This study investigates the crossover effect of work-life balance (WLB) in the relationship between the management of small and medium-sized enterprises (SMEs) and their employees. SMEs are smaller in scale and have fewer employees than large enterprises, resulting in a close relationship between management and employees. In SMEs, it is easier for employees to observe the daily behavior of the management. Therefore, if management’s WLB satisfaction is high, the positive attitude of the management will be transmitted to the employees, and it is thought that this will improve employee WLB satisfaction and motivation. In this study, business managers (90 people) in Osaka Prefecture and the matched data of employees (1,054 people) were used for analysis. The results showed that the management’s WLB satisfaction level had an influence on the degree of work engagement of both male and female employees. However, a crossover effect between management and employees’ WLB satisfaction while observed in men, was not observed in women. It is suggested that the fixed ideas and paternalism of male management toward female employees may work to suppress the crossover effect on women.