How To Have a Difficult Conversation with Your Boss…

difficult conversation boss

Scariest. Thing. Ever.

But how many of you have struggled at one point in your life with a supervisor? Surely one or more. I’m so blessed right now because I have an amazing supervisor. Having a supervisor you trust and admire and look to for help and guidance is the most amazing feeling. Tom Rath talks about this in his WELLBEING book. “Having a good boss is just as important as having a good doctor.”  And if we are following that advice, we may come to a place in our career where we need to have a difficult conversation with our boss.

Your doctor is responsible for your physical health, and making sure you take care of yourself. Your boss/supervisor is responsible for your professional health and ALSO making sure you take care of yourself. A supervisor who does not seem invested in this is not worth working for. But that’s easier said than done, I know! You can’t always choose your supervisor. And there may come a time during your tenure in a specific position at a specific company when you struggle with your boss. And you have a choice. You can look for another job; or you can be proactive and strategize a way to talk to your supervisor about your concerns, needs, whatever it is that’s frustrating you. That’s the basis of today’s post.

How to Have a Difficult Conversation with Your Boss

Where to start? I have a multi-phase process on talking to your supervisor. Keep in mind that if you have a great supervisor, you may not need this advice now. If you have a great supervisor, you’ll just know this in your gut – your supervisor knows you better than you know yourself. He/she sees your potential and tries to improve it. They give you exciting projects to take on, and positive feedback regularly. So if your gut is hurting when you think about your boss, then you probably need this post.

DISCLAIMER – the decision to have this conversation is going to be a risk. I want to make sure you know this from the very beginning. This is not a flawless process nor is it a guarantee. But – when done correctly, with respect and dedication, it can really improve your relationship.

Let’s get started. There are several tasks you need to complete and they are going to take time. Don’t read this post and go out and schedule a meeting with your boss tomorrow. You are going to need to reflect, plan, and prepare.

Task #1 – EMOTIONS

Because it’s more than likely a feeling that triggered you, right? Something that was done or said made you feel something negative. Let’s explore this…

You need to write down what is troubling you and/or why you feel detached, why you are frustrated, etc. Write it all down free form and don’t hold anything back. When you have finished doing this writing, put it away and leave it be for a couple days. You are, essentially, purging everything negative from your system, but hopefully it’s not just about how much you hate this person or how mean he or she is. You need to be very specific.

“When my supervisor calls me out in front of the team, I feel shamed and undervalued.”

“When my Director tells me I’m not being reasonable or realistic, I feel disappointed and discouraged.”

“The way my supervisor gives me feedback is making me feel low in my self-esteem and self-worth.”

You see what’s happening here? What’s the pattern in those statements?

When So-and-So Does This, I FEEL This.

See? You are describing the behavior you observe and the feeling you get. Having this conversation with your supervisor cannot be personal; it has to be about behaviors and how they make you feel. You absolutely cannot go into your meeting with your feelings on fire – you need to have very specific things identified so you are NOT emotional.

Task #2 – THEMES

After you’ve let your sadness and anger settle for a few days, dig up your scribbles. Read them through quickly, let it settle, and then read them again, carefully. Have your pen and paper ready to write down themes. What do you notice in your concerns?

Under valued
Not encouraged
Lack of engagement
Taking credit for YOUR work
Lack of positive feedback
Unrealistic expectations

It pains me to even write these, because my hope is that every manager/supervisor behaves like a leader and avoided these situations.

But I digress. You’ve found your themes. Pick the two (or at very most, three) that have been the most debilitating for you. Now it’s time to qualify them.

Task #3 – EXAMPLES

Take a piece of paper and make 2-3 columns. Give each column a heading, and write your theme there. Now reflect on specific instances when your supervisor made you feel this way:
Duty Weekend – so-and-so made suicidal ideations – on the duty phone my supervisor yelled at me and hung up.

Staff meeting before the big presentation – i asked a question – he made fun of me

Big event coming up that I was in charge of – she called me three times a day to ask about various details. I couldn’t get anything done

You may find there are several examples or just one BIG example that really got you down. But being able to identify specific situations where you felt uncomfortable or distrusted can help your supervisor understand where you were coming from.

Remember that this process is all about perspective. Chances are, while you are reflecting about these situations, you may even identify behaviors of your own that exacerbated the situation. Which could lead to a totally different conversation with your boss later on.


You need to outline exactly what you wish to say to your supervisor and it needs to be professional, respectful, and organized. Using your emotions list and your examples list, it’s time to craft ONE TO TWO statements for your meeting.

The statements should be specific to the example (day, time, location if possible), should include a sense of feeling, and then ask a question of what could have been done differently.

“During the week before closing, in our staff meeting, I asked what I thought was a clarifying question about the procedure you wanted us to follow, and you chided me about not understanding. The team laughed, and I felt embarrassed. I am wondering how I might have made this situation less embarrassing for me.”

