For a knowledge- and skill-centric organization, the process of knowledge management encompasses three important and closely related elements: (i) task assignments, (ii) knowledge acquisition through training, and (iii) maintaining a proper level of knowledge inventory among the existing workforce. Trade-off on choices between profit maximization in the short run and agility and flexibility in the long term is a vexing problem in knowledge management. In this study, we examine the effects of different training strategies on short-term operational efficiency and long-term workforce flexibility. We address our research objective by developing a computational model for task and training assignment in a dynamic knowledge environment consisting of multiple distinct knowledge dimensions. Overall, we find that organizational slack is an important variable in determining the effectiveness of training strategies. Training strategies focused on the most recent skills are found to be the preferred option in most of the considered scenarios. Interestingly, increased efficiencies in training can actually create preference conflict between employees and the firm. Our findings indicate that firms facing longer knowledge life cycles, higher slack in workforce capacity, and better training efficiencies actually face more difficult challenges in knowledge management.