3 simple rules for easily upgrading all your business PCs to Windows 11

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An absolutely fascinating report detailing how Microsoft’s IT team deployed Windows 11 for their employees was recently published. The gist is that Microsoft upgraded a staggering 190,000 devices to the latest Windows operating system in just five short weeks. While the speed and scale of this rollout is impressive—and as a consultant who’s deployed multiple corporate-wide Windows OS upgrades for many business customers over the past ten years—the fact this massive device upgrade had a 99 percent success rate is a remarkable accomplishment.

At a high level, there are three key learnings that every business small to large can glean from Microsoft’s own Windows 11 employee upgrade program. Those learnings are essentially rules that businesses can follow for their own upgrade program to get Windows 11 successfully onto all of their eligible devices. Most importantly, the same tools Microsoft IT used for their upgrade program can be used by any-sized businesses currently using Microsoft 365 Business Premium. By the end of this blog post, IT pros and entrepreneurs will know the 3 simple rules their business can follow to execute a proven, no-drama upgrade to Windows 11.

Windows 11 Upgrade Rule 1: Assess your IT environment and plan accordingly

Planning is crucial for any Windows OS upgrade rollout success. As we noted in a blog post published late last year, there are some devices that won’t meet the hardware requirements to install Windows 11. Not all of these devices have what most IT professionals would consider “old hardware,” but rather they lack an integrated Trusted Platform Module (TPM) to meet Windows 11’s stringent cyber-security requirements. Any devices without a TPM would be ineligible for the Windows 11 OS upgrade.

To help businesses quickly and easily find which corporate devices are eligible, Microsoft suggests using the Update Compliance tool to automatically scan all Windows 10 devices and assess if the device has a working TPM 2.0 along with flagging any other potential “gotchas” before upgrading. The Update Compliance tool is delivered via the cloud and is available at no added charge in the Microsoft Azure Active Directory portal for all Microsoft 365 Business Premium subscribers. That means if your small business has Microsoft 365 Business Premium, then you already have the same tools the global Microsoft IT organization used to find which of their hundreds of thousands of employee devices were upgradable.

Amaxra recommends that any Windows 10 devices found to be ineligible for a Windows 11 upgrade using the Update Compliance tool be flagged for replacement during your company’s next scheduled hardware refresh. Our consultants do not currently suggest remove a working Windows 10 device because we’ve found those legacy devices can continue to run alongside upgraded Windows 11 devices on our customers’ corporate networks. One scenario Amaxra uses to explain it is if your company has 100 total employees and you run the Update Compliance tool to assess your IT environment. Over the course of the past three years, 80 employees have received devices eligible for the Windows 11 upgrade, but 20 employees are found by the Update Compliance tool to have ineligible Windows 10 devices—and your company budget does not allow for buying new PCs until the next fiscal year. Amaxra recommends keeping those 20 employees on Windows 10, upgrading the 80 employees to Windows 11, running Windows 10 and 11 devices in parallel until you can buy the 20 employees new devices built specifically for Windows 11.

Windows 11 Upgrade Rule 2: Automate and communicate your OS upgrade strategy

Compared to previous Windows OS upgrade rollouts, the automation tools available to businesses have never been better quality, faster performing, and less costly than today. Similar to the Update Compliance tool, all Microsoft 365 Business Premium subscribers can use the included Windows Update for Business deployment service. This cloud-based tool empowers IT managers to deploy automated Windows 11 OS upgrades to specific devices during specified timelines. Microsoft notes in their report that the 99% upgrade success rate could be directly attributed to how the Windows Update for Business deployment service leveraged rich data gathered about devices from the Update Compliance tool. The deployment service knew exactly which devices were eligible for the Windows 11 upgrade, which devices weren’t, and all the IT team had to do was schedule the deployment during times that were most convenient for the employees.

Knowing those “times that were most convenient for the employees” to get their devices upgraded to Windows 11 is an important part of the deployment. Every business is unique, and it’s incumbent upon the corporate leaders in both IT and operations to communicate to employees exactly when a Windows 11 OS upgrade will occur—and how long it can be expected to take. Amaxra recommends preparing not just a timeline for the OS deployment, but also a plan for communicating the deployment timeline to all employees.

Windows 11 Upgrade Rule 3: Acclimate employees to using Windows 11

Once you’ve assessed your IT environment and planned out your Windows 11 upgrade strategy, Amaxra suggests offering “what to expect” resources available to employees via email and your corporate intranet that outlines the subtle differences in the Windows 11 user interface compared to Windows 10. Even though most Windows 11 user interface changes help user productivity, some employees don’t like any changes no matter how small. The most successful Windows 11 corporate upgrades are the ones where your employees are doing their best work rather than opening trouble tickets with your IT staff to ask: “Why is the start button on the center of my taskbar on Windows 11?”

While large enterprises often have dedicated staff for employee education, many small to midsized businesses (SMBs) do not. One useful and free resource Amaxra recommends SMBs to use is Microsoft’s overview of the enhanced productivity features in Windows 11.

Amaxra can help your SMB plan out your Windows 11 upgrade strategy

These 3 simple rules for a companywide upgrade to Windows 11 are proven by Microsoft’s own IT organization. However, the consultants at Amaxra know IT resources for SMBs are typically limited and precious. We know this blog post can help put you on a path to successfully rolling out Windows 11 at your company, but we also recognize that some SMBs could use a little more guidance during that upgrade journey.

Amaxra is a Gold-level Microsoft partner with expert consultants to help you deploy Windows 11 upgrades and other cloud-powered business solutions.