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How to Have Courageous Conversations

How many courageous conversations have you had recently?

We ask because now more than ever is the time to stand up and speak up — and also listen.

In order to help you have more courageous conversations — that are hopefully filled with actual progress, kindness, and understanding — we reached out to Kjirsten Mickesh, co-founder and CEO of ConnectHuman, which she started with her son Taylor.

ConnectHuman’s mission is to create human connection that improves well-being and performance. Connection Zoo, their kids’ product, teaches social and emotional skills to prepare kids for a happy, healthy life. Which, you know, we could probably all use right now regardless of age, right?!

Kjirsten has been a student of human and organizational behavior for years, having led HR at global companies. In addition to her leadership on the Connection Zoo brand, she is a speaker, consultant, and coach, with specialized training in social and emotional intelligence.

We are delighted to have a guest post from her today on how to have courageous conversations. (And, after you read, be sure to save a copy of her Courageous Conversation Guide with more info and activities here!)

How to Have Courageous Conversations

By Kjirsten Mickesh, co-founder and CEO of ConnectHuman

I have a favorite pillow. Each night, I crawl into bed already imagining the comfort I will experience with my pillow. I lay my head back, it sinks in, and the sides of my pillow come up around my ears as if it’s tucking me in and hugging me good night.

There are a lot of things going on in the world right now that are really uncomfortable. Our emotional well-being and relationships are being tested. It’s hard to make sense of what’s happening and why. This is the perfect time for courageous conversations, yet so many of us are not talking about what we’re thinking and how we’re feeling, except on social media, which was not intended for meaningful, high stakes conversations.

What Is a Courageous Conversation?

It’s the one you don’t want to have, because it can be uncomfortable and the stakes can be high (relationships, reputation, emotional suffering). These are the conversations that can leave you feeling vulnerable or exposed.

Why then would a courageous conversation be a good idea?! When you lean in with courage and invite someone to explore with you, you get to see the world as it is — not just to you, but to others, as well. When you join others in their space, and you feel with them, you create shared understanding and build stronger emotional bonds. Courageous conversation, done well, connects us.

“You see the world as you are, not as it is” – Anais Nin, author

Conversations with people we live with, work with, or play with around topics that trigger emotion and surface differences, are best done face-to-face. But that takes courage.

The 6-Step Courageous Conversation Process

I practice* a 6-step process with the acronym PILLOW to help me engage in courageous conversations about any challenging topic, from COVID, racial justice, identity, grief, or mental health … the list goes on and on.

(*I use the word “practice” very intentionally; this is hard, and I don’t always get it right.)

Courageous conversations will be uncomfortable, and your PILLOW can support you through the discomfort.

Pause. Slow down to prepare yourself, allowing for self-awareness and intention setting. Are you in a place emotionally to have this conversation? Is your intention to win or to strengthen your relationship? Ego is not your friend during courageous conversations; humility, empathy, and curiosity are.

Invite. Make your opening line an invitation, not an attack. Send the message that you value your relationship. Within the conversation, invite the other person to share their perspective, even if — especially if — it is different than your own.

Listen with empathy to connect emotionally. Listen with your ears, eyes, and heart. It is important to believe that what they tell you is real for them, even if you can’t understand or relate to it. Each of us is the ultimate authority on who we are, how we feel, and what we’ve experienced. Even in shared situations (like COVID-19), there will be significant differences in the way each of us feel and experience it.

Love first. A courageous conversation is about acceptance, understanding, kindness, and care. Put your relationship first.

Open with statements and questions that encourage authentic, courageous sharing. Allow for silence. Your response to what’s shared with you will either open the door for courageous conversation or shut it down. Avoid responses like, “It can’t be that bad,” or “Are you sure?” or “That’s not true.”

Use responses that open vs. shut down conversation:

  • Thank you for sharing that with me.
  • Please tell me more about that, or What else should I know about this?
  • I haven’t had that experience, or I haven’t felt that way, or I have a different perspective. Please help me understand your point of view.
  • I imagine that is ____________ (difficult, hurtful, overwhelming, etc.).

As you listen, continue asking open-ended questions that deepen your understanding and connection. Offer your perspective, encouraging exploration of both similarities and differences.

Walk with them, literally or metaphorically, in their space, hearing and accepting their truth. Invite them to do the same with you, so you can move forward together in support of each other’s needs.

As an adult, you’ve had a lot of time to shape your view of the world, your behaviors, and the way you interact with others. It’s easy to think that your truth is the truth. It feels safer to stay in your bubble, with the people and perspectives that are familiar and comfortable.

