The authors study the dynamics of training and turnover in firms facing both organizational- and employee-level dilemmas. First they establish a simple model that captures those conflicts and incorporates imperfect information and both worker and organizational expectations. Organizations can be both created and dissolved, and employees can move between firms, start new ones, or leave the industry for good. Next the authors summarize the different ways the dilemmas can unfold over time, collated from a number of computer experiments. For example, under one set of conditions, the double dilemma can be resolved for the industry as a whole and productivity then increases steadily over time. Alternatively, the organizational-level dilemma may remain unresolved and workers may contribute at fluctuating levels. In that case the overall productivity stays low. The authors find a positive correlation between high productivity, low turnover, and enterprise size, a relation that has also been observed in the empirical literature on training, stability, and turnover in organizations.