I'm not sure why, but I imagine him with his expression.
As for my process, everything is done digitally. The initial sketch, then the final sketch. Though, if I were doing it traditionally I would complete it then scan, making no digital alterations.
As an example, this is the initial (and only) draft for this particular drawing:
I try to make them as close to the end result as possible since I tend to lose track of my ideas as I work.
Thanks so much for sharing your character, and I hope I answered all of your questions!