This paper explores the dynamics of managing collective problem solving and decision making, and the application of tools and strategies to deal with the emergent complexity of systems in which educators work. Schools and educational programs are complex adaptive systems that respond to changes in internal and external environments. Functioning within such a dynamic system requires a tolerance for ambiguity. The literature suggests that a propensity for risk taking is necessary for productive group problem-solving but may not be sufficient. The "amoeba" model provides several metaphors for managing the complexity of work-related problem-solving, in that like the amoeba, good problem-solving is transparent (few hidden agendas, abundant high-quality communication); is deliberate (done with care and attention); has no permanent "internal structures" (the decision-making path depends on the changing nature of the problem and environment); and can bend and reshape itself to adjust to the environment. The image of a pull-down menu suggests the following nonlinear elements of problem solving: generating ideas, identifying decision criteria, prioritizing items, analyzing the list, and splitting independent items apart to be dealt with separately. Includes a list of eight organizational change "insights." (Author/SV)