Federal IT Leaders (left to right), Maj. Gen. Jacqueline D. McPhail; Luis Lopez; Vaughn Noga; Sid Sripada; and Joe Powers, share their Windows 11 migration journey.

May 20 2024

How Windows 10 Deployment Lessons Should Inform the Move to Windows 11

Experts from the Army, EPA, GSA, OPM and the Department of Education describe how they adapted their experience from 2019 to the current migration.

The journey to Windows 10 in 2019 was rocky for a number of federal agencies, especially given the looming deadline for Windows 7 end-of-support in early 2020. FedTech reached out to federal IT leaders and asked them what they learned from that experience that might apply to the move to Windows 11.

We talked to Maj. Gen. Jacqueline D. McPhail, director of architecture, operations, networks and space, U.S. Army; Luis Lopez, former CIO, Department of Education; Vaughn Noga, CIO, Environmental Protection Agency; Sid Sripada, division director in the Office of Digital Infrastructure Technologies, General Services Administration; and Joe Powers, associate CIO for enterprise infrastructure solutions, Office of Personnel Management.

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Communication Around Your Windows 11 Migration

Teamwork, collaboration and information sharing are essential to ensuring a smooth rollout.

  • “Maximize your user engagement, particularly in experience testing. Take their feedback and use it to tailor how you communicate about the migration to different business areas.” — Powers
  • “Invest in user training. You can move to a new OS where everything is improved, but people need to know what’s in it for them and how to put it to work.” — Lopez
  • “Collaboration among technicians ensures quick resolution of problems through near real-time information sharing.” — McPhail
  • “Communicate often within your agencies, even if it means sharing barriers to moving forward. The transparency provided by a roadmap helps internal communication tremendously.” — Sripada
  • “Develop a comprehensive communication strategy, including operations, IT management, leadership and management, and others. This will include the planned methodology and approach, tentative schedules and courtesy communication for labor unions and other stakeholders.” — Sripada

Planning Requires a Roadmap to Windows 11

Create a detailed roadmap that everyone can follow from start to finish.

  • “Make sure your help desk is prepared for the move. For this deployment, we rewrote our help desk support contract to include surge capability.” — Powers
  • “Plan for adequate lead time and funding to address technology needs and labor resources. We’re working to ensure sufficient upfront planning to reduce the migration window needed to complete the upgrades and streamline the process.” — Sripada
  • “You have to think about application rationalization. Are we currently paying for tools that we’ll no longer need once we have Windows 11? What new features or capabilities does the OS offer, and what should that mean for our IT portfolio?” — Lopez
  • “Establish hardware prerequisite planning early. We’ve already begun necessary Windows 11 hardware requirements gathering, and we’re performing market research activities to understand the marketplace for vendors, resellers and manufacturers, and the availability of hardware and software.” — Sripada
  • “We are collapsing organizational networks into a single service provider that can more easily migrate endpoint devices in bulk using automated tools. New endpoints added to the architecture will automatically be provisioned with Windows 11.” — McPhail

READ MORE: Get additional tips on how to ace your Windows 11 migration.

Thorough Testing that Starts Small and Scales

Identify potential issues early in the process by investing in a pilot program.

  • “We don't like to have people store files on their computers because we want to be able to upgrade them. If a computer breaks, we want to be able to drop another computer on your desk, and it should have all your files there. We sync to OneDrive so we can do upgrades fairly quickly.” — Noga
  • “Beyond laptops and other client devices, include accessory devices as part of your testing. Ensuring monitor, docking station, external camera and printer compatibility is as important as ensuring laptop compatibility.” — Sripada
  • “One of the things we’ve learned is that you have to prepare for it. Take the time up front. We generally pilot within the IT group before we actually deploy it more broadly.” — Noga


Windows 11 U.S. market share as of March 2024

Source: statcounter.com, “Desktop Windows Version Market Share United States of America, Mar 2023 - Mar 2024,” April 5, 2024

Deploying Windows 11 Is a Culture Shift

Pay attention to all of the details during the launch.

  • “Don’t underestimate what the deployment is going to take. We rolled out Office 365 and Windows 10 at the same time, and that was a lot of change for our customer base. This time around, it’s a stand-alone project. We’re focused only on Windows 11.” — Powers
  • “Before you change anything, it’s important to understand how the upgrade is going to affect the user experience. You can’t just say, ‘This new OS is going to work.’ At the least, it has to be comparable to what you had before, and it should be better.” — Lopez
  • “The biggest challenge in the earlier migration was the large number of disparate network and system owners, which increased the complexity of the migration. The Army has converged the majority of these separate organizational networks. We now have fewer network owners who will need to update systems during this migration.” — McPhail
  • “You can't be behind on your version of Microsoft because it becomes exceedingly difficult to do a transition if you're one or two revisions back. We, as a practice, try to maintain the current version.” — Noga
  • “We reinforced the importance of asset visibility and asset management for both hardware and software, along with the need to proactively manage lifecycle refresh processes.” — McPhail

You're Not Done After the Initial Deployment

Follow up with users post-deployment and provide support where it’s needed.

  • “The Army is leveraging a Windows 11–based VDI image to consistently implement software updates and security, and to ensure a seamless user experience between government-provided endpoints and BYOD endpoints.” — McPhail
  • “The Army has messaged the force to only buy Windows 11–compatible devices when purchasing Windows-based devices.” — McPhail
  • “Don’t forget about the post-migration work. You have to be available after you do the update to help people optimize the new system.” — Powers
  • “Make sure your customers know you’re there to support them and to help them when something isn’t working the way that it should.” — Lopez
T.J. Kirkpatrick (Noga) and Customer Supplied

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