Legally astute educational leaders are essential to successfully execute any school's mission. This article relays practitioner viewpoints concerning priorities and preferred instructional approaches concerning legal literacy training. In doing so, the article advances overwhelming participant support for context-focused real-life legal literacy preparation. Remarkably only ten percent of the research participants reported receiving this suggested type of leadership preparation. Administrator-recommended approaches consistent with problem-based instruction would be more familiar to aspiring leaders, inspire greater awareness and confidence, and be more consistent with the sensemaking responsibilities already tied to their existing administrative roles. Finally, with expanding awareness of escalating challenges, including fallout from continuing culture wars and other national conflicts, the article contemplates literacy skills administrators could need in the future.