I've been avoiding this thread because I thought it was in the manga section

Best Shounen Charisma: Naruto
Best realistic leader: Neji - he's already revered as a genius, powerful jounin, good leading ability, 360 anti-assasin vision....he'd be my first pick.

Since the focus is on Shikamaru, I'd give him the role of Head Strategist. Konoha gets a great mind, and Shika gets a holiday.