
Quick answer: Pick one kid whose parents already trust you. Show up at the same time every week, teach one real skill, keep everything out in the open, and back the parents up instead of competing with them.
Think about the man who taught you to back a trailer down a boat ramp. Not your dad. The other one. Maybe it was a coach who had you running the fence line at 6 a.m. in August. Maybe an uncle who let you drive his F-150 around a hayfield when you were thirteen, or the neighbor who handed you a socket wrench, said "lefty loosey," and then watched you figure out the rest.
You probably can't quote one thing he said that sounded like advice. You remember that he was there. Every Saturday, same time, no speeches. That's most of the secret, and it's why you're more qualified for this than you think.
You're the backup, not the replacement
Start with the parents. Always. Every time.
The kid you're thinking about has a mom or dad, or a grandmother raising him, who is already carrying the load. Your job is to make that load lighter, not to become the fun alternative. So the first conversation isn't with the kid. It's with the adult who tucks him in.
Make it specific. "I'm going to the lumberyard Saturday at nine to pick up deck boards. Can Tyler ride along and help me load?" That's an offer a parent can say yes to in four seconds. "Let me know if he ever needs anything" is an offer nobody takes. (More on that in Stop Saying Let Me Know If You Need Anything.)
Then ask what they're trying to build. A single mom with a twelve-year-old boy usually knows exactly what he's missing. She might want him around a man who works with his hands. She might want somebody to make him put the phone down and shake hands with an adult. A dad who only has his kids every other weekend might just want another steady face in their lives during the off weeks. Ask. They'll tell you.
And then honor their rules like they're yours. If Mom says no phone at the table, there's no phone in your truck. If Dad says no energy drinks, you don't buy one at the gas station because "it's just one." The fastest way to lose a parent's trust is to be the guy who undoes their work.
The skill is the excuse
Kids don't sit still for life lessons. They'll sit still for a job.
So give them one. Pick something you actually know how to do and let the time together hang on it:
- Changing the oil and checking tire pressure
- Throwing a spiral, or fielding a grounder without flinching
- Sharpening a pocketknife on a whetstone
- Cleaning and filleting a fish
- Building a birdhouse, then a bookshelf, then fixing the neighbor's gate
- Walking into a store, asking an employee for help, and saying thank you like you mean it
The skill matters. But the real teaching happens sideways. A fourteen-year-old won't look you in the eye and talk about the kid who's making his life miserable at school. He'll tell you the whole thing while you're both staring at a carburetor. Shoulder to shoulder works. Face to face feels like an interrogation.
Let him get it wrong. Let him strip the screw. Don't grab the drill. Hand him a new screw and say, "Slower this time." The lesson he keeps is that a grown man didn't take over or blow up when he messed up.
He's also watching everything you do when you think he isn't. How you treat the cashier. What you say when a referee blows a call. Whether you pay for the coffee you forgot was in the cart. That's the curriculum, whether you meant it or not.
The rules you never bend
This is the part people find awkward. Do it anyway.
- Stay visible. Garages with the door up, ballfields, kitchens with other people in them. Never alone with a kid behind a closed door.
- Parents always know where and when. Text before you leave, text when you're heading back. No surprise stops.
- Keep messages in the open. Copy a parent on texts, or use a group thread. Nothing private between you and somebody else's child.
- Take the background check. Little League and most youth programs run one on volunteers, and many also require a short abuse-prevention course. Do it without grumbling.
- Respect a no. If a parent pulls back, you step back. No arguing, no hurt feelings in front of the kid.
If one of these rules makes you feel insulted, that's the rule doing its job. It protects the kid first, and it protects you second. Any man worth trusting with someone else's child will thank the people who set up guardrails like these.
Kind doesn't mean pushover
The worst version of a mentor is the "cool uncle" who's all fun and no standards. Kids can smell it, and they don't respect it.
Serve the kid by expecting something of him. If practice starts at 5:30 and he strolls in at 5:45, he sits for a drill. If he borrows your fishing rod, it comes back rinsed, the reel wiped down, and no bird's nest in the line. You're not being harsh. You're teaching him the old code: you return what you borrow in better shape than you got it.
Model it too. When you drop him off, he's home on time, fed, and holding whatever he left in your back seat in a bag. Bring his mom a dozen eggs from your chickens now and then. Show up early to the game and stay to break down the field. He'll notice.
And when he mouths off, correct him. Calmly, directly, once. Then move on and don't hold it over him. A kid who learns that an adult can tell him he's wrong and still show up next Saturday has learned something some grown men never figure out.
Girls need this too
None of this is only for boys. The aunt who teaches her niece to change a tire, the woman who coaches the eighth-grade volleyball team, the neighbor who shows a teenage girl how to balance a checkbook and negotiate for her first car. Girls need capable women in their corner, and they need to see what a decent man looks like up close.
If you're a man coaching girls, the rules above apply with extra care: another adult around, parents in the loop, a female assistant coach when you can get one. If you're starting from scratch on the coaching side, What Nobody Tells You About Coaching Your First Youth Team covers the parts the league handbook skips.
Sticking with it when he grunts at you
Somewhere around thirteen, the kid who used to run to your truck will start answering every question with a shrug. Don't take it personally. Keep showing up.
Commit for a full year before you decide whether it's working. One season at minimum if you're coaching. Put it on your calendar like a work meeting, because it matters more than most of them. If weekly is too much, do every other Saturday, but make it the same Saturday every time.
Here's the hard truth about it, though. A mentor who shows up for three months and then disappears does more damage than one who never showed up at all. That kid has probably already had an adult walk out on him. Don't be the second. If you're not sure you'll stick, start smaller, the way Pick the Volunteer Job You'll Actually Show Up For suggests. And when you have to cancel, tell him yourself, ahead of time, with a new date.
What it gives back
You'll find out what you actually know. Explaining why you torque lug nuts in a star pattern to a skeptical eleven-year-old will clear up a lot about your own thinking.
You'll get calmer. Kids test patience, and most of us could stand to have ours tested on a regular schedule.
And you'll mostly go unthanked. That's fine. That's how it worked for the man who did it for you.
But fifteen years from now, some kid you'll never meet is going to back a trailer down a ramp on the first try. He'll learn it from a man who learned it from you.
Cal Brennan
Fitness
Strength coach. Trains fathers, tradesmen and desk workers, which means programmes that survive a bad week.
Watch
Watch how it's done
Picked for this article.
From channels we rate. Plays on YouTube or TikTok.
Big Brothers Big Sisters of Puget Sound
The Value of Mentoring: A Kid's Perspective
TEDx Talks
Inspiring Change: The Magic of Mentoring At-Risk Youth | Armand Lawrich King | TEDxSanDiego
TikTok@the_coaching_dad
🎯 Feel like a coaching imposter? You’re not alone. But guess what? You’re doing better than you think. Here are 3 quick tips that’ll instantly level up your game (no clipboard required): - Actually listen to your players—eye contact goes a long way. - Keep your instructions kid-sized. You’re not le
Read next
