How to Have a Difficult Conversation

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By Gabriel Gonsalves

Personal mastery, leadership development, and spiritual growth with the heart in mind. 

Difficult Conversation

Having a difficult conversation with someone you love can be very challenging. But when done from a compassionate space, it can set you free, deepen or strengthen your connection with someone, and even repair a broken relationship.

What makes this type of conversation so challenging to have, is the great unknown they will inevitably put us in touch with…

How will the other person react when I tell them exactly what I think about them or how they make me feel?

What if I get distraught, can’t control my emotions, say, or do something I might later regret?

What if we open a can of worms, hurt each other’s feelings, and hit a point of no return?

No wonder so many of us avoid them like the plague!

When it comes to having a difficult conversation with someone you love, the problem most of us have is not knowing exactly how to go about it.

I mean, we don’t have good role models of what having this conversation looks like, feels like, and sounds like. I don’t recall ever seeing a ‘Difficult Conversations 101’ class in my high school or college.

So how do you have one? How do you have a difficult conversation with someone you love?

Here’s how to create a conscious, heart-centered conversation that will improve, heal, and grow your most cherished relationships in 9 steps.

9 Steps to Having a Difficult Conversation with Someone you Love

1. Acknowledge your desire, need, or longing

Take a moment to connect with your heart or the part of you that wants to have this conversation by asking yourself, “Why is having this conversation important and meaningful to me?”

2. Clarify your intention

Get clear about what it is that you’re genuinely wanting by having this conversation. Do you want to feel more connected to the other person? Get them to modify their behavior? Do you wish to share what’s in your heart with them? What is it you’re longing to experience by having this conversation?

3. Invite the other person

Say to them, “There’s something I would like to share with you. When do you think or feel would be a good time for us to have a conversation?” If they say no, do your best not to take it personally. Simply tell them, “Can I check back with you next week? Maybe you’ll be ready then? What I have to share is important.”

4. Set the context

Let the other person know what the conversation will be about and what you want by having this conversation. For example, “I value our relationship a lot, and I want to talk to you about what I’ve been feeling lately with regards to you.”

5. Hold a safe space for each other

Create an agreement to hold a safe space for each other by asking, “Can you listen to all that I have to say, without interrupting me, please? After I’m done sharing what I have to share, I’ll do the same for you if you feel like you want to reply.”

6. Get real with the other person

Avoid rehearsing the conversation beforehand, and instead, take a deep breath into your heart and share what’s in it. Share what you honestly think, feel, sense, want, and long for. Lean into your edge by saying what you’re most afraid of speaking and asking for what you’re most afraid to ask for. If you get triggered, lose your calm, or go into fear, go back to breathing deeply into your heart. If possible, sit on the same side of the table and get fully present with the other person.

7. Seek connection above understanding

Stick to the facts and how you felt about it. Say, “When ___ happened, I felt ___.” Let go of the need to be right. Take responsibility for what is yours and be willing to admit any faults or wrongdoings. Let go of the story you had told yourself about the situation, how this conversation would go, and be open to seeing things differently. Above all, seek to listen deeply, feel connected, and empathize with the other person.

8. Agree on a way forward

Determine what will be the next action step or steps you’ll each be taking. Don’t leave the conversation until you’re clear about what will happen next. Ask, “What agreement can we reach?” Be sure to follow through.

9. End with love and appreciation

Complete consciously by appreciating the other person, the qualities you admire in them, and the lessons you’re learning by being in a relationship with them. Thank them for their time and for their willingness to listen and share their heart with you. Finally, remind them how much you love them and what the relationship means to you.

That night, before you go to bed, take a moment to reflect on the conversation you had and about what you learned about yourself and the other person. Then, appreciate yourself for having loved yourself enough to courageously speak the truth of your heart.

From my heart to yours,

Difficult Conversation