In 401 BCE, the Persian prince Cyrus the Younger, seeking to seize the throne, hired an army of Greek mercenaries: the so-called Ten Thousand. When Cyrus died at the battle of Cunaxa, the Greeks found themselves in the midst of the Persian empire, with little hope. This hope became even more forlorn when the most influential leaders of the Greeks were killed in an ambush. Somebody had to take control; but who? Xenophon was not an officer, nor even a soldier. However, he was able to rise to the position of commander of one of the three biggest companies of the Ten Thousand, and later even attained the supreme command. His memoirs provide an interesting, although idealized, case study, which emphasize many essential elements of leadership in a moment of transition. The subtle balancing act with surviving institutions and past leaders, the focus on subordinates’ emotions to build confidence and trust, and the importance of communal ideals and ethical choices are only some of the pillars on which Xenophon built his power. From this case study students will appreciate what is needed for an effective change in leadership to be made, as well as the challenges that face the one attempting to emerge in a new environment.