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This case study examined teacher leaders’ perceptions of their own development and focused on the role of professional learning, professional background, and workplace environment. Former participants of a TLPD program were surveyed three to seven years after program completion and a subset identified as active teacher leaders were interviewed about their TL development and how the program, their backgrounds, and their workplace environments influenced their TL trajectories. Participants found that the program positively influenced their leadership development by increasing confidence and connecting them with education stakeholders. Participants considered their personal beliefs, like having a growth mindset, as one of the most important background factors in their leadership development. Findings from the study have implications for structuring future TLPD initiatives.