This has been a tough year for everyone, and that provides more opportunities for difficulties to crop up at work. Some people are having new or stronger mental health issues, while others are just doing their best to make it through a pandemic. Whatever the reason, there are more circumstances that could mean you need to have difficult conversations with your boss, and it could be that it’s harder than usual for you to have that conversation. If it is harder to talk to your boss, some planning ahead of time can make it easier.

What Is It About

Before you go see your boss, make sure you know exactly what you want to talk about. If it helps, write down your concerns and what you’d like to happen after your meeting. Look it over before you go talk to your boss. You may even decide to bring that paper with you. If you’re flustered, it can be hard to remember what you wanted to talk about, which can make the situation more stressful. It’s also helpful to have examples of your concern so your boss fully understands the problem as you see it. You want to be able to share the problem clearly, so your boss has all the information they need to make changes.

conversations with your boss

Keep Calm

Ideally, both you and your boss could have a conversation like this without getting worked up. However, sometimes tempers flare during difficult conversations. Do your best to keep calm, no matter how your boss responds. Sometimes, it’s helpful to take a moment before you reply, so you can make sure you only say what you want to say. It’s easy to say things in anger that you may regret later. Yelling during a difficult conversation will make your boss, and anyone who overhears, think less of you. If you’re worried about being able to keep calm, try practicing the conversation with a trusted friend, ideally not a coworker.


If you’re having a difficult conversation with your boss, your concerns are valid. However, sometimes you may not have all of the information behind why certain things are happening. Or you may want your boss to do something that they can’t do for reasons you aren’t aware of. It’s important to be able to have these conversations with your boss, but it’s also important to be willing to compromise. What looks like a clear cut solution to you may turn out to be very difficult. Ideally, you and your boss can work together to find a solution to this problem that works for everyone. Even if you don’t quite get the result you want, it will almost certainly be better than if you hadn’t said anything.

The most important part of having difficult conversations is to do it. Nothing will change if your boss doesn’t know there’s a problem. What may be obvious to you could be invisible to them. Other people may also be having the same issue, so if you’re able to speak up about the problem, you’re helping them as well. Often, these difficult conversations with your boss can be hard to start, but once they’re done, you can see that they weren’t as stressful as you were expecting. And if your conversation does turn out to be stressful, it will be helpful to have done the work beforehand to make it less stressful.

Looking for another way to reduce stress in your shop?

Cut Down on Meetings