The purpose of this research inquiry focuses on how school leaders "make sense" of educational reform in their local contexts. In order to do this, an exploratory qualitative case study of two schools that took part in policy reform initiatives directed at ubiquitous use of information communication and technology (ICT) in the Singapore city-state context is undertaken. Using focus group discussions (FGDs), interviews and observations this inquiry investigates and builds emerging explanations to sense-making experiences of actors in the midst of reforms. Using Bruner's narrative analysis, findings from this inquiry provide a picture of how school leaders cope in periods of uncertainty. School leaders in the midst of leading-edge reforms in ICT experience shifting identities, emerging roles and ambivalent capacities. This inquiry proposes a policy learning approach for educational leaders facing uncertain futures.