When NOT to use the Hit-and Run:

Two outs
Remember, the batter is going to make contact regardless of how crummy the pitch is. The batter is being offer up as an out, so with two outs, why would any coach try this play? The batter will probably make an out which means, your team is probably going to be playing defense after the next pitch.

Speedy runner on 1st base
Some kids are just plain fast and are going to steal a base 95% of the time, so why waste the out? With a speed runner on first, he can steal second base on his own. A better strategy would be for the runner to steal second, and then bunt him over to third.

Power hitter at bat
Your four hitter is expected to crush bombs, not give himself up to move a runner one base. Let the big guy hit and move runners using his power.

When to use the Hit-and Run:

Slow batter, average speed at first
Use it to avoid likely double play. If the runner at first can’t steal the base on his own and the batter will probably be thrown out at first on an infield hit, using this play is a safe way to advance a runner. Double plays are momentum swings. When they happen to you, they usually boost the other team’s confidence at the plate.

Batter who drives the ball to right field most of the time
A hitter who can handle the bat well and hits the ball behind the runner is golden. Runners should use caution. If the ball is caught by the right fielder, he will need to get back to first quickly. As he is stealing, the runner needs to take a look at the ball as it come off the bat. If the ball has a chance of being caught as a fly ball, he need to stop and observe the play. If caught, he needs to get back quickly. If not caught, he needs to quickly advance.

Runner on first and second
An aggressive move, which also prevents the double play. With two runners breaking on the pitch, the defense must recover and quickly and focus on the offered out at first. Typically the defense wants to throw to third or second as a first option in order to keep runners out of scoring position.

Runners on first and third
The opposing team are expecting the man on first to steal. They probably have a pitch out called or a fake throw to second, and go the third. Whatever they have called, your hit-and-run play will stop it and confuse them at the same time. Oftentimes it never occurred to the defense that this could happen to them. Well, the runner on third goes on anything hit down, the runner on first was already going, and the batter, if he hit the ball on the ground, is likely to be the out, but after you score. Worst case scenario is you have a run score, a man in scoring position, and an out. Not to bad considering you could have hit into a double play.

The Technique
(1) Make contact
Hit the ball. The hitter must first understand he is swinging at EVERYTHING. Contact is what is expected of him. Furthermore, the batter should expect a bad pitch or a pitchout. Why? Because if it is a good pitch, he shouldn’t have any trouble making contact; it’s the pitches over his head that are tough to hit. On a pitchout, a bat can be tossed if needed, just to make contact. There is no rule against throwing the bat at the ball to make contact. The only rule is if the bat is intentionally thrown and remains in the field of play, and interferes with the fielder. See rule 6.05(h) in the Official Baseball Rules.

(2) Swing down
As far as the swing, hitting to opposite field is a bonus. The number one concern (actually number two after making contact) is to hit the ball on the ground. One purpose of the hit-and-run is to avoid a double play. If the batter hits the ball in the air, there is a good chance that the runner will be doubled up. On a high pitch, the batter should tomahawk the ball, thus swinging down on it. Remember, the batter needs to hit the ball on the ground.

(3) No pick offs
The runner should never get picked off in a hit-and-run situation! The hit-and-run is put on to stay out of the double play. You are giving up your hitter; so the runner will gain a base. The runner does not need a great jump on the steal, since he is getting help from the batter. Once the runner takes off, after the third or fourth step, he should peek to the batter to see where the ball is hit. If the ball is in the air, obviously he should stop, wait for the catch, and go back to his base. A line drive is different. If the runner sees the batter hit a line drive, he should keep going. If the ball is caught the runner will get doubled up anyway; if the ball goes through there’s a good chance he is now standing on third. Now, sometimes the runner will not see where the ball is hit. Then he must go to plan B, which is to watch the reaction of the defense. Usually this will dictate where the ball was hit.

(4) The coach helps the runners
The coach must be loud and vocal upon contact. If the ball is hit up in the air with the potential of being caught, he should yell “UUUUUUUUPPP!” As a bonus, the coach can also yell where the ball was hit. For example, “UUUUUP, Right Field!.” If the ball is hit on the ground, the coach can yell “GO, GO”. Remember the coach is making the call for the next base only.