In January of 1987, noted director, educator and SDC Board Member Mary Robinson met with directors Mark Lamos and Nagle Jackson to discuss running regional theatres. At the time, these two men were the Artistic Directors of Hartford Stage and Princeton's McCarter Theatre respectively. The conversation begins as many of SDCF's one-on-one interviews do, with Lamos and Jackson outlining the origins of their careers as directors, and specifically as Artistic Directors. We find that both men transitioned from performance to direction, and as Lamos puts it "were the kind of actor's you saw and said 'it looks like he should be a director'". These two master artists talk about the lessons they learned in the various posts which they've held at America's leading regional theatres, including: A.C.T; Arizona Theatre Company, Guthrie Theatre, Milwaukee Rep and others. We learn that though there are issues unique to each theatre and community wherein they reside, there are common obstacles and rewards that face all artists and administrators who work in regional theatre. Lamos and Jackson speak about how they've dealt with enhancing subscriber bases, choosing a season, working with Boards of Directors, finding new audiences and engaging their communities, and reaching out to communities that are not regularly exposed to theatre. This is a discussion not to be missed by anyone who's ever had the goal of running or starting a theatre company.