How to Have Difficult Conversations

A core foundation of maintaining an authentic and meaningful connection with someone else (and of living an authentic and meaningful life in general) is the ability to have difficult conversations. 

Of course, it’s easy to avoid communication when there’s tension or conflict. We may be afraid of the uncomfortable things we’ll have to feel, or even of the potential loss of that connection. And yet, failing to express our truth is ultimately unsustainable, because those unmet needs and unspoken pains eventually do surface in unexpected and even more painful ways. In other words, avoiding these conversations often means trading short-term discomfort for long-term dysfunction.

So no matter how difficult you imagine the conversation will be, if this is a relationship you value, it’s important to trust that on the other side of that conversation is more peace, understanding, and harmony. Even if the intended outcome you seek with the other person doesn’t happen, having this courageous conversation is still a step towards greater well-being in your life.

Of course, it is not simply a matter of having the conversation or not. Rather, it is the way you have difficult conversations that often determine whether your relationship survives or thrives. 

So, here is a simple 5-step process that we hope you will find helpful for having difficult conversations: 

  1. Consent: Ask the other person if it’s a good time to talk, and if they have x minutes to be available. If it’s not a good time, ask them when a good time would be. By asking, you’re giving a signal that you have something important to share, and inviting their consent can show that you care about the quality of their presence. 

  2. Fear: If this is a difficult conversation, you are probably carrying some fear around how the other person will react or how you will feel in sharing. Expressing that fear right away begins the process of communicating your underlying desire or need—while also offering your own vulnerability, which can help the other person to feel more comfortable opening up.  

  3. Hope: Let the person know what you hope will happen as a result of having this conversation. Ideally, frame this hope as a desired shift in the relationship: for example, “In sharing this, I hope we’ll be able to understand each other better, and that our relationship will feel more supportive for both of us.”

  4. Share: Here is where you say the thing you want to say. What’s most important here is to use conscious communication: for example, using “I” language to express your feelings, and avoiding any “victim language” that blames the other person for your experience (e.g. “you made me…”). 

  5. Feedback: If you are ready to hear how your share impacted the other, you can let them know how you would like to receive feedback. For example, you might first ask them to share a summary of what they heard to make sure they have understood you correctly. Once you feel heard, you might also ask them to share how they were impacted by what you said, or invite them to share their own perspective on the situation. 

Throughout these five steps, make sure to check in with yourself to notice how you are feeling and what you may be needing. You might find it helpful to take a break before “switching roles” to integrate—and also to invite the other person to follow some of these same steps out if the situation is still charged or you’re feeling particularly vulnerable.

Finally, you may want to close the conversation with a form of acknowledgement or gratitude around the process (e.g. “Something I’m appreciating about this conversation is…”). This can help to balance out some of the discomfort you may still be holding.

What are YOUR strategies for having difficult conversations? Do you have any additional tips to add, or a story to illustrate? We’d love to hear in the comments.


- Text by Solomon Krueger

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Practicing Safe Vulnerability