I would quiz him on his work setup. Find something that would make his life easier and make him go about doing it.

One of the most interesting learning experiences involved automating our anti-virus setup. We where hit bad Code Red and it was all over the place(a rather long story).

We needed a report as to the software levels, if software was installed, and the dictionary levels of all machines. We also needed to know current alerts and current levels of the dictionary files.

This process introduced me to TieRegistry, TableExtract, HTTP::Request, LWP::UserAgent, Net::SMTP, MAIL::Sender, and IO::File. After all that; my horizons changed dramtically and ideas on things to try kept appearing.

It's the old saying: Learn by doing!