This study identifies factors associated with flexible work arrangement (FWA) use in the context of the "Supervisor-Promoted Flexibility" program implemented by an employer in the financial activities supersector. This change initiative involved supervisor-initiated discussions that explored prospects for supervisee FWA use. Discussions increased the odds of FWA use expansion, but changes occurred at different rates among work units. Managers’ gender, age, and attitudes toward FWAs corresponded with changes observed. When managers believed that supervisee FWA use reflected favorably on prospects for their own careers, they were more likely to expand use over time.