Due to his show of strategy skill and creativity during the exams, Shikamaru was made a Chunin by the Hokage. As he knew team seven and who they would be trying to save Shikamaru was order on his first assignment of leading and building a team to retrieve Sasuke and joining Orochimaru. Shikamaru set about building his team, he was only allowed to use Genin due to the attack on Konoha, Shikamaru first enlisted Naruto and Choji and then Later Neji and Kiba. As they set out Shikamaura had already planned an attack placing Kiba at the front knowing his and followed by Choji (Naruto who would give back up), himself and then Neji at the back(abilities would pick up any traps laid for them) making the perfect plan for attack and defense.
But as they moved they where trapped by Jirobo one of Orochimaru’s four men who had taken Sasuke , Sitting down and watching Naruto and Neji striking at the rock formation they where now trapped in Shikamaru formulated a plan of escape, as Naruto struck at one point the others would strike at the weak point that would be on the other side of the trap. When they escaped Choji decied to stay behind and face Jirobo on his own knowing the others would be escaping. Shikamaru told Choji that he better catch up and left with his now only three team mates as they went Shikamaru marked their path so that Choji could follow. As they met each new threat the team broke down one by one to face Orochimaru’s men one on one allowing the team to catch up to Sasuke.
Shikamaru tricked the Tayuya and told Naruto to go ahead and as he was one of the only people that could get to Sasuke and stop him. This left Shikamaru to face Tayuya a female ninja who used a flute to make genjutsu(illusions) and confuse her enemies, as the battle progressed and Shikamaru began to get the up hand, Tayuya summoned three demons to her side, the demons where controlled by her flute and Shikamaru allowed them to attack him to start with, this was a ploy to allow Shikamaru to pick up on what notes created what movements and then he took control of the three with his Shadows control and turned them back on their master who was forced to set them send them from where they came.
Her only weapon was her flute and she began casting genjutsu and Shikamaru found himself having to come up with a new plan of attack, Throwing a kunai he missed and then fell under the Genjutsu. Thinking she had won she removed the Kunai that was now stuck in the tree behind her and began to move to slit his throat when she got close enough Shikamaru lunched his attack. He had been pretending to be caught under genjutsu so that she would move into range for his attack. Shikamaru says "The first attack is always a fake one.. this is a basic strategy"
She had no choice but to use her cursed seal to break free of the attack Shikamaru could feel his chakra fading and knew the battle would be over. Just as he gave up hope a blast of wind broke the air and there stood Temari of the . As she landed in front of him Shikamaru gave a tactical update and with this information she made quick work of Tayuya.
The two of them made their way back to Konoha and discovered that Sasuke had escaped and everyone on the team was greatly injured. Questing everything he had done Shikamaru went to leave Konoha but was met by his father who called him a coward, He said that if he was not there to lead them then some other ninja would have to and he would always question if one of them died could he have stopped it if he was leading. As news arrived telling them that everyone was going to be okay Shikamaru broke down in tears and swore he would do better next time. After he had the news he said good bye to the people of the sand village who had come to help and mentioned how annoying women where when he turned his back to Temari.