Taking a problem to your boss's boss is one of the biggest gambles in office politics. The payoff can be great, but you run the risk of becoming a pariah whose days in the company are numbered. That's why you should take this step only if you believe your future at the company is at stake—because of a negative performance review, say, or because a vital project has been canceled. First, try to get permission for your maneuver. You may get the okay if you frame your request as a search for expert input. Even if your immediate supervisor objects, persevere. Asking to go over their head is as bad as actually doing it so you've nothing more to lose. When you do get upstairs, continue to frame your efforts as a search for advice. Resist the temptation to bad‐mouth your supervisor. If you manage to win the top person over, you'll have gained a valuable ally—one who will most likely be able to protect you from recriminations. If you don't win the top person to your side, start looking for another job.
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