Abstract. 'In the land of the blind, the one-eyed man is king'. This is particularly true in leading the introduction of Systems Engineering in a new domain. This could be in a sector new to Systems Engineering, such as transportation or biomedical. It could also be a new application in a traditional sector, such as system of systems or service engineering in defence. The challenges are many: there are few case studies; immature processes; limited tools and best practice; and data and information are missing. Yet in sectors such as transportation and infrastructure there is a strong demand to do something that will improve value for money -and a one-eyed systems engineer can make a persuasive case for investing in Systems Engineering.So is the one-eyed systems engineer a prophet -leading their organisation through the wilderness to the Promised Land? Are they a pragmatist, supporting the prophet and making sure that they deliver what the prophet has promised? Are they a perfectionist, who knows that if the Systems Engineering process is followed diligently it will deliver significant benefits? Or are they a pirate, selling shoddy Systems Engineering practice to desperate customers? This paper employs Checkland's Soft Systems Methodology to explore the different types of Systems Engineering leadership that the authors have seen across multiple sectors. It examines the associated mindset, approaches, values and personality types of the leaders. The paper illustrates the applicability of the different types of leadership to different situations using examples from the UK rail and defence industries. The analysis demonstrates the importance of deploying the right type of Systems Engineering leadership, illustrating the potential pitfalls of mismatching organisational context and Systems Engineering leadership style, and highlighting the non-Systems Engineering skills and competencies that are essential to realising real value through Systems Engineering.