Well, we talked about the five reasons not to migrate to Windows 8, but instead to skip straight to Windows 10, and since you believe that was 100% solid, let us talk now about what you need to do in order to be prepared for that jump to diez. Or, as we like to call it within the CM community, the process of “please, oh please, do not let Windows 7 happen to me again.”
In all seriousness, Windows 7 was tough for everyone, and I mean everyone within an enterprise IT environment. This OS migration effort was the hardest hitting to date and is one of those topics where no matter who is in the room, you can throw out the comment “good news is, no matter what we talk about, it will be less painful than migrating to Windows 7.” That tells you something, it tells you that no one is very proud of the space our industry slipped into, not how it was handled but the level of complacency which made the task so arduous for most. That space of being basically incapable of providing respective business partners with a proactive, agile, and lean means of keeping technically current at a foundational level.
Mind you in cases where 1E did drove said migration, the zero touch streamlining we provided removed a lot of that complexity and provided automation with enduring value for companies who accepted our help. However, zero touch OSD automation is only part of that ever changing puzzle which is systems management or, more specifically, Software Lifecycle Automation. Hopefully this list either supports, challenges, or brings to light items which you may carry forward when taking on your next migration effort.
Here are the five items which I feel are paramount in order to keep the sins of the past, in the past:

  1. Application Rationalization….. it’s not just a once in every five-to-ten years sort of activity. This is the biggest challenge when it comes to being agile enough to meet the demands of the digital business. This emerging identity of our charge as IT processionals which we are only starting to fully comprehend. Invest the time now to develop a proper technology standards process and team up with your IT partners (security, procurement, systems management, support, and so on) to start standardizing the software accepted into your estate. Help the business understand how this type of proactive process provides a lean environment capable of efficient change when needed with significantly lower cost and support variables.
  2. Design your OS migration with a break-fix in mind. Take the engineering and operations design investment further than simply addressing the ability to move from Windows 7 to Windows 10. Design a dynamic service offering which handles a device reload if necessary down the road. Think of an environment where end users can reload their own PCs if they need to (this still will not fix a dead hard drive though)? Moreover, imagine a world where your support staff may cut troubleshooting off at the 2 hour mark, knowing a fully automated reload is only one hour away which can be independently triggered by the end user. If this sounds like something you can do with your own mobile device, it’s because it is what you can do with your own device and guess what? Your end users can too and already have this expectation of you.
  3. Get your application owner house in order. Most companies have caught on to this but for those who have not. Do you know who is best suited to determine applicability, value, use case fit, and compliance for business critical applications? You guessed it, the business itself! If you do not wield the ability to expose data surrounding software footprint, major versioning, and allotted entitlement; you need to get there. Now the option always exists to funnel all this work into a traditional SAM team but if this is your route, make sure you know who is accountable for what, and that they have the ability to enact compatibility cycles. This component of making sure you have a reliable and easily trigger-able path to preform compatibility testing will save you months of “why can’t you do this for us IT” or “we don’t have the time or resources to invest in this activity until XX date as we have scoped other work so the business can be profitable” (sound Windows 7 migration familiar?). This is a political time bomb if handled reactively and will impact the perception of migration success, so get the work streams to achieve this task into a business as usual run-state.
  4. Map your applications intelligently, there are a whole host of ways to do this (some good, some not so much) but weaving this into your standard application acceptance and packaging process is crucial for portability and allows software to be more of an independent and valuable entity. The outset means that an OS migration, upgrade, and/or reload is just that, an OS function which requires ensuring user identity is retained but should not be more than that and won’t be if application mapping is well maintained as a standard practice.
  5. What technology investments will pair into a Windows 10 world best? This is a question to start asking yourself now and discuss with your major software vendors. If a software product today is valuable but has no line of sight to how they can take advantage of the “mobile-centric” application experience, this is a pretty good indicator of stagnancy or cause for them to provide a very good reason why not. If the function of the application could benefit that is of course, and If no vision forward exists, you may want to look at your options now as opposed to when you need consistency during migration time. This also is a fantastic way to let the business get involved and aid in this decision making process. I am not saying you should ask Adobe how PDFs will amaze you in Windows 10, but I am saying if you have a mobile workforce and you are not asking these questions now, rest assured they will and it will be right around the time when the look down at their smart phone and sigh in disappointment.

So let me know your thoughts out there, this is a gigantic topic and there is no shortage of opinions but this view is provided in the hopes that the author may learn from the feedback just as much as someone may learn from the content above. Windows 10 is a chance for the systems management community to emerge and lead the charge, amplifying how potentially complex and costly exercises like OS migration can usher in an overall IT products and services value uplift and if we do not approach as a community, we will miss out on a ton of possibility.