This concurrent session raises and responds to the important question of how we set goals and structure case work and supervision when—because of generational differences—our students’ educational and professional values may not mirror those we have for them. For example, studies show that, among other things, the Millennial generation, much more so than preceding generations, embraces informality, prizes immediate reassurance, seeks connectedness, and views professors as collaborators in the learning process rather than repositories of knowledge. To what extent should we as clinicians take account of generational differences and factor them into our teaching? Should we consider whether some of the values of clinical teaching are themselves rooted in generational disposition, such that they need to be translated or transformed in order to be made relevant to our Millennial students? How, precisely, can we do so? Participants will take away from the session a tool kit of strategies for identifying and understanding generational differences and for using that knowledge to strengthen the everyday teaching strategies they employ in their clinics. In particular, participants will come away with an understanding of how to interpret and apply the social science literature regarding generational characteristics and generational differences, how to catalogue their own generational outlook, how to understand the generational outlooks of the Millennials and other generations with regard to learning styles and professional expectations, and how to develop strategies for both transmitting core clinical values across the generation divide and limiting the frequency with which generational differences interfere with learning objectives.