Decline and downsizing often create organizational conditions that are tension-filled, problematic, disruptive, and prone to unethical behaviour. It is common for educational organizations to face discontinuity of services and reduction of personnel; therefore, it is important to understand the relationship between declining organizations and the ethical behaviour of educational leaders under these circumstances. In this article, we provide a general description of organizational decline, typical responses to such decline, and highlight the phenomenon of personnel downsizing, with particular attention to the Canadian education context. We offer descriptions of various in situ strategies from several Canadian educational superintendents to illustrate implications for how we might better understand personnel reductions in relation to ethics. We conclude with suggestions concerning ways we might upgrade downsizing with wise judgment and ethical decision-making.