How to Have an Uncomfortable Conversation

As a former people-pleaser and a perfectionist, I did everything in my power to avoid uncomfortable conversations. I was worried I would lose the other person’s respect and love. And I thought it would be easier to twist myself into a pretzel becoming a more “agreeable” version of myself than it would be to have an uncomfortable conversation.


But I’ve learned we just have to have an uncomfortable conversation sometimes. You might be asking what are the nuts and bolts of an uncomfortable conversation? How do you actually do it?


Let’s first look at the ways not to do it.


I used to vomit my feelings on the other person. I didn’t have a structure for the conversation and I normally held my feelings in for too long. The other person would be stunned, because they had no context for where this came from. It was also confusing because it was literally the opposite of my “cool girl” behavior where I tried to be exactly what I thought he wanted.


A successful uncomfortable conversation is not a lecture. It’s not jumping up on a soapbox and proclaiming your opinion as the one and only way. This method is extremely one-sided and leaves no room for the other person to contribute.


Got it? Good. Let’s look at how to have those uncomfortable conversations so they are productive. This is what works best for me, and you should feel free to tweak it to meet your own needs. I encourage people to write down their reflection when preparing for the conversation. It allows you to get everything out of your brain and in a place where you can see it and organize it.


My first step is to prepare yourself with what exactly is bothering you. You can recognize that something is bothering you because you will feel off- it might be low energy, unexplained sadness or anger, it might be thoughts that won’t stop running in your brain. Take some quiet time and sit with the feeling. What is coming up? When did you start feeling this way? Why is it important to you? What do you need to be different?


Next, assess what is your responsibility in the problem. You can’t blame the other person for everything, but you also are not responsibility for everything. That would be over-functioning. Ask yourself, how can I show up fully in my half of this relationship? What needs to be expressed to the other person? Were feelings hurt? Do you need to share a boundary or make a request?


Once you feel like you have a handle on what needs to be said, ask to have the conversation. This gives it a framework, which can feel comforting. Ask the person for a time to talk.


Please avoid accidentally blindsiding the other person with your conversation, and you make sure to have their full attention. It also gives the opportunity to schedule a better time. Yes, I am saying you want to schedule an uncomfortable conversation. You want both people to be able to relax and focus with minimal distractions. It is also helpful to provide a time frame too, so the person knows this isn’t something you intend to drag on into a huge conversation all night long.


This would look like “I have a few things I need to talk about in regard to _______­­­­______. Do you have 10 minutes now or would later be better?”


Now that you are in your conversation, express yourself honestly from your point of view. Avoid pointing fingers. A great way to do this is to use the classic “I feel” statement. For example, let’s say your partner curses so much that it offends you. This looks like “After our conversation the other day, I feel a little angry. I realized that we hit a sensitive area for me. I completely respect your right to use curse words. But may I make a simple request and ask that you not use that language around me? If you’re not able to do this, I will need to leave.”


Let’s break this down.


Acknowledge your feelings. Acknowledging your feelings is part of how you take ownership of your 50% of the relationship. You know those feelings are your responsibility. The negative feelings were an indicator that something was off, and you located the problem. (this is what you did in step one)


Respect the other person’s free will. You will never, ever be able to control another person’s actions. If you show that you respect this, the other person can relax and listen from a more open place.


Make an ask. I like the phrase “May I make a simple request?” The people pleaser in me likes this because it reinforces that I am not asking for something big or unreasonable. You want to be clear about what you are asking from the other person. Be clear and concise.


Set a boundary. If your needs are not met, there is a consequence. You must uphold the boundary as well. If you make a request and your partner does not meet your request on a regular basis, then you must uphold your end of the bargain. Actions have consequences.


There you have it. That’s the structure of how I have an uncomfortable conversation, and why I do it this way. How do you see this applying in your life? Is this useful to you? Reply and let me know!