The Art of Observational Humor

The contestants were ready to evaluate the target speaker in the District 33, Division C Speech Evaluation Contest.  As I was being introduced to present my evaluation, someone opened a door in the back of the meeting room.  The door was next to a parking lot and we were distracted by something that sounded like a loud warning beeper from a truck which was backing up.  Beep.  Beep.  Beep.  We couldn’t see what was causing the beeping because a temporary room-divider curtain blocked our view of the door.  This happened exactly as the Toastmaster said, “And our next evaluator contestant is John Kinde.”  By the time I reached the speaking platform, someone had closed the door in the back of the room.

When there is a distraction in the room which everyone notices, my approach is to address it with humor.  It takes some practice and some quick thinking.  My first words after taking the platform:  “Pardon me while the fork-lift brings in my notes.”  I was instantly connected to the audience and on my way to an effective evaluation.

Observational Humor adds power to a speech or a club meeting.

  – “Observational Humor stretches our imaginations and makes us better listeners.  It’s the icing on the cake!”  Linda Bown

  – “The opportunity to recall someone’s earlier statement, with humor, is priceless.  It’s the height of wit and active listening.”  L. Eric Culverson

  – “The Observational Humor segment of our Toastmasters Club is always the highlight of the meeting.  People love it!”  Judy Moreo

Observational humor, as discussed in this article, is that fresh, customized humor created shortly before you deliver it.  It is humor that is stimulated by what you hear or see before you are introduced to speak.  It’s normally a piece of humor which you didn’t bring to the event but which is inspired by your observations after you arrived. Observational Humor is powerful.  Here are a few reasons why:

Common experience.  The forklift example was effective because it recognized something that everyone noticed.  The foundation of a good joke is common experience.  It’s part of the you-had-to-be-there factor.   This explains why a funny spontaneous line, when you later tell it to a friend, doesn’t get the same response as it did when it first happened.  You had to be there.  With Observational Humor you ARE there.  Freshness gives the humor power as you share a common experience.

The power of tension.  One of the functions of humor is that it relieves tension.  A distraction during a meeting creates a bit of tension which begs for relief.  A well-placed observational joke lets people laugh and release the tension caused by the interruption.

The element of surprise.  The immediate nature of the forklift line also added power to the humor.  There is great value being in the moment.  The line is so unexpected but at the same time the audience is also thinking “yeah, I noticed that beeping sound too.”  They love being surprised with a totally unexpected observation.

Making connections.  In a speech evaluation contest, the more positive points and suggestions that you make, the more competitive you normally will be.  Someone who makes one good suggestion may be at a disadvantage to someone who makes three good suggestions.  What about someone who made so many points that they needed a forklift to bring in their notes?  Making the connection between the notes and the forklift was the key to making the humor tick.

The illusion of freshness.  A great opening line can make the audience feel that your entire speech is fresh and prepared just for them.  Compare that to opening with a time-worn joke that everyone has heard and you can see how Observational Humor has so much more impact.  One of the key reasons to practice Observational Humor is to add a fresh touch to your talks.

Audience bonding.  When you can be in-the-moment, it connects you to the audience.  They know that you are really present and that you are there just for them.

Saranne Rothberg, The ComedyCures Foundation, hones her expert Observational Humor skills presenting a live weekly radio broadcast and 50 events a year

connecting and helping people with therapeutic humor.  She confirms the value and magic of Observational humor:  “It’s powerful because Observational Humor lets me be incredibly playful and intimate on stage.  It goes beyond the joke-joke-joke format.  The audience immediately trusts that I am listening and care about their interests.  They understand that they are not getting a cookie-cutter presentation.  By integrating Observational Humor with their content, you earn their full attention! Then, anything is possible.”

Here are a few more examples of Observational Humor and triggers to creativity.


A great way to uncover humor is to watch for alternate or double word meanings.  At one of our club meetings, the theme for the meeting was Presidential Trivia.  Also, Darren LaCroix shared his mantra:  Stage time.  Stage time.  Stage time!  Later in the meeting I shared this observation:  “Here’s a piece of Presidential trivia.  Zachary Taylor logged more miles campaigning by stage coach than any other President.  His campaign advisor told him the key to success was…Stage time, Stage time, Stage time!”

