6 Key considerations when orchestrating your Windows 11 Pro upgrade

Because Windows 11 Pro has new hardware requirements, your upgrade strategy must both address hardware and software aspects, not to mention security, deployment plans, training, and more. This checklist will get you off on the right track.  

1. Assess hardware compatibility  

Hardware refresh requires careful planning and sufficient lead time. Conduct a hardware compatibility assessment to understand the initiative’s scope, explore upgrade options, and secure necessary resources.  

Refer to Windows 11 Pro specifications and run Microsoft’s PC Health Check app to see if a laptop meets specific requirements.

Additionally, it’s a good idea to develop user personas to understand how employee needs vary depending on their roles and responsibilities. To inform your approach, consider factors such as technical expertise, how Windows 11 Pro features support their workflows, budget constraints, and willingness to upgrade hardware.  

2. Evaluate software compatibility  

Identify which applications are critical to your organization, including productivity suites, specialized industry software, and communication tools. Then, check with the software vendors to see if the applications are compatible with Windows 11 Pro. Also, verify system requirements for each software to ensure compatibility with your new devices. 

Since Internet Explorer and its compatibility mode are not available in Windows 11 Pro, ensure critical applications aren’t reliant on IE prior to migrating your fleet. Plan for the adoption of Internet Explorer mode in Microsoft Edge to support legacy web applications. 

3. Assess licensing requirements  

Review your software licenses for Windows 11 Pro compatibility and check for any additional licensing needs. If your organization uses volume licensing agreements such as Microsoft Volume Licensing, verify if it covers Windows 11 Pro upgrades. Some programs include upgrade rights to new OS versions, while others may require additional licensing fees.  

Collaborate with your legal and procurement teams to ensure compliance with software licensing agreements and maintain comprehensive documentation for the transition. Also, include additional licensing costs in your budget planning to ensure you have adequate resources to support the upgrade. 

4. Understand the impact on your security landscape 

Revise your security policies based on Windows 11 Pro’s new security features to ensure they align with the latest best practices and compliance requirements. Refer to Microsoft’s security baselines, which are pre-configured group policy settings that help expedite the enforcement of security best practices and compliance standards.  

Review and configure user permissions to ensure proper access control. For example, you should implement group policies to manage access privileges for file systems, registries, applications, and other resources. 

5. Develop deployment strategies  

A well-orchestrated deployment plan is essential for minimizing downtime and disruption during the transition. Your timeline should address hardware refresh cycles, software compatibility testing, user training, and other requirements. Also, consider using deployment tools like Microsoft Endpoint Manager to facilitate the process. 

Develop a phased deployment plan based on departments, locations, or user groups and start the rollout with non-critical or less complex segments. Consider setting up a pilot test group to gather feedback and address compatibility, performance, and usability issues before an organization-wide deployment. 

6. Implement training and support   

The transition may be more challenging if employees need to adjust to new hardware and software simultaneously. Develop a comprehensive change management and training plan to communicate the benefits and get employee buy-in. Besides technical competence, address challenges such as resistance to or anxiety about change, which can derail adoption.   

Also, train your IT support team and establish a helpdesk or support system. Most organizations will require additional resources during the first few months of the rollout. If you haven’t already, consider partnering with a third-party IT services provider to ensure IT support readiness. 

Compugen, for example, helps organizations navigate this critical transition with hardware procurement, software compatibility assessments, deployment strategies, change management, and post-deployment support.  

Learn more about our Windows 11 Pro upgrade services and see how we can help you orchestrate a seamless transition with the right hardware and software support. Click here to book a discovery call.