Background and Objectives: The healthcare organization are often fail to realize their strategic goals due to the lack of effective leadership. To address this efficiency, factors can possibly influence the management performance should be identified. Thus, the purpose of this study was to evaluate hospital managers’ leadership style and explore the relationship between leadership style in hospital executive managers and their leadership readiness and leadership effectiveness. Methods: The study sample included the entire (96) C-level healthcare executives currently employed in the Iran University of Medical Sciences, including chief executive officer (CEO), chief financial officer (CFO), chief human resource officer (CHRO), chief information officer (CIO), chief nursing officer (CNO), and chief operating officer (COO). The study instrument was a questionnaire asking about respondents’ leadership style questions, leadership effectiveness and leadership readiness. The collected data were analyzed using Pearson’s correlation coefficient and single variable and multivariate regression. Findings: Transformational leadership was found to be the dominant leadership style among the executive managers. The leadership readiness was found to be significantly correlated with transformational leadership (P < 0.05). Moreover, leadership effectiveness showed significant correlation with transformational/transactional leadership style (P < 0.05). Conclusions: Our study suggests that adopting active management which represents both transformational and transactional managing style can lead to an improved leadership effectiveness in healthcare organizations.