The world needs great leadership like never before. And contrary to popular belief, strength of character can be developed. This article explains why people tend to underestimate the need for leader character and overestimate their personal strength of character. In a recent executive development course, participants from a company took the self-assessment version of the Leadership Character Insight Assessment. The authors noticed that an inordinate number of respondents had self-assessed as 5 out of 5 on all dimensions. These results were at odds with the briefing received from the company’s CEO before the workshop. The CEO had serious concerns about his employees’ performance. After experiencing a change in senior management, the company had moved from a hands-on, command-and-control leadership style to a more open, collaborative approach. After the shift in leadership, employees still functioned in silos, with little collaboration. Despite these problems, participants believed that their self-reported character assessments were true. This allowed the authors to “start an excavation for self-awareness.” As part of an experiment agreed to by the CEO and a pre-selected participant, the authors bullied this participant. This offered an opening for a discussion on the interconnected dimensions of leader character. How was it acceptable to watch and do nothing while a colleague was bullied? Developing character is different than developing competencies. It is like strengthening your body by working out. Unlike physical training, however, there is no limit to how much we can exercise character.