If the organizations in which we work must challenge assumptions about their core business models, shouldn’t we challenge our assumptions about organizational models, leadership capabilities, and learning practices? If we believe what many are predicting, the future of work over the next decade will look nothing like it does today. In fact, those close to technol­ogy disruptions and future work trends predict that nearly 40 percent of the jobs we know today will be disrupted by technology within the next five years. Shouldn’t we be vigorously challenging our assumptions about the organizational learner?