Strategic Silliness: When To Lighten The Mood

The deal was important and could lead to future work. I was impressed with this company, but had some valid concerns. They brought their Chairman to the table to help close the deal.

“Karin, I know you’ll be very impressed with what you see here today. We’ve got a great track record of results, and numbers to back it up. I can’t wait for the team to share more about our programs. But before that, I’ve written you a little song.”

He pulled out a piece of notebook paper with the song he penned, and began to sing. His a capella serenade included why we should give them a shot. The mood was instantly lightened by his silliness. My guard dropped a bit. He sang, I listened more deeply.

“Children have one kind of silliness, as you know, and grown-ups have another kind.”
~ C.S. Lewis

What followed was a highly-professional presentation with data, video, tours, side by sides. They proved they were the best. I hired them. Not because of the song, but not in spite of it either. Silliness has serious benefits.

Well-timed Silliness Can:

  • Break the ice
  • Show you’re real
  • Show you are bold
  • Energize the meeting
  • Showcase creativity
  • Build relationships
  • Create memories

Strategic Silliness Precautions

After my standing ovation to his song, I responded: “Great stuff”. NEVER do that at our corporate headquarters. We both grinned knowingly.


  • must be timed well, with a receptive audience
  • works best with kindred spirits
  • can’t stand alone (surround it with great results and execution)
  • works because it’s unusual and infrequent
  • is tasteful
  • What would you add?