Planning Your Organization’s Windows 10 Upgrade

Eric Riz

by Eric Riz on 7/21/2015

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Article Details

Date Revised:

Applies to:
business strategy, Windows 10

Windows 10 upgrade requires cross-department planning

Upgrading from one technology version to the next is a delicate process that can take a significant amount of time and effort to plan properly. By definition, organizations will upgrade to another software version because of the perceived benefits and enhancements contained in the new edition. While this is fundamentally true, there are many considerations that must be taken into account before clicking that button and upgrading.

When Microsoft announced that they would release the Windows 10 desktop product to the public on July 29, 2015, excitement began to build immediately. As the first release since Windows 8 on August 1, 2012, Microsoft has spent a significant amount of time and effort on the product, aligning it to their mobile-first, cloud-first vision, and incorporating feedback from previous product versions.

While some companies will be on the cutting edge of the upgrade, others will choose to wait until the bitter end, meaning wait until Microsoft announces when they will end support for the product. In some cases, companies will opt to stay the course regardless of the support options, such as when Microsoft ended support for Windows XP on April 8, 2014. To this day, I'm aware of many companies who have intentionally chosen to stay the course and still use XP. From their perspective, Windows is just the operating system behind the specific enterprise system they are using. Banks are famous for choosing this path as their financial systems incorporate their own security and maintenance, two of the main reasons for upgrading. Since their tellers don't use the Windows-based functionality, they will be last to upgrade.

Windows 10 will have long-term impact on the organization, so deciding on whether to upgrade, and if so, when to upgrade, should involve a series of questions, departments and approvals. The table below offers a good starting point for you to begin your upgrade decision. Drop this table into a format of your choosing and begin by starting conversations internally in order to level-set.






Cost Considerations

What is the cost of the upgrade to Windows 10?

Is the cost annualized or one-time?

Will there be training costs associated with the upgrade?





Operational Considerations

When did the organization last upgrade their desktops?

How many users operate remotely?

Does the company lease or own their computers? If they do lease, when does the lease expire?





Enterprise versus Personal

Is the enterprise on a standardized version of Windows (7, 8, 8.1)?

  • If yes, can the entire organization be upgraded?
  • If no, are there specific users or departments that can benefit from the upgrade?

How many users have administrative privileges on their devices, and may upgrade regardless of corporate decisions?





Training Expectations

How many users will be impacted by this upgrade? (Remember that an un-trained user who impacts corporate processes due to lack of training must be considered here.)

What training options are available for Windows 10 user training?

What support will have to be provided to users internally?





Technical Considerations and Impacts

Do each of the devices pending upgrade have a minimum of 16GB of free space (for 32-bit) or 20GB of free space (for 64-bit)?

Are each of the devices pending upgrade running the most up-to-date version (whether 7.1 of 8.1)?

How do we handle exceptions to the above?




With these questions and considerations to take into account, be sure to get the right team in the room for the initial conversations. Though the initial release to manufacturing (RTM) occurred on July 29, 2015, your organization certainly doesn’t have to upgrade until they have sufficiently planned and are ready for the change to occur. With your team compiled, ask questions about alignment to your overall strategy, the 5+ year IT plan (which you hopefully have) as well as the true functional requirements and usage demands of your users.

Topic: Windows 10

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