This paper seeks to better understand the workplace learning that occurs in the executive office (henceforth referred to as EO) of the NACADA: The Global Community of Academic Advising through a conversation with the association's Executive Director, Dr. Charlie Nutt. After providing a context of NACADA and its EO as well as my interview with Nutt, I summarize the interview and analyze it through the lens of important competencies of effective managers as described by Gilley and colleagues.