The right way to upgrade a client OS in the enterprise

Posted: July 25, 2014 in General

Upgrading Windows on laptops/tablets isn’t about imaging or SCCM/LANDesk. The real success factors are often not clearly understood and prepared for prior to the project increasing cost during the project and sometimes missing key benefits or improvements.


Key success factors are:

  • Explore new features of the OS – often a new version of Windows provides new features that can provide key business advantages or cost savings. Technologies such as Direct Access, BitLocker, AppLocker are free for most organizations and can provide substantial benefits when implemented as part of an OS upgrade.
  • Understand the current environment – accurate data about current hardware/peripherals as well as applications used throughout the organizations (especially non-enterprise apps) or which end users are responsible for each application is often to hard to come by. The assessments and discovery tasks to gather this information are very time consuming and are not ideal tasks for an outside vendor who is not intimately familiar with the organization. Starting the data collection well in advance and/or maintaining the data current on an on-going basis is necessary to reduce costs and meet deadlines
  • Understand requirements – the business requirements for Windows projects are often defined in parallel with the project, sometimes extending into deployment and changing key project parameters at the last minute. This approach can be very costly so defining the requirements prior to the project and making sure they are aligned with business strategy (e.g. should users be storing data on local devices? How is the data backed up and shared? How does this integrate with cloud offerings? How do we avoid data leakage?) is a great way to ensure that the final product is a good fit for the organization and project costs are contained.
  • Application testing process – as the most important factor of overall project duration, an effective application testing process can have a huge impact not only on project timelines but on end user experience following migration. A well-defined process that is managed by a competent application analyst/process manager is vital to the success of the application testing effort and with it the overall project.
  • Change management – a client OS upgrade is often one of the most disruptive IT projects for end users. While the OS change itself might be minor, the accompanying upgrade of the browser, core productivity software (Office, Acrobat, etc) and introduction of new OS features can be very disruptive to a large majority of end users. Managing this change, setting expectations, communicating clearly and structuring the project to minimize disruption are important activities that must be prioritized and handled by an experienced program manager or process analyst.
  • Process overhaul – the broad footprint of this type of project invariably impacts many internal processes: support processes, application lifecycle management processes, security processes, on-boarding and off-boarding processes, hardware asset management processes and more. While these processes can be updated following the migration, a typical approach, doing so is much more disruptive and takes quite a while to complete as team members are busy supporting the organization. Reviewing and adjusting processes during the project in coordination with the project team results in a more seamless transition and a faster return to full productivity for the organization
  • Compliance – for organizations subject to regulatory frameworks such as HIPAA, PCI, SOX, GxP, etc, the changes brought by a project such as this can be more impactful. Preparing the compliance teams for the project by including them in the project team from the onset and integrating their requirements and efforts into the project plan will help avoid last minute surprises that can derail execution


The solution that CCO ( uses is to deploy a project team with a lead in each area identified and ensure that the leads are familiar not only with the type of project but the type of organization. We leverage and support existing mechanisms within the organization to ramp up quickly on project portions that are required early and/or present high risk. Communications with all relevant channels including executives, business units and application owners is established at the onset and used for ongoing change management. Complementing roles of logistics/project management and process/change management are either filled by the same resources or a tightly integrated team.


End result for a recent Windows 8.1 project:

  • Meeting project deadlines and delivering a new platform on brand new hardware for thousands of users in less than 6 months
  • Delivering cutting edge features (encryption, cloud backup, always on VPN) and platforms (convertible touch hardware, enterprise tablets) to users with minimal disruption
  • Replacement of iPads for remote workers with Windows based tablets that provide enterprise management and security
  • Overall user satisfaction due to visible project benefits such as cutting edge hardware, up to date productivity tools, cloud data storage, non-password authentication
  • Flexibility within project team resulted in meeting schedules in spite of challenging external factors (cutting edge technology, release of Windows 8.1 update 1 in middle of project, hardware availability issues, limited internal resources)
  1. Cory says:

    Do you have a copy of your project plan you are willing to share? Getting ready to start a Windows 10 upgrade from 7.

  2. Guy Yardeni says:

    Hi Cory,
    Thanks for reading and leaving a comment. The project plans I have will likely not be of much use without a lot of context that I can’t provide due to confidentiality.

    I’ll reach out privately with some information that might be a good starting point.


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