Web development is an inherently interdisciplinary field that offers a unique introductory path to computing prior to more traditional programming courses. While significant earlier work has investigated the challenges that novice web developers encounter, little research is available about teaching while coping with the field's considerable breadth. This paper reports findings from interviews with practicing web design instructors in secondary and post-secondary teaching environments. We present emergent themes related to recruitment strategies, student expectations, teaching techniques, and common challenges. We find significant effort is needed to cope with mismatches between students' expectations of what web design is and the HTML/CSS syntax-oriented view of the discipline often emphasized by teachers. We conclude with implications for new teaching tools that would help better sustain student motivation while equipping them with fundamental skills in web development.