The inspiration behind the research conducted in this conference paper roots back to the 6th European Lean Educator Conference (ELEC 2019) held in Milan. Named “The Lean Educator and Practitioner Mashup”, the conference was meant to explore the latest academics and industrial contribution to lean education, embracing the figure of Leonardo da Vinci as a conceptual leitmotif.Both formal and informal events were paramount in the inspirational process leading to this research, highlighting some relations between lean thinking principles and the character of Leonardo da Vinci.In this regard, analogies have been analysed to study if and how Leonardo’s tools, theories and techniques could describe him as one of the contemporary figures of the Lean Educator or Lean Sensei.The focus of the research was on Leonardo’s tendency to outline the method and process through which his genius developed and manifested, to point out similarities and differences with the contemporary lean thinking and practice and to compare his figure with the one of a Lean Educator first and of the Lean Sensei afterwards.