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I remember seeing a sitcom where the boss had installed some new software and the characters had difficulties using it. I thought it may have been The Office (US) with Ryan's new website, but judging by the episode summary it doesn't look like it.

UPDATE
It was one of the major one of recent years, probably no older than 2005.

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Do you have more details? How old is the show? What do you remember about the cast? –  user209 Mar 14 '13 at 19:48
    
Please add the additional info provided in the comments, to the question. –  KeyBrd Basher Mar 15 '13 at 5:19
    
You really need to be more specific. In what way did they "have difficulty"? What was the software about? Or the sitcom/scene setting? –  DisgruntledGoat Mar 17 '13 at 1:18
    
@DisgruntledGoat It doesn't matter. He posted a (now deleted) comment that said he was trawling for examples of this, he's not looking for a specific show, just an example that he's planning on using for some presentation. –  user209 Mar 17 '13 at 3:18
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Not much to go by but you could try the IT crowd which is known for mocking the lacking computer skills of non-IT-people. Maybe you saw one of those episodes.

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