Overview Series: How to Pilot Windows Vista

Windows Vista® has introduced many new features to the Windows® operating system, all designed to help users work more effectively and easier than ever before.

When an enterprise makes a decision to move to a Windows Vista environment several processes are set in motion. One of the most important is the development of a pilot deployment program. The pilot program serves several functions including testing, evaluating, collecting user feedback, and training users in preparation of the intended deployment of Windows Vista. A successfully executed pilot program will help produce a smooth deployment, accurate allocation of resources, such as budget and personnel, and an accurate estimation of training needs.

Defining the Scope

The first step in a successful pilot should be to define the goals of the program and what is to be accomplished upon completion. Because goals will be used to measure the success of the project they should be carefully considered with the assistance of different stakeholders, including the information technology (IT) department, the support center, executive staff, and possibly individuals that represent the end-user population.

Business Requirements

Some of the goals that should be defined while planning your Windows Vista migration pilot should identify the business needs and requirements that the pilot should address. When defining business requirements for the pilot and the eventual deployment to the production environment, it is important to gather information from departments and groups throughout the organization to see what their goals and needs are, in addition to making sure that their current concerns will be addressed by the pilot. When choosing individuals or groups to include in the pilot, ensure that each can not only “speak” for their department, but that each has the extra time to participate in defining the business requirement.

When defining business needs, several factors should be taken into account, including:

  • Will the upgrade meet existing and planned business requirements?
  • Will there be a cost saving realized by moving to Windows Vista?
  • Will security be affected by the introduction of Windows Vista?
  • Will the upgrade be a benefit to end users?
  • Will mobile users have a better experience than they do now?
  • What will be the upgrade cost in terms of staff hours, money, and other factors?
  • Will security be negatively affected?
  • Will support costs be lowered?
  • Who will be the executive sponsor for the project?

Assessing the Current Environment

Before a migration can be initiated an assessment or survey of the current network environment will need to be conducted. During the assessment phase the goal is to get a clearer picture of the present state of the environment to get a better idea of what applications, operating systems, hardware, and user needs exist. Existing software should be assessed to determine if the applications are compatible with Windows Vista, if a Windows Vista-compatible upgrade is available or, in the case of custom applications, to determine if the applications will work or can be made to work with Windows Vista. When hardware is inventoried it should be determined if the hardware in place is capable of running the version of Windows Vista that will be deployed; for example, Windows Vista Business or Windows Vista Enterprise.

To assist in the assessment process there are several tools readily available that can help during the inventory phase. These include:

  • Application Compatibility Toolkit (ACT) 5: This utility can assist in the inventory and compatibility determination phase of assessment.
  • Business Desktop Deployment 2007: This Microsoft solution accelerator can help you determine various deployment options and scenarios for the current environment.
  • Windows Vista Hardware Assessment 2.1: The Windows Vista Hardware Assessment utility can assist in the inventory of computers on a network and report those results so the project team can determine if current hardware can run the new operating system.
  • Systems Management Server (SMS) 2003: Using SMS 2003, you can collect detailed information on current hardware and software environments across an enterprise.

Tip The Windows Vista Application Readiness Web site is a good resource for determining whether Windows Vista compatibility updates have been released for various applications.

While the assessment phase is in progress, try to address the following questions:

  • Will the current hardware run the version of Windows Vista you want to deploy?
  • Will the current applications being used throughout the organization run on Windows Vista? What about custom applications?
  • Will the current network services work with the proposed environment?
  • What will be the cost of bringing incompatible hardware and software into compliance?
  • What applications or hardware cannot be upgraded?

During the assessment phase it will also become important to determine a baseline for hardware (and in some cases, software). A baseline will be used as a tool to determine a minimum requirement for the computers and/or software you want to upgrade to Windows Vista. It is important to note that a baseline does not represent only the minimum requirements for deploying Windows Vista, but also what will support required business applications that support specific job functions without decreasing end-user productivity. When a piece of hardware or software does not meet the baseline requirement during the pilot phase it will need to be brought into compliance either through hardware or software upgrades or, in some cases, by replacement. In some cases, if the hardware or software is not critical to the operation of the enterprise, it might be retired and not be part of the eventual deployment process.