“The weekend that so-and-so was making suicidal ideations, he/she yelled at me over the phone and hung up on me. While I know I handled the situation incorrectly, this made me feel shamed, frustrated, and disempowered. What should I have done differently so I can prepare for next time?”

In this short statement, you acknowledge that an action made you feel something less than positive (“when you said ___, I felt ___.) And given that this person is your supervisor, the “what could I have done differently” statement keeps you from being insubordinate and encouraging your supervisor to assist you further.

Task #5 – MEETING

Finally. This is when you schedule the time to have your discussion with your boss. You may already have a regularly scheduled One-on-One meeting with your supervisor. If this environment already exists, use this time. It’s safe because it’s your designated time; and if your boss is a super busy director/associate director, etc., it may be the only chance during a week that you have to talk.

If you don’t have a designated time already, then you need to schedule one. Depending on where you work, you may need to arrange this with an administrative support staff, but you may be in a position where an outlook invitation is enough. You know the culture of your department, so proceed accordingly. If you DON’T feel like you know the culture yet, ask your supervisor’s administrative person the best way to schedule such a meeting.

If you are still feeling nervous or uncertain about the meeting, then share your plan with a close friend or a colleague you trust. He might be able to provide you with some additional insight – or provide feedback on your plan. He also might talk you out of it and offer to help you work through the frustration. See what happens – and adjust if necessary. It would not be the worst thing in the world to cancel the meeting if you had to.

On the day of the meeting, dress the role. You are having a professional conversation with your boss, so if that day is a regular “no meeting day” and you might be in jeans or casual dress, change it up and wear something that you might wear if you were meeting with a Vice-President, a Dean, an Upper-Level Manager. Dressing professionally will also give you more confidence during your conversation.

Here’s how you want to outline your conversation:

1. Introduce the conversation:

“I wanted to have a conversation with you because I’ve been feeling somewhat frustrated in my position recently.”

“I have been struggling with something that happened at the last couple of staff meetings, and I felt strongly that I should share it with you.”

“You probably have noticed that I’ve been behaving a little withdrawn or quiet lately, and I wanted to explain myself.”

2. Share the specific experience(s) that have led to you feeling this way – you did this already in the PREPARATION phase.

3. Then…you will be giving your boss the chance to speak. He or she may already be waiting to respond. Or they may be waiting to see if you have anything else to share. But give your supervisor the space now to respond.

And the rest of the conversation is going to happen how it happens. You could experience a variety of possibilities:

a. The supervisor feels terrible and apologizes to you.

b. The supervisor feels aggravated and reprimands you.

c. The supervisor asks you more qualifying questions to get to the heart of the situation.

d. The supervisor laughs in your face.

Once again, you are going to be counting on your gut to tell you if everything is okay. If your gut feels okay, then you can probably thank your supervisor for her time and then either move on to the rest of your one-on-one or leave the office.

If your gut is hurting or having other negative feelings, you are going to have to get your resolve back quickly. And unfortunately, it may mean that you’ll be eating a little crow before you get to leave the room. The best way, in my opinion, to avoid more frustration? Apologize and ask for feedback.

“I’m very sorry that I brought this up. I felt it was important to share my feelings with you. Do you have any suggestions on how I might avoid these reactions in the future?”

“I didn’t mean to behave inappropriately. I was feeling very frustrated about this incident and I felt strongly about sharing that with you. How would you recommend that I work through these issues in the future?”

Regardless of your supervisor’s reactions to your information, you don’t want to leave the room feeling like there is still stuff “out there.” So if that means you have to kiss ass a little…then you have to do that. Because the bottom line is – you still have to work with this person. He or she is still responsible for your professional development.

In many ways, it may seem like I’m ending this blog post on a down note. Again, I will repeat the disclaimer from the beginning: having a conversation of this magnitude can be a risk. In my own experience as a supervisor, I know that if a staff member came to me with these concerns and shared them with me in this manner, I would do everything I could to hear them out and provide them with feedback. I would understand that they took a risk to share these thoughts and feelings, I would congratulate them on being brave enough to talk to me about it.

So I will end this post by saying that I believe in this process for having difficult conversations; should you choose to employ it, you are being a self-advocate and insuring that you are heard, even if nothing changes. You are going to be a different person for taking the chance.

I’m proud of you. Always.

2 thoughts on “How To Have a Difficult Conversation with Your Boss…”

  1. Oh, man…. This post triggers a lot of work PTSD feels. I’ve been there. Had a boss take credit for my hard work. Have been belittled in front of my coworkers, and made to feel as though my work didn’t matter/wasn’t stacking up. This is wonderfully useful advice (and I so wish I had this along with a backbone to open the conversation with my boss back in time!). I’m so grateful for my work situation now. I have a boss who respects me, comes to me for my opinion, and believes in me enough to further my education (paying for my online courses). He genuinely WANTS to see me excel because he knows that will only further ALL of us. It makes a huge difference <3

    Thank you so much for sharing this!

    1. Charlotte,
      Thanks for your comment! I hope that the blog post is able to help others. And thank you so much for reading it. Please keep coming back!

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