In The Educational Imagination, Elliot Eisner presents a theory of educational criticism and a form of qualitative research in education. Central to his theory is the notion of the connoisseur, a particular kind of observer who, on the basis of certain qualities, can be trusted to write an incisive and illuminating account of an educational setting. The theory is illustrated by a range of examples of educational criticism in practice. This paper reflects on the author's attempt to apply educational criticism in a self-reflexive way in the context of a Teaching and Learning Research Initiative project on teaching literature in the multicultural classroom. A number of questions are raised about observation as a data collection instrument, the ethics of observation and reporting, and ways in which a commitment to dialogue can impact on the textual products of criticism. If the observed teacher is an artist, what might they want to say to the connoisseur observer and how might this talking back affect the criticism itself?