This paper is rooted in practitioner experience of working within the non‐profit sector. It is both underpinned by Master’s level research and built on as part of an on‐going sense‐making process for the author in terms of her doctoral research. Focusing on a specific part of the sector – local development agencies, explores how personal theories emerge and the rules of thumb chief executives of such agencies use to develop their practice. This paper draws on fieldwork involving interviews with 20 chief executives and considers the roles of chief executives in relation to learning and development needs. As such, this is not a search for “truth” or for blueprints for managers, but represents a concern for and interest in how people – “puzzled” individuals who have to deal with ambiguous situations day‐by‐day – juggle multiple realities, and what informs their (thinking and) actions.