I think all of the posts pointing to Crosby's work ethic are entirely beside the point that
@Amazing Kreiderman was making. Crosby might spend a lot of time on skills and physical workout. He might spend a lot of time looking at tape. He might be a good leader and teacher of peers. The point here, though, is that even despite those things, he might not have a great handle on what it takes for the average player to make it. Why not? Because every single thing he tries to do, he can do. He might work hard at doing them, but there are no limits on his game at all. I vividly remember after the '09 season, Crosby decided he wanted to become a better goal scorer. Yes, he worked very hard to get to the point where he could score 50 goals the next season. It's just that dedicating himself to the goal is literally the only thing he had to do to achieve it. Gretzky actually did a similar thing when, after scoring 70+ goals in 4 straight seasons, he just decided to go for averaging 2 assists per game the next season and, through hard work and dedication, was able to accomplish it. Both are pretty amazing, but actually sort of illustrate the point.
In general, a player who had to fight for every single scrap has a completely different understanding of how to help young players maximize their potential than someone who can set simply his mind to something, work hard to achieve it, and achieve it every time. That can cause a disconnect with being able to convey things to the players. Your average Tanner Glass has a better chance of actually helping someone like Filip Chytil, despite Chytil possessing far more talent than Glass could ever dream of, than your average Sidney Crosby. Does that mean that Crosby couldn't possibly be really good at helping prospects, maybe even better than Glass? No, it doesn't. But the odds are against it.