How To Have Tough Conversations With Your Friends, Colleagues & Partners

Show of hands for those who value great communication, transparency, and being direct and honest. I’ll go out on a limb and guess that all of you would say yes. Now, keep that hand up if you’re great at all of those things you value: communication, transparency, and honesty. Is your hand still up?

Anytime someone poses that question in a group setting, more than half of the group slowly brings their hand down, and looks around with that look of “ugh, guilty.”

It’s normal — tough conversations are exactly that and there are so many factors contributing to making them tough: ego, not wanting to hurt feelings, insecurity, limiting beliefs, lack of confidence, and the list goes on.

With the help of therapy, podcasts, audiobooks, and simply having the tough conversations, keep scrolling for five scenarios, and how to handle them.

Friendship.

The Scenario

Within the past year, you feel a bit disconnected with a dear friend. For whatever the reasons may be, you just knew it didn’t feel good and didn’t want to lose the friendship. When you went to lunch, you simply said, “I feel like we might be drifting apart right now, I don’t know if that’s true, but I value our friendship and want to make sure we have some space to talk through anything to help strengthen it. How are you feeling?”

Your heart raced the entire time with so many scenarios running through your head that are too long to list. The key to this conversation was staying in curiosity and learning how she or he was feeling vs. judgement.

Your friend asked, “Do you have any specific examples that led you to feel this way?” In your response, not pointing fingers, but rather shared how you felt in the moment — this unlocks deeper concerns and more open-ended conversations.

In the end, you both felt a little disconnected but for no particular reason other than life, kids, and a pandemic, and committed to re-prioritizing our time and investment into each other’s lives. By saying, “You’re an important person in my life and I want to invest more time into this friendship, this is what it looks like…” you have essentially redefined your friendship.

The Lesson

Stay curious, listen to the other person’s responses, and don’t judge those responses. Their truth is their experience, and the goal is to build the next step or chapter. No one was trying to win or one-up the other here, we both came from a place of wanting to understand each other’s feelings and to support one another into the next chapter.

Romantic Relationships

The Scenario

Imagine being in a new relationship where you and your partner have reached your 6-month mark. However, you have reached the point where you aren’t having fun anymore, and the relationship felt very one-sided in a lot of ways. In this particular scenario, you do wish you would’ve spoken up a bit sooner on how you were feeling, to try and work on it, but didn’t, which is one thing you’re still learning. Around the six-month mark, you realized the relationship wasn’t for you but you found it a very hard time breaking it off because he or she was a really nice guy or girl, and didn’t want to hurt his/her feelings. With the help of your therapist, you approached the conversation thinking about how you wanted to feel and how you wanted him or her to hopefully feel and went into it very kind. You didn’t go into it wanting to salvage it, you knew it wasn’t for you, but running in a similar industry circle and cares about ensuring it ended in kindness.

The Lesson

When you know you don’t want to salvage the relationship, It’s necessary to point fingers and offer up scenarios of where it went wrong, especially if you haven’t addressed it in the past. It’s important to acknowledge to not use your voice or bring anything up to try and work on it — that is transparency, honesty, and vulnerability in admitting you were wrong.

Workplace.

The Scenario

Imaging being on a work trip where you were hosting a large event, and you felt something was off with one of your colleagues. Typically they’d be warm, welcoming, and carving out the proper time to hang, but you have experienced them completely the opposite. It was a rather quick trip and one where we didn’t have a lot of alone time, so it didn’t feel right to say anything in the moment. Plus, you were still trying to decide how to feel about it. Every emotion was present: confused, hurt, upset, annoyed, and even questioning what you might’ve done to make them feel that way. When you got home, the feeling was still present, so exactly a week later, you asked for a call.

Knowing our working relationship was great, and they are the type that values vulnerability and bold communication, you simply said, “I know you are the type that values vulnerability and open communication, so I wanted to talk about our recent event. I felt like something was off, and you weren’t your usual self are you okay?” You decided to remove yourself from this one initially and find out what was going on with them if anything. They responded that they weren’t happy in their role, and shared it was no excuse to project that onto you, and felt awful that it impacted you the way that it did.

We decided together we wanted to carve out monthly time to connect and get out of the work-mode grind, and you’re happy to report that this has helped immensely. Sometimes it takes removing the “work” in the workplace to truly get to know one another; though it takes both parties to be willing to carve out time for that.

The Learning

Removing ourselves from the narrative allows the other person to potentially open up more vs. come from a place of defensiveness or shame. No doubt your colleague knew the impact of the behavior because you opened up. Imagine the conversation would’ve gone a completely different direction if you opened it with, “You were really rude to me.”


No matter the scenario, it’s clear that curiosity, owning mistakes, and not judging reactions or responses is key to navigating tough relationships. I’m grateful that each scenario has also led to robust and open conversations, and I give credit to the approach. But I’m curious readers, how do you approach tough conversations? What have you learned? Sound out in the comments below.

Stay safe, healthy, and live life to the fullest.

Xoxo, Messycafe.


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