The exit and entry of executive leadership presents a powerful moment. In the exit of leadership, an institution must reflect on both successes and failures. With a contentious exit, as was the case of John Bowen at Nelson College, which is presented in this chapter, the organization needs to understand what precipitated the call for change and how to successfully move forward. This process should guide the college through the interim process and, more crucially, the hiring process. Though the hiring process was not discussed in this work, it is of incredible value for the organization to act with great deliberation. Of equal importance is the entry of new leadership. The entry process should involve a great deal of information and be conducted with thoughtfulness and purpose. During this process, the executive and the institution must exercise patience to ensure the new relationship between the college and the executive has a chance for lasting success.