As work itself is changing, some of the basic tenets of leadership development are being challenged. The very idea of leading people in jobs is changing with the democratization of work and the continued advance of digital technology. These twin forces are moving work beyond the traditional structure of activities that are organized into stable jobs within a siloed organization. Work is being disaggregated into tasks that can be dispersed inside and outside of the organization — the “uberization” of work. And as AI and robotics increasingly supplement and replace the work of humans, the expectations of leaders — truly understanding the work, how it can be executed now and in the future, and the cost, capability and risk implications of current and future work options — are increasing exponentially.