Why Playfulness Is Your Secret Leadership Advantage

Somewhere between childhood and corporate America, we got too serious. We traded in our crayons for spreadsheets, our questions for conclusions, and our laughter for late-night emails.

But here’s the truth I’ve learned after decades in leadership, sales, and coaching: the best leaders know how to play.

The Best…

• Emails

• Sales meetings

• Offsite planning sessions

• Product launches

• One-on-one calls

• Conferences

Are FUN!!!

Now, I don’t mean turning your Monday meeting into a carnival (although, that might not be a bad idea—think PT Barnum). Allow a spirit of curiosity, creativity, and joy to infuse your work. Playfulness is not the opposite of professionalism. It is the oxygen that keeps it alive.

When I walk into a company struggling with morale, I can usually tell within five minutes whether people are having fun. Not partying fun, purposeful fun—the kind that shows up as laughter in the break room, inside jokes in the group chat, and the freedom to say “what if” without fear of judgment.

Here’s the thing: Playfulness doesn’t distract from productivity. It drives it.

When people feel safe enough to play, they feel safe enough to take risks. And that’s where growth happens. I’ve seen million-dollar ideas born out of “crazy thought” conversations that started with someone saying, “This might sound dumb, I am going to say it anyway…”

Play creates space for experimentation. It loosens the grip of perfectionism and invites curiosity. Remember when you were a kid and built something with Legos just to see if it could stand? That’s what innovation looks like in adult form.

I’ve worked with executives who thought being playful would undermine their authority. “Katey, I can’t be seen as the goofball in the room.” My response? “You don’t have to be the clown—you have to be real.” A genuine laugh, a clever metaphor, a little lightness—it reminds people that you’re human. People work for people.

“100% of customers are people. 100% of employees are people. If you don’t understand people, you don’t understand business.” – Simon Sinek

And humans follow humans, not job titles.

All of my team meetings involved play, laughter, and fun. Some of my favorite team meetings involved Dr. Seuss. The best sales book ever written is Green Eggs and Ham by Dr. Seuss. It is a simple message: be passionate, make friends, get creative, be persistent. We spent the entire meeting breaking down the book. Most people realized that they were taking “sales” far too seriously and realized that it is supposed to be FUN!

My most successful FUN sales adventures:

• Giving away Matchbox cars to doctors as a pharmaceutical sales rep

• Making breakfast before a real estate sales meeting as a mortgage company leader

• Dressing up as a bridesmaid at a Bridal Expo at a coaching client’s booth

• Going running at lunch with a prospect

• Hosting a “welcome to the neighborhood” party for new buyers

• Dance party…virtually or in person…before every keynote or team meeting

I got more… email me!

Here’s your challenge for the week:

• Smile first. Energy is contagious—make yours worth catching.

• Invite laughter. Humor softens hearts and sharpens minds.

• Be curious. Ask “what if” more often than “why not.”

• Model joy. When you show up light, others will too.

• Have FUN. Put your email into ChatGPT and ask it to edit as PT Barnum.

Playfulness doesn’t mean immaturity—it means aliveness.

So loosen your tie. Kick off your heels. Ask the silly question. Celebrate the little wins. The most magnetic people in business aren’t the ones with perfect answers—they’re the ones who make the room feel lighter.

When you bring play to your work, you don’t just make money—you make moments.