Engineering Leadership (EL) is a dynamic undertaking which seeks the alignment of the many ‘ways and means’ to achieve organizational goals, and thus realize advancement in engineering and technological disciplines. This chapter examines the core competencies of the Engineering Leader, the role and ‘fit’ of Systems Thinking in EL, and how an organization might invest in a culture of EL growth. A historic and contemporary review of contributors in leadership and technical management theory are presented alongside applied vignettes. Mental model representations of core competencies and Systems Engineering in EL provide a graphical road-map to think about developing Engineering Leaders.