Confronting Your Boss

You were hired for a reason. Your experience. Your drive. Your ability to deliver great ideas. Your bosses love hearing what you bring to the table. What happens though when it's a critique of your boss needing attention? Heart racing, palms sweaty. When is a good time? Am I even in a position to say anything?
It probably feels like never is a good time to tell your boss you disagree. Maybe you see a different way or are noticing hypocrisies from the top down that are impacting your team. So when and how do you tell the person who holds your fate that you aren’t on the same page?
Trust Your Gut
You were hired for a reason. Your opinions are valid and worth bringing forward. Just like any relationship, it takes work from both sides to keep things healthy. Issues in a workplace will inevitably arise that impact morale. Be an advocate for change. You may even be praised for contributing to a more positive work environment.
Delivery Is Key
Prepare yourself. Talk to someone outside of the workplace to get an objective perspective. Make sure you have your ducks in line.
Appeal to your audience. No one wants to be confronted. So don’t be confrontational. Does your boss prefer a serious atmosphere or are they going to laugh at work memes? Use a style of discourse that they are familiar with. Either way, it’s a time to be professional, concise and kind.
Include yourself, but leave the coworkers out of it. We don’t suggest being vague, no reason to tell a story about “needing advice for a friend”. However, do consider softening delivery by including "I" statements.
Some examples:
Road Blocking
“I see why we have done it this way in the past, but I think it’s worth trying a new approach. We can always go back to what's tried and true.”
Micromanaging
“I always appreciate your feedback; It would mean a lot if I could have some space with the project to give it my focused attention.”
Advocating For Teammates
“In the meeting the other day I felt Sam had a great idea, maybe we can work with them to flush it out.”
Where and when, make or break. Don’t deliver bad news in the break room, bathroom, or in a crowded space. Request a meeting, consider drafting a summary email, and be clear about the time you need to share your thoughts. Be confident, but humble. Your voice matters, but so does your boss’. Be sure to share your thoughts while making space for your opinion as well.
There May Not Always Be A Perfect Time
There is a fine line between giving things time to work themselves out and waiting for a bad situation to get worse. The longer you delay the further you get from relevance. You don’t want to seem like you are dwelling on something from the past.
Maybe It's Not Your Boss You Should Be Telling
This can be a trickier scenario. But some things warrant HR getting involved if you really feel like your position will be threatened for speaking up. You also might not want to out yourself, or your identity, and speaking to a third party for anonymity's sake can be important. Don’t gossip with employees. Don’t bottle it up.
Contributing to a positive work environment directly impacts job satisfaction. If you aren't satisfied it will start to show. It can be better to risk advocating for change rather than risk losing your job from poor performance.
Be sure to build a relationship with your boss and your colleagues from the beginning. If you notice your work doesn’t have something built into the schedule for constructive feedback you should propose it. As issues arise, as they inevitably will, there won’t be as much pressure if a precedent is set and a forum is formed. Remember, we believe in you. You got this!
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