Windows as a Service – User responsibility and interaction

This will be the first post in my series on What you need to do if you want to adopt Windows as a Service. The reason for it is quiet simple – my lab is building as we speak. So, ill start with perhaps the most important step you need to take to successfully implement WaaS in your organization. And its not even a technical one. Most likely ill quote this post in the following once as well, because this is what it comes down to in the end.

But first, what challenges lies ahead for our end-users and for us as IT-pros when it comes to keeping them happy with WaaS (or Windows Servicing)? I can see a few:

  • Training – With new features coming out with every single Windows release end-users will need constant training. And from experience and several migrations between Windows versions, its hard to give end-users the training they need with a 3-5 year interval. How should we manage it now when we get a new version (at a minimum) each year?
  • Application compatibility – This may not sound like an end-user issue, but of course it is. Nothing annoys and stresses users as not being able to do their work. And who gets blamed when something brakes due to a faulty update or upgrade from Microsoft? IT of course.
  • Waste of money and low ROI – All new features sounds wonderful, and I bet your organization can save a lot of money by implementing them, but its not free or cheap to implement something. And if we see issues with training (above) how should your organization get the expected ROI?
  • Added complexity – Today most software and services are not purchased by the IT-department. Its usually other departments that signs up and pays for them – and then (if needed) let IT-manage them. Previously it was kind of easy to look at a service see the “Windows 7 certified” stamp and buy it. Now, the software or service needs to support the WaaS model. It may not be that hard when it comes to some web services (though, Edge could prove difficult) but software that runs on a device running Windows 10 will be more complex to buy then before.
  • Disturbance due to updates and upgrades – Something I always here from end-users are: “Do not, under any circumstance, reboot my device while I’m working!” and “You cant reinstall our machines, it will take a long time and it will take weeks until we are back on track.” And theses quotes are from migrations from Windows XP to Windows 7! How do you think the same end-users will react on having to install a new OS at least once every year? And updates? Large updates… How to cope with them?
  • Demand on higher degree on user interaction – And last but not least, and the point that I’ll build most on the remaining post on. Not only should the end-users accept being disturbed more often, with new updates and operating system deployments. IT will also ask them to do more to help IT?!

So, with those issues up in the air, what to do? And – I want to make sure you understand my point. I believe that I have solutions for every single challenge above – they are there to show you what questions you probably will face in your own environment, if you aren’t already. Now, let’s go and give you some answers:

Application Knowledge, Responsibility and testing


The first challenge I want to address is perhaps the biggest of them all – and Ill get back to this one in another post in this series, but then from a technical perspective. How can we create an WaaS based environment with high availability, the performance and the functionality the end-users are expecting?

Lets begin with trust. I’ve always said that there are one organization that always will take the biggest risk with the WaaS model – and that’s Microsoft. If WaaS don’t work, if applications and services starts malfunctioning after a new Windows release, organizations will start looking at alternatives. It’s in Microsofts interest that everything works as good as possible. At the time of writing, I do believe that Microsoft still has a way to go before everything is fine and dandy. Even if they are, very, rare – I hear customers that have applications and drivers crashing after a Windows upgrade from one Windows 10 release to another.

And that wont be acceptable in the long run.

But to reach the point were new Windows releases are stable, and not causes issues for our end-users both Microsoft and us as partners and customers to them needs to do our homework. I won’t open the box on responsibility here, should Microsoft or applications vendors adapt? Its a hen & egg questions again. There are however things we can do today.

An issue I face in every single migration project I get involved in is lack of knowledge around applications. Many IT-departments have a decent overview on what applications that are running in their organization, but they know very little about them. They usually know how to install them and which server a client-server application uses. But in many cases, not more than that. And in my opinion, they shouldn’t! Its not fair on IT-departments to demand that they need to understand each and every application, because in most cases they are not involved when a new software is bought somewhere else in the organization.

So – its important that when you embrace the WaaS model, you also find someone in the organization that knows each application. Usually, this or theses people don’t work in IT, but they know how the application is used and how it supposed to work. Now, you know who to contact if something seems to be wrong with an application. And no, this person shouldn’t necessarily be a kind of “second line support”, but its more important than ever to understand the organization you work in and their needs.

With knowledge comes responsibility. Again, this may or may not be the same person but its vital that each and every application have an owner. Someone that are responsible for the application, how know how to contact the vendor and have a responsibility to report to IT when something seems wrong, especially after a OS-upgrade.

That brings us in to a cornerstone in the WaaS model in your organization. Its impossible to do a full-out test of all applications each time a new Windows version is released. I do encourage my customers to not do that in their migration projects as well. Instead of assuming that all applications will be incompatible with the new OS (which is basically what you say when you want to test them all) – assume that they are compatible. You can read more about this in my previous post on the Fail Fast approach. But this way of managing your migration projects needs to become a part of you everyday work as well. You can look at the migration project as a pilot for how I believe you need to work in your organization moving forward. When the project ends, some of the roles in the fail fast approach may disappear (Project Managers etc) but the process it self and perhaps even the task force need to exist after the project has ended. Instead of a project manager you may have someone with responsibility for an application, or a SDM, a help desk manager, problem manager, incident manager or whatever doing that work. And your end users needs to be aware of this.

