Interest in human experiences, especially positive experiences, has been increasing ever since positive psychology gained a foothold in public attention. In this research, higher education administrators from Finland and the USA ("N"?=?13) were asked to describe positive or successful situations or chains of events in which their leadership had a significant role, in order to find out what kinds of situations administrators found the most rewarding. The participants were asked further to discuss feedback and its importance in their work. The ultimate aim was to consider the notion of caring leadership from the viewpoint of practical leadership action.