COVID-19 teaches us lessons about leadership, the most important of which is to put more women in charge. This Article provides an interdisciplinary analysis of these lessons, which come at the very high price of many forever disrupted and lost human lives. COVID-19 is a global tragedy. COVID-19 can also be a cruel, relentless and unforgiving teacher of valuable lessons about leadership. During COVID-19, leaders had to quickly mobilize many resources and convince many people to change their established behaviors and familiar routines. Leaders had to rely on effective and persuasive communication to achieve buy-in and voluntary compliance by a diverse public. This is because enforcement of non-compliance is effectively infeasible. This Article introduces the phrase, thoughtful leadership, to describe such leadership and leadership communications. In response to COVID-19, some leaders have been compassionate, courageous, data-based, decisive, and kind. These leaders’ communications with the media and the public were calm, caring, clear, empathetic, honest, science-driven, and transparent. This Article applies to leadership mathematician Eugenia Cheng’s category-theory based notion of congressive qualities, such as being collaborative, communitarian, cooperative, curious, empathetic, inclusive, open-minded, modest, other-regarding, and prudent. This Article analyzes what leaders who were more successful during COVID-19 did and said. During COVID-19, women were many of the most admired and more successful leaders. These female leaders of cities, states and nations were exemplary. There were also some exemplary male leaders. This Article considers explanations and theories about why so many women leaders were among the most successful during COVID-19. This Article profiles in some detail three exemplars of leadership: New Zealand prime minister Jacinda Ardern, Secretary to the Governor of New York Melissa DeRosa, and New York state governor Andrew Cuomo. Finally, congressive and thoughtful leadership are also applicable to parenting and teaching.