Many large organizations encountered difficulties when transitioning their users to Windows 10, leading to the abandonment of biannual upgrade plans. As a result, numerous enterprises remained stuck on Windows 1809 and are now racing against time to upgrade before losing support. With our extensive experience in enabling large IT transformation and digital workplace modernization programs, we’re already simplifying the planning process for a smooth and efficient Windows 11 migration in large enterprises. Here, we have streamlined all the crucial components into a simple 14-step process outline that will guide you through the entire project.
1. Plan the plan
Large-scale operating system (OS) migrations and IT transformation projects don't begin on Day 1. To increase the chances of success, it is important to engage with project stakeholders early on and establish objectives, milestones, and potential risks. Creating a preliminary plan is crucial as it sets expectations for stakeholders and leadership, ensuring everyone is set up for success. Be sure to download the Windows 11 Project Plan Template for a detailed and fully customizable plan you can put into action right away.
2. Build your project scope
Defining the project scope for your Windows 11 migration can be a challenging task. The project team must determine what the final state should look like and identify the necessary infrastructure to support the user base. By setting clear boundaries and guardrails, project teams can avoid ‘scope creep’ and ensure the project stays within budget, timeline, and resource capabilities. Compared to Windows 10, initiating a Windows 11 migration should be quicker since OS upgrades are now considered a business-as-usual (BAU) activity. This makes it easier to build a compelling business case for the project.
3. Select your internal and extended project team & structure
It is crucial to involve the BAU team from the project's early stages as they will be responsible for taking over once the initial migration is completed. Plan the structure of the project team and define roles and responsibilities. The team size may be smaller compared to previous migrations due to the increased sophistication and prevalence of automation. The focus should be on critical activities rather than manual-intensive, repetitive tasks, which can be automated. A mix of internal and external resources can be included, leveraging skills not available in-house or to supplement resources for specific project aspects.
4. Choose your target infrastructure and platforms
While many aspects have changed since planning your infrastructure and platforms for the initial Windows 10 migration, the importance of a well-designed and carefully architected platform remains the same. The platform serves as the foundation for delivering the OS, applications, and Modern Workplace environment. Ensuring the architecture is right and testing multiple deployment use cases are critical for a smooth migration and a successful operating environment post-transition. Consider utilizing our Windows 11 Assessment Service to gain a complete view of app compatibility, project scope, and, if required, target platform analysis. With this information, you can quickly and confidently categorize and assess your environment for Windows 11 based on specific rule sets, significantly speeding up the process.
5. Design, build, test & manage your gold operating system image
Preparing and testing the "Gold Image" is a crucial step where speed is essential. Enterprises often spend more time than anticipated on this step, resulting in delayed releases and a prolonged process due to subsequent updates, hotfixes, and patches. It is essential to have a clear vision of what the gold image should include and how it interacts with the end-user environment. Choose the technology for managing the gold build, which will make the rollout and any deployment changes easier. Clearly define the requirements and build the gold image with all the necessary components, including applications, drivers, configurations, security products and settings, policy and profile settings. Thoroughly test the image with all its configurations against the back-end infrastructure to ensure everything functions as expected.
6. Rationalize your application estate
Improving application management has been a significant goal for many organizations in recent years. Consequently, the hygiene and health of the application estate have improved, with applications categorized, normalized, and rationalized regularly. However, if you haven't kept up with regular upgrades, you may be dealing with a significant amount of Shadow IT that has accumulated since the last OS migration. Reducing application sprawl is necessary to manage the process effectively. There are various tools available for this purpose, ranging from free Microsoft tools and services to sophisticated automation solutions. Consider using automation solutions like Juriba's AppM Packager and AppM Tester to streamline application testing, packaging, and package conversion challenges.
7. Application testing & readiness
After categorizing, normalizing, and rationalizing your application estate, proceed with application packaging, testing, and readiness. While having applications already packaged in MSI or AppV format was sufficient for Windows 10 migration, adopting Modern Applications is beneficial for Windows 11. Automating application packaging, testing, and ongoing management can save critical time, cost, and resources. A typical enterprise OS migration involves around 1,500 applications, making it crucial to efficiently run all in-scope applications through a smoke test to identify any problematic ones. Automating application packaging and testing can significantly reduce the timeline, as evidenced by a recent customer example showing a 96% reduction in time. Managing the volume of applications and their impact on user and device readiness can be daunting for project managers. Prioritization, sophisticated ring planning, and managing the right applications at the right time are crucial for project velocity. Investing time early in the process will pay off later, as applications are often the most common project bottleneck. It is important to integrate your migration management tooling seamlessly with your application packaging and testing tooling for an end-to-end solution.
8. Plan your T(minus) timeline
IT managers know the complexity of interdependencies between users, applications, devices, processes, and other project elements. Conflicting projects running simultaneously can complicate matters further and potentially halt the entire project. In such cases, organizations tend to allocate more resources to speed up manual processes. To mitigate these challenges, it is important to understand the processes involved, how they impact the timeline, and the criteria that must be met before proceeding. Consider dependency checks, readiness criteria, and other factors. Automate inefficient processes and optimize dependencies to accelerate the project. Remember that automating a flawed process only speeds it up, not improve it.
9. Plan your scheduling methodology
Choosing the right scheduling methodology is often overlooked but essential. Define the deployment schedule, potential risks, capacity constraints, and more. This step requires allocating roles and responsibilities within the project team.
10. Agree your end-user engagement plans
End-user engagement plans play a critical role in migration planning, as they define a significant part of the user experience. Plan the communication and interactions with end-users, considering automated emails, email tracking capabilities, self-service options, and feedback mechanisms. Large organizations may need to send multiple emails per user during an OS migration project, so it is important to consider tracking mechanisms and manage the volume effectively.
11. Decide which software tools will best support your migration efforts
Over the years, the number and sophistication of supporting software tools have increased. Many enterprises now rely on these tools for user directories, software and hardware management, app workflow management, and request and problem ticket systems. While these tools provide valuable data, managing an extensive tool stack and obtaining a comprehensive view of all activities has become challenging. For a successful Windows 11 migration, consider having a Data Warehouse that centrally stores all relevant information, such as hardware/software inventory, application usage, and device warranty dates. Properly plan the integration of tools with internal processes and existing tools. Ensure your team has the necessary skillset or sufficient time to learn how to use the tools effectively to maximize returns on investment.
12. Plan your deployment logistics
Inadequate planning of deployment logistics can put projects at risk, especially when the scope exceeds physical feasibility. If you engage service providers for delivery logistics, establish a clear collaboration plan. Whether managed internally or with a service provider, closely monitor capacity utilization, as underutilized resources can lead to budget overruns.
13. Scope reporting & dashboarding
Reporting and dashboarding are essential elements of any project, yet they are often an afterthought. Many project managers spend excessive time gathering, analyzing, and presenting data, only for it to become outdated shortly after. Defining key performance indicators and reporting requirements enables effective progress management. Automate reporting and provide real-time actionable insights to measure progress, identify bottlenecks, and enable permission-based reporting based on roles and responsibilities.
14. Deliver a successful project wrap-up & BAU handover
Handing over the project to the Business-as-Usual (BAU) or digital workplace management team requires careful consideration. Simply transferring the project without proper transition planning is inadequate. The BAU team typically operates with limited resources and no project budget. To ensure a smooth transition and future upgrades, involve the BAU team as much as possible throughout the process. Provide them with proper documentation, share lessons learned, and facilitate knowledge transfer. Utilize tooling that seamlessly supports future Windows 11 Servicing upgrades.
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