13 Tips To Help You Speak Up To Your Boss In Tricky Situations

Dear Val,

I work for two women bosses who are experienced, extremely capable, and excellent at their jobs. There are many good things about working for this team: they back each other up; they communicate wonderfully; and they are organized, efficient, and caring.

The two women are best friends. One of them is happily married with children. The other one? She is dreadfully unhappy with her husband. How do I know this? Because we all work together in one big room. My co-workers and I hear everything the two of them say. They certainly make no attempt to keep this between them or talk quietly.

The two women are also very critical of their bosses, make inappropriate jokes and comments, and disclose confidential information to each other in front of us. It's a small company with no human resources department. If I made any kind of anonymous complaint, it would be immediately obvious that I or one of my co-workers had submitted it.

I know far too much and have heard way too many strange and funny stories about this woman's husband! She complains about him constantly.

As for the jokes about their bosses, I wish I could unhear some of the racier ones. Usually, when it gets unbearable, I make my quiet way out of the room, but I can only do that so many times a day.

I need quiet time to work. And it's difficult to work with a whole heart for bosses who are so unprofessional.

How can I address this? Should I approach them together or separately? Should I tell their bosses, the owners of the company, that this amount of talking and gossip has made getting work done problematic? Is there a professional way for me to approach them?

– Drowning in Noise and Gossip

Dear Drowning,

I wouldn’t like that either! I’m sorry you’re in that awkward position. I’m getting frustrated myself, remembering a similar situation I was once in. I feel for you.

There are two issues here, and I want to name them both:

1. It sounds like your bosses' behavior is interfering with your work productivity since you need quiet to work. Quiet is a legitimate need.
2. It sounds like you’re feeling stuck working in an environment that feels somewhat offensive to you.

Either case is delicate to bring up because these are your bosses and you work closely with them. And yet leaving these issues unresolved can interfere with your livelihood and your career. That’s a big deal.

Let’s look at some options for resolving your situation so you can find the best course of action with the least amount of risk.

Speaking Up in a Tricky Situation

Addressing a matter like this requires some delicacy on your part. I have a feeling you can do that well. From the way you wrote about your bosses, I get the sense you are very considerate of others, so that natural tendency will help you handle this situation well.

I discussed your problem with a friend (and fellow introvert), Christine Dutton of Dutton Consulting, who has 20 years of human resources experience and is currently a human resources consultant.

We came up with these tips to make it easier for you to speak up and to increase the likelihood of getting the results you want:

1. Keep in mind that any boss should want to know if your productivity is being compromised. It’s in their interest to address your concerns. That’s on your side.
2. Start by talking to your bosses. It tends to work best when we try to address an issue directly with the person first, before going over their head---whenever possible.
3. Meet with each boss one at a time, one meeting immediately following the other.
4. Consider having this conversation early in the day so you’re not worrying about it for the full day and building up anxiety.
5. Write down what you want to say in advance. Introverts often find that writing their words before speaking is helpful.
6. It's best to be brief, concise, and positive. Choose your battles. There is always gossip in the workplace. The confidentiality concerns and the racy conversations are the priority issues. And be clear that you need more quiet in order to work effectively.
7. It's important to sandwich the conversation by sincerely saying that you have a lot of respect for their work and their competence. Open and close on a positive note.
8. Acknowledge that what you need to say is hard to say. Tell them you want to put it all out there before they respond. Then you can take your time, and it will be easier to speak because you gave yourself some breathing room. And remember to breathe!
9. Let them know what you are uncomfortable with, without judging anyone. State the facts, and focus on your feelings of discomfort.
10. Right after, write down notes about each conversation, including what you each said.
11. Know that it’s okay if things don’t go smoothly or you forget to say something. You’ve done your best. You can always go back to the conversation later.
12. If things don’t change, then it makes sense to go over their heads.
13. You may need to leave the environment eventually if you want to lose the gossipy culture. Better to try first. If you feel you have to leave and you have documented the situation and your efforts to change things, you may be able to collect unemployment, depending on many factors.

What If It’s Harassment?

You're being harassed if you're being subjected to conversations of a sexual nature. If you ask for it to stop and it doesn’t, then you are in a legal situation with legal protections.

From Christine Dutton:

“If it’s a harassment situation, it is best to treat the harassing behavior like any other kind of behavior you would like to change. Be direct, let the person know what your concerns are in a sincere manner, and ask them kindly to stop. If things change, great!

But if they continue the same behavior, that is when it’s a legal situation.

This applies to cases where there are risqué or innuendo-filled conversations happening in the work environment. If things escalate, you should go above your bosses’ heads.

Be careful to document any retaliatory behavior that happens because retaliation for reporting sexual harassment is illegal. It is up to you if you would like to just talk about the behavior or actually use the words, ‘I find these situations sexually harassing.’”

How I Handled a Similar Awkward Situation

My similar situation from years ago wasn’t quite as delicate, but it was still awkward. It did get resolved to some extent. I want to give you a taste of it in hopes it'll help.

I needed to work in quiet, but my department head wanted to have commercial radio music on the overhead speakers that everyone could hear. I could feel the tension coming from her every time I asked her to turn the radio off. Then it was on again the next day, so this was a daily battle. I tried to grin and bear it, but the tension was mounting inside me. At the time, I didn’t fully understand my need for quiet, so it was hard to stay confident about this. Now I know it’s nothing to apologize for!

Eventually, it came up in a staff meeting with the higher-ups in the room. At that meeting, my department head came up with all kinds of ways for me to deal with the music, none of which felt like reasonable solutions to me. Finally, one of the leaders stepped in and said that productivity was more important than the radio, and that was that.

I wasn’t popular with her, but at least I got some quiet. I could finally work without feeling agitated and distracted.

Honestly, I was glad to leave that workplace eventually for this and many reasons like it. I learned some good lessons about my needs and how to fight for them.

I hope you find a great solution because you seem to like your bosses. I wish you the best.