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Upgrading an operating system can, in many cases, be exciting. New features! New enhancements! UI improvements! But with that comes the big questions: is my system compatible? Will my software work with it? Are there drivers for my hardware? These are daunting questions for an individual user but when you work in IT and are responsible for upgrading the entire office, it can be a logistical nightmare. But that doesn’t mean it can’t be done and with some careful planning and forethought, you should be able to upgrade your office with little difficulty.

The first step to doing an upgrade is to make a list of all the steps that will be required for you to complete it. Having a list will help you determine where to start and what order to complete the tasks in. There is nothing worse than getting knee deep into a system upgrade and discovering that you missed a critical step during the planning stage. Your list should include identifying how many computers will be upgraded, where they are located, when will be the best time to perform the upgrade, and any hardware or software issues you may encounter.

You will now, as with any organization, want to work on determining the cost. There are the direct costs of the project such as the salaries of the personnel involved and the cost of the software. There are also the indirect costs like food for the people performing the upgrades and the potential costs of travel for getting employees to remote sites if necessary. The more accurate these projections are at the beginning, the better you will be able to manage those costs as the project moves forward.

With that aside, it is now time to identify how many computers in your organization will require the upgrade and where they are located. This will tell you how many licenses will be required and also give you an idea of what order to upgrade the computers in. I have found that typically the best time to perform these upgrades is over the weekend or some other time when people aren’t going to be using their systems. You don’t want to be performing these upgrades during the day when people are using their systems or on a weeknight when people will be needing them the next morning. Also, if the computers are spread out amongst multiple locations, you will need to make sure that you have two to three support people available before, during, and after the upgrade to help resolve any issues. It is much easier to handle any issues in person rather than remotely.

From personal experience, I can tell you that whenever you are completing an upgrade, it may be best to first test it on a few select systems that are representative of the majority of the computer in your organization. This way, you can identify any issues, such as driver or software incompatibility, with the upgrade on that system prior to executing it system wide and help to prevent them. You also will want to gather all of the necessary drivers to make sure that your hardware stays compatible with the new OS. In most cases, the drivers should be upgraded along with the operating system but it’s still a good idea to have a copy that you can use separately if necessary.

After identifying the best time to complete the upgrade, for argument’s sake we’ll say it’s the weekend, it will be time to gather together everything you will need to complete the upgrade. For this post, we will say that all of the computers are currently running Windows 7 and you are wanting to upgrade to Windows 8. From experience, the best way to do this is by using the Windows Server Update Services (WSUS) provided by Microsoft. I could write an entire separate paper on how to use WSUS and what it can do so, if you choose this route, I recommend that you go to to learn more about this invaluable tool. If WSUS isn’t an option, or if you prefer to use another method, I also recommend imaging. Information on how to do this is available at

When you know how you’re going to deploy the upgrade, and after you have done testing and determined that the upgrade will work, it’s now time to make sure that everyone’s system and other data is backed up and secure. This step is absolutely critical. If anything goes wrong during the upgrade process, you need to be sure that the information that was previously stored on the computer is still accessible. I will never forget when I upgraded my Windows machine from XP to 7 and lost the psychology paper I had spent two weeks writing. I had to recreate the whole thing in four hours. I managed to pull it off but I wouldn’t have had to if I had been smart and backed up before I upgraded.

Once you are confident that everyone’s data is safe and secure, you will want to start deploying the upgrade but do it in a way that you’re not targeting all the networked computers at the same time. Start with one or two that are within your Local Area Network to make sure that the deployment goes smoothly. If there are any issues, you can make adjustments as needed locally and then continue with the larger deployment over the network. It’s very difficult to say how long this will take but it’s best to stay close in case there are any issues.

And when I say issues, there are many. So much can go wrong that you can’t plan for. Recently I was assisting the IT department at my job with upgrading a few select computers to a more recent version of Windows when, about 30% into the installation process, the whole thing froze. It just stopped. We were baffled. We had literally just done the same upgrade on other computers at a different branch not a week earlier with no issues. Well, after wracking our brains and comparing system configurations, we determined that the computers we were upgrading simply didn’t have a good enough processor to run the upgraded version. That was our mistake. We failed to compare the newest specs against what the computer was running and it cost us several hours of downtime and manpower. We installed a lower powered version of the OS on the computer and it was up and running within an hour.

Once the upgrade is complete, you will want to afford some time to the end-users to test the systems and make sure that everything Is up and running properly. This will usually consist of the users performing the tasks that they normally perform on a daily basis to find out if there are any glaring issues. The most effective way to gather this information is to set clear expectations for the users and what you are wanting them to report. As long as you provide them with guidelines on what to report and how to report it, the information you receive will be consistent and useful.

After the users have reported any issues, and you have taken steps to correct them, you can consider the overall upgrade complete. There will always be things you encounter after the fact, when you think all is said and done, but that can be said of any large scale IT project. I’m hoping that this guide has helped you to understand some of the steps required to prepare for and execute a network-wide OS upgrade.