Stealing bases is great fun. Where else can a kid get to act like a complete little rascal, in front of his parents and everybody, and not only get away with it but get cheered on and rewarded to boot! For a kid, successfully stealing a base is truly one of the finer things in life.

Some managers take much of the joy out of base stealing by setting up complicated rules and signals in vain attempts to control when their players will and will not try to steal. This author disagrees with that approach because we are not dealing with adult baseball players. We are dealing with kids: enthusiastic, emotional, energetic, happy, and somewhat crazy kids. Kids can be led, encouraged, and influenced, but it's hard to control them. When it comes to base-stealing, it's impossible.
That is why this author advocates a very simple base-stealing policy:

1) Be sure to tag up on foul balls.
2) If you think you can make it, go for it.
3) Never get thrown out standing up. ( Slide, even if there is only a 1% chance of making it.)

The runners will succeed more often than not, it drives the opposing pitchers crazy, and it is huge fun. In business management, this is known as building a "bias towards action." (You can spend a lot of money to learn that.)

A manager has to keep track of many things during a baseball game. It is easy to miss a good opportunity to give the "steal" signal. This stifles initiative. Kids have good instincts. They read body language better than we adults do. This is why quite often the base runner is actually the best judge of when and when not to "go for it."

Base-stealing is a controversial subject. Many managers will disagree with this author. Do it your manager's way.