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Digital Transformation

The Move to Windows 11: Planning and Execution for IT Leaders

What’s your plan for migrating employee devices to Windows 11 before the Windows 10 end of support deadline in October 2025? As every good corporate IT leader is aware, even relatively small-scale Windows operating system migrations require careful planning, testing, and deployment to avoid business disruptions.

If you’re reading this blog post in 2024 and thinking: “October 14, 2025 is at least a year away and I have plenty of time,” then would you be surprised to learn that it took some enterprises three years to upgrade to Windows 10 before the 2020 support cutoff date? Stephen Kleynhans, a research VP for Gartner in circa 2017, emphasized the complexity and time-consuming nature of any companywide Windows OS upgrade, stating that IT departments “can’t wait until the eleventh hour because they require months for user acceptance and application compatibility testing before they can even think about a broad rollout to employees.”

Even though Microsoft engineers have worked to make the process of upgrading from Windows 10 to Windows 11 much smoother than it was going from previous Windows operating systems to Windows 10, the reality is that most businesses rely on third-party apps that are critical to business operations. Each of those apps still require testing to ensure proper functionality before rolling out a new operating system—which often results in a lot of work for IT departments during any Windows migration.

Maximizing Business Potential with Windows 11: Security, Reliability, and AI

Many CIOs are now considering their Windows 11 migration as a strategic opportunity to enhance security, hardware reliability, and AI-driven efficiencies. Unlike older operating systems, Windows 11 introduces a suite of advanced cybersecurity features that enables IT departments to better secure and monitor a fleet of corporate-owned devices. You’ve likely heard that Windows 11 requires a Trusted Platform Module (TPM) 2.0, a secure co-processor that’s used to safeguard sensitive data and cryptographic keys. However, you might not have heard why you can’t just add a TPM 2.0 card to a Windows 10 computer and achieve the same security results: Windows 10 was designed with TPM 1.2 in mind. Because Microsoft engineered Windows 11 for the new hardware, retroactively adding TPM 2.0 support to Windows 10 would require significant changes to the OS architecture, affecting stability and compatibility.

Speaking of newer hardware, Windows 11 delivers significant improvements in reliability and performance with the latest generation of AMD and Intel processors. Advances in low-power/high-efficiency processors along with the ability to take full advantage of multiple processor cores in Windows 11 means businesses can expect less downtime due to hardware failures and reduced maintenance costs, ensuring smoother operations. The recent introduction of devices equipped with processors dedicated to accelerating AI services, such as Microsoft Copilot, locally rather than in the cloud also marks a leap forward in operational efficiency. These AI capabilities automate routine tasks, provide advanced analytics, and enhance decision-making processes, translating into considerable cost savings and productivity boosts for businesses.

Planning for Windows 11 Migration

At a high-level, a strategic migration from Windows 10 to Windows 11 involves:

  1. Hardware Assessments: Evaluate current hardware against Windows 11 requirements to identify necessary upgrades or replacements. Consider a medium-sized financial services firm using a mix of desktops and laptops acquired over the last five years. To determine readiness for Windows 11, the IT department conducts a comprehensive hardware assessment. The CIO discovers that 40% of their devices don’t meet the minimum hardware requirements for Windows 11 and have no dedicated hardware needed for running AI models locally rather than in the cloud to support the firm’s strict data compliance rules.
  2. Application Compatibility Testing: Test critical business applications on Windows 11 to ensure compatibility and smooth operation. This is important for any organization that relies on a custom-built app to avoid compatibility issues that would cause business disruptions. In some cases, Microsoft will help IT teams to test and refactor their homegrown apps for Windows 11 through the App Assure with FastTrack program.
  3. User Training: Develop a plan to train IT staff and end-users on new features and changes in Windows 11 to maximize adoption and minimize disruption. There will always be “that user” who hates change. So, you should be prepared with a training program that includes instructional videos, quick reference guides, and live Q&A sessions to cover the new features and changes in Windows 11. If possible, set up an internal support portal on your company’s intranet to address any post-migration issues.
  4. Data Backup and Recovery: Ensure comprehensive data backup and recovery plans are in place to protect against data loss during the migration. Because the migration tools are so good now, it is rare that an organization would lose any significant data during an OS upgrade. But why chance it? Before your migration begins, schedule a disaster recovery drill and verify the integrity of your backup systems.
  5. Security Policy Updates: Review and update security policies to leverage Windows 11’s enhanced security features. For example, a law firm upgrading to Windows 11 could enable hardware-based isolation for sensitive documents, configuring more stringent authentication measures like MFA, and updating their endpoint protection strategies to integrate with these new security features. When making any policy updates, you must also include user education about new security protocols as part of the “Training and Support Plan.”
  6. A Phased Rollout: Consider a phased approach to the migration to manage risks and address issues without affecting business operations. For example, start with a pilot group of IT staff and power users on Windows 11, followed by departments with the least dependency on legacy applications. User feedback from each phase can be gathered to adjust your rollout plan, address issues, and ensure that support resources are adequately prepared for each subsequent phase. This approach allows IT departments to manage the migration process more effectively and ensure a smooth transition for all users.
  7. Post-Migration Support: Establish a support structure for addressing any post-migration issues and questions. Proactively assigning IT support resources that are dedicated to the Windows 11 migration ensures your employees can get the most out of the new OS, which helps with the return on your investment because you’re increasing overall productivity and minimizing business disruptions.

The Windows 11 Migration Checklist

Success requires a thorough and organized approach to each critical step in the migration process. Here is a handy checklist IT leaders can use to make sure the basics are covered:

TaskDescriptionCompleted ? (Y/N)
Hardware AssessmentEvaluate all devices for Windows 11 compatibility, focusing on TPM 2.0, CPU, RAM, and storage requirements.
Application Compatibility TestTest all critical business applications on Windows 11 to identify any compatibility issues.
User Training PlanDevelop a comprehensive training program for users on new features and changes in Windows 11.
Data BackupEnsure all data is backed up and verify the integrity of backups before starting the migration.
Security Policy ReviewUpdate security policies to leverage Windows 11’s enhanced security features.
Pilot DeploymentConduct a pilot deployment with a select group of users and gather feedback.
Phased Rollout PlanPlan a phased rollout, starting with less critical departments or systems.
Post-Migration SupportEstablish a support structure for addressing any post-migration issues.
Inventory UpdateUpdate the IT asset inventory to reflect the migration to Windows 11 for all devices.
Performance MonitoringSet up systems to monitor performance and user feedback post-migration.

Develop a Windows 11 migration plan with Blue Mantis

No matter where you are in your Windows 11 migration journey, Blue Mantis can help busy IT leaders to:

  • Assess and select future-proof devices.
  • Explore options for financing and training services.
  • Plan the configuration and deployment of your Windows 11 devices.

We can even help you with sustainably and securely disposing of your old Windows 10 devices. Connect with us today to discuss how we can migrate your device fleet to Windows 11 well before the October 14, 2025 end of support cutoff.

Jeremy Bello

Senior Solutions Architect, Microsoft

As a Senior Solutions Architect specializing in Microsoft technologies, Jeremy leverages his extensive background in virtual desktop infrastructure, data center virtualization, cloud architecture, and networking to devise creative solutions for intricate business challenges that are practical, effective, within budget, and that meet client goals.

Jeremy began his career in IT as a printer technician, then worked his way up to server administration, and then later moved on to consulting roles, applying his business and technology acumen to client business challenges. 

Most recently, he spent eight years expanding a Managed Technology Services provider, playing a key role in strategic planning across the organization. Under his direction and the direction of his leadership peers, the company grew both organically and through multiple acquisitions.