Abstract. Work can either become a source of stress, or fulfillment, and it has serious societal impacts beyond that of individual. Employers need to maintain healthy workplaces not only due to law requirements but also for the productivity of their organizations. Psychological well-being of employees can be improved either by reducing organizational stressors or by increasing individuals’ resilience. Elimination of stressors, of course, requires their identification first. Self-report questionnaire has been the predominant, if not exclusive method for that, however it is not perfect. Here, I propose a new strategy for measuring work stressors by exploiting the byproducts of most available workplace technologies, i.e. organizational communication and collaboration metadata. I base my measurements on theories and findings of occupational stress research and discuss the benefits and limitations of the proposed strategy with respect to the state of the art. Finally, I address how this measurement strategy can guide organizational interventions. To the best of my knowledge, this is the first study that discusses the utilization of workplace technologies for measuring organizational stressors. The proposed strategy has important theoretical and practical implications in human resources management.