As self-described “educators,” in our formal instruction of students and teachers and our more recent outreach to a wider array of clients, we have focused on systematically using the full range of system dynamics tools to become, and assist our clients to become, better thinkers and modelers. In a conscious effort to build that capacity through collaborative problem solving, we have devised a “ladder of engagement.” It is a structure and sequence of activities supporting a powerful and integrated process by which continuously “better questions” allow us to: (1) probe progressively more deeply into describing the behavior of the system (a rung of KNOWLEDGE); (2) identify the system’s features (feedback loops and delays) controlling its behaviors (UNDERSTANDING); and (3) locate and evaluate leverage points in the system where intervention can effectively and efficiently affect its behavior (INFLUENCE). In addition to the ladder's hierarchical structure, at each rung or level the process explicitly incorporates feedbacks designed to develop an iterative learning process that continually reinforces the linking of answers to better questions and the parleying of one’s facility within a limited sphere of interest into broader abilities and motivations to pursue more diverse challenges and “enduring” and generic problems.