This paper aims to describe the education and career pathways of a group of nursing deans in the late 20th and 21st centuries. The study explores nursing deans to understand the career development process and to develop recommendations for succession planning. Methods: A qualitative interview captured the oral histories of 30 nursing deans from Canada, United Kingdom and Australia in 2011 and 2012. Career and educational pathways were mapped, tabulated and exemplars used to emphasise key education and career decisions. Results: Findings show that there are four distinctive pathways to becoming a nursing dean and these are: 1. Same university pathway: Clinical work to teaching and thence the promotion and leadership in education route and pursuit of deanship in the same institution; 2. Different university pathway: Clinical work to teaching thence the promotion and leadership in education route and pursuit of deanship at a different institution in the same country; 3. Different country pathway: Clinical work to teaching thence the promotion and leadership in education route and pursuit of deanship at a different institution in different country; and 4. Health pathway: Clinical work to clinical management to dean route. Conclusion: The career and educational pathways of the 30 deans described will inform aspiring deans and highlight the importance of doctoral qualifications, management experience and leadership qualifications. Importantly, these aspirants need to determine the particular institutional culture into which they aspire to commit to becoming a dean of nursing.