Staying ahead of the pitch: an old baseball metaphor that means to anticipate where the ball is going to go so that the batter can score a hit. But to anticipate changes in a field as robust and challenging as information sciences, reflection and contemplation are often key to good planning. With simple day-to-day management of libraries already being a full-time task, true leadership and planning often comes with a real, physical break from the workplace and daily routines. With this in mind, the leadership retreat should be employed by librarians to give themselves the luxury of deep reflection, camaraderie, and thoughtful planning in environments conducive to such work. This article outlines a simple process that can be used to run a planning retreat, at a reasonable cost, and within a modest time frame. To outline this process, a case study involving the University of Oklahoma-Tulsa Schusterman Library will be described.