There is no part of human existence that loss and grief do not reach, and the workplace is no exception to this. This article is therefore concerned with some of the implications of loss and grief in work settings in general and for workplace leaders in particular. By way of example, it explores in particular the needs of bereaved caregivers returning to work and the potential for stigma to emerge in relation to employment and bereavement. Central to the article is an argument in favor of the need for change within the workplace, specifically within the structures and systems that support bereaved caregivers returning to work. This article critically reflects on the leadership management challenge of supporting bereaved caregivers returning to, or seeking, work and addressing the problem of stigma in relation to employment and bereavement. Some structural and policy changes are highlighted to assist employers and bereaved caregivers faced with this situation.