Leaders play a critical role in the development and execution of Total Worker Health (TWH). Small businesses, in particular, can benefit from strong leadership support for TWH as the burden of work-related injury, illness and fatality, as well as poor health and well-being is high in this population. In the present study, we conducted a program evaluation of a TWH leadership development program for small business leaders using the RE-AIM framework. The goal of the program was to help change leaders' behaviors around health, safety and well-being practices following the theory of transformational leadership. Two leaders from each business participated in pre-training activities on their own, a 6-hour in-person training, and three months of access to virtual training transfer activities, including coaching and goal tracking. Our results suggest that the TWH leadership development program is effective at improving leaders' self-reported TWH leadership practices and that the in-person training was implemented successfully. However, leaders did not report improvements in their personal health and in fact reported increased levels of work stress after the program. We also observed some challenges when implementing our training transfer strategies. Our study suggests that leaders may benefit from attending TWH leadership trainings alongside other colleagues in their organization to facilitate a shared vision and goals for TWH in their organization. As a next step, it will be important to determine the program's effectiveness in changing business TWH policies and practices, employee perceptions of TWH and leadership, and employee health and safety outcomes.