This article considers the importance of leaders being securely attached. A securely attached leader can establish relationships with self, others, and the world in a safe and trusting way. This plays an important role in supporting the development of a secure working environment for the teams with which they are working. When a leader builds up a relationship with a team, based on secure attachments, there is space for social and emotional balance. This evokes curiosity, an eagerness to learn, and the urge to explore. Leaders who themselves have experienced (elements) of unsafe attachment may encounter challenges in being able to offer psychological security, not just for themselves, but also in relationship to their team members. The authors look briefly at the current era of transition in the world and its impact on leadership in organizations. They focus on theories around attachment and examine some issues around insecure attachment and leadership. They conclude by offering several concrete interventions, which can be deployed by TA facilitators, to help leaders develop a more secure base in themselves and thus offer a secure-based relationship to their teams.