How to Tell Your Boss Anything: 11 Tough Conversations to Have

Some have more casual relationships, while others have more formal ones. Whichever group you fall into, there’s usually one steady constant: tough conversations with your boss can feel awkward and stressful. 

Love your boss or hate 'em, they are likely the gatekeeper to your salary, your schedule, and your next big moves within your organization. While we've already covered how to ask your boss for anything, this article is a little different.

This will cover how to tell your boss important details that have the potential to change things—like that you're making a big career move, that you need more support, or that your family is growing. 

The Dos and Don’ts of Talking to Your Boss 

According to the Boss Barometer Report, only 30 percent of workers find being honest with their boss to be easy. However, the same report found that 81 percent of employees felt respected by their bosses.

If you feel you have a mutually respectful relationship with your boss, you can probably have easier conversations—once you pull the bandage off the first time. 

But what if you hate your boss? What if your relationship is tenuous at best? In that case, you can combine the below advice with our advice about dealing with bad bosses. 

To ensure a smooth conversation next time, check out this brief list of dos and don’ts when preparing for a tough conversation. 

The Dos of Talking to Your Boss 

The Don’ts of Talking to Your Boss

11 Tough Conversations to Have With Your Boss 

While every situation is different, we rounded up 11 of the toughest conversations employees have with their bosses, along with tips to navigate them. 

1. How to Tell Your Boss You’re Unhappy

Before you speak to your boss about being unhappy, take some time to dig deep and understand why that might be. Are you unhappy about the projects you’re working on? Or is your unhappiness due to coworkers?

Prior to your meeting, make a list of what specifically is making you unhappy so that you have examples to share with your boss. Additionally, take it a step further and jot down a few solutions so you can discuss those with your boss during your conversation. 

Once you provide potential solutions, consider asking for advice or help. 

2. How to Tell Your Boss You’re Looking for New Opportunities (+ If It’s a Good Idea to Do So) 

When applying for a new job, you may feel a bit guilty and inclined to tell your manager. However, I would carefully consider if it’s in your best interest to tell your boss that you’re looking for new opportunities.

If it’s an internal position, then certainly let them know (because they’ll likely find out from HR anyhow), but if you’re looking externally, it may be best to keep that to yourself since it might lead to questions about dedication to your current role. 

If you had previous conversations with your manager about wanting to grow in your current role without any results or movement and choose to share that you’re looking elsewhere, it likely won’t come as a big surprise. 

Either way, if you decide to let your boss know, make sure to focus on the following and keep it positive:

3. How to Tell Your Boss You’re Quitting

Even if you’re thrilled to leave your current company, telling your boss that you are quitting is HARD!

Here are three key points to touch on during your conversation: 

Following this conversation, be sure to send an official resignation email copying your HR team so they have it on file. 

Pro Tip: Keep in mind that it’s in your best interest to leave on good terms. If you have concerns about your time at the company, talk to your HR department about an exit interview.

4. How to Tell Your Boss You’re Overworked + You Need Support

It can be challenging to ask for help, but if you’re consistently working overtime, it might be time to reach out to your boss and ask for support. First, send your boss an email outlining the issue, and ask to set up a time to speak so you can come up with a solution together. 

During your conversation, be sure to focus on the following: 

And of course, feel free to seek out advice or solutions from your manager as well. They might have some tricks up their sleeve to help you out.

5. How to Tell Your Boss “No”

For those of us who are chronic people-pleasers (hello, it’s me) it can be challenging to say “no” to taking on additional work.

While we don’t recommend you shout “no” at your boss the next time they try to add something else to your already full plate, we do encourage you to have a productive and solution-oriented conversation with your boss.

Rather than saying "No," which is a full sentence, you may try the anti-improv approach, where you say "No, and..." 

Here are a few things to consider: 

6. How to Tell Your Boss You’re Burned Out 

Burnout is considered an official medical diagnosis and should be taken seriously by your manager. When approaching a conversation about burnout, Confidence Coach Steve Errey says that this is the one time when you should not worry about immediately problem solving the situation at hand.

