<img src="https://secure.leadforensics.com/51024.png" style="display:none;">

Office 365 and Windows 10: Your Stepping Stones To A Successful Evergreen IT Implementation

For many years, Evergreen IT has been imagined by many CTO's and CIO's as the cure-all for their IT management issues. But sadly, many organizations have tried and failed to implement Evergreen IT, and seemingly nobody got close to achieving the goal until now.

However, with organizations migrating to technology such as Windows 10 and Office 365, the building blocks for successful Evergreen IT Implementations are there, and achieving it is becoming more likely.


To understand why, let's first have a look at why previous efforts to build Evergreen IT have failed:

Evergreen IT Needs Supporting Baseline Technology

You just cannot expect to start Evergreen IT without appropriate supporting technology.

This begins with a continual and always up-to-date way to understand what your IT landscape looks like (hardware as well as applications), and how it is being used. Once you understand that, you will need the right technology to analyze this information and make it actionable. 

Many enterprises have no or little continuous software or hardware management tools in place, and manage ad-hoc projects rather than perpetual upgrades and maintenance. By not managing the lifecycle of what you have, each project has to deal with the legacy of multi-year technical debt, and consequently, projects take longer and increase in scope as the team understands the additional dependencies for delivery.

Evergreen IT Needs Supporting Processes In Place

To be able to continuously manage your IT landscape, you not only have to know what you are dealing with from a technical perspective to identify what you need to replace or upgrade, but you also need to be able to execute the appropriate processes that support the activity.

To do this you must have the requisite request, approval, licensing, financial, communication and deployment processes established. They must be agile and fast enough to execute on an ongoing basis, with proper process management in place to support workflows and approval chains.

Evergreen IT Needs Executive Buy-In

As you can see from above, Evergreen IT is not a project that can be siloed into your IT organization: It requires organizational change throughout your company.

Perpetual projects mean that your end-users will be subject to additional levels of IT change than they are used to. For many organizations, this could be as high as 15 – 20 change events per annum, ranging from the usual patching and application updates through to hardware refresh and major application change. The consequence of higher levels of change is potentially higher levels of risk that changes break the environment.

This is why an appropriate buy-in for the cost of resources and a top-down acceptance of Evergreen methodology is critical for implementation success. Without the necessary acceptance and support that Evergreen processes will be in place, businesses will be subject to constant interruption without correctly understanding the benefits.

Evergreen IT Needs User Buy-In

End-users do not always like change — and more often than not, they will even resist it  — especially in a corporate environment where, unjustly, so many see IT purely as an enabler to perform their primary job function.

However, end-users do sometimes like shiny new stuff, and at home are much more accepting of changes that are pushed down to them (think Windows 10 consumer and iPhone/Android application and OS updates). Therefore, Evergreen IT has to manage the mix of new IT adoption with the elements of change at the end-user level.

End-user complaints will be one of the biggest barriers to Evergreen adoption if your changes become disruptive to the business.

Evergreen IT Needs Supporting Budget

To determine your potential Evergreen IT budget, you can follow these simple rules of thumb: Think about how much you have spent on IT implementation projects over the last five years. It is a significant number.  Now divide that amount by 5. This is the type of spending you will need to justify to your management team on an annual basis. By shifting an organization from a primarily reactive and project-led model to a new proactive and perpetual maintenance model, major changes in budgeting methodology and a potential increase in the initial headcount may be required.

As an example, consider the trend of moving in-house infrastructure and applications to the cloud. As this strategy gathers momentum, moving the organization to an OpEx rather than CapEx financial model as part of Evergreen IT efforts, while removing many of the barriers to IT adoption (e.g. many large enterprises have a 30-90 day lead time for a server to be placed in a data center) will help organizations move towards more agile and continuous IT management. 

       Read Also: Why Evergreen IT Must Be Part Of Your Long-Term IT Strategy


As you can see, it is critical that an organization invests in the right technology to enable Evergreen IT, but at the same point, this initiative will fail without executive management and end user buy-in, as well as the proper processes and budget in place to make your dream of Evergreen IT a reality. 

Windows 10 and Office 365 Help Evergreen IT Become Reality

While Evergreen IT is an organization-wide initiative and will eventually impact your entire IT landscape, the actual Evergreen IT implementation cannot be achieved in one hit. It is wise to choose one or two elements and start to manage them using an Evergreen IT methodology, to prove that your organization is capable of achieving the shift.

If you have to choose two core elements of your IT infrastructure that lend themselves very well to implementation in an Evergreen IT fashion, obvious possibilities are Windows 10 and Office 365. Microsoft has been pushing hard to deliver the technology required to support these technologies 'as a service' natively, which makes them a great candidate for initial adoption.

Office 365

Office365-1.pngOffice 365, Microsoft's online productivity suite, enables employees to host their email, calendars, contacts, and much more in the cloud.

Before to migrating to Office 365, businesses were required to purchase and implement the equivalent of productivity solutions such as Office Professional Plus, Exchange, Lync, SharePoint, Yammer, and OneDrive in a traditional on-premises model.

