The Midland Area Wellbeing Coalition aims to foster individual, workplace, and community wellbeing. To support this mission, we designed the Leader Wellbeing Training (LWT), a research-based intervention equipping leaders to embed wellbeing practices within their organizations. Grounded in positive psychology, the LWT integrates the PEMRAH framework, the U.S. Surgeon General’s Framework for Workplace Mental Health & Well-being, and the APA’s Psychologically Healthy Workplace model. Through a three-part workshop series, leaders engage in experiential learning, strengths-based reflection, and systems-informed approaches to drive sustainable culture change. The program emphasizes psychological safety, modeling vulnerability, and practical application, empowering leaders to cultivate environments where employees can thrive. This paper describes the Coalition’s context, relevant literature, and the intervention’s design, while addressing limitations such as time constraints, cultural resistance, and sustainability challenges. We propose the next steps for piloting and scaling the program, with a focus on continuous improvement and measurable outcomes. By educating and empowering leaders, this initiative advances the Coalition’s vision of creating a thriving, inclusive community where everyone feels good, struggles well, and functions effectively.