He's definitely not an experienced user, at least not with Linux or the command-line. He just has a lot of experience with computers. My point was that this isn't a grandma situation: 'Ok, so this is called a FILE. Your website is made up of lots of different files. Files are kept in directories, which are like folders, and end with /…'

PS: This actually makes me think interesting thoughts about the meaning of the word 'user', the many different senses in which we use it, and the many overlapping ways one could be said to be an experienced user, such that many experienced users all have entirely distinct skill sets with no overlap.

You can do a lot of stuff without ever touching the shell, and there's a good chance he's even used the shell before, just not in a Unix environment (probably Windows, which is significantly different, though the transition isn't too hard). Besides, nobody said he was "experienced", just that he wasn't a novice.

A longtime smalltalker is definitely an experienced user.