Individual coaching has been in the business world since the 1980s. Team coaching is a more recent entrant into the world of learning and development. This paper presents a case study of team coaching from the perspective of a team coach who was engaged by the team leader to improve the quality of the team members’ relationships and of goal attainment. A qualitative case study method was utilized, and data were gathered using structured interviews, observations, and personality and leadership assessments. The general finding of this study was that team coaching can be a highly effective means of development. An unexpected finding was that when coaching a team of leaders, including their leader, team coaching can positively impact leadership development at both the individual and collective level. Building upon the case study and reflections on circumstances that the team leader experienced after the team coaching engagement concluded, the author proposes the application of complexity theory and its associated tools in a team coaching process model for working with leadership teams faced with highly unpredictable and chaotic situations.