We hear much about the “democratic ideal” as if it were unreachable within the walls of the organization. Of late, apologists have begun suggesting that there is no need to worry; democracy exists; it is just that it is often hidden from view right within the requisite hierarchical structure. Top managers are sharing their leadership roles with others in the organization. This provocation will take the opposite position that hierarchy and democratic leadership are predominantly incommensurate and that closer inspection would show that hierarchical conditions largely persist and that when democratic leadership occurs, it does so only with the conditional permission of those in control. The essay goes into detail regarding plural models of leadership, shows where they fall on the hierarchy–democracy continuum, and outlines how leaderful development might be able to prepare learners for real democratic experience.