When examining Odysseus's actions in books 9–11, we should remember first of all that he is telling the story of his own exploits to the Phaeacians. We can discount the possibility of his belittling his own role through modesty. Modesty about one's own accomplishments was barely even a concept in Homeric Greece and is certainly not an attribute of Odysseus. However, there is a strong possibility of his heightening the conflict and exaggerating the circumstances for dramatic effect.

The battle at Ismarus in book 9 shows Odysseus as a wise leader but not a strong one. This is a pattern throughout the Odyssey. Odysseus is right, but his men disobey him anyway, with a mutinous attitude that eventually leads to their deaths in book 11. Odysseus is constantly portrayed as better suited to being an adviser and counselor than a leader in his own right. This is shown again in the episode of the "bag of winds" in Book 10. Odysseus is in the right, but he cannot command the obedience of his men, who open the bag against his instructions.

Odysseus is wrong and shows poor leadership in refusing to leave the land of the Cyclopes in time to prevent the capture of himself and his men, but he is resourceful in his method of escape. This is the type of situation, requiring cunning and subtlety, which reveals the best in Odysseus. His final revelation of his name to Polyphemus may seem like gratuitous bravado to a modern reader, but Homeric heroes were deeply concerned that their exploits should be known, and Odysseus is doing exactly what Achilles, Diomedes, or any of the heroes with whom he fought at Troy would have done. If he behaved like this more often, he might have the respect of his men, allowing him to command their obedience and be a truly effective leader. As it is, they disobey him for the final time in book 11 by eating the cattle of the sun, and he no longer has the responsibility of leading them after they all drown on the voyage from Thrinacia. It is surely the definition of a bad leader that he fails to preserve his men from death.

At Ismarus, Odysseus "urged [his crew] to cut and run," to take their plunder and leave immediately, but they wanted to stay and have a party instead. He calls them "mutinous fools" because all they wanted to do was get drunk and eat the longhorn oxen there. During this time, the Cicones collected all the allies they could and returned to Odysseus's crew's encampment, slaughtering six crew members from each ship. If Odysseus were a better leader, it seems to me that he could have compelled his men to follow his directions and leave.

Next, when the crew reaches the island where the Cyclopes live, they "[press him], pleading hard" to take some food and return to their ship. However, Odysseus wants to see "what gifts [the cave's owner would] give" to him. In other words, his greed seems to overwhelm his thoughts about his men's security and safety here. This is not a sign of a good leader.

Odysseus uses good judgment when he tells the Cyclops that his name is "Nobody," but then he reveals his actual name and taunts the monster as his ship rows away. His words "made the rage of the monster boil over," and it nearly resulted in Polyphemus sinking the ship or capturing the men. Odysseus, however, continues to taunt him, tempting fate and incurring the wrath of the monster's father, Poseidon, in the process (not a good leadership moment).

Odysseus' Leadership in Books IX-XII

1. He and his men attack Ismarus and sack the city, killing the men and sharing the wives and plunder. In one way, Odysseus is characterized as a good leader because he commands that everything be shared equally. On the other hand, he is a bad leader because his crew does not follow his orders, revealing his control is at best weak. 
2. After a dreadful storm, Odysseus is characterized as a good leader when he recognizes the dangers of the appealing Lotus-eaters, and he therefore forces his men back on board. 
3. Then, he and his men land on the Cyclops' island, at which point they are trapped by one of the monsters, Polyphemos. He is a good leader because he manages to outwit the Cyclops and escape with his men and many supplies. However, he is also a bad leader because, in his pride, he reveals his identity to the Cyclops. This endangers his entire crew. 
4. His crewmembers' betrayal following their stay at Aeolus' island goes unpunished, which could reveal Odysseus as a bad leader who does not hold people accountable for their actions, or as a good leader who forgives people's mistakes. 
5. Odysseus' quick thinking allows him and his ship to escape the Laestrygonians' attack, characterizing him as a good leader. 
6. On the Aeasean island, Odysseus' commitment to hunting and keeping his men safe shows that he is a good leader. Later, when Circe captures Odysseus' men, he refuses to abandon them to their fate, again making him a good leader. However, his decision to expose his men to Circe's power again is disturbing; although no harm comes of it,  this is an ambiguous characterization. 
7. Odysseus' conversations with the ghosts characterize him as a good leader who listens carefully to advice. 
8. Odysseus' protection of his crew against the sirens is a mark of good leadership. 
9. Odysseus' inability to strike down or control Eurylochus makes him a bad leader and leads to serious issues in their quest.