Over the past few decades universities and colleges have undergone changes that have increased the complexity of academic managers' roles. There is some evidence now that these managers have come to experience significant role ambiguity, conflict, stress, and other negative effects -and that their wellbeing has been compromised. However, the literature about such matters is incomplete and sometimes contradictory. The study reported here was undertaken to contribute to existing understandings about the condition of academic managers in tertiary education by profiling a previously unstudied population -Greek and Cypriot department chairs. The specific focus here is on stressors in the workplace, and we present findings from an exploratory study and compare them to findings from a recent parallel Canadian investigation. The cross-cultural insights gained help to enrich current understandings about the stressors that managers experience in the workplace.