or computers that get handed from one person to another and this is taking up a lot of IT cycles, you probably want to look at building a desktop image if you don’t already. A well built image can reduce your deployment time substantially and advancements in imaging technology mean that it’s no longer necessary to spend hours saving user data off an old computer, cloning the hard drive of a reference computer and then restoring the data you saved. Having only one image to maintain even if your organization uses diverse hardware is more of a reality than ever.
4. Are our corporate applications going to work? The Microsoft Application Compatibility Toolkit (ACT) is a free download that can help you evaluate and mitigate application compatibility issues. Applications that can’t be upgraded may be able to be shimmed or run in Windows XP mode.
5. How will employees’ files be moved? Knowing where employees are storing their files is critically important. How many times have you heard: “I didn’t put that file in the System32 directory – the computer did it!”. Once you know where files actually are, a plan is needed to ensure that user files and user settings are migrated. Bob won’t care if the rollout is a complete resounding success if his desktop wallpaper isn’t as he left it!
6. Will Office 2010 or IE 9 be rolled out at the same time? Often this is the perfect time to make other adjustments and upgrades to the desktop infrastructure along with Windows 7. There is all sorts of information on deploying Microsoft Office 2010 and Internet Explorer 9 that can be used in the planning. If the Microsoft Desktop Toolkit (MDT) is being used for the deployment, Office 2010 can be added to the MDT environment.
7. Is this a good time to assess and update policies and security? As in #6, deployment projects present good opportunities to revisit and revise other areas of the desktop infrastructure. What policies are in place and what can be improved? Are there group policies that we could benefit from to better manage and streamline our desktop environment? Are there security enhancements that we can take advantage of?
8. How will remote users get updated? Instead of remote employees like the sales teams shipping their notebooks in to get upgraded and incurring downtime, consider swapping out old hardware for newly configured machines or sending them a bootable USB with the Windows 7 image on it to do the upgrade themselves.
9. What’s the impact going to be to users and the helpdesk? Will there be any planned downtime and how will this be communicated to users? As with any change, there will likely be a short term increase in calls to the helpdesk. Is the helpdesk appropriately staffed and equipped to handle questions? Using tools such as the Windows Troubleshooting Platform and the Problem Steps Recorder can help resolve issues quickly and diminish ongoing helpdesk calls.
10. What’s the ongoing maintenance of the desktop infrastructure going to look like? Taking control of the desktop environment is a huge step in streamlining staff productivity, improving processes and freeing up IT time to devote to developing new ways to use technology and IT know-how to business needs. Tools like those found in the Microsoft Desktop Optimization Pack (MDOP) and practical guidance found in the Microsoft Operations Framework (MOF) can help.

I’ve included a lot of information in the above 10 questions and each one could be a separate article on it’s own. That’s why the conversation doesn’t end here.

On the next AlignIT Manager Tech Talk, Jonathan and I will be discussing how to de-risk your Windows 7 deployment with Dave Kawula, a Senior Consultant with 1E and a guy who has more knowledge of desktop deployments in his pinkie finger than most people have in their whole heads. Join us LIVE on Thursday, January 12 from 12-12:30pm ET for De-Risking Your Windows 7 Deployment.
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