Challenging Your Superior

1 Oct

Challenging your Superior

In any facet of life, challenging someone in a position of authority is intimidating. Supposed insubordination can get you in a lot of trouble, especially in the workplace. However, challenging your superior, in certain instances, is not only acceptable, but also tremendously beneficial. The key is knowing how and when to do it.


No matter what, you must approach your interaction respectfully. Blatantly interrupting your boss is never a good decision. Although it isn’t easy, finding a way to craftily interject is important. First: make sure the conversation breaks for a moment. Direct interruption is never excusable. Second: speak only when you have the attention of your superior. That way, you’ll probably have the attention of everyone, and you won’t have to challenge your superior twice. Third: balance your respectful tone with a hint of confidence. Meekness implicitly gives your boss, professor, or manager license to write off your idea.

Word Choice

Those in a position of power should be open to new ideas. Regardless, insulting your boss’s proposals could shut him or her off to your ideas and put you on bad terms. Acknowledging the positives of an idea before proposing your conflicting suggestion, could pave the way to acceptance of your suggestions.


My middle school basketball coach used to say, “If you’re going to take a shot while I’m speaking, you better make it.” Just the same, if you’re challenging your superior’s idea or plan, you better have something great to say. Make sure to think about your suggestion and supporting evidence before putting anything out there.

Challenging your superior in a careful, insightful and confident way will garner you respect and admiration. Great ideas are great if you’re an entry level employee or a CEO. The challenging part is knowing how to present them.

by Michael Cohen


One Response to “Challenging Your Superior”

  1. Jonathan Emden October 3, 2011 at 1:56 am #

    I appreciate how succinct your argument is. Leading with ‘respect’ was smart, since that’s a contentious issue when challenging a superior. The only area where I was confused was the anecdote about your middle school coach. While I think incorporating a story is a wonderful approach, I couldn’t quite grasp what the coach was conveying and how that applied to challenging another. That said, your use of editing is great; you said exactly how much you wanted to without being too wordy.

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