National Boss Day is October 16 each year. When the holiday falls on a weekend, it is generally celebrated on the working day closest to October 16.

National Boss Day offers employees an opportunity to recognize those in supervisory positions. Popular ways to say "thanks" include cards, a lunch in the boss's honor, flowers, or gift certificates. It is a time for many workers to appreciate their employers.

The concept of National Boss Day began in 1958 when Patricia Bays Haroski, then an employee at State Farm Insurance Company in Deerfield, Illinois, registered the holiday with the United States Chamber of Commerce. She designated October 16 as the Special Days because it was her father's birthday. Haroski's purpose was to designate a day to show appreciation for her boss and other bosses. She also hoped to improve the relationship between employees and supervisors.

Four years later in 1962, Illinois Governor Otto Kerner backed Haroski's registration and officially proclaimed the day. The event’s popularity is growing outside the United States and is now also observed in countries such as Australia, India, and South Africa.