Tip When building a baseline it might be helpful to visit https://www.microsoft.com/windows to review the system requirements for each edition of Windows Vista.

During the assessment phase you should also consider whether to do a clean installation versus an upgrade. See the "Infrastructure Preparation and Deployment" section of this guide for more information on this option.

Choosing a Pilot Group

The next phase of the deployment will be choosing a group of users to participate in the pilot program. This group of users and the hardware they use will allow the actual deployment to be tested in an environment that will simulate the production environment. Choosing appropriate users and hardware is critical; choosing inappropriate participants can result in meaningless data or, in some cases, mean missing a potential problem that could be critical during actual deployment.

Selecting Users

After project goals have been determined and needs have been assessed, a group of users will need to be selected as the pilot group. The pilot group will represent the larger enterprise and user segments within it that will be affected by the upgrade. Members of the pilot group should be carefully considered to ensure that they will accurately represent your user population, and that they can provide the necessary feedback to make the project successful.

When choosing a pilot group, consider the following best practices:

  • Choose users that represent a larger segment of your user base. For example, choose a small number of users from the Accounting department that would perform the average functions of that group, such as using certain software packages or hardware.
  • Try to include users who are currently using earlier versions of the operating system, such as Windows 2000, to determine if the computers can be upgraded to Windows Vista and retain functionality.
  • Consider including users with applications that need to be evaluated for compatibility with Windows Vista.
  • Choose users that can allocate time to providing feedback and information to the pilot management group.
  • Include users who would see the greatest benefit from upgrading to Windows Vista. One example of this would be mobile users who would benefit from BitLocker disk encryption.
  • Look for users who understand and embrace new technology.
  • Consider an opt-in approach to include users in the program.

Tip When using an opt-in approach consider seeking approval from an individual’s supervisor or manager to avoid affecting a department negatively.

In some cases choosing a group of users can also be done by determining who is not a good candidate for inclusion. Determining who is not a good candidate for a pilot can be just as important as determining who is a good candidate. The wrong candidates might yield no usable data or, in some cases, adversely affect the organization or the pilot.

When evaluating the suitability of a candidate consider the following:

  • Do not choose users whose departments would be adversely effected by potential downtime, decreased performance, compatibility problems, or other factors.
  • Avoid choosing departments or users that have custom software or environments that have not yet been tested with or certified to work with Windows Vista.
  • Carefully consider the inclusion of mobile users or “road warrior” types that might be away from the office for extended periods and away from technical support.
  • Do not upgrade users who perform mission-critical functions for the enterprise.
  • Consider the timing of using a candidate for a pilot; for example, a user who works in accounting and who needs to work on end-of-the-month reports during the pilot period should not be included.
  • Do not include entire departments in a pilot, to avoid shutting down a group in the event of a critical issue during the pilot.

Choosing Client Computers

The other aspect of choosing a pilot group is choosing the right client computers for the program. When choosing hardware for the pilot include only PCs that meet the minimum requirements to run the version of Windows Vista you want to deploy (Windows Vista Ultimate, Windows Vista Business, Windows Vista Enterprise, etc.).

When choosing client computers consider all factors, such as devices that the user might use with the PC. Look for hardware such as mobile devices, scanners, printers, docking stations, and so on that might be attached to the system at different times. Each will require a specific set of drivers and applications to work properly.

Tip To assist with choosing client computers to use in the pilot, consider using the Windows Vista Upgrade Advisor to scan a system to see if a particular version of Windows Vista is appropriate for the PC, and to highlight potential problems with hardware and software.

Planning the Pilot Deployment

After the current operating environment has been assessed and suitable users and hardware located, you can move toward planning the actual pilot deployment. When planning the pilot deployment it is important to keep a few key points in mind.

First, make sure there is an adequate mechanism in place to solicit feedback from the pilot program participants. During the pilot the collection of information is vital to the success of the eventual enterprise deployment. By the time the planning phase occurs you will already have selected the users and computers that will participate in the program and, if the selection has been done correctly, these users will approximate the final environment. Because the pilot environment will simulate the production environment feedback from participants should fairly represent the issues that will be seen during the eventual enterprise deployment. Remember, feedback gathered during the pilot will be used to identify and resolve problems during the pilot and before final deployment.

