Analyze the Scylla-and-Charybdis passage as a forced choice between two costly options, and evaluate it as a model of leadership under constraint.
Odysseus is warned that his route home runs through a narrow strait guarded on one side by Scylla, a six-headed monster fixed in a cliffside cave, and on the other by Charybdis, a whirlpool violent enough to swallow an entire ship. He cannot avoid the strait and cannot fight either monster -- the only real decision is which side to sail nearer. He is advised to hug the side nearer Scylla, accepting the near-certain loss of six sailors, one for each of her heads, rather than risk Charybdis, which could sink the whole ship and kill everyone aboard.
This is a distinct kind of dilemma from earlier trials: there is no clever trick available, as with the Cyclops, and no advance safeguard, as with the Sirens. It is a forced trade-off between a smaller, certain loss and a larger, uncertain catastrophe -- the kind of decision real leaders in emergencies still have to make, and it is worth sitting with the discomfort of Odysseus's choice rather than resolving it too quickly.
Mastery looks like: They can explain why this episode is a forced trade-off rather than a puzzle with a clean solution, and can connect its structure to a real-world example of a similar dilemma.
Common stumbles: Looking for a "trick" that avoids all loss, the way the Cyclops episode had one, when the entire point of this passage is that no such trick exists here.