We study the interactions between supervisors and workers via evolutionary game-theory. We develop a simple model where workers select their effort level and decide whether to comply or defect. Supervisors, in turn, have two different functions: first, they act as coordinators and convert team-effort into output; and second, they act as monitors and induce workers to comply. In doing both, they may either behave as “motivators” through charisma and persuasion (authoritative style), or as “punishers” through authority and control (authoritarian style). In our framework, motivators encourage independence-seeking and reward compliers through inspiration and engagement, while punishers take all relevant decisions and reprehend defectors when these are caught shirking. The message is that authoritative leadership improves both productivity and worker’s well-being. For this to happen, supervisors must improve their charisma, while workers must develop their decisional skills. When either of these conditions is unmet, a variety of welfare-depressing situations may emerge.