Upgrading to Windows 11 isn’t just about getting the latest operating system, it’s an opportunity to improve security, refresh your devices, and modernise the user experience. But the transition needs to be done right.
We sat down with David Barbagallo, our expert ASI Solutions Principal Consultant, to unpack the key steps for a successful Windows 11 upgrade. From planning to deployment and user adoption, David shares what’s critical at every stage and how to make the process smooth for your IT team and your people.
Why upgrade to Windows 11?
“Windows 11 brings more than just a new interface,” David explains. “It delivers real improvements in security, performance, and manageability, all while creating a more intuitive experience for users.”
With enhanced endpoint protections, native support for modern hardware, and tighter integration with Microsoft 365, Windows 11 positions organisations for the future.
However, to ensure a smooth transition, a structured approach is essential.
Step 1: Scoping the upgrade
Before implementing Windows 11, it’s crucial for organisations to assess their readiness. This includes evaluating the current IT environment, ensuring hardware compatibility, and determining the best deployment strategy.
Key considerations include:
- The scope of devices to be upgraded
- Potential network restrictions
- The need for a phased or company-wide rollout
Additionally, aligning the upgrade timeline with user training and support plans is essential for a smooth transition.
David’s recommendation:
If devices are due for replacement soon, consider aligning the upgrade with new hardware rollouts to deliver a better user experience and reduce upgrade-related risks.
Step 2: Readiness assessment & compatibility checks
Next comes readiness. David stresses that compatibility should be non-negotiable.
“Nothing derails an upgrade faster than discovering incompatible devices late in the process. Use the tools available, Intune, PowerShell scripts, Endpoint Analytics, to get clarity early.”
Readiness checks include:
- Windows 11 compatibility reports: Not every Windows device is compatible with Windows 11. Organisations will need to identify which devices in their fleet support Windows 11
- System requirements: At least 64GB of free disk space and Windows 10 (version 2004 or later with the September 2021 update)
- Application compatibility: Identifying potential software conflicts that may impact installation
- Network considerations: Assessing bandwidth requirements for remote employees (8GB+ download per upgrade)
Step 3: Choosing a deployment approach
There’s no one-size-fits-all method for deploying Windows 11. Organisations can choose from multiple deployment methods, each offering varying levels of control and automation.
“The best method depends on your environment. Some clients prefer the control of SCCM, others are embracing Intune or letting users self-serve the upgrade. It’s about finding the right balance between control and convenience.”
Step 4: A phased rollout strategy
A structured rollout is key to ensuring minimal disruption during the upgrade to Windows 11.
Starting with a small testing group is critical for identifying initial compatibility or performance concerns as well as identify any adoption issues that may arise during the role.
The advantage of using a phased approach also allows IT teams to gather user feedback, adjust support resources, and refine training materials, to ensure a successful transition to Windows 11.
Always test first with a small group, then pilot with 5-10% of users to discover any issues early and resolve them before rolling out organisation wide.
Step 5: Managing user experience and IT support
A successful upgrade isn’t just about the tech, it’s about the people. A well-planned upgrade should enhance employee satisfaction with minimal disruptions.
“Communicate early, train proactively, and make support easy to access,” says David. “You want employees to feel empowered, not confused.”
Key considerations:
- Communication plan: Notify employees about the upgrade timeline and any changes to their workflows
- Training & adoption: Align upgrades with internal training initiatives to ensure employees understand the benefits of Windows 11
- IT support plan: Define escalation processes for resolving post-upgrade issues quickly
- Security & compliance: Ensure endpoint security policies are updated and enforced post-upgrade
How ASI Solutions can help
At ASI Solutions, we take the complexity out of IT upgrades.
Our experts can:
✅ Conduct readiness assessments and compatibility checks
✅ Develop a tailored deployment strategy based on your organisation’s needs
✅ Manage the entire upgrade process, from testing to full deployment
✅ Provide end-user training and post-upgrade support
✅ Ensure a seamless and secure transition to Windows 11
Ready to streamline your Windows 11 upgrade?
Download our Windows 11 Action Plan, a practical, step-by-step checklist based on expert advice from our Principal Consultant.
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