Upgrading Software: The factors to consider

How to Plan for Your Next Software Upgrade

upgrade softwareThere comes a time for every company to bite the bullet and investigate upgrading their systems. Regardless of whether you’re talking about hardware or software, upgrading is never so much an “if” as much as it is a “when”.

In this case, we’ll just stick to what is typically the easier choice: upgrading software.

I say “easier”, but what I really mean is that there will be more of a choice. For example, if your company is using Windows Server 2003, you probably know that Microsoft will soon stop supporting its security and vulnerability patching cycles.

This is typically the pattern of software releases and it usually comes many, many years after the initial release (and the release of multiple other versions of the OS). So, when it comes to upgrading software, it will always depend on the type of system rather than the year of manufacture.

When planning to upgrade software, there are a great number of factors to consider. For this read, we’ll stick to what I consider the most important (in no particular order):

  • Cost
  • Plan
  • Test
  • Retraining
  • Implementation
  • Configuration


When it comes to the IT field in general, it’s not so much a money-making department as it is a necessary tool for the modern world. To keep that tool in working order, maintenance is required. Software patching, can only take you so far. Carefully weigh the benefits for upgrading versus staying put. Software support lifespans and the need for greater flexibility and efficiency are a key reason to keep software not only patched but on the most current format.

Taking advantage of cutting edge software technologies tends to have unforeseen advantages and can lead to profound changes within an organization. So, when it comes to cost, I think it’s a wise choice to also weigh the cost of not upgrading to that new version of an OS, or mail system. In a world filled with ever challenging security threats, it’s best to choose based on the cost “Not” to upgrade rather than the cost to do so.


Have a plan, and test new installations regularly. This will make upgrading an asset and trial tested process for future use. In the IT field, it’s best to always have a testing system available for any software – that’s a given. This will make the choice to upgrade easier by giving you the ability to see not only how the software will perform in your environment, but how it will be adopted by the people expected to run the systems on a daily basis. These are processes that every organization should have regardless if you want to upgrade any software currently.


Retraining may be seen as a takeaway from upgrading, yet in my perspective this is a necessity that cannot be over emphasized as important. This should be taken as a chance to improve not only systems but people on a regular basis. Having been a part of such a staff, I can attest to the productivity a well trained and experienced staff can accomplish. Pushing to invest in the most recent and cutting edge software will clearly display this, and keep systems running efficiently.


During implementation planning, you need to consider how to install and configure your new software and determine whether there will be any system downtime. Yet as our software systems have evolved, so have the process changes that make software deployments easier than ever.

So, if you’re having the “upgrade conversation” at work, it’s probably already time to take action and update that software!

In the case of Windows Server 2003, get your team on board with Windows Server 2012 R2 and realize the ease of live server migrations and remote administration. Upgrade your Exchange server for added administrative functionality with web interfaces. Don’t wait for the added pressure of product support timelines and always be prepared in this ever changing IT world.

2015-03-20T09:09:10+00:00 March 20th, 2015|

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