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From The Trenches – Upgrading to Windows 10

By Edward Jorczyk posted 10-03-2016 11:31


By Ed Jorczyk, DIrector of Information Technology, Bowman and Brooke LLP
and Josh Lazar, Director of Information Technology, Community Legal Services of Mid-Florida

The release of the Windows Anniversary Update further fine tunes Windows 10, adding some new features and addressing some pain points.  Let’s take a look at the stages of deploying Windows 10 and give you some things to consider.

One of the first things to determine is your upgrade path.  Moving to Windows 10 and Office 2016 is probably not a big move if you’re on Windows 7 and Office 2010/2013.   In our experience, the main challenge is not with the OS upgrade along, but a change to a later version of Office that accompanies the upgrade. The focus on your upgrade path should be to focus on the OS and Office alone.  For example, you probably do not want to switch document management systems or any other major software at the same time as you roll out Windows 10 and/or upgraded Office.

Identifying a core IT team is essential to a successful upgrade.  In a small firm, it may be a team of one and that one person may be you.  A medium to large firm may have a core team with representatives from training, help desk, applications, and infrastructure.  This is the team that will be making the key decisions on how to deploy and configure Windows 10.  Let’s focus on the medium to large firm as we move through the upgrade path.

At first, your desktop deployment team will work to get a standard image developed with your applications using tools such as System Center or Microsoft Deployment Toolkit.  They’ll need to assess the compatibility of your devices and applications with Windows 10.   The new Windows Upgrade Analytics service can help you with this process by automating the inventory and providing you with a workflow.

Once you have a working image, your core team will want to review the numerous group policy options that are available for managing your systems.   Review the Microsoft Security Compliance Manager includes pre-configured GPO’s to jump start this process of securing Windows.  You should also review the other group policy settings that are available for Windows, Office, and other applications.

Feeling good about your image?  Time to move to your beta testers.  The typical setup for beta testing includes the core IT team and others within the help desk staff that frequently test new software.  With Hyper-V built into Windows 10 Enterprise, testers can even run their legacy desktop in a virtual machine.  Since IT staff can make poor testers, a pilot group outside of IT is recommended after passing the beta test. 

Now it’s time to involve your attorneys and staff.  Identify some key individuals in an office where you have good IT support.   It’s best to include staff that are tech savvy and those who are not so technologically inclined.  They are typically the staff that will give you the best feedback.  This is a time for them to identify issues with your configuration of Windows and your applications.  And it’s also a time for you to test your training approaches and materials.

Is it still looking good?  Expand your pilot group and involve more users and more offices.  Include locations with less on-site IT support so that your help desk staff gets experience supporting real users using the new platform.

Finally, it’s time to go for gold!  Target no more than one office per week.   Have additional IT support on-site for the first couple of days to deal with immediate issues. 

What about training?  Many people may already be using Windows 10 at home.   Even if they’re not, the jump from Windows 7 to Windows 10 isn’t too much of a difference.   You may want to provide a variety of training approaches and let your users choose the approach which is best for them.  Many of the tech savvy ones will be able to be productive immediately.   A one or two-page quick reference guide may be all that they need.    Some more be comforted by a webinar highlighting the changes.   Others may need more one on one assistance.   Whatever you do keep the training basic.  There’s no need to show them everything that’s new in Windows 10 on day one.  The new start menu, the search bar, and a dip into the task view might be all that is necessary for successful first training session.