How to Stand Up to Your Boss (Without Being A Pain in the Ass)

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Former Apple evangelist Guy Kawasaki says swearing in the business setting is alright “once or twice a year.” But don’t do it more often than that, because “pain in the asses do not advance.”

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What’s the Big Idea? Everyone wants to make their boss happy, and there is a simple, albeit irritating prescription for that: When your boss asks you to do something, you should drop everything and do it. According to Guy Kawasaki, that’s how to “enchant” your boss. But what about when your boss is wrong? That’s a much trickier situation. First of all, “if your boss is asking you to do something that’s truly stupid, immoral, or illegal, you’ve picked the wrong boss,” Kawasaki says. And yet, even a good boss is going to be wrong some of the time. Kawasaki offers this scenario: <blockquote> Your boss may not know all of the facts or may not be aware that if you don’t finish that manual, then you can’t get the manual printed and so you can’t ship the products and so are you going to hold up shipping so, you should say ‘Are you sure you want me to drop writing the manual and do what you’re asking because this is the consequence?’ In that kind of situation, the prudent thing to do is to explain the consequences of what you’re asking me to work on. </blockquote> There are other instances, however, where “you may want to shoot the moon,” as Kawasaki explains, “in order to stand up for a principle.” Let’s say your boss is asking you to do something that is “so head-smackingly stupid that you have to swear about it.” Is that a good idea? Kawasaki thinks it is, under certain circumstances. “If anything,” he says, “it will show that you’re awake, and you’re aware, and you’re not asleep at the switch and you’re not just some kind of sycophant.” What’s the Significance? While it is permissible to stand up to your boss, and you may allow yourself a swearing outburst several times a year, don’t make a habit of it, says Kawasaki. In other words, no one wants to be around someone like Alec Baldwin’s character Blake in Glengarry Glen Ross (<a href="http://www.youtube.com/watch?v=y-AXTx4PcKI" target="_blank" rel="noopener">“Put that coffee down!”</a>). If swearing is part of your general personality and you are someone who “fights everything” and “resists everything,” then Kawasaki says you are basically “a pain in the ass.” And those people do not advance.

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