How To Have A Difficult Conversation With Your Manager

Manuela Pauer

March 05, 2022

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We are faced with all sorts of difficult conversations at work.

One conversation I get asked about a lot is how to have a discussion with your manager or colleague about something crucial you want to change. For example, talking to your boss about your workload.

If you are planning to have a crucial conversation with anyone who you are not managing directly (for example your manager or a peer), you want to take a collaborative approach.

You can start by simply envisioning both of you working as a team to find a solution to the problem.

Let's take the example of talking to your manager about your workload.

Here are 5 steps you can take in order to have a collaborative conversation with your boss:

1. Schedule a time to talk

Schedule a time to talk to your boss 1:1 and indicate what you would like to talk about (for example, about your workload.) If you have a regular meeting already set up with your manager, give them a heads up that you would like to talk about your workload in your next meeting.

2. Describe the mutual benefit

When you start the conversation, frame the issue in a way that shows how the conversation will benefit both of you. The goal is to work as a team together to find a solution to the issue.

You could say for example: "If I continue to work like this, I will burn out and quit. I know that doesn't benefit either one of us, so I would like to find a solution with you."

3. Listen to understand their point of view

Give them a chance to share their point of view first.

You can say for example: "I would really like to understand what you think about this situation."

Then focus, be quiet, and let them talk without interrupting.

4. Express your point of view

Once you have heard the other person out, start with what is at the very heart of the matter for you. What is your experience with this issue?

For example: "I have tried my best to get all the projects done on time, but it has required me to work every single weekend for the last month. I am feeling stressed and exhausted. At this rate, I am getting really burned out. I really like this job and I do believe in our mission. However, I also know that I don't do my best work when I have to juggle so many projects and I will not be able to keep up this pace. For me, it is really about finding a more manageable balance, so I can do my best work."

5. Brainstorm alternative options

Open up a dialogue. For example: "I would really like to find a solution that works for both of us. What are some options that we can consider?"


It's normal not to feel comfortable with difficult conversations at first. Practice makes perfect! You can practice these steps with a friend, so you get familiar with the structure. The more you do this, the easier it will get.

Manuela loves helping mid-level professionals create a career and life they love through career exploration and life coaching. You can sign up here for her newsletter with monthly tips and occasional course announcements.



Opinions expressed by the author are not necessarily those of WITI.

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