651 Copyright © 2014, IGI Global. Copying or distributing in print or electronic forms without written permission of IGI Global is prohibited. Chapter 48 DOI: 10.4018/978-1-4666-6046-5.ch048 Leading and Learning in the Digital Age: Framing and Understanding School Leader Challenges ABSTRACT This chapter investigates how Heifetz’s (1994) model, applied to the work of school leaders, has led to key insights. The framework helps practitioners and education leadership faculty who teach aspiring and practicing school leaders better understand the nature of adaptive and technical challenges that leaders encounter day-to-day and their approach to making sense of them, managing them, and helping other adults to do the same. The authors employ the adaptive-technical analytic framework to examine a case that is representative of real world problems that leaders have been wrestling with, based on their prior research. Through Heifetz’s lens, the authors deconstruct the case to illustrate how framing the problem as adaptive and/or technical directly informs the leader’s work. Embedded refective questions create opportunities for readers to pause and apply this model to Principal Georgina’s case. The authors encourage leaders to apply a framework and questions like this in their unique milieus. INTRODUCTION With the explosion of technology in the digital age, access has eased work—in many ways—in that educational leaders everywhere can instantly connect to their stakeholders, tap resources from around the globe with the click of a key board and create learning communities without the constraints of brick and mortar. This is what we call the “light” side of technology. We want to acknowledge that advances in technology have enriched the work of leading and learning. And yet, as much as life has changed in our post-modern society, there are enduring issues, Patricia Maslin-Ostrowski Florida Atlantic University, USA Eleanor Drago-Severson Teachers College, Columbia University, USA