Leaders need many competencies to drive diverse and transcultural workforces by building strong work and positive intergroup relationships. This is particularly true for running organizations which grow in social, cultural, and technological diversity. Love, defined as compassion (Schopenhauer), is a form of caring, a form of altruism which emphasizes concern for the self and the other person’s well-being. In contemporary globalizing work environments, while technologizing and digitalization are at the forefront of the approaching Fourth Industrial Revolution, love, compassion, peace, and sustainability are advancing as key components in the art of collaboration for a sustainable, future world. This chapter presents findings from a qualitative research study in which 22 leaders were interviewed on their views of love and leadership. Leaders explain how they define and interrelate the two concepts and how love impacts on their leadership in theory and practice. Findings show that love is split into concepts of interpersonal, intrapersonal, object-related, and toxic or nonexistent love in a work environment. Leaders know how to express and detect love at work. They understand love as an emotion which connects people across cultural group membership and supports individuals in finding solutions and working together respectfully and openly. Additionally, love can help employees to transform negative emotions into neutral or positive ones. Finally, extraordinary leaders are defined by the respondents as those who go beyond the regular and customary and are driven by concepts such as a loving attitude, love for humanity, inclusiveness, and unconditional love.