A lazy person; a pencil that is still sharp has obviously not been used, and is therefore not doing a lot of work. It also sounds like a compliment, so you can troll people with it.
Why are you here? You really are the sharpest pencil in the pack, aren't you?
This is what a person says when he is making a tentative appointment.
"I'll Pencil" (because the appointment can be erased) "you in" (to my schedulebook).
Ozzy: Hey, can I come up to your big fancy office and make fun of you?
Boohiss: Er. I'm kinda busy this week. Tell you what, I'll pencil you in for 4:30 on Thursday.
To pencil someone into a schedule but using a light amount of pressure. This way, as you know they will always cancel, when you erase, there is no visual indent of their name in your schedule.
Guy: sorry I keep cancelling on you, would you like to go to the cinema on Friday?
Girl: yes, I'll lightly pencil you in.
Guy cancels
Girl to friend: I am glad I only lightly penciled him in, as there is no indent to remind me that he cancelled AGAIN!