How to Have Difficult Conversations With Your Boss

There are a few times when having work conversations can be difficult if something is going on that needs a delicate approach. If you have been overlooked a few times for promotion or have suffered a workplace injury, it is time to hire a personal injury attorney.

Conversations with your manager or boss aren’t always easy, and they can be the cause of a lot of stress before they happen.

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Why you should have difficult conversations with your boss

Often a boss is so busy being a boss; they don’t see what is happening on the shop floor. They aren’t always aware of workplace conflicts, imbalances in the distribution of tasks, and more.

Difficult conversations can get you what you want in terms of work-life balance, more fulfilling responsibilities, better relationships with peers, and of course, a higher salary.

So here is how you can get those difficult conversations started.


Requesting a meeting will give you a time slot for the sole purpose of the conversation. This is a much better option than trying to get a chance conversation in the coffee room or saying something in passing. When you request the meeting, keep in mind any other people that you might need to be there – like HR, for example.


Try not to approach the meeting from a superior and a subordinate point of view. Instead, shift your mindset into having a constructive conversation between two colleges in the same company.

If you head into the meeting feeling less than, you are more likely to be nervous and upset.

Shift your mindset so that you head in for a positive conversation.

Write it down

If you have trouble remembering what you want to say, write it down. You can take the notebook in with you to carefully cover all of your points. If you are questioned about the content of the meeting at a later date, you will have your note to support you.

You can also practice getting your points across with a trusted person or into a mirror. As you practice, you might also like to prepare for the solutions you may offer and consider if they might suit you.

This roleplay of the conversation can be very beneficial and help you positively prepare for the discussion.


Try to avoid dancing around the topic and leaving room for any miscommunications. During the discussion, clearly state the topic you wish to discuss and use straightforward language. If there is room for miscommunications, what you think you are saying and what they hear can be very different.

Start by thanking them for their time, and then follow up with the topic. Leave no room for doubt about what the meeting is for.

It can also be helpful if you enter the room with an idea of what you believe is a fair and suitable solution for you.

Perhaps you are primarily looking for ways to improve your work-life balance? Check out this post for help: Working women and their work-life balance.


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