By moving to Office 365, customers no longer need to manage their own mailbox, SharePoint, file storage or telephony on in-house equipment, since Microsoft looks after all security patching, software upgrades, bug fixes, and capacity expansion. Instead, organizations are able to accelerate the deployment of the latest versions of Microsoft solutions and automatically stay up-to-date with the latest features. 

In the Forrester Report, The Total Economic Impact of Office 365, the analyst company states:

Moving to Office 365 makes organizations inherently more flexible. IT organizations can more quickly provision users and roll out the latest features to make workers more productive. One organization reported using Office 365 to more quickly integrate two merged companies. It said, “It has given us tremendous agility.”

Furthermore, the study names reduced IT support due to the elimination of hardware and software with Office 365, savings due to replacement or elimination of third party software and services with Office 365, and reduced fees due to decommissioning legacy hardware with Office 365. 

By implementing Office 365 instead of a traditional on-premise solution, an organization can save Windows Server licenses, Exchange Server licenses, Lync Server licenses, SharePoint licenses and vast amounts of storage. Besides the enormous benefit of consolidating and saving on licenses, these servers also do not have to be maintained or managed, driving a reduction in operational staff.


In addition to the above benefits, Office 365 customers see improvements in their IT and data security, their disaster recovery, uptime, and reliability. 

But what does this mean for Evergreen IT?

On the face of it, the infrastructure management headache is removed, Microsoft (or your Microsoft partner) will manage it all for you, and you simply pay a monthly subscription fee for a service which continues to expand with added functionality.

Great for the server side of the estate, but you also need to consider the bit that remains in-house: your software applications, security considerations, access to the mailbox from personal devices and your internal dependencies on the mail, file and sharepoint and unified communications service.

For example, an upgrade to the core Office 365 product might necessitate an upgrade to the local version of Microsoft Office on every machine in your organization.  But will all your macros, Access databases and Office dependent applications still work correctly on the new version? Likewise, Microsoft could deprecate a function or API call on the central Office 365 platform that you rely upon in your web application, or change a powershell script that runs a critical business process.

This is the fundamental reason why adoption of any 'as a service' product means a change in operations for your organization. For ongoing success with Office 365, you will need a good understanding of your inventory, its dependencies, and how any change might impact it. Think about how quickly you could shift from Office 2013 to Office 2016 today. Even a major patch to your existing version of Office would probably involve a significant project and testing effort.

Click here to download our Office 365 Migration Project Plan Template

Windows 10

When Microsoft launched the newest (and last edition) of its Operating System, Windows 10, it touted it as an OS-as-a-Service — in other words: from now on, depending on which service channel option you choose, you will receive all security updates and feature upgrades as soon as they are available, or at least within a clearly defined timeframe.

While Windows 10 can never be under the same level of control as the central Office 365 platform, the methodology behind the new Windows 10 servicing model is pushing hard towards an Evergreen Operating System installed base.  No more big-bang migrations! And since all updates and upgrades are cumulative, you are able to bring any PC or device up to date instantly.


In conjunction, complementary services such as Windows Server, SCCM, Active Directory, and InTune are all moving towards an 'as a service' approach, and shaping towards the cloud.  In fact, over the next five years, we expect to see further significant reductions in on-premise infrastructure and solutions for end-user device management as all Microsoft products can be managed from the cloud.

But what does this mean for Evergreen IT?

In the same vein as Office 365, this shift towards Evergreen IT has its consequences for your IT department, its processes and procedures. For a start, assuming that most of your devices will be on the Current Branch for Business (CBB), you are now in a perpetual upgrade cycle with Windows 10.

Choosing to retain an old version after the cut-off places you out of support ... immediately. So for every branch update that you consume, there is potential impact on your local applications, your web applications and your hardware compatibility. It also has impacts on your build engineering, your application packaging and your supporting infrastructure.

What this means is that every time a new anniversary update is released, there is the potential that it could break something in your IT environment. In previous times, we had total control over this process. We would start a project, get the associated buy-in and set some dates for delivery that we thought were achievable. Under Windows 10, the clock is ticking immediately. If you are not properly tested on the new update, you risk potential business disruption.

So part of the shift to Evergreen IT on the desktop includes a significant shift in how we manage that desktop estate. If you do not know the answer to who, what, where and when with regards to your device upgrades and their compatibility with the latest release, you could risk a very unhappy and disrupted user base. 


There is no doubt that IT has been crying out for a more predictable, better-maintained and secure desktop operating system and mail / unified communications platform. Microsoft started with a shift in patch management with Windows Update, and has now driven the big change with Office 365 and Windows 10 with more to follow, including the realisation of infrastructure as a service. These are platforms which truly embrace the concept of Evergreen IT.

However, while this continuous management approach of IT assets, processes, and infrastructure solves the crippling problem of living through inefficient, costly, and lengthy cycles of big-bang migrations, and resource-heavy operations teams, it brings with it a new set of challenges that must be addressed. Perpetual maintenance to N-x versions involves a critical understanding of your current IT environment and how it might be impacted by the forthcoming change.

It is a cultural shift that we will explore in future blog posts.

New Call-to-action