The purpose of this study was to identify the factors that influence managers to take advantage of coachable moments in day-to-day management. Interviews with ten managers found that time, skills, and relationships were key factors considered by managers, but that these were considered within the context of potential “risk” to the manager. This paper elaborates on these findings and makes recommendations for further research into how managers consciously assess the risks associated with coaching, in order to decide whether to take advantage of an informal coaching opportunity.