Some key points to keep in mind during the planning phase include:

  • Provide an easy way to gather and solicit feedback from participants in the pilot program.
  • Provide a way to document all pilot results for future capacity planning and full-scale deployment.
  • Identify computers and applications that might be at higher risk of encountering problems during an upgrade because features have changed or are no longer supported.

Remember that the purpose of the pilot program is to simulate and gather information about the deployment of Windows Vista into the production environment. Keeping this point in mind will ensure that your team is focused on addressing the issues of deploying Windows Vista instead of focusing solely on software testing.

Testing and Deployment Phase

When the planning phase has been completed the pilot can move onto the actual testing and deployment phase. The testing phase represents the move from a lab or test environment to the actual deployment to “live” desktops where users will get their first hands-on experience with the product.

Prior to actual deployment it is recommended that testing be done to see how Windows Vista will run on current hardware and with standard software. Testing during this phase can be done in a controlled lab environment that approximates the standard enterprise environment so the affect of an issue will be minimized. Testing during this phase might also be done by selected IT staff who might have an additional PC on which to run Windows Vista while they still have a primary computer running the current operating system such as Windows XP.

Ideally the testing phase should consist of two parts: in-the-lab testing and limited production testing. In-the-lab testing phase environments that closely simulate the actual production environment will be configured and used. In a lab environment rigorous testing should be conducted to minimize problems, in addition to taking advantage of the isolated lab environment where problems cannot spread. The second phase of testing, or limited phase, will consist of the previously mentioned IT staff, support center, and other “power” users who can not only provide useful feedback, but who also have secondary computers that are used for production work. When these phases are complete the wider pilot deployment can begin.

Creating a Test Plan

When testing Windows Vista it is important to put a structured testing plan in place to check the compatibility of software applications, the compatibility of hardware, and to catch any early problems or issues. The goal of early testing is to catch as many problems and issues as possible and address them before deploying to the pilot group.

During the testing phase have a set of specific goals established that need to be accomplished. During this process of settings goals it will be helpful to refer back to the earlier goal-setting document for the project and expand the business requirements and technical requirements. Specifically, your testing plan should include:

  • A list of specific technical and administrative goals to accomplish that are agreed upon by members of the pilot team and are based on feedback from various departments.
  • A way of measuring results—for example, milestones—in addition to a way of prioritizing problems that need to be addressed.
  • A method of classifying problems that will determine if an issue will halt the deployment until a resolution is found, in addition to classifications for less-critical problems.
  • Schedules that will determine when major milestones should be met.
  • Assignment of responsibilities; for example, who will be in charge of testing what feature(s).
  • A mechanism or process for reporting any problems or issues that manifest during the testing process.

As mentioned earlier, the testing phase should focus more on testing applications used throughout the enterprise and how they will respond in a controlled, isolated environment like a lab. The group participating in testing Windows Vista should ideally consist of individuals who are technically savvy, such as senior or experienced IT personnel or end users. Additionally, the group of users that will participate in this phase should be kept small which in some cases might mean between 20 and 30 users.

Any feedback on problems or issues during this phase should be carefully examined and considered for potential implications in the production environment. Remember, what might appear to be a small or isolated problem in a lab could grow into a critical problem during a full-scale deployment.

For more information on creating test plans, consult the Business Desktop Deployment 2007 references which can be found at: https://technet.microsoft.com/en-us/library/bb490181.aspx. Each BDD reference guide offers specific guidance for creating test plans and stabilizing the deployment environment.

Creating a Pilot Deployment Plan

You should have a plan in place that will address how issues are dealt with during the course of the pilot and the eventual deployment. Inevitably problems and issues will occur that are minor, in addition to issues that are more serious, each of which will require a different level of care and attention. During the pilot consider having a mechanism in place to prioritize problems so they can be evaluated and addressed appropriately. Consider a process that logs problems as high, medium, or low. For example, a problem that makes the deployment fail might be considered high, whereas one that causes a minor display problem with an application that only a few users use would be categorized as low. After the testing phase and later, limited deployment, revisit these issues to determine if they need to be addressed immediately or if they can be postponed.

