Sometimes people really don't know why they want to learn Perl. This may not be the case with your group, but I've found that in any teaching, making the subject relate to the student is always a good first step. This guy is an operator right? I'd suggest trying to figure out what sort of work he's been doing, and show him how perl can make his life easier. Lay out examples of what you want to teach that are relevant to what he's been doing for the last 20 yrs. of his life and it will be much easier for him to grasp the fundamentals. Want to teach him about data conversion? Figure out an instance where he's done manual data conversion in the past and then show him how to do it in perl. That'll gaurantee an "ah-ha" moment.

Folks with little or no programming background can learn and use perl, but it's far more difficult if they don't have some way to apply the theory to concrete examples of it's use.
I didn't learn Perl to learn Perl. I learned it to make my life easier. Now I'm using it to make other peoples lives easier too.

~monk d4vis
#!/usr/bin/fnord

ps. If that doesn't work, try beating them harder.