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).