Know when there's a weak arm and when there is a strong arm behind the plate.
When Stealing, Know The Catcher
If you've decided that your runner is capable of stealing, double-check the opposing catcher's arm/throw ratings. While no catcher has a 100% success rate of throwing runners out, you probably shouldn't tempt the best.
Look for a weak catcher and get ready to run!
Which catcher is the hardest to steal on in the league?