What Coaching My Kids’ Teams Taught Me About Running a Company
I’ve spoken at the United Nations. I’ve shared stages with John Maxwell and Deepak Chopra. I’ve built companies across 18 countries.
But nothing has taught me more about leadership than coaching my daughter Ella’s softball team and my son Brayden’s baseball team.
I know that sounds like something you’d read on a motivational poster in a dentist’s office. But I mean it. The lessons that have stuck with me the longest…the ones I actually use every single day running a company with 500+ people…those came from standing on a dusty field watching a nine-year-old try to figure out a batting stance.
Here are five of them.
1. Meet People Where They Are
When you’re coaching kids, you learn something fast: not everyone learns the same way.
Some kids are visual. You show them what a swing looks like and they get it immediately. Some are verbal…you talk them through the mechanics step by step. And some kids? You just have to let them do it wrong fifteen times until their body figures it out.
If you try to coach every kid the same way, half the team checks out.
Running a company is identical. I manage a team spread across Atlanta and Cagayan de Oro in the Philippines. Different cultures. Different communication styles. Different ways of processing feedback.
Early on, I made the mistake of managing everyone the way I wanted to be managed…direct, fast, get-to-the-point. That works great for some people. For others, it felt abrupt. Even cold.
Coaching taught me to slow down and ask: how does this person learn best? How do they receive feedback? What motivates them…recognition, autonomy, structure?
The answer is never the same twice.
2. Reps Over Theory
I’ve never once given a kid a PowerPoint on the physics of hitting a baseball. Not once.
You know what works? Reps. Get in the cage. Take a hundred swings. Then a hundred more. Feel it. Adjust. Repeat.
Practice beats planning every single time.
In business, we love to plan. We build strategies and frameworks and roadmaps and project timelines. And look…those things matter. But I’ve watched too many entrepreneurs spend three months perfecting a plan and zero months executing it.
At Outsource Access, when we’re rolling out a new process or onboarding a new client, we don’t try to make it perfect on paper first. We run it. We see what breaks. We fix it. We run it again.
The field is the classroom. Always has been.
3. Build Confidence Before Correcting Technique
This one changed everything for me.
There’s a kid on Brayden’s team…great athlete, tons of potential. But early in the season, his mechanics were rough. Everything in my brain said fix the mechanics first.
But his confidence was fragile. If I started the relationship by telling him everything he was doing wrong, I’d lose him. He’d stop trying.
So I did the opposite. I found what he was doing right and made a big deal out of it. His effort. His attitude. A good throw here. A solid at-bat there. I built him up first.
Then…once he trusted me, once he believed I was in his corner…I started introducing corrections. And he took them. Because he knew the feedback came from someone who believed in him, not someone looking for flaws.
This is the single most transferable leadership lesson I’ve ever learned.
When a new VA joins our team, the first few weeks set the tone for the entire relationship. If we lead with everything they need to improve, we create anxiety. We create someone who’s afraid to make mistakes…which means they’re afraid to take initiative.
But if we lead with what they’re doing well? If we show them we see their strengths? They open up. They get creative. They start solving problems on their own.
Confidence first. Correction second. Every time.
4. The Best Players Aren’t Always the Best Leaders
Every team has a kid who’s clearly the most talented. Fastest arm. Best bat. Most natural ability.
And sometimes that kid is also a great teammate…encouraging, lifting others up, leading by example.
But sometimes? That kid is the worst influence on the team. Rolls their eyes when someone makes an error. Gets frustrated when things don’t go their way. Talent without character.
In business, I’ve made this mistake more than once. I promoted the person who was best at doing the work, assuming they’d be great at leading others who do the work. Those are two completely different skill sets.
Your best salesperson might be a terrible sales manager. Your most productive VA might struggle as a team leader. Performance and leadership are not the same thing.
Coaching taught me to look for something different in leaders. Not just skill…but how they make the people around them better.
5. The Campfire Moments Are the Real Moments
Here’s what nobody tells you about coaching your kids’ sports teams.
The games aren’t the best part. The practices aren’t either.
It’s the campfire talks. The early morning car rides to tournaments. The conversations at 6 AM when we’re both half-awake and Brayden says something that just stops me in my tracks. The quiet moments after a tough loss when Ella processes what happened and figures out what she wants to do differently.
Those are the moments where real connection happens.
And here’s the business parallel that took me years to understand: the real culture of your company doesn’t get built in the all-hands meetings. It doesn’t get built in the strategic planning sessions. It gets built in the small, unscripted moments.
A five-minute check-in with a team leader in the Philippines where you ask about their family. A message to someone recognizing something small they did that nobody else noticed. A conversation that has nothing to do with work.
Those moments are the foundation. Everything else is just structure built on top of it.
The Overlap Is Bigger Than You Think
I used to compartmentalize. Business Brad over here. Dad Brad over there. Keep them separate.
Coaching broke that wall down. Because the lessons aren’t different…they’re the same lessons applied in different contexts.
Meet people where they are. Prioritize reps over theory. Build confidence before correcting. Separate talent from leadership. And never underestimate the power of the small, unscripted moments.
Whether you’re building a team of VAs across the globe or helping a bunch of kids learn to field a ground ball…it all comes down to the same thing.
People first. Always.
Every week in my newsletter, The Full Potential Dispatch, I share lessons like these…where business, family, and personal growth intersect. Real stories, real frameworks, zero fluff. Subscribe here and join thousands of leaders working to realize their full potential.