The end-users needs to know that they are responsible to report any issues that may arise after and update or an upgrade. Its no longer OK to think about an issue like this: “Someone else will report on it and IT just has to solve it, ill sit here and wait.” Unfortunally I know that this way of thinking isnt uncommon, but its something that has been left behind from an era where IT knew everything about the IT-environment, and that’s not where we are today.

So, a practical way of looking at it:

  1. Make sure you end-users KNOW when a new update or upgrade is deployed.
  2. Use a ring approach (more on that later on and in other parts of this series) to catch all applications as soon as possible with minimal disturbance of end-users.
  3. Ensure that the users know to whom, when and what to report if something isn’t working as intended after an update or upgrade.
  4. And make sure that the end-users know that it will be taken care of as soon as possible.
  5. Pause, stop or reorder the roll out so that end-users that have the malfunctioning application don’t get the update or upgrade causing it until its resolved.
  6. Have a continuous dialog with the end-user(s) that reported the issue on your progress and especially when you believe that it has been resolved.
  7. And, last but not least, show gratitude to the user(s) that reported the challenge and let them know that what they have done is important for the entire organization.

As I see it, this is the only manageable, time & money-effective way of managing applications in a WaaS environment. And I could almost promise you that this in the long run will save you money compared to the massive application-testing-projects that we usually see in our migration projects.

And how can we get this knowledge and information out in your organization?

Ambassadors and internal evangelist


To be honest, and please correct me if you believe that I’m wrong, most IT-departments today don’t have such a good reputation in their own organizations. Its not because they are doing a bad job, on the contrary. My experience are that most IT-departments are passionate about their organization and do everything in their power to support the rest of their organization. So, why don’t they have hero-status? Mostly because of a lack of dialog between the IT-department and the rest of the organization, which I’ll come back to further down in this post.

But, now, imagine that you would like to introduce something new in your organization. Something that will change how IT-manages devices, apps and users and that will affect the end-users. How would you communicate this to the organization? Again, many end-users lacks the trust to the IT-department and their experience is usually not to good when it comes to IT changing stuff. So, who do they trust? The answer is simple, they trust their peers.

So, to successfully market Windows 10 and Windows as a Service (because this is pure and simple internal marketing) we need to find users that knows the organization and each individual department. That understands their challenges and are willing to promote your new platform and management style.

When I work in migration projects I usually recommend that first and foremost look at organizational knowledge and understanding rather than technical knowledge. The reason is simple (and this is the most important piece of advice in this entire series):

End-users always needs a WHY. Why is this changing & why should I be interested in promoting it?

Without a why, you will never be successful in implementing Windows 10 in your organization. And the best people to help you create that why is your future ambassadors or evangelist. They can see, if you explain the tech to them, how this could benefit their individual departments. That in return will help them to carry out the word on why this is happening and how each end-users could benefit from it. That will make a change in a migration. It will create a need in the organization that they weren’t aware of before, but they always had the need.

So, the role of the ambassador(s) is to give insight to the IT-department on the needs of the organization. They’ll add valuable information on how, when and who to migrate and manage Windows 10. The end-users will see the ambassador(s) as just that – their voice.

The ambassadors will also promote the technology, or rather the use of it, in the organization and ensure that the end-users understands how and why they should help IT manage the platform (for example from an application perspective as stated above).

I would also encourage IT-departments to be transparent to the ambassadors. Tell them about the challenges, the choices that needs to be made, the questions you  can’t answer. This will build trust, and that’s truly vital for a successful WaaS implementation.

Training and user adoption

Moving on to training. I’m an MCT and training, education and knowledge-sharing has always been something that I’ve loved to do. But the ear of classroom training sessions is almost over. So, with Windows 10 and Windows as a Service we need to find new ways of training our end-users (and IT, but that’s out of scope for this part of the series) in a continuous way.

The ambassadors (above) will have an important role in this as well. Because they now what’s important for their respective department they can help you do what Microsoft does: Choose Hero-features.

Each Windows version (and Windows 10 in itself) consists of a huge number of new features and functions, large and small. Its impossible to train all users on all features and functions – and for Microsoft its impossible to market everything. Therefore you have the choose the features that are most important to each part of your organization – and start by training them on that. These features is usually called hero-features, because they will make an instant change (and improvement) to the end-users day-to-day work. Because these hero-features are tailored to each organizational part based on their needs, it will also ensure that the ROI of the training is fast and high. The user adoption will be higher when you put the training into context and show the users why to use it as well as how.

The training should be accessible for all users and easy to use – without demanding a large investment of time. I have good experience with Nano-learning, but also with short videos (5- 7 minutes at most) in an internal video-channel for example. This will ensure that users actually do their training (and yes, you should choose a way to deliver the training so its possible for you to follow-up on is).

