I believe that all players, especially under 14, should understand the role of each position on the team. Give these free softball coaching drills a try and you will be pleased with the results!
When there is less than full team at a practice session I take the opportunity to practice situational play ( as well as reinforcing fielding skills) by using one fielder only (left or right side) and the full infield. Using one outfielder allows us to have live base running.
With a coach hitting the ball (for better control of the training environment) we ask the players to field the softball and make the throwing response appropriate to the position of the base runner(s).
After a limited number of repetitions (perhaps 5) using the initial fielding positions we rotate all the players one position higher in the position order of one through nine. If possible I start and end the drill with each player in their most often played position .
Any player needing specific instruction on an appropriate situational response is given that instruction and the same play is repeated once more only.
I feel this drill provides each players the opportunity to become confident of both their own positional role in various situations and enables the player to understand what the other players will be doing as the playing simulation develops. (such as who takes a cut-off throw, where to position themselves as the cut-off player, how to re-adjust during a play that is broken by a slowly developing defensive response, poor throw/catch, etc)