The current rhetoric about accountability, making adequate yearly progress, and focusing on quality classroom instruction obfuscates the core challenge in becoming a superintendent: How does one use the entry and transition process to learn what the real challenges and issues are in a school district? Can entry be used as a time for personal and community learning and for signaling how leadership will be exercised in one's administration? How can this time be used to build relational trust, the component of leadership that Tony Bryk and Barbara Schneider, co-authors of Trust in Schools: A Core Resource for Improvement, have found to be the strongest predictor of long-term school success? The approach to school leadership being promulgated in the United States does not take into account the challenges leaders face during entry and transition--namely, learning the context. Yet learning the context has everything to do with whether leaders succeed or fail in the long term. In this article, the author shares how he has approached entry and transition in very different ways in the two superintendencies he has held. He points out that taking time to learn the context before starting to act impacts how future decisions will be made, perceived, understood, and acted upon.