IT and cybersecurity teams have had a long-standing battle between functionality and security. But why? To understand where the problem lies, this book will explore the different job functions, goals, relationships, and other factors that may impact how IT and cybersecurity teams interact. With different levels of budget, competing goals, and a history of lack of communication, there is a lot of work to do to bring these teams together. Empathy and emotional intelligence are common phenomena discussed in leadership books, so why not at the practitioner level? Technical teams are constantly juggling projects, engineering tasks, risk management activities, security configurations, remediating audit findings, and the list goes on. Understanding how psychology and human factors engineering practices can improve both IT and cybersecurity teams can positively impact those relationships, as well as strengthen both functionality and security. There is no reason to have these teams at odds or competing for their own teams mission; align the missions, and align the teams. The goal is to identify the problems in your own team or organization and apply the principles within to improve how teams communicate, collaborate, and compromise. Each organization will have its own unique challenges but following the question guide will help to identify other technical gaps horizontally or vertically.