Focusing on the current timetabling process at the University of Toronto Mississauga (UTM), I apply David Wesson's theoretical framework in order to understand (1) how increasing enrollment interacts with a decentralized timetabling process to limit the flexibility of course schedules and (2) the resultant impact on educational quality. I then apply Robert Birnbaum's leadership ideas to improve UTM's timetabling process. I propose the provision of strong centralized leadership in the timetabling process instead of the current central service support of a decentralized process. (Contains 1 table and 5 figures.)