Academic Advisors experience it every day - a student is denied entry to her desired transfer program, another falls below the requirements for his program of study and faces potential dismissal; our advisee has chosen a major that is clearly a very poor fit. How do we tell a student he may not be ready for the next step in his intended path, or she might want to consider an alternative direction? In this 85-minute, 2010 slidecast presentation, returning presenter José Rodríguez (Florida International University) is joined by Susan Kolls (Northeastern University) to discuss effective communication behaviors to help us understand how to deliver bad news to students. José and Susan examine the role of the advisor in teaching students to reassess, redefine, and redistribute their goals and intentions, and offer ways to package the news in the best possible light, strategies for better student understanding, alternative paths, and follow-up strategies.