Telling Your Boss, “You’re Wrong”- and Surviving

Of the many hard conversations you must have at work, quite possibly the hardest is the one when you know your manager has erred and you have to tell her or him. 

In that conversation, you must balance a lot of interpersonal dynamics, from managing up and communicating your point of view constructively to not over-stepping boundaries or upsetting the power balance in your working relationship. To be sure, the risks of sticking your neck out are challenging. However, if your communication skills are on point, the rewards could be great – your supervisor’s trust in you, as well as his or her admiration of your professionalism may grow. 

Before plunging in to highlight someone’s mistake, consider these do’s and don’ts: 

  • Do reflect on your office culture. Is constructive feedback, in any direction, encouraged? 
  • Do be ready to offer a fact-based fix or solution. 
  • Do think about letting this go if the error is not serious, will not have long-term impact or will not come back to bite you. 
  • Do adopt the tone of expressing a “concern” rather than an accusation. 
  • Do not be an arrogant know-it-all. 
  • Do not start the conversation without preparing how you will frame and deliver your message. 

Remember, regardless of what the boss does next, once this tough conversation is over, it lingers as part of your long-term working relationship with him or her. To make the outcome a positive one, call on all your abilities to convey maturity, empathy, and humility. 

In this case, using those high valuable soft skills might have a solid impact on your organization and your career. 

Whether you are new to the job market or a seasoned professional, the Ignite Career Center, a program of Jewish Community Services, can help you go farther and get there faster.  Our highly experienced Career Coaches provide individuals of all backgrounds and abilities with the customized services and tools they need to stand out from the competition.  For information, call 410-466-9200 or contact us through our website

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