During the years I've been in IT, I've encountered quite a few instances where users think they understand how to handle their computer data. But more often than not, they need a little guidance.
In the days of Windows 98 and before the advent of imaging software at our company, preparing a desktop took an hour and a half and laptops took three hours. You had to install the operating system, do the Windows updates, reboot, then install the applications, do any reboots that were necessary, then install the antivirus client. Laptops went to specialized users, so they had more applications than the average desktop user.
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Then, when the machine was ready, there was the touchy issue of data transfer from one device to another.
"Nick" was a longtime employee of the company and reasonably computer savvy -- or so I thought. When the time came for him to get a new laptop to replace his old, lousy one, I was a happy fellow. No more patching up his old clunker. He told me, "Don't worry about backing my stuff up and transferring it to the new machine -- I'll take care of it."
On the surface, this sounded like a dream setup, but it should have been a red flag.
After the customary three-hour setup, I handed the laptop over to Nick. About an hour later, he called me and said, "I think I blew something up. Come and see me."
Sheepishly, he told me what he had done. Since the company didn't have a very good server-side backup solution, months before Nick had run out and bought a tape drive to back up his data. Smart. He then told me that he backed his machine up on a regular basis. Smart -- sort of. I saw that he was backing up the whole machine on his tape drive, not just mail, documents, and Web bookmarks.