After each introduction of hero-features its also important to have the ambassadors talk about it and using the features in their day-to-day work. This will inspire other as well. And if a user feels comfortable with a new hero feature, they will usually move on by themselves (if they feel the need) and adopt other features of the OS or application = higher user adoption, better ROI and more happy users.


Self-service and “choose your ring”

In the old days a migration from, for example, XP to Windows 7 wasn’t a choice – it was something that was force on the end-users. In some ways, so are Windows 10 – but it doesn’t mean that we cant enable the users to have a choice. An illusion of choice is better than no choice at all.

That’s why self-service in one way or another is mandatory in the projects I’m involved in. It can be self-service for the project only or that we start the implementation of a self-service solution parallel to the Windows migration.

The most common services I encourage to provide to end-users are:

  • Choose when to migrate your PC from what you have to Windows 10. This will ensure that the migration is done when it suits the user and will save you some time and money by not having to send out technician to aid the users.
  • Self-service of applications. Migration projects are a good time to remove unused applications or upgrade old once. Instead of doing a huge job (which in many cases of course can be automated) with inventory and users/pc-application mapping – the end-users choose applications by themselves.
  • Upgrade your PC. The next step after the migration, and useful both when doing Windows Servicing or Upgrades using task sequence.
  • Choose your own ring. I strongly encourage you to use at least a few internal rings in your organization for migrations, upgrades and  updates of Windows. To enable the users to choose what ring they want’s to end up on, your are empowering them to manage their own PC. If a user always want’s to be the last one to receive updates for some reason, let them. Or if someone that are really interested in new technology (even people outside of IT are) let them be in the CB-branch. The choice is important and you will get happier end-users as a result.

And you could of course add even more services to your self-service solution (or solutions).

User feedback

Last, but not least – to be honest perhaps the most important subject is user feedback. From the start of the migration project and continuously after that – you need to get real end-user feedback.

To find you Why (ambassadors section) you need to learn from your users. To get the how you need to ask what’s best for them – as well as when its suitable to do something. I know from experience that Finance/accounting rarely wants to reinstall their machines close to the end of a quarter or year. In education you burn a lot of bridges by suggesting a migration in the end of a semester and so on.

To create trust and a better environment both for you in IT and the rest of your organization you need to have a genuine dialog. Listen to what users has to say, and don’t let that feedback disappear into a large black hole. Take your time to explain why you do some things but, even more importantly, also explain why you don’t do other things. In my experience IT-departments are to restrictive when it comes to explaining their pains and challenges. This only creates an image of IT as uninterested and boring – so start being transparent.

Value your end-user feedback and show them that it is valuable. I promise you that you will see an increased trust and user happiness if you start listening and talking to users. And can also promise that you will get inspiring challenges to solve, pushing your technical knowledge to the limit. Which is something I know that many IT-pros would like to do more often.


So, how can we start a dialog? The best way is to create a group at the start of a Windows 10 migration project. They usually consists of users that are potential ambassadors, but the essential thing is that they know your organization. Sit down with them, explain your thoughts on the coming project and then ask them what they would like to gain from it. Embrace their feedback and add it to your project objectives. Ensure that they always have someone to contact in the project during the time and invite them to review your delivery during the creation process.

When the project is finalized, create a good way for end-users to give you continuous feedback and have regular meetings with the group (or a group) that was involved from the start. Ask, listen, reject (and explain why) or embrace the information and implement solutions in an never-ending process of feedback.


This is the first post out of many on how to successfully embrace the WaaS model of Windows 10. It’s probably the least technical one, but perhaps also the most important. To sum things up I would say that there are three things to take away:

  • Open up the dialog with your organization. Both you and the end-users will get a better environment in the long run.
  • Ensure that each application have someone that takes responsibility for it and have knowledge on how its actually used.
  • Enable your users to do more and give them the power (or illusion – your choice) to decide more for themselves.

I have addressed all the challenges that I started of with in this post, and given you advices on how to change the way you involve your end-users. Ensure that these “soft” parts are in-place early in your implementation – but if you are done already or have just started, its not to late.

Please let me know if you would like me to explain anything in more detail or if there’s something I have left out.

Next post will probably be up next week, but the topic isn’t decided yet. What’s most important to you? If you want to know more, start by reading my post on: What you need to do if you want to adopt Windows as a Service – which will be the focal point of this series.




As a Solution Architect, Simon inspires customers, partners and colleagues to create the best possible workplace for their users. His main focus is the Windows platform – but todays workplace consists of so much more than that. As an MCT he is passionate about teaching and sharing knowledge. He’s a frequent speaker, blogger and podcaster – as well as a penguin fanatic.

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Posted in Application Management, Microsoft, Training, Windows 10, Windows as a Service
One comment on “Windows as a Service – User responsibility and interaction
  1. […] Windows as a Service – User responsibility and interaction […]

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