This chapter uses the dynamic of being a non-executive director (NED) as a process for leadership development. Context here is significant. The participants are owner-managers of growing businesses. Their context is demanding but also isolating from the lifeblood of leadership development – a variety of contexts, a variety of ‘leaders’ to observe and a variety of demanding inter-personal challenges. The process we explore in this chapter is that leadership learning can be enabled by participating in a peer learning community as a NED. We theorize the development of a NED through the lens of communities of practice. In particular, we look at how a community of owner-managers collectively shape their practice, their capacity and confidence through engagement in a year long journey as non-executive directors.