In this chapter genuine leadership stories derived from the organizational setting are used to explore each element of the ‘leadership moment’. The stories reflect the experience of a consulting practitioner who works with leaders to improve leadership effectiveness in businesses. The organizational context is found to play a critical role in shaping the way an individual considers her or his leader identity and responsibilities. Noted is that every leader in an organizational context is also a follower (except for a founder), drawing attention to the challenge of making a clear distinction between leader and follower in the workplace. Purpose is seen to be a necessary component of the organization, which then shapes and regulates organizational leadership. Perception is viewed as a game changer to the thinking of leadership providing the dynamic quality needed to understand how our perspective of leadership can change from moment to moment. Attention is called to the importance of trust and respect in the leadership moment.