How to Have a Difficult Conversation With Your Boss
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This is a big topic.
And for some context, not every single boss is able to be successfully communicated with this way.
The unfortunate reality is that some bosses are terrible, defensive, and have low EQ. For example, some people feel threatened by any level of feedback and cannot receive it gracefully or without feeling attacked. I wish that were not the case for anyone in a leadership position, but here we are.
These tips and this approach will work for any boss, but are especially useful for bosses who are difficult to have difficult conversations with.
These are some tools and tips to make a challenging conversation with your boss/leader/manager/supervisor easier.
Whether it’s an issue you are having in your job, or some difficult feedback to share with them, it’s crucial to have some skills to be able to navigate a hard conversation with a leader — or with anyone for that matter.
A “difficult conversation” can be a myriad of things; challenging feedback for your boss, or about your job, or about a coworker, etc. It’s anything that feels like it could be emotionally high stakes or dicey because you don’t know how the other person will respond, which causes you to be fearful or have anxiety about their reaction or the outcome because it could have potentially negative consequences.
“The more skills you have in your tool belt when approaching a tough conversation, the higher chances you give yourself of a successful outcome”
The more skills you have in your tool belt when approaching a tough conversation, the higher chances you give yourself of a successful outcome. Here we go:
First thing: approach a difficult conversation in cold blood.
“In cold blood” meaning without much emotion. It’s important to initiate a difficult conversation when you are calm, not when you’re fired up or in the heat of the moment. Ideally, you want to be and remain as emotionally neutral as possible.
Throughout the conversation, it’s important to stay emotionally calm. Don’t get excited or raise your voice, or have big reactions to how they respond. Energy is contagious and it’s critical to make sure that conversation (at least on your end) does not get “turned up to ten.” Keeping your emotions and voice level at or below a two or three out of ten is good practice for keeping conversations productive and calm.
Make sure it’s a good time to talk.
Springing an important conversation on someone when they don’t have the time or focus, or they’re just in a really bad mood can be detrimental to the success of the conversation. Approach by asking for permission to have the conversation, make sure they’re free and that it’s a good time.
Approach the conversation seeking advice.
This is an approach that I have used with a lot of success. Entering into the conversation with something along the lines of:
“I have a situation/something that’s been on my mind that I’m not 100% sure how to navigate and I’d love to get your perspective and some advice from you. Is now a good time?”
As much as possible, you want to have that other person be in an open and receptive space to hear what you have to say. Asking for guidance/advice/input is an easy way to put someone into a mindset of being helpful rather than defensive.
“Asking for guidance/advice/input is an easy way to put someone into a mindset of being helpful rather than defensive.”
Even if the conversation is about them, like delivering tough feedback to them, it’s an accurate thing to say because the truth is that you have to get their perspective and input if you’re going to resolve whatever you’re dealing with.
“I’m here for guidance.”
“I’m seeking your wisdom.”
Starting a conversation this way immediately puts someone into a more interested and less defensive state about whatever they’re about to hear. It’s a great way to avoid putting someone on the defense right off the bat.
It doesn’t hurt to be vulnerable.
“It’s okay to let them know that you are nervous or worried to bring something up that could potentially be challenging for the two of you to discuss.”
It can be incredibly disarming to be humble and vulnerable within the context of this conversation. It’s okay to let them know that you are nervous or worried to bring something up that could potentially be challenging for the two of you to discuss. Here’s some ideas of how to frame that:
“Before we dive into this, I want to mention that this conversation makes me a little nervous to have because you’re my boss and I care what you think.”
“I’m not sure how you will respond to this so I am feeling a little anxious about having this conversation, but I think it’s valuable to have together.”
“I want us to have a good, healthy, working relationship and that’s why I wanted to bring this up with you.”
Being vulnerable and honest with your leader about anxiety or worry you’re feeling about this conversation can be a really helpful ingredient to keep them from feeling defensive or attacked. Hopefully your vulnerability will result in them being more vulnerable in the conversation as well.
