Managers act as change agents on the frontlines of the day-to-day implementation of change processes at the same time as having to manage daily operations. This double role puts them under pressure to both implement change processes efficiently and emphasizes the need for tools and techniques to develop the change competencies of managers. This chapter addresses this issue by presenting a case study of a change management competency intervention. The intervention lasted four days of workshops and consisted of dialog exercises and serious-game simulations. The participating managers were presented with change dilemmas related to key change concepts such as change phases, change resistance/readiness, and balancing change and stability, with the aim to improve their change competencies. Drawing on interviews with managers participating in the training we analyze how the intervention challenged the managers’ perspectives on their change management and fostered learning and development of change competencies. The key role of sensemaking processes are analyzed to nuance and theorize the complexities of developing change competency.