Please set up automatic system imaging for your server (e.g. Slicehost backups). The biggest barrier to learning is fear, so it helps him to know that he can pr

Please set up automatic system imaging for your server (e.g. Slicehost backups). The biggest barrier to learning is fear, so it helps him to know that he can press the "undo button" for the entire system at any time. Other than that, I recommend letting him watch you use the terminal for 20 minutes to show him what proficient console use looks like. Advanced commands can be Googled later, and those "Unix Cheat Sheets" and cram tutorials were always simultaneously too complex and too simplistic for me to ever find useful. A working understanding would be more valuable.