I wonder how awesome, Shikamaru's dad, Shikaku is at strategies. You've got to figure he must be amazing since he's a Jonin Commander and the one ninja Tsunade chose to take with her when the Shinobi Alliance first met up.
Shikaku was the only active shinobi summoned to the meeting over the next hokage and he nearly had Kakashi elected then, if not for Danzo's jutsu. Shikaku beat Shikamaru in shogi the one time they played while Asuma had never come close.
Shikaku is probably the Head Strategist who Tsunade consults with concerning larger battles.