Windows 11: IT admin shares his upgrade experience

June 28th, 2022

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The launch of Windows 11 in October 2021 brought a fresh new UI onboard and was touted by Microsoft as a brand-new interface to put users’ content front and centre, featuring more accessibility features, and built for hybrid work. 

Paul Warren is an IT professional working in the M365 Modern Workplace space with a specific focus on Digital Transformation especially all things Insider (Windows, Office, Edge). He has experience working in the government sector as well as across multiple clients as a Solutions Consultant.

PB Tech spoke to Paul to hear his thoughts on the Windows 11 adoption trends he’s seen in the industry just under a year post-launch.

Months after the release of Windows 11, what's the response from enterprises regarding Windows 11 adoption, both from an admin and user perspective?

Paul: So naturally IT folks were keen to jump on board quickly. But I’ve noticed that one of the really cool things with technology being so out there these days, people have actually come to me and said, “When are we getting Windows 11?” 

Getting early adopters from both the technology and the business is really crucial for success. In my organisation, we have Pacific Island sites as well as sites in New Zealand.  A great example of this is half of our people in Fiji are now on Windows 11 because they were eager to make the transition. They just said, “We'd like to do this.”

With previous Windows operating system (OS) updates, do you feel like there's been the same level of enthusiasm and end-user knowledge around Windows 11 compared to Windows 10?

Paul: Yes. I think one of the things Windows 11 has going for it is it's got a fresh new user interface (UI) and there's a group of people who get excited about that and want to be able to experience this. Some people already have it at home. Businesses often lag, years or sometimes up to a decade behind with Windows. You look back to Windows XP, to Windows 7, and lots of businesses wait right up to the end of life to upgrade. From day one, Windows 10 came out with a constant “as-a-service” model. The twice-yearly upgrades with Windows 10 prior to 2022 and now yearly for both Windows 10 and Windows 11 mean that you can keep that cadence going. Upgrading Windows actually becomes, dare I say, quite easy. 

From an IT management standpoint, what have you found the experience of upgrading to Windows 11 to be like?

Paul: There are always going to be issues specific to every environment. I experienced issues, but I’ve also been able to address these issues relatively early by using Windows Insider builds before Windows 11 was released (and continue to do so for every future release of Windows 11). Being able to address issues quite early and get support from Microsoft has been crucial. Every place I’ve worked, I’ve run Insider programs, with the key reason being, that it buys more time to get in front of issues. A good example of this was a significant issue with Intune, Windows 11 and the VPN we use. We picked this up early in the Insider builds and worked with Microsoft to address the issues a lot earlier than would have happened if we waited for the GA release (this would have also impacted more people too). Being able to validate it before general release to the wider company is so important. 

What have been some of the worst-case scenarios you’ve had in your experiences upgrading previous operating systems?

Paul: The one top of mind is app compatibility. If you look at the upgrade from Windows XP to Windows 7, or Windows 7 to Windows 10, legacy applications have always struggled with those upgrades. But currently, if an app runs on Windows 10, it’s extremely likely that it's going to run on Windows 11. If you find that it doesn't, then Microsoft has a service called AppAssure to address that. If your organisation has enterprise licensing, Microsoft will help you with that and they'll do it for free.

From an admin perspective, how do you feel like Windows 11 ranks in terms of like the security and manageability controls? 

Paul: One of the key concerns around Windows 11 that a lot of people talk about is some older hardware can't run it. The main reason for that is Microsoft wanted to build an operating system that was secure by default rather than needing IT admins to turn things on. Things like Credential Guard are now enabled by default. 

The CPU family has to be of a recent generation. And these requirements are to cater for modern security threats going forward.

From an IT admin perspective, what are some of the reasons to upgrade to Windows 11?

Paul: There are other reasons to upgrade as well - the ability to access newer features in the operating system, features like Snap Layouts, being able to dock and undock and your screens staying where you left them. 

New accessibility features are also being highlighted. There's one that has just been released to Windows 11 that's going to provide live captions in the operating system. We've already got something like this in Microsoft Teams calls but this is now being extended to Windows, so as an example if you're watching a video on a corporate website with no subtitles, it will do that.  Live Captions will also work offline as well. Microsoft is really investing in accessibility features, which is awesome.

How do you deal with the challenges of getting your organisation to buy into a new operating system upgrade?

Paul: I’ve mentioned building up a community of champions who are keen to be early adopters.  I have a Champs group made up of people from all over the organisation and are people who really are keen to use new technology early. Being part of this group means there are going to be moments where things may not work at times, so having a tacit agreement where you go, “Hey, look, I'll get you on early, but there may be issues. You're going to have to tell me these issues and we'll work together to sort those out,” is key to being successful.

I use tools like Yammer Communities to keep the conversations going. I've got a Windows 11 community where I'm asking, “Hey, what's your favourite feature? How do you feel about Snap Layouts or Live Captions?”

Just asking probing questions as well as encouraging people to post if they're having problems helps. People in this community are now also starting to post tips etc, which really helps with adoption too. 

Another important challenge for a lot of organisations is these types of questions that need to be answered:

“Why do I have to upgrade?” or “What's in it for me?”

Having an idea of the answer before initiating the conversation to upgrade will help with breaking down the resistance that you might face because you will need to build a business case for it. 

Most will have the standard enhanced security, better real-time collaboration, and higher efficiency reasons, but being able to answer that “What’s in it for me” question is important, and this is where your insider community will give you insights to help build the case to upgrade.

Based on the feedback from your early adopters, do you feel like Microsoft has done a good job with Windows 11 in presenting an OS upgrade where there is something for everyone in terms of both the IT admins and the end users?

Paul: From an IT admin perspective, making things secure by default rather than having to go and turn features on is a really good call.  You're always going to get users who say, “I don't see the point of an upgrade”, or have a perspective of, “I'm just here. I get my cup of tea from the kitchen, I do my work, and then I go home,” and may very change-resistant.

But that group is getting smaller and smaller. I look at the younger generation coming through from university, they've got every device under the sun and they expect their workplace to be able to provide a modern operating system. 

Another change I encourage is moving from the old-school way of deploying applications along with exerting control over every single application installation, towards giving end users a bit more control of their devices and providing a mechanism where people can install their own applications from a Company Portal.  That’s something we can do now that we’re moving to Autopilot and using the OS that comes with the device rather than just baking apps into an image.

What are some of the biggest mistakes that companies tend to make when upgrading to a new operating system?

Paul: Assuming what people want rather than getting an understanding of what they actually expect – it’s so important to be engaging with your early adopters, understanding the user experience and what is working or not working for them.

For example, if or when this pandemic ever ends, people won’t be charging back into the office again. So, you're going to have to cater for people in this new hybrid work environment. 

Using management tools like Microsoft Endpoint Manager (Intune), I've been able to upgrade people's devices to Windows 11 while they're at home, or in places with bandwidth limitations.  But it’s more than just about being able to upgrade an operating system, using Intune really helps with maintaining and securing it along with providing a really great user experience.

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