How To Choose the Right Windows 11 Upgrade Strategy

While Grow America no longer worries about the support cutoff deadline, many small businesses do, and they face a time crunch. When support ends for Windows 10 on Oct. 14, it will no longer provide free software updates, security patches or technical assistance for the operating system. 

Windows 10 still accounted for 21% of the OS footprint as of July 2024, when Forrester Research’s 2024 digital workplace survey was taken. While that percentage has certainly decreased since then, a sizable chunk of employers have yet to move to Windows 11, says Forrester analyst Andrew Hewitt.

But it’s not too late. Small employers still have time to migrate to Windows 11. They can purchase new computers with Windows 11 preinstalled, or they can upgrade current PCs to the latest OS, provided their existing hardware meets Microsoft’s minimum Windows 11 system requirements.

Check out this guide to Windows 11.

Windows 11 Upgrade Options as Deadline Looms

The greatest upgrade challenge for small businesses is a lack of hardware compatibility for Windows 11, but if the hardware supports Windows 11, the transition is usually easy, Hewitt says. “It does require some testing, especially for custom applications,” he adds.

Windows 11 offers enhanced security and a better user interface, among many other features, helping to improve productivity. It’s optimized for best performance on the latest hardware, so buying new Windows 11 PCs is a good investment if budget allows, according to Bob O’Donnell, president and chief analyst for TECHnalysis Research.

Today’s computers have a four- to five-year life span. Purchasing new computers with the latest specs future proofs organizations and makes it easier for them to take advantage of emerging artificial intelligence applications, such as the Microsoft Copilot generative AI tool, he says. In fact, when Forrester asked IT decision-makers why they were refreshing their computers, the top reason was to take advantage of AI on their hardware, Hewitt says.

“Even if they’re not going to use AI features immediately, they are prepped for the future by getting better PCs,” O’Donnell says.

Organizations that need more time to upgrade to Windows 11 do have a fallback option: Subscribe to Microsoft’s Extended Security Updates program, through which Microsoft will continue to provide security updates for a year.

RELATED: Streamline your upgrade to Windows 11.

How Grow America Transitioned to Windows 11

At Grow America, Palumbo migrated to Windows 11 by extensively testing the new OS before rolling it out to the organization’s nearly 100 employees, who work remotely across the United States and in offices in New York City and Cleveland.

The organization, which invests in affordable housing and creates jobs nationwide through small-business lending and training, is standardized on cloud-based applications, including Microsoft 365 and Adobe Creative Cloud. Palumbo, therefore, didn’t have to worry about existing software not working with the new OS.

“Our core applications are not dependent on a specific version of Windows,” he says. “They’re dependent on internet access.”

In summer 2022, Palumbo began equipping employees with new Lenovo ThinkPad laptops as their computers reached year three. He upgraded about three employee laptops a month until he completed the Windows 11 migration last summer.

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The migration was much easier than moving from Windows 7 to Windows 10, which had significant user interface changes and hardware driver incompatibilities, Palumbo says. By contrast, even though Windows 11 is a completely new OS, the changes are subtle.

“Windows 10 was a completely new aesthetic and required more hand-holding, while Windows 11 felt more like a cosmetic upgrade,” he says. “It wasn’t as big of a lift.”

Managing a mix of Windows 10 and Windows 11 machines during the migration was easy. Palumbo used Microsoft Endpoint Manager to manage the laptops and push software updates and security fixes to devices.

To ensure a smooth transition, Palumbo configured the new computers, tied them to employees’ Microsoft Entra ID accounts for single sign-on access and installed the necessary drivers.

After shipping them to employees’ homes, he says, he scheduled a meeting: “We carved out 30 minutes to show them around. I pointed out the changes in Windows 11 and I addressed their questions.”

How To Upgrade Existing PCs With Windows 11

The Broadway League took a different approach with its Windows 11 migration. While it did buy some new PCs, the national trade association for the Broadway theater industry largely upgraded existing Windows 10 computers with the new OS.

That’s because the organization upgrades PCs every five years, and most computers were still current, says Neal Freeman, the Broadway League’s chief digital and technology officer.

About 10 of its oldest computers didn’t meet Microsoft’s Windows 11 hardware standards. The organization replaced those aging PCs with new Lenovo Windows 11 desktops and laptops.

Freeman monitored usage for several weeks to make sure mission-critical software worked. The Broadway League relies on Microsoft 365, Adobe Acrobat and other software as it advocates for theater owners, negotiates labor agreements with unions and co-produces the Tony Awards.

The organization’s 34 full-time employees and a handful of interns found that the full suite of Microsoft software worked flawlessly after the migration, he says: “Windows 11 was mature by the time we implemented it, so we monitored it for a few weeks and determined it was OK to deploy it to the whole environment.”

The organization uses a managed service provider for tech support. In early 2024, Freeman worked with the MSP to load Windows 11 onto the remaining 30-plus computers.

There were a few hiccups, however. The new OS was a free download. The MSP used a patch management tool to remotely install Windows 11 Pro during off hours. The upgrade worked for most PCs, but about 10 devices would not take the update.

For those devices, Freeman used Windows Installation Assistant to manually install the OS on each computer. Even then, several would not update. “It would chug for an hour and say, ‘Something went wrong. Please try again,’” he recalls.

Through trial and error, the MSP pushed scripts that forced the remote installation to work.

“We worked out a process, and eventually it succeeded,” says Freeman, who completed the Windows 11 migration in early 2024. “It was a little frustrating, but it wasn’t difficult. We got it done.”