Phase One – IT Staff and Support Center

When the initial lab testing has been completed Windows Vista can be deployed to the first group of pilot users, which ideally will be the IT support team. Making the IT staff the first recipients of the deployment satisfies several goals, including deploying the product to a small, initial group of easily monitored desktops and users. Members of the IT staff also are useful as early adopters because their high level of technical knowledge and skill will make the deployment easier and the task of dealing with any technical or usability issues much easier than with a nontechnical group.

During and after initial deployment to the IT group be sure to gather information on the overall success of the process for later use and analysis. As with any information that is generated during the pilot process analyze any issues that arise and use the results to make any necessary fixes, adjustments, or updates to the next phase. Another invaluable aspect of diligent information gathering and processing is that it can be added to a support center database to use in addressing the same or similar issues later on during the pilot and during the enterprise deployment of Windows Vista.

When this phase is complete and any critical issues are analyzed and resolved, the next step is to deploy the Windows Vista operating system to the next group(s) of users.

Phase Two – End Users

The next step in deploying Windows Vista during the pilot is to get it to the various users that were selected to participate in the project. Based on the number of users during this phase and the number of IT staff available to help it is recommended that you adopt a phased approach to ensure success. When a phased approach is used problems can be addressed easily and deployment processes refined to make the process more effective. An additional benefit of a phased approach is that it will better approximate the actual deployment process to the production environment. The likelihood of deploying Windows Vista across the enterprise at once or to very large groups is low in most cases.

During this phase consider the following points to ensure the safest and smoothest possible deployment:

  • Take each department’s schedule into account and plan your pilot around critical work times to mitigate the chances of problems affecting business operations.
  • Upgrade smaller and easily managed pilot groups at a time to monitor and address problems effectively as they arise.
  • Document all issues that occur during the deployment process so that they can be addressed during future deployments, and to prepare support center and IT staff for problems when full-scale deployment occurs.
  • Identify problems that result from application compatibility, in addition to those related to incompatible or insufficient hardware.
  • Keep track of issues that occur as a result of lack of end-user knowledge or skills so training can be developed.
  • Initially start with smaller, easily controlled groups that can be easily monitored and contained to catch any remaining issues that were not discovered during previous testing.

Infrastructure Preparation and Deployment

The next phase of the pilot process is determining deployment and infrastructure requirements and any other requirements to make the deployment successful. The project team should address how to deploy the operating system image to the intended desktops and laptops that will be running Windows Vista. There are several options you can use to deploy Windows Vista:

  • Zero Touch Installation (ZTI) deployment is a non-interactive option (one that does not require user interaction). This type of deployment would be ideal for organizations that have the appropriate support infrastructure, such as Microsoft® Systems Management Server (SMS) 2003 or Microsoft Operations Manager (MOM) 2005. This type of deployment requires much more planning and infrastructure, but does eliminate a lot of the issues associated with end users interacting with the deployment.
  • Lite Touch Installation (LTI) deployment requires some user interaction to complete the process, and might be ideal for organizations that do not have tools like SMS 2003 or MOM 2005. This type of deployment is also effective for client computers that might be remote, have special security policies, or don’t have the network capacity to handle ZTI.
  • The final option for deployment is to perform a standard manual installation running the Windows Vista installation from a source DVD or from a central location like a network share. This option requires the greatest amount of user interaction. Because user input will need to be provided during the installation, this option also has the greatest potential for problems; users might make mistakes when entering information during the installation.

When a deployment option has been selected and the infrastructure prepared, the next step is prepping and building an image of the new operating system. When building an image it is important to take into account the various hardware platforms and environments to which you will be deploying and build the image appropriately. The image should include all necessary drivers, software, and other features that will be part of the deployed environment.

Tip You can learn more about the various deployment options on the BDD 2007 site. Specifically, the Infrastructure Remediation Feature Team Guide (https://technet.microsoft.com/en-us/library/bb456421.aspx) offers guidance for infrastructure preparation.

In environments that have more than 25 users the infrastructure will have to be put in place to support volume activation of Windows Vista. The new activation services used in enterprise environments are the Multiple Activation Key (MAK) and the Key Management Service (KMS). These services will require the deployment of a dedicated server to manage licenses or adding the role to an existing computer.

