I had the parent of a new player on the team send me a text, and ask what their son needs to work on. We've only had a week of training, so it's very early in the season. Nonetheless, this is a hugely positive sign, in my opinion. This is a parent who is involved, and critical (in a good way) of their son.
These parents are my favorite to work with. Their players are not always the best on the team, but they are also pushing them towards the next challenge. My least favorite question from parents is "Why didn't my son/daughter start the last game?" or "Why isn't my kid a starter?" The way this question is phrased usually insinuates they think their kid is already deserving of that spot. They've already written another player off in their head, or assume they know more than you do. The question is, in their mind, a rhetorical one.
The types of questions I love to hear are "What does X need to do to earn more playing time?" In both this question and the above ones, the parents are looking for more playing time. However in the last question, coming with humility and a willingness to work, shows a willingness to submit to the process of improvement. Playing time, and anything worthwhile in life, should be earned.
This is very much something I strive to weave in to the culture of my team. There's this weird idea that takes root in the minds of some that if you ask for something, you deserve it. Playing time, to play a different position, taking free kicks, you name it. Youth sports should be focused on a quality process, not some immediate outcome. This goes for the role of results in the youth game, individual improvement/playing time, style of play, etc. Asking and getting more playing time is not nearly as valuable for the team or the individual as earning it.