Knowing the full gravity of the situation will lead to a higher steal success rate.
Know the Situation
If you feel good about your runner, their battery, and the count, the last thing to check is the situation. Is the risk of an out worth the extra bag? Does a successful swiped bag drastically increase my odds of scoring? Will opening up first base take the bat out of my best hitter, due to an intentional walk?
In general, you should be stealing as part of a larger game plan, not simply to rack up stats. You may be getting a guy into scoring position late in a close game. It's sometime helpful for avoiding a double play.
Essentially, stealing bases is a fine art, not just on the base paths, but in the dugout. They can help you win, of course. But you can just as easily "run" yourself into a loss.
What are your tips on stealing successfully in The Show?