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Pro Tips From The Windows 10 Summit: How To Get Your Executives Fired Up About Evergreen IT

Do you dread having to pitch Windows 10 Service Management to your executives? Will they perceive it as yet another service they have to dole out cash for or think it is Business-as-Usual and not understand why you need additional resources and budget to upgrade to the latest version of Windows 10 every six to twelve months?

You are not alone! While most IT executives now understand the many benefits of Evergreen IT, businesses can't seem to wrap their heads around it — and consequently withhold their support and money! This is such a hot topic that I decided to pick this as my thought leader seminar when I was invited to speak at the Ivanti Windows 10 Summit.


Below, I have summarized some key insights on how you can make a few simple tweaks in your pitch to not only get them to understand why continuous upgrades are a requirement in this fast-changing environment, but to get them excited about it!

[Watch the entire session on-demand here.]

1) Use Storytelling As The Key To Getting Attention

Throughout my career, I have watched many salespeople and I realized that the one thing great sales people have in common is that they are amazing storytellers. They take their audience on a journey that aligns with their needs and goals.

The same is true for IT.

Gartner VP Analyst Robert Naegle put it best in his recent webinar Tell An IT Value Story That Executives Will Care About: "To communicate IT’s value, IT leaders must know what business executives care most about."

Rather than telling your executives that you have to move to Windows 10 before Windows 7 support runs out in January 2020 and you need about $5 million for the upgrade, we need to tell our executives a story and map that story to concrete business values they care about. Remember — it is not about what we do, but the perception of the impact of what we do.

Generally, every executive goal can be rolled up into one of these three categories:

  • Drive more revenue through new or better services and products,
  • Create more cost efficiencies and savings by making their operational engines as lean and mean as possible, or
  • Mitigate risk.

If you put yourself in the shoes of your management, the same request (but framed with the focus on the business outcome) could sound something like this: “Our business is evolving and we need to be more agile in providing tools that enable our teams to collaborate better and drive more revenue. We can achieve this by rolling out Windows 10 with Microsoft Teams which should strongly impact the bottom line.”

2) Paint A Vivid Picture To Illustrate The Cost Of Doing Nothing

Because of the looming end-of-support date for Windows 7 in January 2020, a lot of organizations start charging into Windows 10 — without ever properly defining their Evergreen IT strategy. They will change the image multiple times during their ongoing rollout without going back to remediate the older versions of the OS. As a result, you can end up with up several different versions of Windows 10, as you can very easily see from our Windows 10 Timeline Graphic below. Just imagine the red line is your current development cycle. This would mean you are maintaining five different Windows 10 versions.


Consequently, this lack of strategy is creating a very messy environment that is hard to maintain — resulting in an awful lot of work for our project team and application packaging and testing team any time you want to make the slightest change in your environment, such as rolling out a new application. Visualizing this complexity and cost to your executive management without going too deep into the technical details is crucial to gaining their support and buy-in.

3) Directly Translate Evergreen IT Benefits To Executive Challenges

According to a recent Ivanti survey, executives name these top four challenges when it comes to their IT:

  1. Reducing time spent on routine tasks and working across multiple systems
  2. Improving both IT and compliance, and limiting exposure to risk
  3. Ensuring maximum end user up-time
  4. Minimizing hardware, software, and other IT costs

Thankfully, Evergreen IT is a direct answer to all of the above. As you can see from the slide, there are significant benefits that come with Evergreen IT. But resist the temptation to simply list them. Be sure to take the extra step and translate its benefits to those challenges!

ivanti slide

For example, Evergreen IT allows you to establish your IT department as an internal service organization. As a consequence of the more centralized and tighter management, possible Shadow IT (which can eat up 30-40% of enterprise IT budgets according to Gartner) is minimized. However, this doesn't really mean much on its own to a business value-driven executive. But if you explain how this leads to a hybrid mix of business agility and IT management, I guarantee that your management will be all ears.

Let's walk through each of the challenges mentioned above and see how Evergreen IT addresses them:

  1. Evergreen IT reduces time spent on routine tasks and working across multiple systems by permanently rationalizing the number of systems and applications you are using. Since your estate is tightly managed and you are spending significantly less time on fire drills, you can automate labor-intensive routine tasks, e.g., your application packaging and testing process.
  2. It improves IT and compliance by limiting your exposure to risk. Most executives are afraid their organization isn't agile enough or won't be able to react quickly to unknown compliance, (cyber) security, and vendor risks. Because Evergreen IT keeps your entire estate always within its life cycle and up-to-date, your risk exposure is kept to a minimum.
  3. Continuous upgrades ensure the maximum end user up-time by making sure that your applications and hardware are up-to-date and performing. This way, your end users receive the best service in terms of up-time and performance.
  4. Consequently, Evergreen IT minimizes hardware, software, and other IT costs by virtue of the effort and resource reductions mentioned above.

This is by no means an exhaustive list but simply an illustration of sample arguments you could make. The important thing to remember is to find the key challenges YOUR management is struggling with and address them!

Next Steps & Getting Started

At this point, I hope you are excited about getting the chance to talk about Evergreen IT to your executives and that we sparked some ideas on how you can present your business case. Here are a few things I want you to keep in mind as you get started:

  • Check out our Ultimate Guide To Evergreen IT Management as your one-stop resource.
  • Start by changing the way you think about managing end user IT.
  • Understand that this is a cultural change, not just a technological change.
  • Define your Evergreen IT strategy and get business buy-in 
  • Apply for budget and create a function in your Business-as-Usual group with responsibility for managing Evergreen IT. Create a roles and responsibilities matrix to show who needs to do what and when to remain in cycle.
  • Define your end-to-end timelines and workflow for each Evergreen IT service.
  • Put tooling in place to support your repeatable process. This should include:
    • Continual Assessment (Discovery/Inventory/Applications/Hardware/Lifecycle)
    • End-To-End Process Support (Who, What, Where & When)
    • Application Testing & Remediation Workflow
    • Self-Service Deployment (Capacity Constrained)

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