How to Push Back on Your Boss

Do your best to understand the goal or motivation behind the boss's request. If you understand the true motivation, you're in a better position to offer alternative courses of action. Explain how one or more of those alternatives will accomplish the goal as well as if not better than the request. One of the reasons that boss's sometimes make bad requests is that they're moving at 350 miles per hour and haven't stopped to consider the impact of what they're asking for. It's likely that they'll still be moving at that pace when you push back. If you want to be heard, you're going to have to keep it short enough to keep their attention. If you get denied after a couple of attempts at a push back on any given request, you have to decide whether you're going to hold 'em or fold 'em. Use your holds judiciously and save them for big things. Fold on the little things. If you're constantly going to the mat with your boss on every request, you'll eventually get shut out of the decision making process. What's your take? How do you know when to push back on the boss's questionable requests? What's your best advice for doing it effectively?