Venn diagrams are illustrations used in the branch of mathematics known as set theory. Invented in the 19th century by John Venn (1880), they show all of the possible mathematical or logical relationships between sets (groups of things). They are particularly attractive as pictorial representations of leadership issues in schools because they represent the interaction between key states and the emphasis required by a leader across the states as a response to individuals, contexts, etc. In this way they act as the landscape over which the talented leader exercises variable leadership styles, demeanour, and process. This paper seeks to explore how the use of Venn diagrams can add clarity to complex leadership and management scenarios. In particular, it argues that Venn diagrams, as a method of critically analysing the interaction between key factors, can be immensely beneficial to school leaders. (Contains 8 figures.)