How to Tell Your Boss, ‘You’re Wrong’ — and Still Remain Employed

March 17, 2021 JCS Career Center

Talking honestly to bosses demands special navigational skills from employees. (Photo courtesy Flickr, Internet Archive Book Images)

By Sherri Sacks

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 them.

In that conversation, you must balance many interpersonal dynamics, from managing up and communicating your point of view constructively to not overstepping 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 their 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, and will not come back to bite your boss or the team.

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 your boss does next, once this tough conversation is over, it lingers as part of your long-term working relationship with them. 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.

Sherri Sacks is a career coach and certified resume writer for the Ignite Career Center of Jewish Community Services.