Although it is typical that employees encounter multiple supervisors during their careers, little is known about how employees’ experiences with prior supervisors shape their reactions to their current supervisor’s leadership. The present study examines how (in)congruences between current and prior supervisors’ task-oriented leadership as well as laissez-faire leadership relate to an employee’s trust in the current supervisor. Using polynomial regression and response surface analyses in a time-lagged sample of 159 employees, we find that incongruence between current and prior supervisors’ laissez-faire leadership reduces an employee’s trust in the current supervisor. This incongruence effect is particularly pronounced if the current supervisor exhibits laissez-faire leadership to a greater extent than the prior supervisor did, but it also holds if the current supervisor shows less laissez-faire leadership than the prior supervisor. For task-oriented leadership, by contrast, we do not find a similar pattern of incongruence effects; a current supervisor’s task-oriented leadership is positively associated with employees’ trust, regardless of the prior supervisor’s respective behavior. In sum, these findings provide new insights into how “shadows of the past” may shape an ongoing supervisor-employee relation.