Millennials (Generation Y) and the Generation Z population comprise the majority of occupational therapy student cohorts and new graduates entering the workforce. While fieldwork education has historically prepared students for generalist, entry-level practice, there is still a gap between what students versus employers feel are career-ready skills and qualities to be successful in the workforce. This manuscript presents evidenced-based strategies for educators, occupational therapists, and managers to enhance the preparation and professional development of occupational therapy students and new graduates. Use of coaching philosophies, emphasizing practice-ready skills, and a growth mindset are methods to target the strengths of Generations Y and Z members and address areas of growth as they prepare to enter the workforce. Emphasizing human relationships over task completion or skill mastery helps uphold the values of millennials and the Generation Z population that they can make an impact in the workplace. Modeling practice-ready skills, explicit discussion of “soft” skills, and use of guided discovery supports these generations’ understanding of basic workplace etiquette and culture. Using a growth mindset philosophy can help foster initiative and self-awareness, which are potential areas of growth for these generations. These strategies can then promote healthy, productive collaboration in the workplace and, ultimately, enhance the client-provider relationship.