Migrating to Windows 10 and modern management at the same time sounds nice, but is it practical?

It would be wonderful to transition to modern management at the same time as we move to Windows 10, but as we learned in the past, it's possible to do to much at once.

While spending much of my time lately thinking about modern management, I can't help but wonder how long it will be until it takes hold. Because Microsoft is so heavily invested in it, I'm certain it will happen. It's just a matter of "when" that will happen, or "what" the reason for companies to migrate will be.

Right now it's a tough sell. Modern management is a Windows 10 thing, but companies are still running Windows 7 in large numbers, and those devices can only be managed in a traditional way. It's easy to say "You should transition to modern management as you migrate to Windows 10," but, as we learned when we predicted that the migration from Windows XP to Windows 7 would be the catalyst for widespread VDI adoption, it is possible to do too much at once.

If you recall, we thought migrating from Windows XP on physical machines to Windows 7 on VDI would be great because we'd simply create one image that all our users could share. We could turn everyone's old PC into a thin client, push out their new VDI desktop, and be up and running.

We were wrong, and for a whole bunch of reasons! First, this is what we were thinking in 2009, right when Windows 7 was new (not in 2014 when we absolutely had to migrate). In 2009, VDI was doing its best to exceed everyone's expectations of cost and complexity, and not in a good way. VDI was hard, and required new skill sets that we had yet to acquire to solve technical challenges that we'd never seen before.

At the same time, Windows 7 posed key challenges that we weren’t aware of. There were new profiles, application compatibility problems, and new hardware requirements, among other things. None of these were actually new, having come out with Vista, but since we all skipped Vista and stuck with XP, we never actually learned about them.

Any IT admin had their hands full with just one of these projects, and to attempt both seemed downright insane. What seemed like a great idea at a high level turned out to be a nightmare when you looked a bit deeper, and I can't help but remember this experience when I think about the move to modern management.

Consider that IT organizations, already likely taxed keeping up with their existing systems management, will have to learn modern management at the same time. The Windows 10 migration, while easier from an application standpoint, presents new challenges in the form of updates, branches, profiles, and hardware requirements, not to mention security and a new filesystem—all of which should be learned before migrating to modern management.

With that in mind, I want to caution anyone who thinks that the looming End of Life for Windows 7 on January 14, 2020 will be the catalyst for modern management to think again. Yes, it's possible that some companies will want to transition incrementally as they roll out Windows 10, but don't underestimate how terrible it would be to have two management systems operating side-by-side for the next two years while simultaneously learning about all the subtleties of Windows 10.

Odds are, most companies will be so consumed with migrating away from Windows 7 that the transition to modern management will wait until that project is complete. It's possible Microsoft sees it this way, too, because while co-management indicates the direction they want to go, it's not currently the kind of thing that's going to make everyone immediately start trashing SCCM servers as they rush to Intune.

That said, the EOL for Windows 7 will be a factor in the adoption of modern management (which is what we seem to be calling this as it pertains to Windows. Overall, it still part of Unified Endpoint Management), I just don't think it will happen simultaneously. Because we're not subjected to the same roadblocks with the Windows 10 migration as we were with the Windows XP to Windows 7 migration, it's reasonable to expect that before that red-letter date in 2020, the overwhelming majority of desktops will have been migrated to Windows 10.

By the time that happens, modern management capabilities from Microsoft, VMware, and others will have matured. At the same time, admins will be well-versed in the challenges of managing Windows 10 via traditional methods. With a better understanding of what it takes to manage Windows 10, and with IT resources not focused on a migration, it's here that I think modern management begins to hit its stride.

While I can't put a date on it, I will say that the closer a company is to completing its Windows 10 migration, the more they'll be thinking about modern management. If I'm Microsoft and VMware, I keep chugging along, talking to customers of increasing size and complexity, and rolling out enough modern management to learn what customers need, but I'm setting my sights on January 15, 2020. We should all be on Windows 10 by then, and we should all be ready for a change.

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