If teaching at its best is an art (Davis, 2005; Sarason, 1999; Grumet, 1993; Eisner, 1985; Barone, 1983; Greene, 1971; Smith 1971), then instructional leadership of teaching, done best, must also be based in art (Behar-Horenstein, 2004; Klein, 1999; Eisner, 1983 & 1998a; Blumberg, 1989; Barone, 1998). The author examines possible applications of an arts-based approach to instructional leadership (Blumberg, 1989; Pajak, 2003; Barone, 1998). Building on the research base regarding instructional leadership as art form, the author combines the Feldman Method (Feldman, 1995) of critique, Eisner’s (1998) notion of connoisseurship, and Ragans’ (2005) articulation of the elements of art and the principles of design to construct a practice that captures both the technical craft of teaching and the aesthetic dimensions evident in artistic pedagogy (Eisner, 1983; Sarason, 1999). Preliminary results of an ongoing implementation study are presented.