He Was Trying to Be Funny

I was at an awards ceremony.  It was the kind where everyone received something, a lighthearted moment to recognize each person’s contribution.

The person handing out the awards had a tough job:

1. Come up with something for everyone.

2. Make it entertaining.

3. Keep it moving.

   
   

They nailed the “everyone gets something” part.  But in their effort to add humor, they missed the mark.  Several “funny” awards dredged up past mistakes, awkward moments, or embarrassing memories.  The kind of things that maybe you’d laugh about in a private, trusted conversation, but not in front of a crowd.

I watched faces change in real time.The smile that froze. The eyes that dropped.The quiet shift from feeling seen to feeling exposed.

The Leadership Lesson

Humor is powerful.  It can break tension, strengthen connection, and create a sense of belonging.

But when humor is careless, it can leave invisible bruises that last far longer than the moment.

As a Self-Aware Leader, your words carry more weight than you may realize. The way you speak about someone, privately and publicly, shapes how they see themselves and how others see them.  A “light” comment meant to entertain can subtly alter their self-image and even impact their reputation.

What feels harmless in the moment can echo long after the laughter fades.

Before you joke at someone’s expense, ask yourself:

• Will this make them feel valued or vulnerable?

• Is this a memory they would celebrate or one they’ve worked to move past?

• Am I making them the hero of the story or the punchline?

  
  

Better Ways to Blend Humor & Recognition

• Make the joke about a shared experience, not a personal misstep.

• Highlight strengths with playful exaggeration  “This award goes to our coffee connoisseur, whose barista skills fuel half the department.”

• Avoid old wounds  If you wouldn’t want it on a billboard, don’t put it in an awards speech.

• Keep the dignity intact  Humor should leave people feeling bigger, not smaller.

  
  

Reflection Questions

• Have I ever used humor that could have unintentionally embarrassed someone?

• How do I ensure recognition moments are uplifting for everyone?

• Where can I use humor to highlight strengths instead of shortcomings?

  
  

You matter. Especially when your words make people feel ten feet tall. 💛

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