How often have you felt that your organization doesn't understand the role of an Agile leader and the transformation support they require? It is very unlikely that your Agile leaders will simply "figure it out", "get with the program", and learn from "trial by fire". Although few people doubt their importance, many do not understand the specific coaching and executive support necessary for these "Middle Leaders" to drive a successful transformation. In addition to being ready to lead others in their new way of working, the Middle Leaders need to be prepared for the personal transformational they will go through as their organization adopts Agile, DevOps, or other transformation frameworks. They need coaching specific to their role to learn/relearn metrics and reporting, developing new roles and responsibilities, and being ready to lead their teams through the organizational changes that will take place. While many factors lead to the success or failure of an Agile transformation, Middle Leaders are a key element. Many of those designated as transformation leaders are experienced supervisors, managers, and mentors, but with the exception of an organization's executives, while being new to the role of an actual leader. The Middle Leaders are in the unique situation of being "stuck in the middle", as they feel pressured from both above and below. Their team members require additional, sometimes critical, guidance since their work assignment, organizational structures, and even culture are now in flux. Executives tend to rely more on their leaders for guidance and understanding on how the transition is progressing, requiring their assistance to gain a deep understanding of what their teams, stakeholders, and customers think of, value, and need from the transformation.