The Biggest Evergreen IT Management Challenge & How To Overcome It

This article is a collaboration with Juriba

Ever since the introduction of Windows-as-a-Service, enterprises have sought for ways to manage their IT in an agile enough manner to keep up with the increasingly faster pace of technological change. Since then, many Microsoft enterprise products, such as Office 365 ProPlus and Windows Server, as well as other applications, like Bloomberg, are releasing monthly or bi-annual updates.

Unlike the old world of ‘big bang project-based upgrades’, this means that IT teams have to manage much smaller, but continuous streams of iterative improvements (often in parallel) rather than overhaul the entire estate every few years.

Now that most large organizations have completed their Windows 10 migration and turned their attention to managing ongoing Windows 10 upgrades, many IT project managers have realized that traditional IT project management methodologies cannot manage change at the required pace and have looked towards more agile project management concepts. This is where the term ‘Evergreen IT’ was born.

Evergreen IT Management Has Its Challenges

Although managing an enterprise IT environment in an Evergreen IT way has a vast number of benefits, this agile IT project management methodology also comes with challenges. While, traditionally, we had years to chip away at a mountain one migration at a time, we now have to manage a constant stream of change:

  • Understanding what we are running can be a challenge, especially with multiple, disparate (and often conflicting) data sources for information.
  • Tracking who, what, where and when for asset management (users, devices and applications) can be a huge challenge without good, consistent and near-time data.
  • End user engagement becomes a critical cornerstone for efficient delivery of change (pull vs push methodology)
  • Business buy-in for the additional change processes; application testing/remediation, device scheduling & refresh,
  • And the list goes on and on.

You can imagine Evergreen IT as a set of fine-tuned, well-orchestrated conveyor belts. If you are not extremely methodical, you will quickly end up in chaos.

Most Challenges Boil Down To Not Having An Optimized Process Framework

The above-mentioned challenges often boil down to a single roadblock: not having a repeatable, automated, scalable, and industrialized process framework.

Let’s look at what that means:

  • Repeatable. This refers to the reusability of the process. Can the same process be used again to manage the same or a different Evergreen use case (e.g., a hardware refresh or an application rollout following an Office 365 ProPlus upgrade) without any problems? Can the tooling used support managing a repeatable process?
  • Automated. It is a key requirement to eliminate as many labor-intensive manual tasks as possible and replace them with automation to be able to keep pace. For example, sending, tracking, and auditing T-minus emails to end users is a great example of the types of tasks that should be automated.
  • Scalable. The process framework needs to be able to scale up or down, depending on the current requirements. Sometimes, we will need to upgrade tens of thousands of users on a new OS while running a hardware refresh program at the same time, and other times, things are running at a calmer pace.
  • Industrialized. Possibly the most important requirement is that your process framework be industrialized. This means the process needs to be optimized and tied into other relevant business processes (e.g., purchasing approval, logistics, support). It needs to be optimized to accelerate the process using mathematical algorithms (e.g., determining the fastest migration path based on application testing readiness). Thirdly, it must be robust and supportable by the right tooling.

Juriba’s Evergreen IT Process Framework

At Juriba, we have developed our own Evergreen IT Process Framework. It breaks the entire Evergreen IT Management process into five distinct steps:

  1. Inventory & Analysis,
  2. Assess & Prioritize,
  3. Ready,
  4. Schedule, and
  5. Deploy.

The graphic below shows the process on the example of a Windows 10 Servicing project, but this Evergreen IT Process Framework can be used for many different use cases. To make it easier for you to manage this process, we have made our customizable Evergreen IT Management project plan template available.

From a high-level point of view, you start by creating a live inventory of all your in-scope elements, analyzing it, and defining your potential roadblocks or bottlenecks. These could be anything from applications that need to be tested or remediated or delivery timelines for to-be-ordered devices.

This allows you to start prioritizing your upgrade paths. Once those are identified, you work through your readiness tasks and get ready for scheduling and deployment. The next step is all about end-user communication, self-service validation, and managing the scheduling and logistics. Finally, you deploy by either pushing or pulling before wrapping up to start the cycle again.


Successfully managed Evergreen IT comes with enormous benefits, but without the right process framework, it can end in complete chaos. It definitely is worth the investment of time, energy, and resources to carefully define each step, formally document them, and then implement the process in an Evergreen IT Management solution that will enable you to manage all the different use cases.

Barry is a co-founder of Juriba, where he is focused on using his experience in IT migration to help drive product strategy, pre-sales and service delivery. He is an experienced End User Services executive that has helped manage thousands of users, computers, applications and mailboxes to their next IT platform. He has saved millions of dollars for internal departments and customers alike through product, project, process and service delivery efficiency.

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