Anyone who's worked in organizations for any length of time has had the experience of being told to do something by the boss that seems like a bad idea. A recent example might be the experience of White House press secretary Robert Gibbs who looked outside his office last week to find Barack Obama and Bill Clinton asking him to unlock the press room so they could conduct an impromptu press conference on income tax reduction extensions. They got a lot of press alright but a lot of it was for Obama leaving the podium after 5 minutes and Clinton continuing for 20 more. A mixed bag of coverage at best.
Based on this behind the scenes account from the New York Times, it sounds like Gibbs had some concerns and tried to push back on his boss. You may not be in the position to have to redirect the wishes of two US presidents at the same time, but if you're working with or for leaders who are powerful in their own right, there are inevitably going to be times when they ask you to do things that are against your better judgment.
Here are some thoughts about how to push back on your boss when that happens:
Ask, "What's your goal?" Do your best to understand the goal or motivation behind the boss's request.
Offer alternatives. 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 good as if not better than the request.
Keep it short. 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.
Know when to fold 'em. 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?