If one thing the movie "Office Space" taught us is that your boss might be annoying, clueless and ignoring their demands might be the best thing you could do for your career.
In reality, that mentality and subsequent actions on your part isn't going to do you any favors in their eyes, and quite frankly could lead you to the unemployment line faster than you can say "want ads."
But the truth is you aren't always going to get along with co workers, your boss included, and having a difference of opinion isn't something you should shy away from, along with telling your superior that the answer is sometimes going to be "no" when they ask you to do something.
As far as disagreeing with your boss, you can do so without putting your job or reputation in jeopardy. A good, competent and assured boss isn't going to take your disagreement as insubordination by any means, but rather is going to be open minded and want to hear what your perspective is on any sort of decision or project.
They don't necessarily always believe their way or the high way as their mantra. You also, however, need to make sure you state your case underscored with facts and not unsubstantiated opinion. Disagreements can turn into positives, sending you back to the drawing board and perhaps making the decision or whatever is being debated better. That sort of atmosphere breeds success rather than just having one vision, one mind and one decision maker. If that's the case, why bother having a staff to begin with?
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