In 2011, The Australian Institute of Teachers and School Leadership (AITSL) established a set of standards to guide the preparation and development of principals informed by three leadership requirements: vision and values, knowledge and comprehension, and personal qualities and social and communication skills. Despite the existence of a national framework, approaches to leadership preparation in the State of Victoria continue to be described as ad hoc and often disconnected, given the absence of any compulsory principal preparation program. As a result, the preparation of early-career principals is very much left to each individual through a number of opportunities, such as middle leadership roles, coaching and mentoring, and university courses, amongst others. Whilst many of the aforementioned opportunities would appear to be adequate, little is still known about early-career principals’ perceptions and evaluation of these opportunities in preparing them for the principal role. In Sweden, the principal training has been an education in constant change, but there has been systematic training of school leaders since the mid-1970s and today the training of principals is institutionalized in Sweden.The National Principal Training Program (NPTP) is currently hosted by seven universities at the request of the Swedish National Education Agency and is based on an agreed national target document that coordinates their expectations. It is offered for the first time when the participant has commenced a principal position. Some appointed principals have gone through voluntary recruitment training or pre-service preparation programs as teachers, and some have experience as teacher leaders, deputy principals, or substitute principals. In contrast, others had no leadership training or experience before their participation in the mandatory national principal program. The national program is a 3-year mandatory in-service program and consists of three courses. Through a comparative analysis, the purpose of this study was to understand how two very different leadership preparation pathways equipped early-career principals with the necessary skills and knowledge as they took on their first principalship, through the eyes of the leaders themselves. This study sought to answer (1) how early-career principals perceive the quality of their leadership preparation and what it has meant once in the principal role and (2) what differences and similarities exist between early-career principals’ perceptions of their leadership preparation in Australia and Sweden, and how we can understand it from a leadership development perspective. Preliminary findings confirm that in both contexts, principals valued exposure to mentoring opportunities and building their principal literacy in areas, such as school laws, jurisdictions and school improvement initiatives. Similar tensions were also perceived and revolved around the complexities of engaging in leadership preparation while managing a full-time job, limited exposure to ‘real’ problem-solving and a willingness to develop expertise in people management. This study has implications for the preparation, development and retention of future school leaders regardless of the pathway taken to reach the principalship. In addition, this study adds to the knowledge base on global perspectives on leadership preparation, with particular insight into how current pathways are perceived by those who undertake them.