Presidents, provosts, and law school deans often have sleepless nights where they lie awake thinking about a multitude of problems, issues, and opportunities ahead for their institutions. "Managing up" is an important aspect of leadership for any role, so understanding the institution's challenges from your boss' perspective is critical. Legal education remains in a state of turmoil and change. There are relentless pressures to deliver on outcomes (and sometimes rankings), inputs, finances, and reputation, all in the context of economic inflation, a looming enrollment decline, and political challenges to higher education. In this session, a current dean will talk about what keeps him awake at night with the goal that it will help attendees better understand the challenges of legal education and how technology fits into the big picture. The session will also explore how IT directors, law library directors, and faculty and staff can best interact with their deans, provosts, and presidents.