Health Information Management (HIM) professionals play a critical role in Canadian health settings. HIM professionals maintain the health information vital to providing quality patient care and they often serve in bridge roles that connect clinical, operational, administrative, and financial functions (AHIMA, 2015). Despite the importance of HIM to health care, HIM professionals are not represented at higher levels of management where their knowledge and expertise should be welcomed. Research on the reasons HIM professionals do not achieve and perform leadership roles in Canadian health settings is considerably limited. This study explored the factors that influence leadership development of HIM professionals in Canada. The focus on leadership in this research concerns the identification and selection of leaders into formal and hierarchical roles within healthcare environments. Four bodies of literature were reviewed for the study. They related to the HIM organizational environment, gender issues, societal factors, and the individual characteristics of certified HIM professionals. A conceptual framework, which was derived from a review and analysis of literature, guided the presentation and discussion of the findings of the study. A sequential explanatory mixed methods design was employed. Respondents for the quantitative phase of the investigation were certified HIM professionals (n = 381, 93.7% women) and HIM students (n = 50; 80% women) who completed survey questions to assess their opinions related to career advancement and leadership development as well as standardized measures of leadership attributes (i.e., Multifactor Leadership Questionnaire-5x; Avolio & Bass, 2004) and personality characteristics (HEXACO-60; Ashton & Lee, 2009). Participants for the qualitative interview phase of the research were HIM professionals (n = 14; 85.7% women) and health leaders (n = 7; 42.9% women). The interviews were conducted to obtain more detailed specific information that could not be gained from the results of the quantitative data collected for the study. In short, the interviews helped to further elaborate or explain the survey data collected for the study. A constructivist grounded theory (GT) approach was employed to analyze interview data. Theory in the form of a multi-factorial conceptual model that identifies and explains influences that maintain the status quo and current leadership gap for HIM professionals is presented. Candidate factors of the model include (in no particular order): (a) individual characteristics, (b) issues related to gender, (c) education, (d) organizational culture, and (e) perceptions of HIM as a profession. These factors were reinforced throughout by the four themes that arose in the GT phase of research. The four themes were invisible but important, career lifecycle, leadership, and gender. Although the identified factors almost certainly interact with one another to limit HIM leadership development and career advancement, certain of these factors appear to exert a profound negative influence. Implications of these findings include consideration of raising the entry-to-practice educational requirement for generalist HIM professionals and development of senior HIM career pathways to support HIM practice and policy related to electronic health information systems, health funding, and resource allocation. It is vital that a critical mass of HIM professionals embark on their career with plans to achieve senior decision-making roles.