The search for growth and sustainability in any organization largely depends on its ability to carry out digital transformation and agility processes. These processes are essential to adapt to an increasingly changing and competitive business environment, allowing companies to be more efficient and effective in creating an unbreakable bond with their customers. This manuscript addresses the importance of detecting and eliminating anti-patterns in organizational culture for a successful digital and agile transformation. During the early stages of the transformation process, prejudices and paradigms rooted in the organization can become an obstacle to change. The goal of this writing is to offer a practical guide for leaders and teams in organizations seeking successful cultural transformation. Effective strategies are proposed to overcome the challenges faced by organizations during this early stage. In summary, the key steps to be followed in the initial stages of digital transformation with agility are described, including the importance of establishing strong leadership, defining a clear vision and scope of the transformational process, among others. A set of recommendations will be provided to overcome recurring anti-patterns, such as lack of stakeholder participation and commitment, lack of proper planning, and confusion of roles and responsibilities.