Humor has always been a part of my life. In fifth grade, I created my own joke book and sold copies to my friends for 25 cents each. In high school, they had to create an entirely new category just for me. I was voted “Class Joker”—because “Class Clown” didn’t fit. I told jokes; I didn’t make armpit noises.
In college, I performed an original stand-up comedy routine at our campus-wide talent show. Some 30 years later, I still remember the entire routine. My first joke went like this:
“In college, I thought I might work toward becoming a brain surgeon … but I didn’t have an open mind.”
Today, as a school principal, humor continues to play a major role in how I lead. Our job is stressful—no doubt about it. But it should never become so stressful that we lose sight of the joy, laughter, and funny moments that happen every single day in schools.
The role of the principal is simply too demanding not to have some fun along the way.
Now, I don’t believe teacher evaluations are particularly fun. But they are familiar. So, in honor of evaluation season, let’s borrow that process—Observe, Evaluate, and Score—and flip it into a framework for leading with humor and humanity.
Observe
Start by noticing the humor in everyday school life.
Think about the moments we all recognize:
- Handing out “Intent to Return” forms
- Passing through the teachers’ lounge
- Delivering treats during Teacher Appreciation Week
These moments don’t have to be routine or forgettable. They can be lighthearted, affirming, and fun. When we intentionally notice—and share—those moments, we remind our staff that joy still belongs in the work.
Evaluate
Next, take time to reflect on who you are as a leader.
Ask yourself: “What are the three characteristics that define me?”
For me, the answer came quickly. I see myself as:
- Fun
- Relational
- Trusting
Once I identified those traits, they became my filter. Whether I was communicating with staff, posting on social media, or creating content for my community, I stayed grounded in those three qualities. The result? Consistency. Authenticity. And connection.
And model! Model! Model!
Score
Finally, score points with your community by being real.
Create authentic content through the use of social media that reflects who you truly are. When your leadership traits are clear, your message naturally becomes relatable. That authenticity builds trust—and trust opens the door to influence.
Engage positively with your audience. Like their posts. Comment on their ideas. Acknowledge the risks they take. Follow back! (While I’m thinking of it…you can follow me on TikTok @nickholtvlwer and Instagram @nick_holtvluwer.)
As you do, your community grows. Your influence expands. And you gain access to the collective wisdom, creativity, and inspiration of others who are walking the same path.
An additional bonus to broadcasting a fun and positive culture out into the world is that it helps with hiring the best teachers. We ask every applicant what they know about our school. Many times a candidate will answer with: “I love your videos and I want to be a part of this school community!”
Leadership doesn’t have to be heavy all the time. Humor doesn’t diminish credibility—it strengthens relationships. And when we allow ourselves to laugh, we create schools where people feel seen, supported, and excited to show up each day.
We grow as leaders when we step outside our comfort zone. So take some risks! After a 30-year hiatus, I am back at open mics and comedy clubs performing stand-up comedy again.
Let’s face it, in the education world, we never run out of material.
Because leadership really is a funny business.
