This article emphasizes the importance of a CEO’s leadership in successfully implementing organizational redesign efforts. It notes how “CEOs must take a proactive lead in organization redesign due to its profound impact on culture and employees. Only the CEO possesses the comprehensive view necessary to minimize unintended consequences.” The authors present five guiding principles aimed at aiding CEOs in surmounting challenges related to organization redesign, such as prioritizing conceptual design before delving into specifics. Alongside the principles, two frameworks are introduced to facilitate the management of organization redesign through different stages, from identifying catalysts of change to execution. The authors further present a framework outlining four behavioral archetypes, illustrating how CEOs might lean into or impede organization redesigns during distinct phases. To prepare for an organizational redesign initiative, the authors advocate that CEOs evaluate their susceptibility to factors potentially impeding their leadership throughout the process. The four questions are: 1) Do I possess unwavering belief in this endeavor? 2) Will I listen to the right people without letting the process go off track? 3) Am I prepared to make tough decisions where needed and stick to them? 4) Am I in control of all the levers I will need to pull? For those undergoing an organizational redesign effort, this article provides useful ideas for CEOs and leadership teams.