Tip To determine which activation option is best for your particular environment visit the Windows Vista Volume Activation Technical Guidance site.


The success of the pilot program largely depends on having established channels to communicate information between all parties involved. Clear and frequent communication can help the project team access the budget, personnel, and other resources they need for the project.

When setting up communication channels consider the following:

  • Identify key stakeholders or department leaders that can speak for their respective groups and get the necessary help or resources from their team. These leaders will also be responsible for communicating to the pilot group any concerns that their teams have or problems they are experiencing.
  • Executive representation is another vital aspect of communication and assuring the overall success of the pilot project. It is important to include a company executive because they can obtain the necessary budget, allocate additional personnel, and give the pilot project representation at the highest level of the organization.
  • Information gathering and recording channels are vitally important to the future success of the pilot and enterprise deployment because they provide ways to report status and other information to the team. As discussed earlier, issues will arise during the pilot because of technical problems and because of unfamiliarity with the product, among other things. Giving participants a way to report information to the project team is vital because this information can be analyzed and used to improve the deployment process, in addition to being used to plan training and other tasks.

Tip The Business Desktop Deployment 2007 solution accelerator includes a sample Communication Plan job aid that can be used as a basis for your own project communications.

Training Requirements

An inevitable part of upgrading to Windows Vista is that users and support staff alike will need to learn how to use and support a new operating system. Some tools are provided in Windows Vista to assist new users with the upgrade, including online help and other features that describe how to leverage the power of the product. However, in most cases additional training will be required.

Before support staff and end users are introduced to Windows Vista the project team should take time to provide some initial training to ensure a smooth transition. Recommended approaches to train users for and during the pilot are varied, but consider the following approaches:

  • E-learning that can be delivered online or using a DVD or CD.
  • Seminars and clinics designed to give users a quick introduction to Windows Vista and how to perform day-to-day tasks.
  • Short instructor-led seminars or half-day training events that train users on the basics of using the new operating system.

Note An added benefit of this particular format is that attendees will generate information on usability and technical issues that can be addressed by the pilot team.

On-demand help that, for example, can be provided by a dedicated support center line set aside for participants in the pilot.

One of the benefits of gathering feedback and information during a pilot is identifying areas that are problematic for users and support staff. When building a training plan be sure to review all documentation and issues reported during the testing and deployment to determine which aspects of the new operating system need to be addressed.

Tip Organizations that are part of the Microsoft Software Assurance program might qualify for special incentives such as training from Microsoft Certified Partners, or consulting services from Microsoft itself.

Post-Pilot Analysis

The final step in the pilot process is to evaluate the overall success of the project and to identify areas for improvement. Early on in the process goals were defined by the project team, goals which at this point should be revisited to see which were met and which were not. Although specific goals for a pilot project will be as unique as the organizations that deploy Windows Vista they do serve the important function of measuring success.

Another part of the post-project analysis is revisiting business requirements to determine if the project satisfied these. Business requirements generally will require more careful analysis of data to determine the affect of the deployment on the business environment.

During the post-pilot analysis the following tasks should be performed:

  • Review project goals to see which goals were achieved, which were not, and why.
  • Analyze business objectives, such as cost savings from using Windows Vista, and the amount of resources that were used to complete the project.
  • Detail problems that arose during the pilot, how they were dealt with, and whether these issues still need to be addressed.

About the Author:

Sean-Philip Oriyano has over 14 years of experience in the IT field covering topics such as networking and security. Throughout his career he has held positions such as support tech, systems engineer/administrator, technical writer/content developer, CIO and instructor. He has performed freelance consulting and instruction for numerous clients and industries. Over the past few years, Sean has taught for organizations such as Northrop-Grumman, Autodesk, and Lockheed-Martin, as well as the United States Air Force and US Air Force Academy. Sean has also authored or contributed to white papers in the field of IT and mechanical engineering and is currently working on his first book. In his spare time Sean enjoys ice hockey, opal mining, vacationing in Las Vegas, and Skydiving.

Sean is certified as a CISSP, MCT, MCSE, MCSA and MCDST as well as a member of the EC-Council and BECCA.

See Also

Other Resources

Application Compatibility
Windows Vista Hardware Assessment
Windows Vista TechCenter
Desktop Deployment TechCenter