How To Have Difficult Conversations
or should we call them courageous?
But how do you actually have difficult, or courageous conversations?
Well, let me start by saying: I don’t really know, either! I find this shit so hard.
Which, by the way, is exactly why you’re reading about this, here. I don’t write about things I know. I write about things that confuse and puzzle me. I go on my own quests to make sense of the world, whether that’s friendship, boundaries, how to quiet my inner critic, or my way of thinking.
So to set expectations: I’m not going to give you a full guide for how to have difficult conversations, sorry. In a strange way, this might be even better.
Because here’s what I realized after just a few hours of exploring resources on how to have difficult conversations:
the internet (and library) is filled with resources. You can figure this out!
this shit is hard. Most of us don’t know how to do this. All we can do is try our best and learn. If we put a little bit of effort into it, we are doing something right.
there are small things we can try and remind ourselves of. One conversation at a time.
We got this!
Here are a few things I found to get you (and me) started. My hope is you’ll feel a bit more confident that you can figure this out.
Before the Conversation:
Consider reframing it from a difficult conversation to a courageous conversation.
Remember, conflict is normal.
Acknowledge that you might not agree (and that’s okay). You will however understand each other’s point of view.
Ask yourself what your ideal outcome is from the conversation. Do you want to be heard? To feel closer and connected again? An action plan? Agreement? Understanding each other’s perspective?
Take responsibility for yourself first. be honest and consider: how have you contributed? What can you do to change the situation?
Self regulate (“turn the temperature down”). Being aware of your own attachment style might help. See for example Secure Relating.
Remind yourself of signs you might get activated and prepare a phrase in case you need to or want to take a break from the conversation.
Consider when and where to have the conversation. A neutral place, maybe walking next to each other instead of sitting across from each other.
Remember that often, courageous conversations go better than expected. Keep an open mind and heart.
During the Conversation:
Listen (really listen) and seek to understand first.
Brainstorm solutions together (don’t be too attached to how you want to resolve things).
Start with I statements: When you [action], I felt [feeling].
Notice when you’re getting activated, take a break if needed.
Remember your ideal outcome. You don’t need to have it all figured out in one conversation. Feeling heard and understood might be enough for now.
Remind yourself what’s important to you about having the conversation. It probably has something to do with how much you both care about each other.
I hope you found this helpful and you’re feeling a bit more confident that you can figure this out.
You can journal on these questions or talk it through with a friend (just make sure you’re clear about what kind of support you are hoping for: venting or preparing for a conversation). I’ve had clients bring difficult conversation with managers to coaching, but there’s no reason to not also bring examples from your personal life.
Until next week!
Take care of yourselves + your loved ones.
Hanna
Resources
BBC Woman’s Hour Podcast: How to have difficult conversations
Non-Violent Communication: https://www.cultureally.com/blog/nonviolent-communication-a-guide-to-empathetic-conversation
Webinar: COURAGEOUS CONVERSATIONS: A GUIDE FOR HAVING TOUGH (YET PRODUCTIVE!) CONVERSATIONS (focus is on the workplace, but lots of practical specific tips)
Book: Conflict Is Not Abuse by Sarah Schulman (just started reading)
Book: The Art of Fighting by Priya Parker (coming out in September)




I write about this here on Substack, and for Psychology Today (my column is called Getting Comfortable with Conflict). Here are my three big-picture tips for having tough conversations:
1. Know that they are going to be uncomfortable and stressful, and that is okay. Persist through the discomfort. It's like when you clean out your closet, there's a part where everything is all over the place and it's a huge mess, and you're like, why did I think this was a good idea?? But eventually, it lets you get to a better place where you can see the discomfort was worth it.
2. See tough conversations as an opportunity to strengthen and grow relationships. You're not causing a rift. You're trying to fix one. If you can do that successfully, you will level up the relationship -- you now know that you can work through hard things together. And if you can't, honestly, the relationship was already broken and now you know for sure.
3. These are skills that you develop over time with practice. And you're never going to be the world champion difficult conversation-haver, so just accept that it's going to be imperfect every time. But keep practicing.
Calling it a courageous conversation instead of a difficult one is a great perspective shift. Difficult = fight, courageous = being honest.