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This month, we want to address an issue that many of us are facing right now: how do we have difficult conversations?

There’s a lot happening in the world right now. And when big things are happening, we find ourselves having big conversations; ones that will probably make us feel uncomfortable. But in order to move forward, we need to figure this out. So, how do we go about having productive, civil conversations with one another?  Particularly those that we disagree with?

Tune in this month as we take a look at some of the ways we can help to make the world a better place for everybody just by developing our conversation skills!

If you’re new to The Conspiracy Chronicles, this is Ever Widening Circles’ monthly newsletter! We take a birds eye view at some of the big issues we’re facing around the world, shine a light on thought leaders tackling the problem, and will give you some ways that YOU can connect to the #ConspiracyofGoodness in our world! So, let’s get to the good stuff, shall we?

Image: Two coffee cups sitting in front of a cactus

The Problem

Let’s face it, nobody really wants to engage in conversations that make them uncomfortable. Most people are pretty averse to finding themselves in emotionally charged situations. Especially, when those situations involve loved ones, colleagues, or friends.

It’s not easy to engage people on topics that you may disagree on. Yet, for issues like addressing racism, politics, or talking about polarizing current events, these conversations are essential if we want to make positive progress.

In an effort to avoid ruffling feathers, many of us resort to silence. We just won’t bring up tough subjects around certain people. But too often, our silence can be taken as apathy or agreement, even if that’s now how we meant it to be. So, what are we to do when we want to approach important but difficult conversations and keep our relationships intact?

Silence is rarely the answer. Too often it can be taken as apathy or potentially agreement. Well, let’s look at some of the steps we can take to make our words more meaningful as we approach difficult conversations in a way that preserves people’s dignity and may actually lead to lasting change!

Where do we even start?

Let’s start by setting the scene: how do we even begin these important conversations? Do we just blurt out our feelings and a list of facts and statistics to our family members? Well… here’s a few ideas on what you can do leading up to seeing them.

First up, assess how you’re feeling about this conversation.

For example, talking about race and racism can be a difficult subject for many people. But if you are wanting to have a conversation with a family member, friend, or your child about the subject, first assess your comfort level—think about it as a sliding scale from “I would rather not talk about it” to “I am very comfortable about it”. (You can use this scale to consider any big topic you want to address with another person.)

Next up, try answering these questions for yourself. “The hard part of talking about ____ is….” “The beneficial part of talking about ____ is…”. Once you’ve taken a moment to reflect, you can now prepare yourself more for the conversation–read up on important history, or topics that might come up, search for resources specific to the topic at hand. 1

Now that you understand why you’re having the conversation and have come to the table informed, it’s time to think about how and where you want to have this conversation.

The best way to have a difficult conversation is in person.

Do not have difficult conversations in the comments of a Facebook post or through a text exchange. We are wired to communicate best in small numbers face-to-face in real time. Given that we are in a time where social distancing is key, you may not be able to sit down face-to-face with people. In that case, the best thing you can do is set aside time that would be uninterrupted for both of you to have a video call over a service like FaceTime, Skype, or Zoom. When situations are emotionally charged, visual contact is key! Without being able to see your conversation partner you miss out on seeing people’s body language and responding to their micro-expressions. 2

It’s also important that you and the person you are talking to are free from distractions. Even something as simple as checking a text can derail a conversation.

So, now you’ve got your conversation set up, it’s time to get in the right headspace. Here are a few that the experts at the Harvard Business Review suggest:

Expect a positive outcome. (I know, this sounds like wishful thinking but it will help you start the conversation in a positive mindset.)
Begin from a place of curiosity and respect.
Reframe your purpose from convincing to learning. (Nobody ever changed their favorite sports team because somebody yelled at them, why do we expect the same of people’s opinions?)

When you’re ready to begin your conversation, it is helpful to verbalize your intention. Remember, you are entering this dialogue from a place of curiosity and learning, so something like, “I’d like to learn more about your thoughts on ____. “ and ask what they’d like to get out of the conversation, too.

You’ll also want to be clear with your conversation partner about the process, saying something like “I want to remain open-minded and non-judgemental. Will you let me know if I slip up at this?” 3This opens up the conversation to become a two-way street. Showing vulnerability and acknowledging that this is not an easy conversation allows both people to be more at ease and potentially help to diffuse tensions.

When your conversation begins, you may find yourself or your partner tensing up. It’s important that you recognize when this happens. “After all, a disagreement can feel like a threat. You’re afraid you’re going to have to give up something — your point of view, the way you’re used to doing something, the notion that you’re right, or maybe even power – and your body, therefore, ramps up for a fight by triggering the sympathetic nervous system.” 4

Once someone’s body goes into fight or flight mode, rational thinking begins to decrease which is the opposite of what you are looking for in a difficult conversation.

So, check-in with yourself often: is your heart rate rising? Can you feel your blood pressure going up? Are you talking faster? Remember, you can “catch” the emotions of other people, so if you are starting to feel a rising sense of pressure, your conversation partner probably is, too.

