Mastering Difficult Conversations is a Powerful Step in Transforming Your Relationships

How intentional conversations bring you closer together.

Published in
3 min readOct 29, 2020

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For most of my life, conflict terrified me. I viewed it as a signal that something had gone wrong in the relationship. As a people pleaser, I tended to appease the other person rather than disagree. It felt easier to sacrifice my needs than it did to have an uncomfortable discussion.

What I didn’t see was that the conversation I was avoiding could actually bring us closer. In reality, not being willing to share how I was hurt or what I needed from the other person, meant I was holding back. I wasn’t bringing my entire self into the relationship. As a result, I hid aspects of myself to protect the part of me that was upset or conflicted. But, the truth is, we can’t strengthen or improve a relationship when we aren’t showing up to it fully.

It’s our responsibility to teach others how to treat us.

To teach, we must communicate. We must express our needs, our boundaries, and our limits. Tolerating someone’s behavior does not benefit them. Rather, it robs them of the opportunity to support us. It withholds the information they need to adapt their behaviors. In the end, it deprives us both of the relationship that could be possible.

Difficult Conversations are the Building Blocks for Richer Relationships

Think of it this way. We’re either building a wall between ourselves and the other person, or we’re building a bridge.

The wall is built through avoidance, tolerance, appeasing, and passiveness.

The bridge is built through vulnerability, expressing needs, curiosity, and assertiveness.

Difficult conversations build bridges. Resisting open communication, retreating from the relationship, or tolerating behavior that doesn’t work for you; these actions build walls.

So how do you go from resisting to initiating these dialogues? I find it helpful to ask myself this question: What if having the hard conversation is the most loving thing I can do for myself and the other person? This helps me to step out of fear and resistance and into love and curiosity. From this place, I intentionally plan for the conversation.

How to Prepare for Difficult Conversations

Take time to think through the conversation in advance while in a calm state. This will lay the foundation for a more productive conversation and a healthier relationship.⠀

  1. Determine your intention. What is the purpose of this conversation? What do you hope to achieve by having the dialogue regardless of the outcome?
  2. Be both teacher and student. Teach the other person what your needs are and how to communicate with you. Stay open and curious to learn about the other person as well. Allow them to teach you how to treat them.
  3. Focus on what is in your control. You do not know how the other person will respond, but you can control how you show up to the conversation.
  4. Find love and compassion for the other person. You care about this person, if you didn’t you wouldn’t be engaging in this conversation. Take a birds-eye view of the situation and get curious about what is going on in their mind. Reach beyond your pain to see what they might be experiencing. Are they hurt, fearful, sad, and why? Curiosity is a really important skill to master.
  5. Prepare for all outcomes. Hopefully, the conversation will go better than you imagined, but if it doesn’t, how will you handle it? Plan out what you will do if you experience pushback when setting your boundary. If the other person isn’t receptive, how will you respond? Planning for multiple scenarios will help you stay focused on your intention for the conversation. Remember, you can always pause the conversation and try again at an agreed-upon time.
  6. Evaluate. After the conversation, take the time to reflect on the conversation in detail. By reviewing and evaluating, you will understand what went well, what didn’t go well, and what you will do differently next time.

As you begin having these conversations, practice kindness towards yourself. This is a new skill you are building. It will take time and many conversations to master. Don’t beat yourself up if it doesn’t go as planned. Learn from it. This will ensure that the next time will go better.

Want a tool to help you prepare, check out the free Navigating Difficult Conversations workbook I created.

Originally published at https://annaolson.com on October 7, 2020.

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Writer for

As a certified life coach, I help individuals understand who they are so they can build the life they desire.