Why Would I Want to Spend My Time Coaching It?
This is a good question and the answer might be that you don't. It can be difficult to work on everything in youth baseball with the time restraints that a spring season has. For 13 and older and Pony teams that allow leading off, it can be a great way to get kids who aren't that fast a stolen base. This can not only benefit the team but provide a thrill for that kid that doesn't usually get a chance to steal a base.
What to Look For
A delayed steal is taking advantage of an opportunity given to you by the opposing team when they simply aren't paying enough attention to the runner. This can be the catcher, pitcher, middle infielders and best of all a combination of those players.
Catcher that likes to frame the pitch
Some catchers like to frame the pitch and they will actually stare down their glove as they frame the pitch. They lose at that point the ability to notice that the runner is going as their focus is directed at their glove.
Catcher that lobs the ball back to the pitcher
Some catchers will receive the pitch and then slowly stand up and lob the ball back to the pitcher. This is a good opportunity to take advantage of that slow throw back to the pitcher. Combine that with middle infielders that aren't backing up and you may have an easy base.
Pitcher that is emotional and doesn't pay attention when the ball is thrown back
Some pitchers live in their own world and really are unaware of what is going on around them. They may receive the ball back from the catcher and immediately start fixing the mound or walking around with their head down. Combine this with middle infielders who are not backing up and you have another great opportunity to steal a base.
Infielder(s) that don't pay attention when the ball isn't in play
This is a good one to focus on. If the middle infielders do not back up the throw from the catcher to the pitcher and better yet, if they simply don't pay attention once the ball is not put in play, then you have nobody who will beat your runner to second base and you have an easy delayed steal.
Third baseman that playing up for a bunt or deep
Again your looking for a player that isn't paying attention after the ball is not put in play. Combine this with a catcher that is framing the pitch for example and you may have a good opportunity to take third. With the shorter throw on this one I may reserve this for players that are good baserunners and have some speed.
So now we know some things that we're looking for, how do we coach the kids to execute?
This really comes down to a timing play in leagues where kids can lead off. You want to teach kids to take their normal secondary lead which is usually two shuffle steps after the pitcher starts delivering the pitch. Then teach the players to take one more shuffle step before taking off at full speed for the next base. The idea is to make everything appear like a normal secondary lead and not a steal. The third shuffle step gains some distance and allows the players on the opposing team to do what we expect them to do and not be prepared. Then after the third shuffle it's an all out sprint for the next base. I've embedded a couple of videos below so you can see it in action.
This next video gives you an example of a catcher who lobs the ball back and a pitcher that doesn't pay attention. The timing is a little different as the runner has to wait for the catcher to start his throw back to the mound. This is the kind of timing that would be needed in Little League. Get a secondary lead, pause, maybe take a step while waiting for the defense to do what you've seen them do and then run full out.
Delayed Steal Drill
I've added a delayed steal drill to the drills section to help you teach the timing involved in the delayed steal. It can also be used to mimic the situation you're trying to duplicate in a game situation.