The article will report on the process and outcomes of shadowing encou
nters with urban principals. The authors provided extensive on-site pr
ofessional development for 58 school principals with the support of th
e Edna McConnell Clark Foundation's Program for Student Achievement be
tween 1991 and 1994. The authors developed a Shadowing Encounter Instr
ument and procedures to facilitate assiduous reflection among urban pr
incipals. The shadowing instrument provides urban principals with oppo
rtunities to think critically and reflectively about their practice. T
he data gleaned from the shadowing encounter are disaggregated so that
the principal can readily see routine daily behaviors across three sp
ecific domains: instructional leadership, school management, and stude
nt social behaviors. The instrument also assesses the predominant lead
ership style of the respective principals, The article will conclude w
ith policy recommendations directed to urban school districts and agen
cies concerned with the task of facilitating critical reflection among
urban school leaders.