Here’s another example using alternate word meaning.  A speaker gave a speech on fire safety, telling us what to do if we were trapped in a hotel room and the building was on fire.  My observation was:  “Let me give you a fire safety tip for the next time you check into a hotel.  Do what I do.  Ask for a non-smoking room.”

One more example.  A speaker told us that when she was in high school, hot-jock Bob Baxter (not his real name) wouldn’t give her the time of day.  My observational line later in the meeting:  “I ran intoBob Baxter last week.  I asked him, ‘What time is it?’  And he gave me the time of day.”


Poking fun at yourself is usually a safe way to get a laugh.  At a club meeting a speaker referred to a celebrity speaker who talked fast and delivered high-content.  This frustrated audiences because they couldn’t take notes fast enough.  My observation later in the meeting: “If you haven’t seen me before, I’m a slow speaker.  Which I know will frustrate many of you.  Because I won’t say anything you’ll want to write down.”


When I’m doing a longer Observational Monologue I like to put matching Book Ends at the open and close of the monologue.  Here’s an example.  First, here’s what happened at the meeting.  A speaker said that the military gave him a career and a wife.  Also, our club membership had been growing and several women had recently joined the club.  Six months earlier, Vicki was the only woman attending meetings.  Here’s the line that opened my monologue:  “I found it interesting that Bill’s time in the military gave him a career and a wife.  The military also gave me a career.  But I was home sick the day they issued wives.” 

And here’s the line I used to close the monologue:  “Attendance at our meeting has been growing.  Our club used to be known as Vicki And The Guys.  I arrived a little late this evening and noticed that we had several women in the group.  And I thought, ‘Maybe they’re issuing wives tonight!'”


If you hear someone say something that gets a laugh, you might be able to piggyback on their joke to get a laugh of your own.  At a club meeting, a speaker told an old joke about a fence around a cemetery.  The fence was there because people were dying to get in.  Later in the meeting I delivered an Observational Humor line:  “There must be something wrong with me. Today I passed by a cemetery with no fence around it…and I had no urge to get in.”


Always keep watch for anything unusual which could lead to a humor connection.  At a meeting at The White House (a meeting venue in Las Vegas owned by the American Payroll Association), I noticed that the lectern was made of clear Plexiglas.  You could see through it.  Later in the meeting, I delivered my observation:  “By the way, here’s some interesting trivia.  The lectern here at The White House was bought at an estate sale…at a nudist colony!”


At a meeting someone commented that I looked like a mortician in my black suit.  Another speaker talked about book publishing and mentioned ISBN numbers used on the back of books to track their sales.  He also encouraged us to write a book, closing with the advice:  Don’t die with a book still in you.  Later, my Observational Humor combined three observations:  “Someone mentioned that I looked like a mortician in my black suit.  Actually, I do own a mortuary.  We offer coffins with ISBN numbers on them…for speakers who die with a book still in them.”


Saranne Rothberg shares a powerful Observational Humor moment:  “The key to developing on-the-spot humor is fearlessness, commitment and the skill of profound listening.  Let me give you an example.  I spent seven hours in a military van with two Marines enroute to our ComedyCures Veterans’ program.  During that ride I was like a fly on the wall, observing their vocabulary, content, tone and how they joked with each other.  The next morning at our live event, I was able to immediately draw from those observations. As I opened the show, a blind and paralyzed 83-year old Veteran with a malfunctioning hearing aid cried out that he wanted to commit suicide.  He couldn’t hear the show.  His name was Joe.  I joined Joe in his wheelchair, gently cupping his face and his hand with the broken hearing aid.  ‘Joe Sweetie, I’m not going to continue this program until we fix your hearing aid.’  Then in my best military voice I yelled:  ‘Joe! We leave no man behind, Joe!’  Joe, and his fellow injured comrades, laughed for about five minutes.  And then, Joe proposed to me!  Leveraging the military’s fierce loyalty, code of conduct and lingo helped me diffuse a live-event crisis with Observational Humor. I bonded with my audience and created a spontaneous comedy platform that permeated the rest of the show.  Observational Humor had an impact stronger than anything else I could have done.”  Notice how Saranne combined courrage with quick thinking to hit the mark with humor.


