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This research aims to provide much needed insights into school administrators’ psychological safety challenges and elicit research evidence to build a psychologically safe and healthy work environment for school administrators in British Columbia (BC), Canada and similar contexts. The data are from interviews with 20 school principals as a follow-up on a large provincial online survey on school administrators in BC. Findings in this paper focus on school administrators’ accounts on their psychological safety and examine how safe school administrators feel psychologically when taking risks, making decisions, and having a difficult conversation, and what strategies they employ to cope with psychologically unsafe situations.