If you’re thinking that the transition from Windows 10 to Windows 11 is as simple as applying a long Windows update, you’re mistaken. Organizations have a giant task ahead of them as the Windows 10 end of life date of October 14, 2025 approaches.
The reason this upgrade isn’t easy is because there are so many factors involved:
An upgrade across your organization is not going to be easy. In this article, we provide a checklist for a successful transition from Windows 10 to Windows 11—and some of the many things you will need to think about as you make this transition.
A migration to Windows 11 can take a long time—on average about 8 weeks mostly due to IT resourcing. Supply chain issues will also likely worsen closer to the end-of-life date. It’s imperative that you start planning your upgrade now.
This may be a combination of internal IT staff, external IT resources (such as your MSP, a consultant, etc.), and non-IT stakeholders within your organization. Everyone’s roles and responsibilities should be clear.
As you design and scope the project, you need to account for the following:
Make sure your key decision makers have signed off on the upgrade project.
Create an updated list of all user accounts, roles, and access levels. Verify that all necessary credentials and permissions are documented.
Create a project plan that includes all the tasks that need to get done, who is accountable for each task, interdependencies, and milestones. Plan the upgrade during off-peak hours to minimize disruption, and ensure all critical operations have contingency plans in place.
It’s taking 2-3 weeks for hardware to come in these days because of inventory shortages and supply chain issues. This timeframe will likely increase as the end-of-life date grows closer.
Communicate the upgrade schedule and process to all employees. Provide clear instructions on what employees need to do before, during, and after the upgrade.
Make sure that you have performed a full backup of your critical data and files, and verify that your backups can be restored if needed. Double-check that all backups are complete and accessible while ensuring there is a verified restore point for each device.
Here’s where the magic happens—the upgrade from Windows 10 to Windows 11 on your eligible devices or the deployment of replacement devices with Windows 11 activated on them. Installing Windows 11 is not like turning on a switch, and there are a few steps you should follow.
Offer help desk support for any issues or questions related to Windows 11, monitor system performance and user feedback, and promptly address any issues that arise. Keep track of common problems and solutions to streamline support. Your helpdesk should be prepared ahead of time for an uptick of user issues during and after the upgrade.
Document any changes made during the upgrade process. Update IT policies, procedures, and inventory lists to reflect the new environment.
Distribute training materials or resources to help employees familiarize themselves with Windows 11, and schedule training sessions if necessary.
Various options exist including trade-ins, donations, recycling, or physical destruction. Your IT staff or vendor can help you decommission devices in a secure, responsible manner that meets your needs.
Meet with IT staff, your IT vendor, and key stakeholders to review the upgrade process. Identify lessons learned and areas for improvement.
Fine-tune system settings and configurations for optimal performance on Windows 11, and schedule regular maintenance checks to ensure a continued smooth operation.
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By following this checklist, organizations can manage the transition from Windows 10 to Windows 11 smoothly and effectively, minimizing downtime and ensuring a positive experience for all users.
Questions about end of support for Windows 10 and its implications on your organization? Reach out to VC3 today.