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How to Have a Hard Conversation With Your Boss

So, you want to have a hard conversation with your boss but have no idea where to start. I get it — talking with a superior can be super stressful! In an ideal world, communicating your needs would be easy, but cold work environments and intimidating higher-ups can make it incredibly difficult to do just that.

But that doesn’t mean you shouldn’t try. Below, I’ve compiled a few tips for having those hard (but necessary) conversations, from sorting through your thoughts to scheduling the meeting and practicing your pitch until it’s perfect.

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Collect Your Thoughts

Depending on your workplace, you may only get one chance to have a serious conversation with your boss, so you’ll want to make it as productive as possible. Therefore, it’s crucial to get your thoughts in order beforehand. I recommend free-associating for a bit: What’s bothering you at work? What problems are you facing? What do you like about your role? What do you hate? Why do you feel compelled to speak to your superior? When you feel like you’ve got some solid answers, compile them in a document and organize them as you see fit.

Get Specific

Once you’ve collected your thoughts, get specific. What I mean is that if your answer to the “why” you want to speak to your boss is because you’re “unhappy,” probe the feeling until you can pinpoint its source. Telling your boss that you’re overwhelmed with an inequitable distribution of work between you and a colleague is a lot more powerful than telling her that you’re simply “unhappy.” One of those situations can be changed, while the other can only be empathized with. Bolster your conversation by making a list of three to five specific issues you want to address. Then, brainstorm potential solutions to those issues, which you can present to your boss.

Make a Plan

With thoughts teased out and specific ideas on lock, it’s time to make a plan. You don’t need to write out a word-for-word speech or prepare a presentation, but it’s not a bad idea to drum up a few bullet points you know you want to hit. This could be especially beneficial for those of you who need to keep up your nerve in front of an intimidating boss. And to the point above, you don’t know how many of these conversations you’ll get to have, so use the time well.

Schedule a Meeting

With a set of goals and structure in mind, you can now set up the meeting. To indicate the seriousness of the conversation, send an email instead of requesting the meeting in person. Keep the tone warm and professional, asking after their week and/or recent work before making your request. Below, an example, with an imagined boss named Barbra Streisand:

Subject: Meeting Request

Hello Barbra, 

I hope your Monday is getting off to a great start! I just wanted to send a quick message to see if you were available for a chat sometime this week. I’ve got calls tomorrow at 11 a.m. and Thursday at 2 p.m., but I am otherwise free and happy to meet around your schedule. 

Thanks so much! I look forward to speaking with you. 



Short, sweet, and to the point. No need to divulge what the meeting is about, as you’ll want to keep a few cards close to your chest.


With the meeting successfully scheduled, it’s time to practice what you’re going to say. Again, there’s no reason to write out a formulaic script, but I’d rehearse the important bits a few times. If you’re feeling anxious, you may even want to run the scenario with a friend or roommate. They can provide feedback and help you figure out how to tackle a range of different responses from your boss. More than anything, this step is about getting comfortable with and owning your truth, whatever it may be.

Be Bold

And when you finally get into the room, be bold. It’s okay to be nervous (or scared or overwhelmed), but don’t forget that standing up for yourself is totally and completely badass! You are your best advocate, so stick up for your interests and goals with focus, precision, and passion. Even if the conversation goes south, or your boss is unwilling to bend, the fact that you showed up for yourself is nothing short of courageous. So, get in there tiger, and do what you’ve gotta do!

And that’s that on that! For more work-related content, check out our guide to quitting a job.

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