How to Improve Your Boss’ Sense of Humor


Want to incorporate more office humor but don’t think your boss has a sense of humor? Wouldn’t it be great if you could develop his sense of humor and as a result make the workplace more fun?  Well you can, to some extent.  But before we talk about how you can improve someone else’s humor (as well as your own), it’s important to understand what a sense of humor is.

Making Sense of Humor

A common misconception is that a sense of humor is the ability to be funny.  This would suggest that Jerry Seinfeld has a sense of humor, but boring, old Uncle Benny does not.  But this is wrong for two reasons.  First, the ability to be funny and to make others laugh is having the ability of humor, not a sense of humor.   Second, humor does not necessarily mean laugh-worthy or even funny.  Humor can be anything that causes amusement, not just laughter (check out What is Humor? for more).  So a sense of humor is merely “the trait of appreciating the humorous.” (Thanks WordNet)

And just like the other six senses–sight, touch, hearing, speaking, taste and the ability to see dead people–everyone’s sense of humor is different.  Whereas some people have 20/20 vision, others have 20/40.  The same is true of humor sense, we just don’t have a fancy scale in which to measure it.  Seriously we don’t, scientists have tried.  I propose we just count number of times a person laughs during the movie Airplane!–the higher the number, the better their sense of humor.

But there is one difference between humor and the other senses.  While 0.6% of the world population is completely blind, that is has no sense of sight, there isn’t anyone that has no sense of humor–even Ebenezer Scrooge found something he could laugh about.  It’s just that different people have different views on what is humorous, and to what degree, but they all have some sense (of humor at least).

Developing a Sense of Humor

So if everyone has a sense of humor then how do you develop it?  Good question young grasshopper.  When you are developing muscles, you aren’t creating them from scratch, but growing and expanding them.  The same is true when you develop a sense of humor–luckily without all the weights.  You are simply building on what is already there and expanding it further.

Building and expanding your sense of humor is as easy as being exposed to different types of humor and consciously seeking it out.  By watching comedies (such as the Top 10 Comedies of All Time…Or at Least to Date), reading cartoons (like Cartoons Worth Reading), or taking a corporate recess (with funny images from around the Web), you’ll find new points of view and things to laugh about.

The next step is to then work to see the humor in life through your own experiences.  What anecdotes do you have from your own experiences that exemplify the humor of life?  Cultivating and sharing these stories can further your own sense of humor, while at the same time “provide a way to bond with others, look at different things in a different way, and normalize your experience, and keep things from appearing too overwhelming or scary.” (Thanks

Developing Someone Else’s Sense of Humor

And that’s all fine and dandy, but the promise up top (at least according to the title) was to develop someone else’s sense of humor, not your own.  After all, if you’re here, you probably figure you’re already on the right track (and I would agree).  So how do you help someone else see the light…side of the office place?  Keeping in mind that you can only help someone who wants to be helped, there are a few things you can do to develop your boss’ sense of humor.  Note: I’m using the context of wanting to develop your boss’ sense of humor, but this would also work for developing your spouse’s/mother-in-law’s/judge’s sense of humor.

1. Ask the Question “Why So Serious?”

Since we already know that everyone has a sense of humor, if you don’t feel like your boss is expressing his at work, you want to understand why.  Some of the older cultures in the corporate world still don’t know the benefits of humor, but luckily you do.  They don’t know that humor can reduce stress, burn calories, improve creativity, increase productivity, and much much more.

If your boss runs a “tight ship” and sucks the humor out of work, share with him some of these benefits or point him to this site–I’d be happy to talk with him.  There’s a famous anecdote about Abraham Lincoln sharing a humorous article during a special session with his closet advisors.  After sharing the article, no one laughed but Lincoln, who then added, “Why don’t you laugh?  With the fearful strain that is upon me night and day, if I did not laugh I should die, and you need this medicine as much as I do.” (Thanks YouMe Works)

Is your work situation really more dire than a Civil War?  Is your boss really smarter than Abraham Lincoln?

2. Discover Their Sense of Humor

In order to bring your boss out of his shell to share his sense of humor, you want to start to understand what he finds humorous.  This is best done by finding out what he finding out what he does outside of the workplace–not by asking “What do you find funny?” (most people wouldn’t be able to pinpoint it anyway).  Instead, ask “What’s your favorite TV show?” or “What kind of books do you read?”  This can give you insight into what he sees as humorous.  If he watches The Office, then he enjoys satire; if it’s Are You Smarter than a 5th Grader? then he either likes feel-good challenges or likes to feel smart.  If he doesn’t watch TV, then find out how he spends his time–unless he lives in a shed out in the middle of the woods with no electricity or plumbing, he likely does something outside of work.

3. Expand Their Sense of Humor

Once you’ve found your boss’ sense of humor, you can work to expand it by recommending new shows, movies, or books to watch/read.  The easiest way I’ve found to find new, but similar content is to take advantage of the recommendation functionality of applications like TiVo, Netflix, or  If the boss says he loved the movie Breakfast at Tiffany’s, then search for it on and check out the “Customers Who Bought This Item Also Bought” section.

4. Bring Their Sense of Humor Out

The ultimate goal of developing someone’s sense of humor is to then be able to share it with others.  In the context of work, this is about bringing more fun into the workplace, as well as getting to know your boss better.  At an individual level, this can come through conversations with your manager.  By sharing personal humorous stories with your boss, you can then ask him to return the favor.  It doesn’t have to be in the vein of “Tell me something funny” but rather “When was the last time you laughed so hard you cried?”

At a corporate level, you can bring humor into the workplace through things such as a bulletin board where everyone, including your manager, shares their favorite work-related cartoons.  By having everyone get involved, not only do you have more diverse sources of humor, you also build a sense of community (check out X Ways to Have Humor in the Workplace for more).


So now you not only know what a sense of humor is, but also how you can develop it further, both in yourself and others.  While you can’t help everyone, you can equip yourself to make the best of any environment.  And at the minimum, if you can’t get your boss’ to expand, you at least have your own sense of humor about his lack of sense of humor.  And for the uber-serious in the workplace, just share this quote from Sydney Smith:

“You must not think me necessarily foolish because I am facetious, nor will I consider you necessarily wise because you are grave.”

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