Leadership is studied from a business, military, and personal perspective. This chapter addresses a topic plaguing most organizations with a shortage of prepared leaders for the future. A listening to collaboration exercise introduces the concepts of leadership, collaboration, and “leaderless” groups. A discussion focus method encourages participation and engages all members. It can be used in a variety of settings to encourage those who generally do not speak up or contribute openly. A best boss strategy is used to get participants to discuss the importance of quality interpersonal skills in a physical or virtual classroom. A learning through dialogue strategy can be used to inculcate team leadership skills in middle level managers, while promoting self-reflection and collaborative learning. A touchpoint activity sets the stage to discuss how a team's work flow affects service effectiveness and efficiency. The chapter discuses the strategies with case examples.