June Montgomery, April 1 2026

WHY THE HARDEST CONVERSATIONS MATTER MOST


I have been thinking quite a bit about the world today, and somehow, people appear not to be talking about it. Have you ever had a conversation you often feel before you ever speak—the ones that sit still in your mind waiting for the right moment, the right words, and the right tone? Is it fear that keeps you silent? These conversations have a specific name. They are known as courageous conversations—those conversations about politics, diversity, equity,conflicts, race, racism, inclusion, religion, identity, etc. Yes, there are many more topics, but this list is just a start for the purpose of this blog.

Courageous conversations are often avoided. Because of this wide-spread avoidance, I’ve often thought the reason was fear or simply not caring. I discovered that it goes much deeper than that. I learned that those topics actually activate deep psychological, social, and cultural forces. Why? As humans, we are wired to belong or be included. Courageous conversations risk—rejection, conflict, one’s reputation, a personal attack, anger, guilt, shame, just to name a few. Who would want to deal with these risks?  In addition, many people were never taught how to communicate effectively—how to have difficult conversations. That’s a major risk and concern in any situation when effective communication is needed. So, what can we do?

Give it a try! Courageous conversations feel uncomfortable, but they often produce some of the most meaningful personal and social growth. When done well, the benefits are great. Here are some of the benefits.

Courageous conversations:

·       build honesty and transparency

·      show respect for differing perspectives

·      strengthen bonds

·      help one to understand lived experiences different from your own

·      provide the opportunity to learn, respond, and explore

·      build confidence

·      help one become more open-minded

·      help one develop the ability to remain calm under pressure (This, in itself, is a skill).

You do not have to agree when having a courageous conversation—but you should stay open. 

What are a few things NOT to do when having a courageous conversation?

·      Don’t try to “win” the conversation.

·      Remember it is a dialogue NOT a debate.

·      Listen to understand, NOT to only respond.

·      Don’t attack or label the person.

·      Don’t generalize people. (using words, “like you always”)

·      Don’t raise your voice with sarcasm, anger, or hostility.

·      Don’t shut down and walk away. (This one is a classic).

·      Don’t dismiss everything the other person says.

Courageous conversations show us who we are and the bravery inside of us to step into uncertainty with flawed courage.

 

Remember: Quiet rooms invite real heartfelt talks. Growth rarely occurs in comfort zones.

 

Question: What’s one courageous conversation you’ve had (or want to have)? Hit Contact—I’d love to hear your story.

Written by

June Montgomery

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