This case study focuses on a diverse group of eight unacquainted individuals from six countries: United Arab Emirates, Israel, Greece, Russia, Lithuania, and the United Kingdom. Three out of eight members were practicing coaches, and only one had some professional group and team coaching experience. From October 9 to December 3, the group had eleven video calls: one mandatory introductory meeting, three optional reflective sessions, and seven mandatory coaching sessions (due to burnout issues, I attended only five). The group met every Wednesday at 12 or 12.30 BST for an hour and a half, except for the reflective sessions on Mondays. Also, the group members participated in daily discussions on the group chat. During the introductory meeting and the first coaching session, the group discussed how they could become a team and questions associated with contracting, theory, and assignments. The remaining sessions were dedicated to well-being (our core topic) and associated themes, such as authenticity, savoring, strengths, and relationships. Six out of eight members coached the group for at least one time. The group did not share an overarching goal, except for becoming a team, as suggested in the module handbook. In this paper, I took two perspectives (i.e., the observer and the coachee) to discuss the sessions that I attended (i.e., the introductory meeting and five group coaching sessions). From an observer's point of view, I discussed our contracting-related ethical challenges against the best practices in multi-stakeholder contracting (see Section 2). The observer's perspective also allowed me to take a broad yet critical look at the major group/team coaching theories and studies (see Section 3). In Section 4, I took the coachee's perspectives to analyze the four coaching sessions facilitated by my colleagues. The sequence of sections corresponds with the phases of our group development, ranging from discussions around contracting and theory to the actual application of various approaches and interventions in a group coaching setting. For a more detailed breakdown of my reflections, please refer to Appendix A.