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6’4″, Tattooed, and Kind

September 10, 2025 Jenny Riddle Leave a Comment

It’s Tuesday night, and I’ve just walked into the indoor pickleball courts at Lifetime in Oak Brook. I’ll be honest: I wasn’t quite sure what I was getting into. Would I be able to hold my own? And what would the people be like?

Having played tennis for most of my life, I know that world and can easily adapt—or at least act as if I know what I’m doing. But pickleball? A whole new milieu. I wasn’t sure if I could pull it off here, but I knew one thing: I was going to die trying.

I’d been invited to join a more advanced league by the head pickleball coach at Lifetime. The crowd? Mostly men, with just three women in the mix—a number of the guys were young enough to be my kids. One 6’4”, tattooed, ridiculously athletic player stood out immediately—Josh.

You could see his advanced technique in the way he warmed up—power, precision, confidence.

The league runs round-robin style: three courts, new partners each game. In round two, I was paired with Josh. Inside my head I was thinking, “Jen, don’t blow it.”

And here’s what surprised me: He wasn’t just good. He was generous.

“Great shot,” he kept saying. From the moment we stepped on the court, he’d smile, look me in the eye as he tapped my racket after each point. He even encouraged the other team after a good rally or when they made a strong play.

Not once did he make me feel like the newbie I was. His encouragement made me want to play harder and rise to the occasion.

That night, Josh reminded me of something I’d just read in Harvard Business Review about what they call a “super-facilitator”—the kind of person who makes everyone around them better.

Here’s what that looks like in real life:

  • Pay attention. Josh wasn’t just watching the ball; he was watching me. He noticed what shots I could handle and encouraged me when I stretched my skills. Great leaders do the same—they notice potential and meet people where they are.
  • Communicate. A smile. “Nice shot.” A quick tap of the racket. Small words and gestures, but they sent a clear message: I see you, and I believe in you. Leaders who express belief in their people give them the courage to step up.
  • Share the spotlight. Josh never hogged the game. He gave me chances to take shots, even when it meant risking the point. At work, as in sports, the best leaders make space for everyone’s contributions.

And here’s one of the coolest things the research reveals: when leaders clearly communicate their belief in people, those people actually become their best selves.

And the good news? Research shows that being a “super-facilitator” can be learned. Whether you’re leading a team at work, mentoring a colleague, raising kids, leading a book club, or just showing up for your friends, the truth is the same: people thrive when someone sees you, believes in you, and gives you room to shine.

Later that night, recovering on the couch with a large ziplock bag full of ice on my arm, I told Bill how much I’d loved the positive vibe at the pickleball league. Everyone had been encouraging, especially Josh.

Thinking about all the kind young men there, I cheekily said to Bill, “I wish our girls had been there tonight,” though I’m not sure they would’ve appreciated me trying to play matchmaker at the pickleball courts.

But what really struck me was this: it was a reminder that kindness and empathy are alive and well—at least on the pickleball court. And yes, after two and a half hours of working my tail off, I practically limped to my car. But it was worth it.

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Jenny Riddle is a dynamic speaker, trainer, and communication expert who has a special way of helping people not just communicate, but truly connect .
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