5 IT experts reveal their Windows 10 upgrade strategies

You wouldn’t think there’d be much of a debate about something that’s free. This summer, when Microsoft released Windows 10 and made it available as a free upgrade – and subsequently setting a new record for user adoption of a new computer operating system – many IT executives took a deep breath. Free is never free. There are support costs, management issues, security problems and a host of other deployment snafus that can crop up. 

Yet, the new OS is a major step forward. Microsoft resolved many of the troubling usability issues that plagued Windows 8, such as a confusing “tile” interface and hard-to-find settings. Many features – including a more streamlined update process that won’t interfere as much with daily work – are designed for the enterprise. It’s even easier to do “in place” upgrades. 

To help put the finishing touches on your upgrade strategy, CIO.com talked to several experts (including those at Microsoft) about how to make a deployment as smooth as possible. We asked about general guidelines, security issues, usability, training and other considerations for enterprise users. Here’s what we found out. 

Most of the experts agreed that the most important reason to upgrade has to do with how the new OS is designed to run the same on many platforms, from laptops to phones to tablets. That’s a major consideration for deployment in the modern office environment. 

[Related: User guide to Windows 10

“The ability to run and manage different form-factors with the same operating system will increase the presence of Windows tablets and phones within organizations,” says Thomas Koll, the CEO of Laplink Software, a migration tool. “After the surge of tablets for ‘quick and easy use’ the need for integrated devices will grow. Enterprise apps can be built once and deployed (and optimized) for all devices, although it is not necessarily that easy.” 

Charles King, an analyst with PUND-IT, says another benefit is that Microsoft worked closely with Intel to make sure the new OS matches up with future CPUs, like the sixth-generation Intel Core processor. That means end-users will experience a speed boost since Windows 10 is optimized for that chipset once it becomes available. 

One of the biggest changes related to deployment, however, has to do with in-place installs. Jim Alkove, the corporate vice president for Windows Enterprise and Security at Microsoft, says the new operating system does not require IT staffers to do a clean install, and that this applies to every device in the organization, not just enterprise desktops and laptops. 

“Windows 10 can help end ‘wipe and replace’ deployments of the past with streamlined in-place upgrades and high application compatibility,” he says. “We’ve significantly improved deployment and device management in Windows 10. We offer a unified Mobile Device Management (MDM) platform across all Windows 10 devices, from phones to laptops to IoT devices.” 

Security issues always come to the forefront with any new OS. Hackers know there are vulnerabilities to exploit after initial release, so any good deployment has to include monitoring and analysis to see if there are any new attacks. Interestingly, with this OS roll-out, some of the security issues are related to Microsoft’s own policies and update schedule. 

Frank Palermo, senior vice president for the Technical Solutions Group at the IT consulting company Virtusa says the wording of the policy suggests that the intent is to protect personal data when it makes sense to do so. (Reading between the lines, it means Microsoft still has to turn over the data is there is a federal request related to a crime.) Palermo says there are other concerns about how Microsoft plans to use end-user data for advertising. 

“Things like browser history, favorites and even passwords are now automatically synchronized to Microsoft’s servers,” he says. “There are also concerns over customized ads. That’s because each Windows 10 device is now branded with a unique advertising ID to let ad networks profile users.” 

King says Microsoft sees Windows as a service now, similar to a cloud app in the enterprise. That means more updates in the background to address features and security issues, many of which might not be as obvious to end-users. That’s a good thing, he says, in terms of protecting data and minimizing exploits, but could become an issue for early adopters who have to put up with multiple updates in the first few weeks and months. There could be interface changes as well, which could impact training and usability in the next few months and into 2016. 

Microsoft has made Windows 10 much easier to use than Windows 8. Settings are now available through the Start menu (you can even right-click to access them faster). The operating system can switch automatically between tablet mode and desktop mode depending on the device you use. For example, if you use an HP Elite x2 laptop, you can remove the screen and use it as a tablet; the OS automatically switches to tablet mode with full-screen tiles and apps. 

[Related: Who's upgrading to Windows 10

All of the analysts agreed that this is a major step forward and should ease deployments. End-users won’t be as confused and won’t need as much training. Koll says many large enterprises did not even deploy Windows 8, and since Windows 10 brings back the Start menu, they can skip the entire debacle of training for the tile interface. 

That said, Palermo says IT leaders should still address usability directly. 

“Business leaders that decide to upgrade their company systems should schedule a training session with employees to go over the differences between Windows 10 and their previous OS,” he says. “This will not only create a more seamless transition, but it will also help companies maximize the benefits of Windows 10 to improve performance across their organization.” 

Other than the benefits to consider during roll-out, any security issues and the training opportunities, there are a few other important factors. Chris Miller, the CIO at managed service provider and Microsoft partner Avanade, says to look closely at business application migration. He suggests picking a few important business apps that will be the easiest to migrate to the new platform and create a deployment strategy around them. 

“Despite significant efforts by Microsoft to foster compatibility, we expect that some applications and devices may have issues with Windows 10,” he says. 

King says companies should do an inventory of all existing computers and mobile devices. This is an important step, he says, in knowing how the OS will impact business operations. Some older computers might still be running Windows Vista or Windows 7 and might not even support Windows 10. In other cases, users might need extra training for the new interface.


John Brandon

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