When it comes to learning Observational Humor, there is no substitute for discipline.  Give yourself the challenge to create an Observational Humor line every time you attend a meeting.  A Toastmasters meeting is perfect, but you can do it at any kind of meeting.  Much of my early practice came at Chamber of Commerce breakfast networking meetings.

As you sit with paper and pen in hand, keep your eyes and ears open for humorous connections.  Look for other people’s comments that get a laugh.  You can often piggy-back on their good lines.  As you take notes, look for connections with a humorous twist.  Then look for a spot in the meeting where you can have a chance to speak and use just one observational line.  Perhaps you’ll be introducing a guest.  Or making an announcement.  Or giving an award.  Drop in your observational line and then segue to your official business.

With Observational Humor the principle of Less-Is-More comes into play.  If you are able to come up with three observational lines, pick your best one and use it.  If you can create ten lines, a good choice is to use just the two or three best ones.  Making a quality cut and using only your best lines can make the difference of having a reputation as someone who is always funny rather someone who is funny only 30 percent of the time. 

At my home club, PowerHouse Pros in Las Vegas, we’ve added a formal Observational Humor segment to our agenda to help all members strengthen their humor skills.  It’s the best way to learn how to create original humor.  And it’s great fun.

How to add an Observational Humor Master to your club meeting.

1.  The role of Observational Humor Master is normally a replacement for the Joke Master position included in many club agendas.  In my opinion, the Joke Master at a typical club meeting is neither very funny nor a good learning experience.  The Observational Humor segment, on the other hand, is very entertaining and a great learning experience. 

2.  The Observational Humor segment is a regular part of every meeting.  It’s on the printed agenda and one club member is assigned as the Observational Humor Master.

3.  The Observational Humor segment is scheduled near the end of the meeting so that we have a chance to observe as much of the meeting as possible before we share our humorous observations.  Specifically, we position the segment during the General Evaluator’s wrap up.  After the Observational Humor segment is complete, the General Evaluator concludes his or her remarks. This placement is designed to keep the humor in good taste and it will be critiqued by the General Evaluator if some of the humor crosses the line.

4.  The position of Observational Humor Master is rotated only among the members who want the challenge.  Before the Observational Humor Master presents his/her monologue, the floor is opened to all members to present their observational humor lines.  “Does anyone have any Observational Humor to Share?”  At a typical meeting of 25 members, about 7 members will have observations to share.  No one is forced to do Observational Humor.   The Observational Humor Master will close the segment with a monologue, maybe three to ten jokes. 

The entire Observational Humor part of the meeting might take 10 minutes.  We have not had a problem with members having too many observations to share.

5.  The purpose of the Observational Humor segment is to improve our general humor skills.  It helps us to see the humorous twists and to master the art of structuring and delivering humor.  It helps us tune our humor radars.  The purpose is not to make members standup comedians.  The goal is to sharpen club member Observational Humor skills to the point where they’re able to drop in one observational humor line into almost any speaking situation they find themselves.

6.  It takes time.  By experience, we’ve discovered that it takes time for a club to get the knack of Observational Humor.  The first few times you try it, it’s quite possible that you won’t have any members who want to share a humorous observation.  Give it time.  We’ve found that after a year, some of the members start to get quite good at it. After having Observational Humor as a formal part of our club’s agenda for five years, we now have about ten people who are quite skilled at it.  It has become one of the highlights of the evening and we have a reputation for great humor at our meetings.

Over the years I’ve seen great growth in the members who participate in the Observational Humor part of the meeting.  So give it a try.  It’s a learned skill.  You can practice it as a club or you can hone the skills by yourself.  It takes a little work, but I guarantee you it’s worth the effort.