As much as leaders like to wrestle with the decisions of the day, sometimes it would be nice if someone would just say, "This is what you should do." Absent the directive nature of giving instruction, the question our group wrestles with is, "Should you?" What does "should" mean to you? Is it simply a question? Is it a word wrapped in regret? Maybe it means action you are being told you should take. Shoulding all over the place can harbor frustration. Once leaders step away from should and head toward action, magic can happen. There are times and places for should and there are times and places it does not belong. Our journey starts with shoulding one's self, includes policy observation, and arcs back to behavioral change. While we won't say "you should listen," we do offer that you might gain insight if you do listen to this episode.