This chapter is important because Shepherd leadership is not much taught in popular business or leadership textbooks. There is inadequate understanding and practice of compassionate care-Shepherd leadership quality-in sectors such as education and healthcare. Education is an important sector as it impacts students’ learning. Teachers with Shepherd leadership qualities motivate students to outperform, and be creative and work persistently to improve themselves, their communities and society. Healthcare is an important sector because providing healthcare has significant impact on personal and public health, development and economic growth to attain major employment. Additionally, research reveals that caring and compassionate leadership is lacking in organizations because it forms resilience, nurtures a team spirit, enhances engagement, and may reduce employee turnover. This chapter sheds light on the importance of compassionate and caring leaders in religious and educational organizations, healthcare, the army, and business organizations. This chapter will discuss mainly Shepherd leadership and aims to define it and will explore where it is mostly utilized and in what type of organizations has this leadership been applied and successful. This chapter also compares Shepherd leadership with Servant leadership, a closely related leadership, and other popular leadership styles in today’s organizations. Lastly, this chapter will touch on the challenges of Shepherd leadership.