“Work” has been paid less attention to as a key factor of project leadership. Project leaders need to better understand their work for successful project management. This study proposes Roly-poly Model as a tool for identifying distinctive characteristics of each work type (Zone 1, Zone 2, and Zone 3) to bring new insight into the determination of an effective leadership style. Operational work (Zone 1) tends to need more directive or coaching leadership, task work (Zone 2) tends to need more facilitating leadership, and project work (Zone 3) tends to need more supportive or delegating leadership. The project leadership based on the understanding of the qualities of different work zone highlights the competency of exercising the leadership right for the main work, which leads to the creation of sustainable project value and ecosystem. The proposal of the Roly-poly Model for project leadership is expected to help project managers exercise more effective, positive leadership and value in the future.