If you are in the IT industry and you haven’t figured out yet that new versions of operating systems, programs, languages, deployment technologies, etc.. are going to keep coming, then I’ve got an unwelcome surprise for you.

And those changes are coming…


  • Windows Server 2003 -> Windows Server 2003 R2 / 2.5 years / small jump
  • Windows Server 2003 R2 -> Windows Server 2008 / 2 years / bigger jump
  • Windows Server 2008 -> Windows Server 2008 R2 / 1.5 years/ small jump
  • Windows Server 2008 R2 -> Windows Server 2012 / 3 years / huge jump
  • Windows Server 2012 -> Windows Server 2012 R2 / 1 year / small jump
  • Windows Server 2012 R2 -> Windows Server Next (estimate) / 2.5 years / huge jump

If you collapse the “r2” releases, you’ve got about 3.5 to 4.5 years between major changes. However, those major change sets are growing.

If you are still running 2008/2008R2 in the next few years, you will be coping with a sea of changes:

  • PowerShell v1 or v2 to v5+ - including re-written parser and tons of new features (including DSC) and delegated administration endpoints (and WMF5 is shipping quarterly, with lots of changes and updates)
  • Features on Demand
  • Scale Out File Servers
  • Virtualization improvements and containerization
  • .NET Core (and ASP.NET on Linux) - yeah, Windows Server won’t be the only choice for ASP.NET apps.
  • Software defined networking

Oh Yeah, and Cross Platform…

If you think changing from Windows Server 2008 to 2012 will be tough, how are you going to feel if you are told, “Oh, by the way, we are going to switch our application tier to Centos 7 because Engineering wants to ship containers.”

Own Your Career

If you want to stay relevant in the technology space, especially in the IT administration and operations space,

  • YOU need to stay on top of technology.
  • YOU need to make sure your team is pushing forward and prepared for the next change.
  • YOU need to make sure the systems you are responsible for are positioned to take advantage of those changes.

Or YOU might have a hard time finding a new role when change invalidates your skillset. Relying on your boss or your company to be prepared is a “nice to have”. You cannot count on it - but your career depends on it.

If your environment is running Windows Server 2008/2008R2 and you are not actively working on a migration strategy (where you were directed to or not) - you are in for a world of pain when your business demands that you get there.

And if you are on Windows Server 2003… I think there is a law against that somewhere… I’d go somewhere that cares about staying relevant.

And yes, I said “whether you were directed to or not”. You are a professional and that’s just part of the job.