October 16 is National Boss’s Day. How Will You Observe it?

Mike Hoban
5 min readOct 14, 2020
Photo — Blue Compass Interactive

Everyone has a “boss” and there are millions of them out there in the work world even though almost none have the word “boss” in their title. A couple of interesting factoids about bosses and Boss’s Day:

  • You have a woman named Barbara Horoski — not Hallmark — to thank for the October 16 observance. In 1958, Ms. Horoski, working for her father as a secretary for State Farm Insurance, registered the name with the U.S. Chamber of Commerce to acknowledge the hard work and dedication of leaders/supervisors everywhere. Why October 16? It was her father’s birthday.
  • Hallmark started offering Boss Day cards only in 1979.
  • According to the U.S. Bureau of labor Statistics (BLS) there were an estimated 8,054,120 people in management occupations in May 2019 in the U.S.
  • The word “boss” is derived from old Dutch and German words (baas; baes; bas) meaning “master of the house” or similar. When popularized in the U.S in the early 1800s it was consciously differentiated from the term “master” as used in slavery connotations.

Although the word “boss” has seen use in a pejorative sense, such as the stereotypical “Boss Hogg,” the greedy, unethical county commissioner in the old TV series Dukes of Hazard, I’ve found that most people in the workplace use it in a neutral way, such as, “Nancy’s been my boss for 3–4 years. Or “The customer is the boss.” Recall Michael Scott’s ironic mug in The Office series which said, “World’s Best Boss.” Boss is simply a denotation of a natural hierarchy.

In fact, to help observe Boss’s Day there are many websites with mugs, trophies, cards, bobbleheads, and assorted chotskies for sale. Gift items range from the standard suck-up items extolling the boss’s wonderful qualities to gag gifts, such as the card which says “Thank you for being my boss. You’re the first boss I haven’t wanted to push down a flight of stairs.” Nice. Another says, “Good luck finding better co-workers than us.” Still another: “I can’t be held responsible for what my face does when you talk.”

Very classy.

And of course, every boss also has a boss. A CEO’s boss is the board or the owners. In a democracy the head of the country’s boss is the electorate. Or at least that’s how it’s supposed to work.

“Boss” — Sometimes it’s a no-no

Some organizations, though, are very intentional in eschewing the term. A well-known financial services company I worked with for years assiduously avoided the term and used the phrase “responsible for” to refer to a formal manager or leader and “responsible to” when referring to one’s own manager or leader.

Words matter in firms with strong company cultures and in that firm if you were an outsider and used the term “boss” — even in a casual sense — it was considered a faux pas. Ditto for the word “subordinate.” Our consulting firm made sure new associates put on the account understood that language before they made an appearance.

In this new era of Work From Home (WFH) and self-management, the role of the “boss” continues to evolve and many employees will not even meet with their boss in-person for long periods of time. For leaders/managers it can be a challenge to stay connected in an emotional and trustworthy way to the people they are responsible for. It’s no accident that “How to lead virtually” training courses have become very popular.


Even the word “supervisor” is being used less these days inside organizations in the super-connected world although it is still used extensively by frustrated consumers who seek an escalation to their problem (“I’d like to speak to your supervisor”). Consider the elements of the word. “Super” means above or over and the “visor” part has to do with the act of seeing. Hence, “supervisor” literally means to oversee in a physical way.

That made sense in an industrial world with factory floors and centralized administrative offices. It makes less sense today with many WFH employees and leaders alike having on-line metrics, on-line just in time training support and employees connecting with customers electronically. “Overseeing” takes on a new meaning and it is more of a coaching relationship rather than making sure a subordinate is at their workstation doing their job.

I‘ve been in the business world for 45 years and over that period I had about 40 direct bosses. City of Detroit in the 1970s; Chrysler also in the 70s; Inland Steel in the 80s; a consulting consortium in the 90s (hi Wally!); DDI in the 90s until recently. Many different kinds of bosses who had many different styles of leadership. Some were older and some were younger. Many have retired and some are in different places. Some have passed away.

In looking back I can say there were only two jerk bosses among all of them and they were both with the city in the 70s. That’s not to say I was not given bad guidance from any of them about how to handle a situation. But they were good human beings, they took an interest in me and helped me to become a better professional and a better leader. And I think I have been blessed in that way because I know many colleagues over the years who did indeed have multiple jerk bosses.

So to all 40 or so bosses I’ve had over the years, Happy Boss’s Day. You made a difference in me.

About the author: Mike Hoban is a leadership coach and advisor who also writes about business topics, sometimes in a whimsical way. In addition to his 35+ years experience as a leader, consultant and business owner he has also published extensively in Fast Company and also wrote a business column for 12 years. Many of his recent commentaries — including several about leading during the COVID crisis — can be found on his LinkedIn page: https://www.linkedin.com/in/mike-hoban-b5756b6/ He can also be reached at mjhoban99@gmail.com.



Mike Hoban

Mike Hoban is a West Michigan-based leadership coach and advisor who also writes about business topics.