I'm constantly anxious about putting pressure on kids. It came easier to me at a young age, but also I was always the kid who wanted to play catch or shoot hoops outside with my dad every waking moment. I wanted to work on whatever would make be better. And it's hard to know how much of that was me and how much was the influence of my dad getting me out there at an early age. From my dad's perspective, it was more me than him. So for that reason, I tend to be more hands off. I'll try to pick times long after a game is over to talk about things that happened. I'm always ready to go out and practice, and I let the kids know that. But I rarely pick what we're going to do.
At the same time there are certain moments where a kid needs to push through and you know that they'll be glad they did. Because if they don't get over a certain hurdle, they'll never be able to contribute, and once they do, things will come more easily. At a young age it's, e.g., overcoming fear of the ball as a hitter and stepping toward the pitcher rather than toward third base, learning to put your glove up and trust that you can protect your face rather than trying to catch everything with your glove below your waist like a grounder, catching a basketball with your hands rather than with your arms.
With our oldest there was one day my wife was working with her on hitting in softball when she was 9. A lot of it was fear of the ball and stepping to third. It was a very frustrating day with much gnashing of teeth. I stayed away and let Mom handle because, even though she was maxing out her knowledge, I knew that only Mom was going to be listened to. But by the end of the day she was making contact, and that sparked a big change. She's not likely going to play at the high school level, but she's getting much more enjoyment out of playing now that she's contributing more at bat and on the bases.
On the other hand, getting B8 work on catching the ball with his glove up was a chore last year. He tends to want to do the things he's already good at. He's definitely not like one of his teammates who asks me to throw the ball to a particular location so he can get better at catching those. I didn't push it as much as much of me wanted to as I saw him falling behind his peers even though he showed more natural ability the year before. But he looks more comfortable this year. He's still not where I was hoping he'd be. But I think he also is just naturally developing that skill a little later. (I think playing basketball last winter helped him get comfortable protecting his face, which was the main thing I was hoping he'd get out if.) But he improved enough to be able to still contribute.
The next step is pitching. He has one of the better arms, so he was interested in pitching. But he was frustrated because the first time he tried pitching, throwing strikes didn't come easy to him. So he never wants to practice it, even though the team needs more pitchers. In the end, I don't care if he doesn't want to pitch. But I care if he does want to pitch and just isn't doing it because it was hard at first. So it's a constant internal tug-of-war for me.