I live in Minneapolis, home to George Floyd, who was recently murdered by police. Many of the courageous conversations I’ve been having lately are related to racism and racial justice. I have had courageous conversations with my kids, my white friends, my brown and black friends. I’ve listened to their voices with humility, curiosity, empathy, and love. My eyes have been opened to experiences I will never have that are very real and happening around me every day. As a result of what I’ve heard, I am changed. I see the world differently now, but I still have a long learning journey ahead of me to better understand how I can go beyond just being informed to being an ally and advocate.

Courageous Conversations Are for Kids, Too

Courageous conversations aren’t for adults only. As a parent, the conversations you have with your kids help shape how they see and experience the world. The most connected, meaningful conversations I had with my kids when they were little were at bedtime. I would lay with them in their beds, in the dark, with no distractions or agenda. As they relaxed, they would more openly talk about how they were feeling, and share what happened for them that day.

We had deep conversations about God, about death when great grandma Jean died, about 9/11, about kids in the park using bad words, and about why women have big breasts and men don’t. 😊

We still have courageous conversations in the context of their young adult lives, as they continue to figure out who they are and how they will show up in this world. The earlier you give the gift of courageous conversation to your kids, the more you will receive it in return as they grow and develop their independence.

Having regular PILLOW conversations strengthens the health of all of our relationships. It’s not just the big-world-event conversations that matter. Ideally, we would build all our important relationships on a foundation of openness and sharing and make courageous conversations a habit.

My son and I created Connection Zoo to help families establish a fun, playful routine that builds a practice of talking about feelings and needs. It’s much easier to have tough conversations when you’ve practiced together.

Feel well, be well, do well. Be courageous! —Kjirsten Mickesh

P.S. I have a Marriott Hotels pillow, in case you’re wondering. (You can order them online). And, if you’d like to give it a try, you can save a copy of my Courageous Conversation Guide (with more info and activities) here.

More Resources

FTC disclosure: We often receive products from companies to review. All thoughts and opinions are always entirely our own. Unless otherwise stated, we have received no compensation for our review and the content is purely editorial. Affiliate links may be included. If you purchase something through one of those links we may receive a small commission. Thanks for your support!


  1. “Communication is the shortest distance travelled between the two.”

    I strongly believe that the conversation should be open and our focus always should be to make sure that we create an environment where everyone is comfortable to share things with us.

    Usually, we listen, judge and react to the conversation and our reaction paves the path to the openness in the next conversation.

    For example: One day my son shared an incident he faced with his friends and my reaction to that would have been shocking to him. By that he may have realized this is something we should not talk about in open.

    And , that is the recipe for disaster.

    Instead, I held my emotions and talked to him normally as if it was a casual thing and encouraged him to discuss more things that happened in school. This way, I laid the comfortable situation for him to talk more about what’s going on and gonna happen in future.

  2. fnaf world says:

    The article you share here is awesome. I really like and appreciate your work. I read your article deeply, the points you mentioned in this article are very helpful thanks for sharing.

  3. Juicergirl says:

    This is what I need to hear now. I have been bottling up and unable to share. But after reading this I think it is time I had some courageous conversations. Thanks from the bottom of my heart. I will be needing guidance from this article to have those communications.

  4. Thanks for sharing this kind of amazing post. It is a great experience to read all about.

  5. Slim Mix says:

    I will pratice it: Pause – Invite – Listen – Love – Open – Walk
    Thank you much

  6. Thanks for sharing this article! It is very difficult for me to start a courageous conversation and share my feelings. This is a very useful article.

  7. Thank you for the information.

  8. Awesome article. I have read it completely and got really impressed. Love to read more similar types of articles.
    Thanks a lot!!

  9. Thoroughly Explained article. Love it!! Waiting for more articles like this. Read it completely and got really impressed.
    Thanks a lot!!

    Loved the article

  10. Loved the article very well Explained!!

    Thanks a lot!!

  11. Mary says:

    Really inspired me a lot and helped me to be motivated. I am a manager at this online store in USA , I needed this courageous conversation for working at my home and in my office. Thanks a lot.

  12. Thank you for this informative piece of work. It’s a must read in times when people tend to compromise and give in due to fear ir just fit in and get by.

  13. Such an amazing piece of info. Something a parent would definitely want for their child to learn. Thanks a lot for sharing

  14. Rupa says:

    It’s a very nice article about courageous conversations !!
    I was looking for a good explanation about courageous conversations and I read many articles on the internet but, this is the best one for me. Thank you…

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