Simplify Your Windows 11 Migration Using Data

How improved SysTrack tools can help IT leaders overcome a few basic migration challenges and ensure a quality employee experience

In the evolving digital workplace landscape, end-user devices and their operating systems play a pivotal role in shaping employee experience. Microsoft dominates the industry with a near 70% market share, according to Statistica, and the release of Windows 11 brings a sleeker user interface (UI), enhanced performance, and improved security features to the enterprise. However, a Windows 11 migration comes with its own unique challenges that organizations will need to overcome before Oct. 25, 2025, to avoid purchasing extended support. 

To simplify the process, Lakeside Software offers improved Windows 11 migration tools to help IT accelerate the journey while keeping employee experience in mind. This post explores how IT leaders can use endpoint data to navigate the hurdles they might face throughout planning and rollouts.   

Windows 11 Migration Challenge #1: Gaining Hardware, Application, and User Visibility for Planning   

The first obstacle to tackle before any endpoint can be upgraded is assessing which devices are ready, need updates, or are not compatible with Windows 11. Unlike its predecessors, Windows 11 comes with higher hardware and software requirements that could be a showstopper for certain devices. Organizations invested in incompatible devices could face financial implications that hit the bottom line if new parts or devices are required at scale.   

Visibility and planning are critical to a Windows 11 migration. Organizations need to assess their estates’ hardware for compatibility and identify potentially problematic applications. This assessment period should also be used to segment employees by persona groups (based on work style, role, geography, etc.) to create a phased plan for migration. Some employee groups could be ready to upgrade immediately while others need extra attention — this allows IT to optimize devices for Microsoft’s requirements while right-sizing software licenses for persona needs.   

Windows 11 Migration Challenge #2: Monitoring Health and Performance in Real Time  

Moving from planning to execution, migration leaders need to keep a close eye on the reliability of endpoints and overall progress. If issues are missed or left unresolved, they could grow in volume as additional migration phases are rolled out. 

When it comes to comprehensive IT visibility, though, not all monitoring solutions are created equal. It takes substantial breadth and depth of data collection across endpoints, applications, and end users to access the full scope of performance throughout a Windows 11 migration. When issues can arise at any second, IT needs that second to be captured (not sampled or averaged) and easily accessed for root cause analysis (RCA) and remediation. From the first to final phase of rollout, real-time reporting of device performance and project progress will help keep a Windows 11 migration on track.   

Windows 11 Migration Challenge #3: Ensuring an Excellent Employee Experience  

Equipping employees with the right education and opportunities for feedback should be part of every Windows 11 migration. Without that vital step, the new, fluent design and touch-control UI updates could prove to be a steep learning curve for some employees and cause negative digital experiences, a dip in productivity, or fragmented adoption. 

Connecting directly with end users to gather qualitative sentiment data alongside quantitative performance data provides Windows 11 migration leaders with a complete view throughout every phase of an upgrade. A direct connection to end users through notifications also allows IT to deploy targeted and timely tips for adjusting to interface changes.

This, along with early assessments of hardware and software compatibility and deep, real-time visibility into the performance, will help organizations navigate successful Windows 11 migrations with a data-driven approach.  

Lakeside customers can access the newly updates Windows 11 Migration DEX Pack through our Customer Gateway.