After a decade-long run, Microsoft will be ending support for the Windows 10 operating system in October 2025. That means the clock is ticking for businesses who haven’t yet upgraded to Windows 11.
The benefits of upgrading to Windows 11 are clear, as are the consequences of sticking with an outdated and unsupported operating system. But migrating to a new version of Windows is rarely as simple as clicking a few buttons, especially for large enterprise businesses with thousands of devices and users.
With this in mind, here are six of the most important steps we follow at Pomeroy whenever we help one of our clients plan and execute their big move.
Assessing your readiness
Getting ready for migration can be a major technical and organizational challenge. On the technical side, you’ll first need to identify any hardware, firmware or software that may cause problems. Often these problems come from old peripheral devices whose drivers won’t recognize a new operating system, or custom software applications that glitch and fail in a new environment. Depending on the number of devices and configurations in circulation, these problems will quickly add up if they aren’t discovered
and dealt with at the beginning of the process.
On the organizational side, it’s also very important to make a formal “deployment plan.” This plan helps eliminate surprises by clearly outlining the timeline, resources and steps involved in the upgrade process, including the most suitable deployment method (in-place upgrades, clean installation, etc.).
Remediating your problems
Once you’ve uncovered your hardware and software problems, you’ll need a plan for solving them before you make the move to Windows 11. Remediation is highly specific to each organization, but common steps include upgrading your system wherever possible and procuring new hardware or software when necessary to eliminate conflicts.
If problem software is business critical or especially difficult to replace, we also help our clients “virtualize” their applications, uncoupling them from the underlying operating system and allowing them to run from any device with an internet connection.
Testing your environment
Before jumping into a full migration, we recommend selecting a small group of pilot users or departments to test Windows 11 in a real-world environment. Feedback from these pilot users will often catch unexpected problems—such as software incompatibility or poorly performing devices—before rolling out the upgrade to the entire organization.
Once you’ve ensured all security features are working well with your pilot group, you may also consider spot testing the Windows 10 “rollback” process on a few devices. This works like a safety net and can be useful if something goes unexpectedly wrong during migration.
Training your users
Pre-migration is the best time to start familiarizing your users with the new features and functionalities of Windows 11. We recommend providing training sessions and access to resources users can access at their own convenience.
Not only does solid training help ensure employees are informed and prepared for the transition, but it also helps them take full advantage of Windows 11 and harness its new features to improve productivity and collaboration.
Streamlining your migration
When it’s finally time to migrate, one of the best ways to minimize disruption is to schedule your upgrades during off-peak hours. But there are so many other variables to consider.
What deployment tools will you use (SCCM, Intune, etc.)? How will you ensure security measures (encryption, antivirus software, firewalls etc.) are configured and up to date on your upgraded devices? The answers to these questions can often make the difference between a smooth migration, and a logistical trainwreck.
Monitoring your system
The work doesn’t stop once your devices are upgraded. You’ll also need a plan to gather post-upgrade user feedback and provide ongoing support and assistance to address any issues that may arise.
It’s also important to closely monitor your post-migration system performance and user feedback to identify and resolve any unexpected issues (spoiler alert: there are always a few). And of course, you’ll need to implement a process for regularly updating and patching your new fleet of Windows 11 devices to maintain security and stability into the future.
With all these moving pieces, it’s no surprise many businesses rely on experienced partners like Pomeroy to handle these steps. Visit our Windows 11 Info Center, or download our infosheet to learn more about how we take the work out of Windows 11 migrations.
