Windows 11 Migration Planning & Pilot - 8 Week Engagement

While Microsoft has worked to make the migration to Windows 11 as seamless as possible, preparing the enterprise for a smooth, seamless migration to Windows 11 requires an appropriate amount of planning and piloting in advance of the production migration. Identifying the appropriate distribution methodologies, performing application and device compatibility testing and creating/distributing user awareness and adoption training materials are some examples of the most crucial steps to ensure a successful migration in the enterprise.

This engagement will ensure a migration to Windows 11 is as smooth as possible using proven methodologies for preparing, testing and executing a pilot migration of devices to Windows 11. Throughout the course of the engagement, the following objectives will be achieved:

Environment Readiness Assessment/Findings Documentation

• Windows Device Inventory
• Windows Application Inventory
• Document Storage Locations
• Existing Security Baselines
• Administrative Templates
• Group Policy Objects
• Device Management Solutions
• Virtual Desktop Infrastructure
• Endpoint Security Solutions
• Disk Encryption Solutions
• Windows 11 Licensing Review

• Establish the “Windows 11 Migration Team” documenting key stakeholders and their roles
• Establish and document groups/rings/users/devices for migration
• Define operational readiness criteria including update success rate targets, timelines, trends, goals and methodologies for monitoring during the deployment
• Identify the most appropriate deployment methodologies for delivering Windows 11 to client endpoints while being mindful of delivery optimization techniques
• Identify and document the necessary steps to prepare the virtual desktop infrastructure environment for hosting Windows 11 images
• Architect any necessary changes to existing tooling or net new solution deployments required to efficiently deliver Windows 11 to client endpoints and virtual desktop infrastructure
• Plan and document ongoing servicing of the Windows 11 operating system platform

• Document inventory of Windows application in-use leveraging Customer provided tooling
• Define criteria for rating applications
• Establish a documented application testing methodology to perform against inventoried and rated applications
• Perform general application installation functionality testing for apps
• Perform upgrade scenario application functionality testing for apps
• Perform Windows 11 feature testing on apps

• Educate IT support staff/frontline help desk teams on knowledge required to support Windows 11 users
• Co-create user adoption documentation on major platform changes for Customer distribution to pilot user groups
• Familiarize/Create buzz, with Customer led “drip campaign” highlighting the benefits for end users

• Reconfigure/update any existing supporting infrastructure solutions to support Windows 11 update delivery to endpoints and virtual desktop infrastructure
• Validate the deployment architecture and perform update deployment testing on several IT designated, test Windows 10 endpoints and virtual machines
• Deploy Windows 11 migration workflow to the first pilot group (not to exceed 20 devices/users)
• Gather and document user feedback post-migration and modify the migration plan, as necessary
• Create a centralized issue tracking system to ensure any migration issues are reviewed and addressed by the migration team. CDI resources will supply up to 40 hours of consulting time to assist with migration issues.
• Perform final knowledge transfer with project stakeholders and closeout project