Get in shape for your Windows 10 migration: 7 things CIOs need to know

By David Smith, - AdviceEmployee experienceInsightProductivity

Talk to someone who’s run a marathon, the last thing you expect them to say at the finishing line is, “I want to run another marathon” (they usually change their mind later!). But that’s exactly how a lot of IT leaders feel post-Windows 7 or 8 upgrade, when somebody says, “when are we upgrading to Windows 10”?

With Windows XP consigned to history after 12 glorious years, many companies have now migrated to Windows 7 and to a lesser extent Windows 8. But Windows 10 offers so much more than an improved look and feel. Outside of headline features like Windows Hello, it’s been built from the ground up as an ‘evergreen’, extendible platform

With dozens of good reasons to migrate to Windows 10, here’s a list of seven things for CIOs and other IT leaders to think about:

  1. It’s never “just an OS upgrade”

Microsoft calls Windows 10 its last ever operating system, as it’ll be adopting an evergreen approach from here on – essentially moving to a “Windows as a Service” model. But you’ve still got to get everyone on it in the first place.

Let’s be honest, an OS upgrade isn’t a straightforward migration so consider the scale of the task before racing ahead. Because OS upgrades typically occur every few years, the list of dependencies that later come to light just seems to keep on growing. These usually include topics such as security, application lifecycle challenges, testing, training and communications. There’s no need to press the panic button, but just acknowledge that your move to Windows 10 is going to require a transformation programme, so take time to plan ahead.

  1. Take the long view to budget

With Windows 10, Microsoft wants to move you out of the infrequent upgrade cycle and get you to a process of continuous updates. That sounds very sensible, but the flipside is that there aren’t compelling events that force you to get the funding to address the next major IT refresh.

What this means for Windows 10 is taking a different approach to your budget. Firstly it signals a shift from large capital intense programmes, to multiple projects on a smaller scale and an OpEx approach to budgeting.

As it takes time for organizations to adapt to change, it’s important to consider what the ‘must-haves’ are for the transformation programme. This isn’t just a Windows 10 conversation around things like biometrics and data leakage prevention, but other perhaps long-overdue fixes for teams and processes across the enterprise.

  1. How does ‘as a service’ work for you?

How does Windows Update for Business, or Windows as a Service, work with your IT team’s ways of working?

Yes, there are cost savings to be made adopting these solutions, but they both come with a sting in the tail in the form of increased pressure around investing in application lifecycle management.

The key point here is that you’ll need to audit your apps – including the bespoke apps that are individual to your business – early in the process. And don’t forget the 3rd party apps you’ve bought ‘off the shelf’. This also extends to the teams, processes and systems that support them. It pays to work with a provider who understands this and is able to review your IT estate first.

  1. How do the new security features fit in?

Microsoft has put a lot of investment in to bringing Windows 10’s native security features up to the standards required by business.  In the past, services such as strong authentication, encryption and data leakage prevention required 3rd party products, complex security design and integration. Often this was at the expense of end user experience, “pushing” users to work around the system to get their jobs done rather than work within the services that had been designed to protect them.

Windows 10 could be an opportunity to consolidate security product vendors and to improve the end-user experience of your digital workplace. To achieve any simplification, you’ll need to build a picture of whether Windows 10 meets your current security policies, and if the built-in features are a match for the defenses you have in place today.  However, user behavior remains the key to understanding whether we have raised the overall security standards of our enterprises. There’s little point in building a wall so high around your services that no one can use them.

  1. End-user attitudes to new biometric security features

Yes, the new security features are extremely attractive. Just consider the password headache for most IT departments, where around 30% of help desk calls are for password related issues. These could be eliminated with Windows Hello.

But we mustn’t forget the end-users here. How do they feel about biometrics?  Could user adoption rates prevent us from realizing the potential cost savings and productivity benefits that biometrics promises?  You only have to scan the media (see the latest piece on Wired) to see that for many, end-user biometrics sound like an invasive technology, requiring them to surrender a little more of themselves and their privacy.  You’ll need to have a plan in place to explain the benefits and the safeguards you have in place to ensure they feel comfortable and in control.

Good internal communications and governance remain key factors for a successful implementation, so seek advice from companies who have handled this before. From a biometric perspective, the success or failure of your Windows 10 migration hinges on how your users take to it.

  1. How can you make the end-user’s experience better?

Review the opportunities to enhance the services you provide to your end-users. Windows 10 offers a chance to give them an experience that resembles what they see in their consumer lives. This familiarity improves adoption rates and provides a more enjoyable experience for end-users.

In turn, this will lead to a more productive and collaborative workforce – a win-win for end-users and customers.

Take the new joiner experience, for example. In many companies, this is a clunky process. But imagine if you just gave new employees an email address, the budget to go out and buy a new laptop, and then when they take it home and login, everything’s automatically configured for them when they switch it on for the first time. Windows 10 can accommodate this scenario, in a secure and seamless way.

  1. Get your head around Microsoft licensing

Microsoft has a reputation for complex licensing arrangements and while I believe it has been simplified, it does help to get advice to make sure you’re getting the most out of your agreement.

Many CIOs need to prepare for the renewal of their enterprise agreement now as many contracts will finish in June (when Microsoft’s financial year ends). It’s not long to get organized, so now’s the time to get help from a company who knows its way around the various licensing options – and the implications for going down certain routes.

Review what you’re using now, be realistic about your upgrade path and focus on where you want to be in a year and three years’ time.


As you can see there’s a lot to think about when upgrading to Windows 10. Going back to the marathon analogy, you’ve got to put your training in before the big race. Working with a good coach can make all the difference. A coach who has previous experience with other runners, knows the course inside out and is able to provide an outside perspective.

So, if you’re looking for a ‘Windows 10 migration coach’, we’re here to help.

For more information, why not head over to our Windows 10 Migration for Business page or check out our Windows 10 Migration Guide.

My colleague Robin Lipscomb also gives further thoughts about how Windows 10 is putting us on a path towards a secure workplace. Click here for the next blog post in the series that looks at the future digital workplace .

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