Occupational therapy educational programs have a high enrollment of students from Generation Y; often referred to as Millennials. In contrast, most occupational therapy program faculty and clinical supervisors are part of older generations that have differing expectations and perceptions related to professionalism. This generational gap makes for a diverse classroom and clinical environment, which can often lead to misunderstanding, assumptions, frustration, disconnect, disappointment, and conflict. Each generational group has a shared culture and set of experiences, characteristics, vlaues, attitudes, and beliefs that influence their behavior, expectations, and perceptions surrounding professionalism. Therefore, when teaching professionalism to occupational therapy students, one must consider the cultural underpinnings and influences related to generational groups and their differences. The capstone project presented and discussed in this document is a manuscript that explores the relationship between culture and professionalism. The manuscript describes how generational culture influences professional behaviors and proposes the use of a critical reasoning construct developed by this author. Based on the language of the Occupational Therapy Practice Framework: Domain and Process, 3rd edition, the proposed construct intends to enhance professionalism and cultural effectivenvess among occupational therapy students and guide them in meeting generational expectations related to professionalism.