Use experience-based language.
Aka “The experience I’m having is…”
Talk about your experience as opposed to (for example) telling them the thing that they’re doing wrong. The quickest way to put someone on the defensive is to label them or make statements about their character. Making claims like “You’re not a good listener,” or “You shoot down all my ideas,” are flame throwers for conversations like these — they light everything on fire.
“The quickest way to put someone on the defensive is to label them or make statements about their character.”
Experience-based language allows you to portray what you are experiencing without accusing the other person or speaking to their character.
If you are sharing that there are times in certain situations where you don’t feel listened to, or that you don’t feel appreciated, no one can respond and say “Yes you do!” When you speak to the experience that you’re having it’s irrefutable — no one can argue how you feel. It keeps the focus of the conversation on the experience you’re having (that doesn’t feel great) instead of labeling them or attacking their character.
It’s also helpful to reinforce that you’re not accusing them of being terrible and that you don’t hate them — I think it’s useful to say that and for them to hear it and to keep the stakes low. Just that you’re having an experience that isn’t great and you want their perspective about what to do about it.
Gently, be direct about the experience that you’re having, give examples if possible, share the impact of that for you and bring it back to asking them for their perspective/advice/input. Here are some ideas on how to do that in a positive way, what makes sense to say will of course depend on the context of the conversation:
“What is your perspective on that, I’d like to hear what you think.”
“I’m at a point where I don’t really know what to do and would like to get your advice or input.”
“What does that bring up for you when you hear that?”
“Is there a way I can show up differently, or change how I’m contributing to the situation?”
“If you were me, what would you do?”
Approaching the topic in this way makes it more collaborative instead of a one-sided conversation. You’re reinforcing that you don’t hate them, you’re not accusing them, you just want resolution. You are also reinforcing that the reason you’re there is because you want to have a good working relationship with them and be excited to work. And hopefully, that level of vulnerability will prevent them from feeling attacked or defensive.
Stay positive and optimistic with your language and remain as emotionally neutral as you absolutely can.
Also, prepare yourself for defensiveness.
If they become defensive or start to get fired up, stay calm and relaxed and keep things low stakes. Reinforce that you just wanted to get their perspective and wisdom, and that you just want to have a good, positive relationship with them, etc. Move toward letting the conversation dissipate, not escalate, as much as you can. Here are some phrases you can say to de-escalate:
“I appreciate your time, I just wanted to talk it through.“
Again, I’m not upset at you, I just figured I’d get your perspective and any advice you’d have to to offer.”
If they blow up on you, do not blow up as well. Be cool. Like I mentioned, not all bosses are created equal and some just don’t have the skill, or lack of ego, or self awareness to navigate a conversation like this successfully. Sadly, it is what it is.
Lastly, especially if you are nervous, write down your thoughts beforehand.
“Hopefully, you can put your leader in a space to talk through your issues in a collaborative manner that results in strengthened trust and a better relationship.”
Follow the map I laid out for you, practice what you have to say, and get your ideas out of your head. It isn’t corny to practice what you’re going to say with a colleague or saying it out loud. Practice what you have to say so you can make sure to keep things focused on your experience, not being accusatory, enter the conversation more neutral. and the words don’t feel as clunky coming out of your mouth for the first time.
Hopefully, you can put your leader in a space to talk through your issues in a collaborative manner that results in strengthened trust and a better relationship. It’s such a valuable skill to have.
If everyone could have conversations like these with their boss, and their bosses received them well, every workplace would massively benefit.
Related Blogs:
Tips for Difficult Conversations & Apologies
A Quick, Simple Hack to Start Challenging Conversations
Stop Avoiding Critical Conversations
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This article was created by Galen Emanuele for the #culturedrop. Free leadership and team culture content in less than 5 minutes a week. Check out the rest of this month's content and subscribe to the Culture Drop at https://bit.ly/culturedrop
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