An Important Rule: 

If you’re trying to convince someone to your viewpoint, insulting them generally doesn’t work. If it does anything, it will be more likely to entrench them against your position. Therefore, this is something that IT professionals should avoid. 

If You Write Your Own Software

or work for an organization that’s core business runs on the software your organization writes, it is easy to miss the issues that folks who typically deploy third party solutions face. Among them is what the vendor will support with regards to operating system, core application components, etc. For instance, an IT pro may be perfectly ready to roll a Windows Server 2012 VM for a new application deployment. However, the vendor doesn’t support beyond Windows Server 2008 R2. Guess what the IT pro is going to deploy? In the vast majority of cases, that server is going to be Windows Server 2008 R2.

As a young IT pro, I often thought, “Hey, I can convince the vendor to support my configuration.” What I quickly learned, however, was quite different. As The Rock says,

“It doesn’t matter what you think!”

If you have to run a particular software package and they have requirements you don’t like, most of the time you have to accept your dislike and conform to the vendor.

When New Features Trump Maintenance

Being a security type, I always want the most streamlined, secure operating system and/or application. However, taking the time to upgrade takes away from time to implement new features unless the new features desired are in the operating system or application that is in need of an upgrade. If the new features come as a result of development or another application, you may not get the option of upgrading when you want. This is especially true when you support a lot of core applications and when business is constantly looking for new features and values new features over maintaining existing systems (even though replacement or fixes or upgrades will be substantially more at a later time). 

Trying to fight this in some organizations is fruitless. The organization will perform the upgrade (or migration to a new OS baseline) when they are forced to dos o. In this case, a bit more wisdom from The Rock,

“Know your role!”

TL;DR Version

We don’t always get to pick when we upgrade OS or application version. There are other factors in play. Don’t assume that one professional’s seeming lack of desire to do so is because of any particular reason. The only way to know is to ask, and to do nicely, without insulting said professional.