At what point do you say to yourself have been an instructor too long? Are there peculiar portents visible only to trainers that tell them they have been behind the podium too long? If you get a second generation student -then yes, you have been an IT Instructor too long! I haven't had that happen to me - yet. But there are other signs out there that clue you in to the "you-have-been-a-trainer-for-too-long syndrome".
One such clue could be if you have trained the same person on two or more successive operating systems. If you taught them Server 2000, then 2003 and now 2008 - than that is definitely a sign you have been at the podium a long time. Another clue could be the training manuals we all seem to accumulate and never throw away. If your collection has NT4, 2000, 2003 and your newly printed 2008 manuals...time for a sabbatical!
I had my own "you-have-been-training-too-long clue" not so long ago. I recently bumped into a student I had trained a number of years ago and we started to catch up each other's lives. This student was a career changer - or rather had been a recent graduate of college and wanted to start a career in the IT field. He was brand new to the field and worked hard at his classes and passed all the requisite tests. He also did some volunteer IT work and had a few entry level jobs to get some experience. He was able to get a great job as the IT administrator for a company after 2 years of working various IT positions. As we were chatting - it became readily apparent that he had mastered his position and was quite good at his job. I wish I could claim credit for his success, but I can't. He did ask about getting one of his subordinates trained though...so in a round-about way, this could be a second-generation student!
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When you can't do what you train...
I'm a firm believer that the best IT trainers can (and do/have) implement what they train. Most IT projects differ greatly in theoretical knowledge of how something should work versus how it actually does work in a production environment.
I'll admit, keeping up both with new technology and new trends in training can be tough, but I think it's key to being a good trainer. When I look for training partners for my clients I almost always ask about their implementation experience and references.
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