I am a co-op student doing my internship and I have been given the dreadful task of upgrading people's Windows Server 2003 or older versions to Windows Server 2008 R2 or higher. However, most users are very aggressive when it comes to letting me upgrade because they may not care about the version of server they are using. For my requirements though I have to do it so I wanted to ask someone what arguments or incentives could I use to successfully convince my users to let me upgrade their server? Does a regular user benefit greatly from stability? Performance increase? What can I use to my advantage to aid me in convincing them?

  • How could you be required to make someone else do something they don't want to do? That's a very interesting internship you have there.
    – joeqwerty
    Jun 19, 2013 at 17:35
  • This isn't a technical problem, it's a people problem. Your incentive is "This update is required by the company. You must comply." (Try to say it in as Borg a voice as you can manage.) -- If that doesn't work, finding ways to motivate your problem co-workers and/or get around their intransigence is really a question for The Workplace.
    – voretaq7
    Jun 19, 2013 at 17:37
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    "resistance is futile, you will be assimilated"
    – joeqwerty
    Jun 19, 2013 at 17:42
  • @voretaq7 It is a people problem but the question I was asking here is technical advantages of Windows server 2008 R2 and disadvantages of Windows Server 2003 or older so that I may convince my users. I believe that it IS a technical question. Jun 19, 2013 at 17:43

1 Answer 1


Windows Server 2003 will be end-of-support in July 2015. There is only two years left in its life. It is a ten year old technology that is crusty and stale. That's all the justification you should need.

  • Thank you @MDMarra . That will definatley be a good scare to give! Jun 19, 2013 at 17:39
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    There will be no more updates (security or otherwise) and if you run into an issue and need to call Microsoft Support, they will not answer questions surrounding Server 2003. They will tell you that it has reached the end of its supported lifetime.
    – MDMarra
    Jun 19, 2013 at 17:40
  • Oh okay. I also found this after taking your suggesiton and googling it: blog.octari.com/windows-server-2003-end-of-support-july-2015-2 Jun 19, 2013 at 17:41
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    Your premise and your approach is wrong. You think that because it's newer then it must be better for the user and that's an ill conceived notion. Your approach that you need to "scare" your users into letting you upgrade their servers is counter productive. Your job is to engage and advise them. Find out why they're running old servers. Find out what their limitations and requirements are for upgrading their servers. Your job is not to "scare" them or to force them into doing anything, especially something they don't want.
    – joeqwerty
    Jun 19, 2013 at 18:02
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    Very true @joeqwerty. My example was more of how management can be sold on it. Once management is sold, you shouldn't have to "sell" the users on it, it should be mandated. If it's up to the users to decide, it's going to be a nightmare.
    – MDMarra
    Jun 19, 2013 at 18:07

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