This document summarizes a presentation on helping entry-level supervisees prepare for mid-level leadership roles. It discusses supervision best practices, challenges for different generations, common supervisor mistakes, and strategies for effective supervision. These include creating supervision plans, communicating style, providing feedback, and maps for navigating departmental culture and understanding where one fits within the larger organization. The goal is to evaluate current supervision skills, identify ways to challenge supervisees, and prepare them for their next roles in student affairs.