A major concern for most leadership development teams is aligning training and development goals to desired outcomes, especially when looking at overall costs to plan and implement effective training programs. Leadership training in healthcare is increasing due to the complexity of duties and the need to deal with conflicting situations on a regular basis. This study explored whether goals and assessment instruments identified and applied by program development managers were adequate to reflect a multi-frame perspective, and whether participant feedback articulates benefits encompassing multiple frames. Four main questions were used in the study: “What potential benefits do leadership development staff who select, design, and evaluate training articulate; and do they capture a multi-frame perspective? How do the goals of the program development managers align with the assessment of evaluation instruments, and do the assessments reflect a multi-frame perspective? How does the perception of training benefits align with leadership development goals and multi-frame perspective? What effect does training in competencies such as, problem-solving, conflict management, and effective communication have on leaders in healthcare?” To highlight a potential link between behavior, change and organizations; Social Cognitive, Human Needs, and Systems Theories were utilized. A mixed-method design applying Interpretative Phenomenological Analysis and Descriptive Statistics was used. Results of the study indicate that the goals identified by leadership development do align with trainees outcomes in terms of: serving as a support mechanism to ensure effective team-building; facilitating growth towards promotion through education and effective feedback; and enhancing leadership core competencies such as, emotional intelligence, conflict management and communication skills.