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Winning ways with Windows 10 updates

We look at how IT leaders can effectively manage the major changes Windows 10 imposes on businesses

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Microsoft is developing features and improvements for Windows at a faster pace than ever before, which means retaining a 10-year support model for its operating system (OS) would severely inhibit its ability to get those features and improvements to market. Therefore, a far more agile operating system is needed, even if the difficulty it imposes on businesses is dramatic.

Windows 10 replaces the five-year to eight-year cadence with a six-month cadence – the Semi-Annual Channel (SAC). Because Microsoft’s Windows 10 updates can be substantial, Gartner recommends that application testing, in some form, be executed for each Windows 10 release that IT plans to deploy.

But this raises the question of how user companies can perform the required amount of testing as often as twice per year? The application testing portion of Windows 7 upgrade projects often exceeded six months on its own, but the process is now expected to occur almost continuously to keep up with Windows 10 releases.

Strategies for application testing

There is no one-size-fits-all magic bullet to the question of how to perform application testing for Windows 10 releases. There are two approaches that Gartner clients have considered that are excessively optimistic or excessively pessimistic.

On one side of the pendulum, the optimistic approach makes an assumption that Windows 10 is Windows 10, so once an application works, it will continue to work. This approach tests all applications as part of the initial move to Windows 10, just as with previous OS releases, but then carries out no testing when SAC updates are released.

However, Gartner believes the changes made to Windows 10 in every SAC release are significant enough that application testing cannot be ignored. Rolling out a new Windows 10 release to computers without ensuring the applications will continue to work can easily lead to frustration and lost productivity while IT rolls back the changes to make the application functional again. When that situation occurs, the company is left scrambling to remediate or replace the application because the Windows release that broke the application must still be applied eventually.

Staffing considerations

The key change to staffing is that Windows 10 creates the necessity to perform OS and application testing on a far more regular basis. This increased cadence involves moving away from previous funding and staffing models, where a large project with dedicated resources, and often with service provider help, could be funded separately. Instead, the IT organisation will move towards smaller, more agile projects, typically with existing IT staff. The frequent releases of Office 365 ProPlus – every six months – cause the same shift in project management. When confronted with supporting both Windows 10 and Office 365 ProPlus, consider the projects together.

Gartner clients have several common questions when discussing the Windows 10 release cycle’s impact for staffing. These questions can almost all be condensed into one overarching question: “What do I have to change to make this work?” The most common approaches are:

  • Reallocation of personnel;
  • Engagement with business units;
  • Process refinement;
  • Release management;
  • Hiring or outsourcing.

Looking at the reallocation of personnel, companies will often opt to take roles normally tasked with Windows image building and security patch testing and redefine those jobs to include frequent OS testing, including Insider Channel builds. Because these individuals are closest to the OS in their normal duties, they are best equipped to participate in OS preparedness projects, including Insider release testing.

As far as business engagement goes, applications are the lifeblood of nearly all business units. Therefore, utilising IT or IT-savvy personnel from the business to achieve successful Windows 10 updates is mandatory. A central IT organisation cannot be expected to understand the fine detail of business applications, and therefore, the business must provide time and resources for application testing for each selected release of Windows 10.

From a process refinement perspective, with each roll-out of a Windows 10 release, the IT department must focus on ways to reduce the time and effort involved in delivering it to the company. Each opportunity to save time and increase speed – without sacrificing quality – must be taken. Gartner recommends documenting all repeatable processes and creating “test scripts” for specific applications to make the next release easier and faster. Continuing to refine those processes and scripts will lead to smoother and safer upgrades as time passes.

Introducing a release coordinator to create a single point of contact for metrics and timelines will greatly enhance release management. It can also alleviate time and effort from multiple tech professionals and management personnel in both IT and business units. This individual will monitor what is new in the OS, create or obtain training materials for users when needed, and assess timeliness and success of each roll-out. This coordinator role can be combined with the same role for Office 365 ProPlus if the company is utilising that product because the feature update cadence is nearly identical.

The least palatable, but not uncommon, approach to get the job done is hiring or outsourcing. Many companies find themselves understaffed in the client computing organisation even before Windows 10 is introduced. By upgrading the endpoint OS once every year or 18 months, instead of once or twice per decade, that issue is dramatically magnified. Often, there is no alternative but to seek additional headcount, in the form of either full-time employees or contracted personnel. However, as processes are refined and IT becomes accustomed to the new pace of change, the amount of time, and sometimes the number of people, required to complete the task will decrease.

Preparing for Windows updates

The previous funding model for Windows desktop OS upgrades is obsolete. A large operating expenditure (opex) infusion plus temporary allocation of IT and business personnel can get Windows 10 into the environment, but will not address the continual time and resource needs of Windows 10 SAC releases. Therefore, an approach that allocates personnel from IT and from the business to perform recurring tasks and testing on each Windows 10 release is crucial to the success of Windows 10 in the company.

By performing risk-based application testing, each Windows 10 feature release roll-out will be significantly smaller than previous Windows projects, such as Windows XP to Windows 7. Therefore, a dramatic increase in overall funding is unusual. Instead, the funding that was allocated in a large, one-time manner for previous upgrades must now be spread across more frequent, smaller projects.

This is an excerpt of Gartner’s “Managing the major changes Windows 10 imposes on your business” report by analyst Mark Lockwood.

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This was last published in May 2019

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