Transformational leadership is one of the most researched leadership theories, but sometimes misunderstood by managers who believe that to be a transformational leader requires them to be charismatic and in some way extraordinary. Similarly, some sportspeople and sports coaches may be truly transformational in their achievements and yet not receive the same recognition as their more flamboyant colleagues. In this chapter, several similarities are identified between managerial coaching and transformational leadership. Some differences were also identified. Where there are similarities, it is argued that adopting coaching practices can help managers to put transformational leadership into practice and gain the associated benefits, whether in business or sporting organizations.