What’s important is taking the time to heal, so the first step is simply opening up to your boss about your burnout. Your boss may ask how they can help, so if you need time off or feel like you can’t complete a project, it’s important to share that immediately. 

For more information on how to treat burnout, please consult a medical professional. 

7. How to Tell Your Boss They’re Wrong

Awkward.

It’s not always easy to speak up when you think your boss is making the wrong decision. Sometimes it's like telling someone their fly is unzipped or that they forgot to take the tag off their new sweater.

It might be awkward and embarrassing in the moment. Ultimately, though, your boss should be appreciative that you're paying attention and that you care enough to speak up. 

This probably depends on the situation, but if you have evidence (quantitative or qualitative) of why they’re making the wrong decision, then that will help you present your case. There are a couple of ways to do this. 

During a Call

If your boss says something you disagree with during a call, consider saying the following: "I see your point and think that’s a really compelling idea. I did some research and found XYZ. Would you be open to discussing a couple of other ideas I came up with based on this data?"

Via a Follow-Up Email

If you don’t feel comfortable speaking up immediately, another good option is to send a follow-up email.

You can use the same outline as above and provide links to any data or research that backs up your claim. Ask if they’d like to set up a separate call to discuss. As long as you’re respectful, a good boss will listen to what you have to say.

8. How to Tell Your Boss You Made a Mistake

If you read the recent #DearIntern Twitter thread, you know that making mistakes is more common than any of us thought.

We just typically don’t like to broadcast mistakes for all to hear. However, when it comes to your boss, honesty is the best policy. 

Rather than making excuses, own the fact that you made the mistake. Provide details on why this was a good learning opportunity for you and how you will be sure to avoid this mistake in the future. 

9. How to Tell Your Boss That They Made a Mistake

It’s uncomfortable to point out a mistake your manager made, but sometimes it’s necessary.

First, do your research to make sure that it was, in fact, a mistake. Also, always assume positive intent. People don’t make mistakes on purpose, so keep the tone positive and gracious when possible.

Once you point out the issue, offer to help correct it or see if there’s anything you can do to help make sure it doesn’t happen again in the future. 

Pro Tip: Make sure that you go directly to your boss with a mistake. Don't start a side thread or tell everyone but your boss. If possible, try relaying this information privately or quietly. 

10. How to Tell Your Boss You’re Pregnant or Expecting

Whether you tell your boss face-to-face or via email is totally up to you and depends on your comfort level.

However, even if you tell your boss face-to-face, you should follow up with written details in an email. If you choose to send an email, here’s an email template you can use inspired by whattoexpect.com:

Greetings [INSERT NAME],


I’m thrilled to share with you some really wonderful news. I’m pregnant! I am due on [INSERT DUE DATE HERE] and I would like to work until [INSERT DATE HERE] before going on maternity leave. 


I plan to take our company’s maternity leave period for [INSERT NUMBER OF WEEKS HERE] and look forward to returning to work after. Over the next few months, I will create a detailed plan delegating projects, tasks, and responsibilities that need to be taken care of while I am on leave. 


Thank you for your time, and please let me know how I can help set the team up for success prior to my maternity leave. 


Best,

[YOUR NAME]

Here are even more tips to help you navigate conversations at work about your pregnancy. 

11. How to Tell Your Boss About Your Health Condition 

If you have a chronic illness or other condition that requires special accommodations, it’s important to loop in HR and your boss so that they can work with you to make sure you and the company thrive. 

When approaching your boss with a conversation about your health condition, be sure to offer potential solutions and ideas about how you can work.

Whether that’s receiving permission to work remotely when you’re having an off day, taking mental health days when needed, or working different hours, as long as you are willing to get the job done, then they should be flexible.

When possible, be open and honest with your boss so they can help you be successful in your current role. 

Need email templates to talk to your boss? Check out this article on how to ask your boss for anything.