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?
Posted in Authenticity & Transparency, Employee Engagement & Energy and tagged , , , , .

Karin Hurt

Karin Hurt helps human-centered leaders resolve workplace ambiguity and chaos, so that they can drive innovation, productivity and revenue without burning out employees. She’s the founder and CEO of Let’s Grow Leaders, an international leadership development and training firm known for practical tools and leadership development programs that stick. She’s the award-winning author of four books including Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates and Winning Well: A Manager's Guide to Getting Results-Without Losing Your Soul and a hosts the popular Asking For a Friend Vlog on LinkedIn. A former Verizon Wireless executive, Karin was named to Inc. Magazine’s list of great leadership speakers. Karin and her husband and business partner, David Dye, are committed to their philanthropic initiative, Winning Wells - building clean water wells for the people of Cambodia.


  1. Silliness should not be at the expense of anyone else. Self deprecating is fine (as long as it’s not too overboard) but belittling someone else rarely sends a positive message.

    • Silliness as a well-timed tool in my government setting. James is right on spot: never belittle someone, or make a joke at the expense of another. I am known throughout the building for my bagpipe imitation, and my ersatz cows and elephants aren’t bad either! But, knowing when and where to share these is as important as being able to sound like a Holstein.

  2. This is EXCELLENT! I have always been one who thought laughing and having fun at work is essential. Obviously, there is a time and place for it, but I can attest to the success of this strategy within our office. It makes going to work everyday that much more awesome! We spend a lot of time there, why not enjoy it.

  3. Positive silliness is a gate opener. Karin, you remind me of a real story. It has nothing to do with me in person.
    The story: A pitch had a qualification conditions that participating companies had a minimum of five years experience in relevant fields. One company had less than two years of experience. The owner decided to participate. On the front page of his offer he had a picture of Neil Armstrong photo landing on the moon with the tagged comment “but how many years of experiences did he have before landing”? The company won the contract

    Show some silliness even before the meeting starts. Karin, yes we need creative silliness

    • Ali, Love that story. Both of our stories involve silly as part of a strategic risk that catches attention. Thanks for sharing yours. Who else has one?

  4. Oh this post has brought back such fond memories. Of when humour and FUN in our offices made being at work even better! The relationships that were built were stronger, and dare I say more effective because we injected FUN. At the right time and situation. Almost too many examples to keep this comment a reasonable length.
    Now that I am in my own work as a coach and consultant, I would say that I have carried that belief to my client relationships with success. Mindful use pays off!
    Thank you.

    • Linda, GREAT. Thanks so much for sharing. I’ve got so many fun memories too (and an office full of pictures 😉 Silly sometimes involves costumes…

  5. A wonderful story, and an interesting little case study

    You had some concerns, so your Amygdala is ringing an alarm bell. Not a big one, but there’s something making noise. Unfortunately for you (all of us:), Amygdala activity causes a negative knock-on effect in higher brain function.

    He sang; alarm subsided; and the rest of the brain was able to listen more deeply.

    Karin’s lesson- brilliant.

    If that science stuff was too boring…

    One of the ways I’ve been known to lighten the mood is to present a chart in a different way.
    Anybody can do this.

    At one point I was a national compliance manager and once a month I had to present riveting compliance reports to the Divisional heads and the VP of Service Delivery.

    I mean, even if you used polka dots on pink and purple pie charts this stuff would still be boring, plus, I needed them to not only be aware of the numbers, but do something about them!

    The solution- a short anecdote (I likened defects within our management systems to barnacles on a sailing boat, collectively, slowing us down), and then- the barnacle graph!

    Sure, it was silly, but it woke them up. For the next month, these leaders were yelling to me in hallways, asking how their division’s barnacles were going, (with odd looks from passers by) and while I wasn’t convinced all of them were genuinely interested in the answer, at least they were now talking about the ‘numbers’. Next step; color the barnacles by division name,,,.

    • Dallas, LOVE the pic. What a great example. Barnacles get stuck in the brain… and give people a wonderful visual to inspire. Thanks for sharing.

  6. Karin- I am visiting again because of the great comment of Dallas. I wish to share my next presentation to be published soon “The half lemon employees”. Getting the juicy output of employees is science and FUN. It is amazing how small changes in squeezing a lemon may increase the juice output. I shall give examples and funny ones too on how to make employees self-seeding and self motivating. Likewise; make meeting juicy as well
    Sweet or sour juice? We shall find out

  7. “So keep fightin’ for freedom and justice, beloveds, but don’t you forget to have fun doin’ it. Lord, let your laughter ring forth. Be outrageous, ridicule the fraidy-cats, rejoice in all the oddities that freedom can produce. And when you get through kickin’ ass and celebratin’ the sheer joy of a good fight, be sure to tell those who come after how much fun it was.”

    I have this quote by our lovely Molly Ivins hanging in our common area. I think humor is essential. It builds bonds with people. James point about never being at the expense of someone is certainly true. I tell my staff,
    ‘we need to take what we do seriously, but never take ourselves too seriously’. Thanks again for a great article.

  8. Humor is part of who I am.

    Only on very rare occasions have I ever gone through an entire coaching call without adding levity to change the mood.

    A few years ago, I had to have a stent put in. I’m one of the healthiest people you’ll see. I was shocked when the doctor’s told me they had to operate.

    Anyways, while prepping me in the operating room, I turned to the surgeon and asked “Have you ever done one of these before?” Nurses, assistants, and doctors all broke out in laughter!

    I couldn’t go a day without laughing at least once.

  9. Back in the day, before being politically correct dampened our spirits, my squad of FBI agents bantered and teased and called each other by nicknames: Bugs, Knuckles, Pinhead, Princess (that was me), etc. I still don’t remember Bugs’ real name…but the point is that we lifted the spirit of the work environment by silliness. We knew each other well enough that we weren’t offended, and the nicknames had a relevancy to their personality.

    About the time being PC became law, the silliness and humor also vanished. Now, we spend more time worrying about offending others, because (gasp) what if their sense of humor is different?

    I totally agree with you, Karin…humor and silliness can go a long way in “stirring the pot of creativity.” I know several (smaller) organizations who don’t hire until the applicant displays some ability to “be silly” and that’s a great way to go….

  10. Humor can be a great training technique as well. Training can be at times stressful and at times boring. Either way it is a required activity. Humor and silliness can really help people. It relaxes the stressed as it did you in your example and it wakes up the bored. I try to use it at the beginning of stressful training and in the middle of boring training.

    • Bonnie, YES! So important in training. I led a training organization, and those folks had some of the best senses of humor around. Fun to work with too…

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