Dear Dan: What’s Your Take on Humor in Leadership

Dear Dan,

I follow, and love, your leadership thoughts. I would be interested in seeing your take on humor and its role or value in leadership.



Dear Curious,

Thanks for the encouraging word and your interest in humor.

On a personal note, sometimes I crack myself up. Check out the image on Talented People Have an Annoying Side. But humor is a double edged sword.

“There is a thin line that separates laughter and pain, comedy and tragedy, humor and hurt.” Erma Bombeck

You can laugh at someone or laugh with them. Additionally, inside jokes make new team members feel like outsiders. Timing and context is everything.

Don’t laugh when:

  1. Others mourn.
  2. New ideas are suggested by novices.
  3. Problems are brought to you by concerned teammates. (Especially, serious teammates.)

Laugh at:

  1. Lunch. Lighten up for goodness sake.
  2. Yourself.
  3. Failure, at least some times. Sam Walton said, “Celebrate your successes. Find some humor in your failures.”


  1. Laughter makes you attractive. Frowning is ugly.
  2. Humor is an invitation to connect. “Laughter establishes–or restores–a positive emotional climate and a sense of connection between two people….” Psychology Today.
  3. Laughter has the opposite effect of stress. Dr. Lee Berk
  4. Laughing limits self-importance.


Sarcasm is dangerous and gets you in trouble. Others have helped me soften my sarcasm, but it’s a beast eager to leap out. Avoid sarcasm in public. Let it out with friends.


Tell a few jokes. Don’t worry that you can’t tell a joke. A bad joke does the same thing as a good one, as long as you know it’s not that funny.


Many leaders could lighten up.

  1. Smile frequently.
  2. Enjoy people.
  3. Laugh.

“I’m not funny. What I am is brave.” Lucille Ball

What’s your take on humor in leadership?

How might leaders interject humor into leadership?