Throughout the Odyssey, Odysseus displays the qualities of a great leader. However, he also makes bad decisions that endanger the lives of his men. I think that there is a definite development in his leadership throughout the epic and that he does, in the end, become a great leader.
The first time we see Odysseus’s leadership on display in the epic is when he recalls his previous travels to the Phaeacians. When he and his men landed on the island of the Lotus-eaters, he drags his men back to the ship rather than leave them behind on the island. He also does the same thing when half of his men go missing on Circe’s Island. He goes searching for them despite the warning from Eurylochus. It's very clear that Odysseus does deeply care about his men and refuses to leave them behind. This is the sign of a good leader.
He also respects his men and desires to honor them even after death. A perfect example of this is Elpenor. When Odysseus meets his ghost from the underworld, he is deeply upset as he was unaware that Elpenor had died. Following their encounter, he returns to Circe’s Island and buries his fallen comrade, as Elpenor requested he do so. It's another act that demonstrates how much he cares for his men. He grieves the deaths of those who died at the hands of Polyphemus as well.
Odysseus also protects his men as best he can. He advises that they put ear wax in their ears, so they aren't tempted by the siren’s song. He also travels past the Scylla rather than Charybdis so that only six men die rather than all of them. Although he does lose six men, he didn't really have a choice and saved as many as he could.
Odysseys can also be a questionable leader. His curiosity is what leads him and his men to be trapped in Polyphemus’ cave. Many of his men are eaten because of his decision to remain in the cave. Although he does eventually save the remaining men by blinding Polyphemus and escaping on the bellies of his sheep, his boastfulness and arrogance doom his men. When he tells Polyphemus his identity, he puts himself and his men at the mercy of Poseidon, the God of the sea.
This event has serious consequences on Odysseus’s reputation with his men. They completely distrust him which has major consequences. When he asked them not to open the bag of winds given to him by Aeolus, his men believed that it was because it contained riches [Odysseus did not tell them otherwise] and they open it, releasing the winds and sending them away from Ithaca. When he later requests that they swear an oath not to eat the cattle of the sun God, they break their oath and do it anyway which results in their collective demise. They even clash on Circe’s Island about what to do because his men are so distrusting of him after what happened with Polyphemus. Although his men behaved stupidly, it is Odysseus’s failure as a leader to earn their trust that leads them to disobey him.
He arrives home to Ithaca without a single crew member remaining. This is his own failure as a leader as his men were his responsibility. However, Odysseus does redeem himself as a leader and a king in the battle with the suitors. He is a teacher and a father to Telemachus who aids with his revenge. Odysseus can lead his son as well as the swineherd Eumaeus, Eurycleia, and Philoetius. They remain loyal to Odysseus and respect him. Because of this, they are successful in defeating the suitors. Odysseus’s identity is kept a secret, Eumaeus and Philoetius barricade the doors of the Great Hall and Telemachus helps his father in the battle. He later successfully prepares his men for battle with the suitors’ families as well.
Overall, I think that Odysseus becomes a great leader of men. We are aware that he was well respected by Nestor and Menelaus when he fought at Troy but as his travels proved, he wasn't the ideal leader. However, once Odysseus reached Ithaca, I believe he was then ready to be a great leader.