In my 30+ years of experience in technology, I have migrated Windows 95 to XP, Windows NT to Windows 7, and now Windows 7 to Windows 10. And they all had one thing in common: I had to come in and rescue the migration projects many times because, initially, in peoples’ heads — even if they are technologists — OS migrations are simply thought of as clicking “Next” a few times.

However, the opposite is true. In my opinion, upgrading to a new operating system in a large organization is one of the most difficult projects you can undertake. It touches every single person, application, and technology in the organization. You have to be extremely methodical and prepared in everything you do to finish the project successfully. Otherwise, your timeline, budget, and everything very quickly get away from you.



Right now, I am knee-deep in one of the largest IT Transformation projects that was ever outsourced to a single vendor. It encompasses migrating 95,000 employees of a global Tier 1 investment bank onto Modern Desktop (Windows 10 and Windows Server 2016) and Office 365, as well as enabling a variety of cloud services. Today, I wanted to share with you some of the most valuable lessons learned in successfully pulling off a project of this scope.

[Click here to sign up for the live webinar with Tony Head (CEO of Accessplc) and myself to go through this customer success suoty in more detail as we explore further key strategies that made this project so successful.]

#1: Experience Is Key

Migrating to Windows 10 is different from all other prior OS migrations because rather than migrating as a big-bang project once every five years, you are instead setting yourself up for success (or failure) in managing future Windows-as-a-Service upgrades. While the average project timeline for OS migrations was traditionally 24+ months, Windows 10 versions only have support windows of either 18 or 30 months. This means that migrations have to happen constantly and much faster. This particular customer has made the decision to migrate every six months.

The key to this is experience — something a lot of enterprises struggle with because this is the first time they are tackling this. But knowing how to set up your migration plans, where to move the dials to accelerate the project significantly, and where not to waste energy and budget is absolutely essential.

#2: You Must Have A Rock Solid Plan

Unlike past migration projects that were planned out in color-coded Excel spreadsheets, you need to have a well-thought-out plan of attack. One good example is Microsoft’s Windows 10 Deployment Ring Concept. Essentially, you deploy Windows 10 in waves: initially to a very limited user base (e.g., technical pilots), followed by a broader pilot (e.g., IT department) and then culminating in a roll out to your business units in broader deployment waves.

However, while this sounds very simplistic, you need to have a tight handle on your guardrails, like application packaging and testing, security policies, and other project framework questions. You also need a plan for user communication both leading up to and after migration.

#3: Yet Think Agile

It might sound counter-intuitive to suggest thinking agile while having a rock solid plan (and, I guess, this is where the experience comes in handy). You won’t exactly know what you are in for until you are in it. It is essential to manage this project with an agile mindset, rather than a Gantt chart. For example, if you look at your application inventory and determine which applications are holding back which users, you can define your fastest migration paths. In other words, start by remediating those apps that allow you to switch as many users to green as possible.

#4: Don’t Skip The Important, Yet Boring Steps

Everyone wants to get to the fun part as quickly as possible and see those numbers on the board climb fast. But skipping important steps and gaining ground too quickly will almost always lead to having to retrace your steps and correct mistakes (which can cost you a lot of time and money) or tread water for a while. For example, it is crucial to spend enough time and resources on ensuring that the applications work with the new platform and fixing them if they don’t work or getting new applications if they cannot be fixed. Another example is not to proceed without executive buy-in and support.

#5: Applications, Applications, Applications

Last, but certainly not least, let’s talk about applications. Many organizations treat applications as an afterthought. They spend a lot of time on which hardware they are going to buy, what screens they should have, or how the build should look, but they ignore applications. This often leads to project downfall. Suddenly, they find themselves massively behind in terms of applications. But applications are first, second, and third in terms of importance.

In my experience, more than 40% of applications will not pass the immediate load test and need further investigation or even remediation. This doesn’t stop the migration per se, but you have to turn your attention to other users that are not blocked by these applications. This significantly hinders your progress.


While some of these lessons seem obvious at first, they are often overlooked or dismissed because they are inconvenient or bothersome. But I cannot stress enough how important these lessons are to the success of your project. Of course, there is a lot more to the story and I would like to invite you to join us on October 21st, 2020 for a live webinar to hear more about our exciting customer case story and share with you more lessons learned.

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