Midmarket IT Leaders Share Strategies On Upgrading To Windows 11

IT executives have either overseen or have plans in place to move their organizations to Windows 11 as Windows 10’s end-of-life nears.

With Windows 10’s end-of-life date just weeks away on Oct. 14, 2025, it seems some organizations are still scrambling to get devices updated.

A recent report from Stat Counter stated that Windows 11 now commands 51.77 percent of the global Windows market share, meaning a significant percentage of devices are still running Windows 10.

Several IT leaders at midmarket organizations shared their strategies on how they are upgrading to Windows 11. Some are overseeing upgrades that involve hundreds of devices.

Overall, most of the leaders said they were taking a gradual approach.

Upgrading To Windows 11: ‘Rush To The Finish Line’

“We have about 350 devices to update and will push that out 50 devices a week,” said James Gephart, vice president of IT and CISO at Passavant Memorial Homes Family of Services.

Gephart said the company is expediting the process because it has “automated the push to upgrade all of our devices.”

Srini Chittamuru, CIO of Movado Group, completed the migration six months ago. Chittamuru said that the company also took a methodical approach to the upgrade. First, the IT team began by rolling out Windows 11 to any new laptops or desktops. Then came the next step—dealing with existing devices.

“Once the OEMs publish the end dates, we start planning and get ourselves aligned with that date,” Chittamuru said. The team created targets by quarter and by week and was able to complete the upgrade, Chittamuru said.

Another IT leader also said his team was conducting a slower rollout. “We’re a nonprofit with limited resources for both staff and technology,” said Ian Brown, director of IT at The Arc Mid-Hudson.

Brown said the rollout was also impeded by the fact that, “We still have hardware that will not run Windows 11 and we are slowly replacing those.”

Brown is not alone in that issue. Windows 11 has some specific hardware requirements that include 1GHz or faster processor with two or more cores on a compatible 64-bit processor or System on a Chip (SoC), graphics card with DirectX 12 or later with a WDDM 2.0 driver, system firmware that features UEFI and is Secure Boot capable, as well as Trusted Platform Module (TPM) version 2.0.

Some concerns about the hardware requirements may have pushed Microsoft to finally offer some temporary relief to organizations that may not have the immediate funds to upgrade or replace devices as needed.

Last month, Microsoft announced its Enable Extended Security Updates (ESU) program, which offers security updates for Windows 10 devices while organizations are enrolled. The program is set to run for three years.

Some IT leaders may find it more of a cost savings to replace legacy devices.

“We retired all Windows 10 machines earlier this year. It was a pretty seamless rollout. New laptops/replacements were all Windows 11, and we did a push in January to move the 30 remaining Windows 10 machines to 11,” said Dawn Marcova, vice president of IT at BFC Solutions.