The Match | Humor
Word: Humor
Sentence:
Humor keeps connection alive when the work gets heavy.
Passage:
When schools, organizations or companies are under pressure, humor is usually the first thing to disappear.
Everything gets serious. Performance meetings. Discipline. Turnaround plans. Adults start bracing before conversations even begin.
My first year at Harper High School, I worked alongside another assistant principal who led curriculum and instruction while I focused on student development and interventions. I learned a lot watching her lead meetings. She built relationships and brought evidence to the table in a way that moved people toward action.
One of her quiet strategies was humor.
One day after school she asked to meet with me. We started casually, talking through the day. Then she paused and said, “I need to tell you something. You stink.”
I froze.
She smiled. “Not your work. Your deodorant. It’s not working.”
She was right. Harper did not have air conditioning, and turnaround work does not move at a slow pace. We were always moving. Always carrying stress.
We both laughed.
But what stayed with me was not the joke. It was the trust.
She cared enough to tell me the truth. And she delivered it in a way that did not shame me.
That laughter was not avoidance.
It was oxygen.
Humor signals safety. It tells people, you can exhale here. It builds connections faster than a policy ever could.
And now I believe humor is a skill. It’s a skill on display:
When a student who had been labeled defiant could joke about my bad jump shot.
When a staff meeting opened with a story that made people exhale.
When we could look at the chaos of the moment and say, “Well… that was something,” and laugh before we solved it.
Not sarcasm. Not entertainment. It’s a leadership skill that helps hard conversations land and keeps people connected when the work is heavy.
I saw it with her.
When humor disappears, what usually replaces it is distance.
And distance is where communities begin to lose each other.
Your Turn:
Where is the work heavy right now, and how might humor help you stay connected?
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8 Comments
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8 Comments
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on February 20, 2026 at 7:24 am
Humor is the lit!!
If you can’t laugh at yourself, who can you laugh at?
You know me, I love to laugh and make people laugh.
It definitely builds character!-
on February 21, 2026 at 10:57 am
You are such a human centered leader! And when you care about people you share more of yourself to them. That openness creates a deep relationship with others cause it shows them that you are the same in many ways.
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on February 20, 2026 at 7:55 am
This passage reminds me of something similar – years ago, in my first “business job”, at a hospital… the CEO, who was a nun, came into my office and asked if I was having “fun” – I thought she was setting me up. I didn’t know how to answer. I cannot recall how I answered, but she filled the gaps by saying, “if you are not having fun, this work is not worth doing”. I think that is poignant. If you are enjoying your “work”, it is no longer work, but something you enjoy doing. The other, more pertinent connection with today’s passage, is that laughter, or just enjoying a little light-hearted fun during the day with a co-worker does release tension. I have worked with many people who are just so serious and that situation sucks the energy out of everyone. No one wants to speak up at meetings; no one wants to team up to solve a problem. Thanks, Chad.
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I love that quote and question by the nun! What is the old saying if you pick a job connected to your purpose you will never work a day in your life? So true, I can imagine you walking around the hospital and making people life and smirk in an environment is built on stress, how important it is to laugh so you can continue to do hard work each day!
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on February 20, 2026 at 8:48 am
Humor and snacks!!!
I don’t attend meetings without snacks. I always bring some , even to my boring PLCs. Snacks often lightens the mood. I have many jokes. I just need to dial back the sarcasm. I am funny, however.-
I love it food and fun! They go hand in hand! Sarcasm can help you through life for sure, and it’s especially when you can bond with someone over a topic that is ridiculous. That sarcasm helps us process the unpredictability of life.
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on February 20, 2026 at 10:12 am
Using humor can make teachable moments memorable. As I was walking in our high school, I heard a student say “We got Obama in this @#%$&!” While I was flatter at the same time I had to use as a teachable moment. When I turned around, the other students just busted out laughing. The young lady started to walk away and I said, “No, you are not getting off that easy, come on back here” in a calm voice. The entire group of students came back as if they were going to jump me if I said anything wrong. LOL I simply said and asked her, “Thank you for the compliment but how could you have said that better?” She said, “Sir, you look nice. You look like Obama.” We laughed. I introduced myself to her. She shared her name and I thanked her for being open to listening and learning. One of the other students in the group said, “dude cool.” A humorous and teachable moment.
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That’s a good story! Kids. They say the things they think without filter sometimes. In this case, it was the highest complement – Obama! She just didn’t know how to articulate that and you used the moment to show and share how to do that to someone. Love it!
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Humor is the lit!!
If you can’t laugh at yourself, who can you laugh at?
You know me, I love to laugh and make people laugh.
It definitely builds character!
You are such a human centered leader! And when you care about people you share more of yourself to them. That openness creates a deep relationship with others cause it shows them that you are the same in many ways.
This passage reminds me of something similar – years ago, in my first “business job”, at a hospital… the CEO, who was a nun, came into my office and asked if I was having “fun” – I thought she was setting me up. I didn’t know how to answer. I cannot recall how I answered, but she filled the gaps by saying, “if you are not having fun, this work is not worth doing”. I think that is poignant. If you are enjoying your “work”, it is no longer work, but something you enjoy doing. The other, more pertinent connection with today’s passage, is that laughter, or just enjoying a little light-hearted fun during the day with a co-worker does release tension. I have worked with many people who are just so serious and that situation sucks the energy out of everyone. No one wants to speak up at meetings; no one wants to team up to solve a problem. Thanks, Chad.
I love that quote and question by the nun! What is the old saying if you pick a job connected to your purpose you will never work a day in your life? So true, I can imagine you walking around the hospital and making people life and smirk in an environment is built on stress, how important it is to laugh so you can continue to do hard work each day!
Humor and snacks!!!
I don’t attend meetings without snacks. I always bring some , even to my boring PLCs. Snacks often lightens the mood. I have many jokes. I just need to dial back the sarcasm. I am funny, however.
I love it food and fun! They go hand in hand! Sarcasm can help you through life for sure, and it’s especially when you can bond with someone over a topic that is ridiculous. That sarcasm helps us process the unpredictability of life.
Using humor can make teachable moments memorable. As I was walking in our high school, I heard a student say “We got Obama in this @#%$&!” While I was flatter at the same time I had to use as a teachable moment. When I turned around, the other students just busted out laughing. The young lady started to walk away and I said, “No, you are not getting off that easy, come on back here” in a calm voice. The entire group of students came back as if they were going to jump me if I said anything wrong. LOL I simply said and asked her, “Thank you for the compliment but how could you have said that better?” She said, “Sir, you look nice. You look like Obama.” We laughed. I introduced myself to her. She shared her name and I thanked her for being open to listening and learning. One of the other students in the group said, “dude cool.” A humorous and teachable moment.
That’s a good story! Kids. They say the things they think without filter sometimes. In this case, it was the highest complement – Obama! She just didn’t know how to articulate that and you used the moment to show and share how to do that to someone. Love it!