This document discusses the dilemmas involved in observing, supervising, and assessing teachers. It addresses four main dilemmas: 1) the "baggage" observers bring with them like preconceived notions of good teaching; 2) the "perception gap" between what teachers and observers see in a classroom; 3) the impact an observer's presence has on a lesson; and 4) the difficulties of objectively assessing teachers in high-stakes situations. It provides recommendations for observers to improve practices like clarifying their own biases, exploring differences in perception through dialogue, keeping a low profile, and reconciling formative and summative assessment roles.