Winchester teaches Leading Self and Teams (BA 1011) at the University of Minnesota's Carlson School of Management. The course focuses on understanding individual perspectives and team dynamics. Specifically, Winchester teaches the differences in personality, identity, values, opinions, and cultures and the role they play when interacting with others, as well as the science behind how teams are structured, team roles, processes within teams, and what leads to effective teams. Additionally, he has published management and strategy cases on Peloton, Roku, and GameStop that are used in undergraduate and master's classrooms worldwide.