10 Ways To Make Your Boss Laugh

People like and trust someone with a good sense of humor.  A good sense of humor shows the boss that you are happy and like your job.  A sense of humor is good for job security.  Developing a great sense of humor is a commitment.  If you wanted to be a good golfer, it’s not likely you’d think that reading one article would do the job.  So it is with humor.  Here are a few thoughts on impressing the boss with humor which will get you started and point you in the right direction.

1.  Analyze the humor style of your boss.  If your boss likes Gary Larsen cartoons, wouldn’t it make sense to clip a great cartoon when you see one and attach it to a memo?  Does the boss laugh?  Does she tell jokes?  Does he smile?  Just because your boss doesn’t tell jokes doesn’t mean that he or she doesn’t have a sense of humor.  She may be a carrier of humor, rather than a creator or initiator of humor.  He may be the first one to laugh at someone else’s jokes.  It’s also a possibility that your boss may never laugh at jokes and yet appreciate and enjoy humor.  Your boss may have MY personality.  I don’t often laugh out loud, but I love humor.  Everyone’s humor personality is different. 

Here’s a word of caution.  If your boss seems to like off-color humor, I’d avoid using that style of humor yourself.  If she tends to tell or laugh at sex jokes, it’s still unlikely that she will want the person she promotes to sales manager to be a teller of sex jokes or bodily function humor.  And just because the favorite movie clip of the boss is the campfire scene from Blazing Saddles (where the cowboys had eaten far too many beans), that doesn’t mean that she will appreciate a whoopee cushion on HER desk chair.  For an upward-bound career, keep your humor clean and know your audience.  Blue humor is a comedy-cop out.  It’s too easy to tell a sex joke.  Leave that style of humor to the lazy and less inspired.  You can do better.  And your career will thank you.  For more on blue humor:  www.humorpower.com/art-bluehumor.html

2.  Understand what makes humor tick.  Humor is primarily about surprise and relationships.  One of the basic principles of telling a joke is keeping the punchline and punchword disguised until the end of the joke.  The punchword is the word that triggers the laugh.  Ideally it should be the last word you say.  And the element of surprise is the reason it’s best not to say: Here’s something funny that happened to me on the way over here.  That’s called telegraphing the joke, and it works against you.

Also a critical concept of humor is relationships.  A good joke or cartoon is almost always a connection of two previously unrelated thoughts.  I arrived early before a speech and noticed two signs over the exit door in the back of the room.  The signs were not related, but posted one above the other.  The lower sign said “Capacity 475” and the upper sign said “Restrooms”…  In my opening remarks I observed that the SIGN over the back door said “Restrooms capacity 475…I guess that means there’s no waiting.”  It got a big laugh.  The humor connected two previously unrelated signs.  Get into the habit of looking for connections and relationships.  It’s the number one skill for creating your own humor.  For more insights on what really makes humor tick: www.humorpower.com/original_humor.html

3.  Get in shape.  Go to the gym.  No, I’m not talking about free weights and admiring yourself in the mirror.  We’re not talking about pumping iron.  I’m suggesting that your humor skills get stronger with exercise.  Many of our blog readers participate in our monthly humor contests.  We normally get between 250 – 600 entries for each contest.  These are people who not only want to have fun, but know that their humor focus is sharpened by writing funny lines until they have none left…and then writing ten more lines.  Just about anything of value takes work.  Developing a relationship takes work.  Becoming talented on the piano takes work.  Getting in better shape takes work.  And improving your sense of humor takes work too.  It’s about commitment and focus.  Check for the contest announced on the HumorPower Blog on April 1 and give it a shot.   Even if you just set aside just a half hour to develop some funny lines…you’ll be preparing your mind to be funnier in the future.  Step into the humor gym and give yourself a workout.  For a look at several of our past contests:  www.humorpower.com/blog/category/humor-contests

4.  Take Mind Vacations.  To make your boss laugh you have to be in a state of fun, to be relaxed.  It’s hard to be funny when you’re stressed out.  When you’re tense, you’re humor tends to be negative.  Sarcastic humor is the result of frustration and tension.  It works against you.  Here are some ideas to keep your mind, and humor, on a higher plane:

a. Keep something that makes you laugh or smile near your phone.  When you get placed on hold for thirty seconds, flip open your favorite book of humor writings or cartoons to lighten the moment.

b. Have a fun photo on your desk, something that recalls wonderful memories.  Maybe you have a picture of your kids at Disney World.  Maybe a picture of your last year’s Halloween costume.  Perhaps a photo will remind you that your dog makes you laugh.

c. Consider breaking the pattern when you’re in a stressful mood.  Do something differently.  If you’ve been with people, spend some time alone.  If you’ve been sitting, take a walk.  If you’ve been in a quiet environment, go someplace stimulating.  If you’ve been indoors, step outside.  Whenever you’re stressed, your body is usually telling you that you need to do something differently.

