Background: This paper explores the leadership and management needs of medical resident leaders, skills that contribute to the success in their role. The importance of leadership development for physicians is reflected in the specific recommendations in the FMEC-MD and FMEC-PG reports of the Association of Faculties of Medicine of Canada and multiple local, regional and national efforts directed towards residents' leadership development. The purpose of this study was to identify key areas for programme development in leadership for physicians by examining the common pitfalls that interfere with success in resident leadership roles. Methods: Twenty chief residents (CRs) were asked to enumerate the pitfalls/mistakes they made, which they felt hindered their effectiveness as a leader. Chi-squared analysis was used to examine the frequency of responses within themes developed from content analysis of the data. Results: The pitfalls spanned multiple categories including leadership (31%), management (28%), communication (19%), role clarifications (13%) and professionalism (9%). Conclusions: Awareness of these pitfalls would be beneficial to CRs and also help inform changes or emphases in leadership training programmes. Our study has identified that leadership development would be enhanced by emphasizing professional aspects of a leader, working across boundaries and proactively seeking role clarification.