When to Execute an Intentional Pickle
An intentional pickle will usually be called when there are 2 outs and you are trying to score the runner on 3rd. If the runner is on 1st, she will break at the pitch just like a normal steal. However, if the catcher throws the ball (which they tend to do because it would be the 3rd out) the runner stops short of 2nd and retreats to 1st. If the short stop throws back to 1st, (initiating the pickle) the runner needs to stay alive long enough to allow the runner at 3rd to reach home. If the runner on 3rd reaches home before the runner in the pickle is put out, the run counts.

If the runner is on 2nd, she will break for 3rd as if she is trying to steal the base. When she gets about two thirds of the way there, the 3rd base coach will yell for her to go back. This creates the appearance that the runner on 2nd made a mistake, which will often cause the catcher to throw to 2nd. When she does, the runner on 3rd scores.