d. Help design a better break room.  This will provide a place for you and your co-workers to have a mini-vacation.  Find some fun posters to decorate the room.  Furnish the room with fun games and puzzles.  Design a bulletin board for fun photos, cartoons and contests.  You’ll make the work environment more fun for you and for everyone else.  The boss will like that.  For more ideas on brightening the break room:  www.humorpower.com/humor_workplace.html

5.  The physical leads the emotional.  And visa versa.  If you want to feel like you’re having fun, act like you are.  If your physical posture is depressed, it will be hard to be funny.  Do you spend a good part of your day smiling?  This is a challenge for me.  I’m not a smiley kinda guy.  I wish I were.  On the one hand, if I’m walking down a dark alley and I see someone approaching me, I’m really good at giving the “don’t mess with me” look.  That’s a good thing.  But if I’m at a party and want to meet someone, sometimes my body language will unintentionally say “don’t mess with me.”  Oops.  It’s something I work on. 

One of the keys to developing a great smile is to do some mirror work.  I’ve done that and it has been very helpful.  Here’s the trick.  We know what a good smile looks like.  We just don’t know what a good smile feels like.  By doing mirror practice, your goal is to create muscle memory, to be able to recreate that great looking smile.  Since doing mirror work, my sessions in a photo studio are so much more productive.   I find it easier to get photos with great smiles.  That’s a step in the right direction towards being more humorous.  For more on smile power:  www.humorpower.com/smile_power.html and also www.humorpower.com/art-smilemyth.html

6.  Story power.  A great way to impress your boss with humor is to be great at telling personal stories.  With this skill you can earn the reputation as a great leader, motivator or sales professional.  Telling a story is the perfect way to build one-on-one relationships and a terrific way to bring a speech alive.  Start by keeping a humor journal.  Record every funny thing that happens to you.  You’ll discover that funny stuff happens to you more frequently.  Actually that’s not true.  What really happens is that you become more tuned to the funny stuff that would have normally gone unnoticed.  Then practice telling your stories your friends and family.  You might even join a Toastmasters club. It’s a great place to sharpen your stories.  I joined when I was 25.  I wish I had joined sooner.  When your story gets consistently good, that’s when you tell it to the boss.  Don’t use the boss for practice!  For more on Toastmasters:  www.Toastmasters.org

And remember, when you tell stories, one of the most effective forms of humor is poking fun at yourself.  Humor targeted at you is almost always safe material.  And stories coming from your own experiences will be original and fun to listen to.  People like others who don’t take themselves too seriously.  For more thoughts on the power of stories:  www.humorpower.com/touch_audience.html

7.  Volunteer to plan a party.  This is a hot idea.  Doing this is what led me to a career in humor.  I was in my 20s and noticed that my workgroup was always looking for volunteers to plan parties.  I found two co-workers (who happened to be really funny, since I wasn’t) and together, for three years, we planned and presented holiday parties, roasts, retirements and going-away parties.  This hands-on party planning experience taught me the nuts and bolts of humor skills. For me it was the beginning of becoming a humor expert. And the boss loved it.  Don’t underestimate the value of this suggestion.

8.  Become a humorous summarizer.  Set a goal for yourself.  Every time you attend a staff meeting, try to create a piece of observational humor by the end of the meeting.  This doesn’t mean you always will use it.  But when the timing seems right, weave your humor gem into your closing remarks.  You’ll get better over time.  And eventually you’ll gain a reputation for being a very funny person.  People will learn to listen to you every time you speak.  This is hot tip number two.  Observational humor skills are powerful.  For more on observational and spontaneous humor:  www.humorpower.com/spontaneous_humor.html   For more on why spontaneous humor is powerful:  www.humorpower.com/art-whysponthumor.html   For a case study on creating observational humor at a meeting:  www.humorpower.com/blog/2006/03/creating-observational-humor-a-case-study

9.  So you don’t tell jokes?  No problem.  Show your sense of humor in other ways:  By a toy on your desk, by a plaque on your wall, by a bumper sticker on your car, by the books on your shelf.  There are ways to show your appreciation for and enjoyment of humor without being a jokester.  Wear a funny shirt on casual day.  One of my favorite shirts is filled with cartoon characters.  Send a humorous greeting card.  Look for ways to share humor other than traditional jokes.

10.  Don’t try too hard.  A lesson you learn from the comedy-improv stage is: The harder you try to be funny, the less funny you’ll be.  When you try really hard to be funny you appear to come from a place of need.  You appear to be desperately craving attention.  And that’s not funny.  I’ve known people who were funny, but who tried so hard to be funny that they weren’t.  Does that make sense?  When you try some humor, just throw it out there as though you were simply testing it.  If nobody laughs, pretend you were serious.  If you do it right, nobody will know.  After all, the best humor comes as a surprise.  So since your boss wasn’t looking for something funny, if you weren’t funny, then he won’t have a clue that you were expecting to be.  Don’t beg for laughs.  Just let it go and learn from it.