This is a good time to employ this strategy that Teaching Tolerance suggests to educators.

Reiterate: restate what you just heard using “I” statements. This allows you to make sure that you are hearing what the other person is actually saying, not what you think you heard. Above all, avoid assumptions!
Contemplate: Count to 10 before responding. Think about your responses and compose what you want to say in response. This helps you truly listen to understand and respond to what was just said, instead of just saying what you want to say.
Respire: Take a breath to check in. Take a few breaths before you respond to help you settle your thoughts and emotions.
Communicate: Speak with compassion and thoughtfulness. Speak the way you would want to be spoken to. Assume the good intentions of your conversation partner and truly seek to understand their point of view. When you disagree with something that is said, focus on challenging the statement rather than the person.

As you go through these steps keep in mind your A-BCDs. These communication missteps can derail a conversation very quickly. Avoid Blame, Contempt, Defensiveness, and Stonewalling. And if (and when) you do find yourself doing this, acknowledge it: “I’m sorry, I was getting defensive, this is a conversation really close to me.”

These are great strategies to keep in mind as you walk through difficult conversations. Remember during a conversation that you wanted to have, you may have to set aside your ego, be vulnerable, and truly hear the other person–even if you don’t agree. Turning a conversation into an argument is hardly ever helpful to the other person. Therefore, if you find yourself heading in this direction, perhaps it’s best to pause, take a break, then come back to it when you’re ready.

We hope that these tips will help empower you to take the first steps in having difficult conversations. Like any skill, it will take time and practice to get things right and to use these strategies consistently. So, give yourself time to practice with people you already have good relationships with and feel comfortable being vulnerable around. You don’t need to be solving the world’s biggest problems, but talking about big topics of the day with somebody else will give you the low-stakes practice you need to have bigger and bigger conversations.

Our Featured Thought Leader Tackling the Problem

Image: Listen first logo

Listen First is an incredible project working to end division in communities across America. They believe, “in the power of starting new conversations that move ‘us vs. them’ toward ‘me and you’ to turn the tide of rising rancor and deepening division. Listen First Project creates opportunities and teaches skills for conversations that tip the scales toward a stronger and more equitable future for our nation and better relationships in our daily lives.” 5

The Listen First Project works to create resources and opportunities to teach conversation skills that move us toward a less divided future. Their work extends to workplaces, schools, and society at large.

Many of the difficult conversations that we need to have as families relate to how our communities will change and grow in the future, the Listen First Project gives us a roadmap for how to navigate those conversations to lead to larger change, and more understanding.

One of my favorite pages on their site gives a great list of tips and principles to follow when having conversations, they also have a guide to conversations that walks you through how to really employ some of the skills we’ve talked about in practice. I strongly encourage you to check both of those resources out.

Things To Do Right Now:

I hope that we have helped you feel a little more comfortable having difficult conversations. So, here are some things you can do to be helpful!

Educate yourself on topics you really care about! If there are topics you are passionate about, learn more. The more you come to the table in a conversation with an open mindset and many angles to present an idea with, the less likely you are to feel overwhelmed or accidentally become defensive! Remember though, a good conversation is about learning, not about convincing!

Sit down and have a conversation! Start with a conversation to help expand the gaps in your knowledge. It might be difficult to admit you don’t’’ fully understand somebody’s point of view. But these conversations are a great way to build toward understanding at a greater level!

Donate! Consider donating to an organization like the Listen First Project or Teaching Tolerance–an organization that works to help educators have difficult conversations about race and racism with their students.
Share this newsletter! When people care, things change. Share this newsletter with 5 of your friends and family! You never know what the ripple effect could be!

Keep up with the community!

Are there difficult conversations that you have been putting off? Do you have a story of a difficult conversation that went well? If so, let us know!

Follow Ever Widening Circles on Facebook, Instagram, and Twitter where we will be posting some of our favorite content and accounts with more information.

Finally, join the #ConspiracyofGoodness Facebook Group to see what other people are up to and share inspiration you come across.

Keep a dose of optimism with you!
Download the Ever Widening Circles app and wake up to good news for a change! Our app is a great way to start or end your day on a positive note!

Check it out for Apple or Android!


  1. Teaching Tolerance. “TT Difficult Conversations.” 2015.
  2. “How to Have Difficult Conversations Virtually.” Harvard Business Review, 8 July 2019, hbr.org/2019/07/how-to-have-difficult-conversations-virtually. Accessed 7 July 2020.
  3. “8 Ways to Get a Difficult Conversation Back on Track.” Harvard Business Review, 22 May 2017, hbr.org/2017/05/8-ways-to-get-a-difficult-conversation-back-on-track. Accessed 7 July 2020.
  4. “How to Control Your Emotions During a Difficult Conversation.” Harvard Business Review, Dec. 2017, hbr.org/2017/12/how-to-control-your-emotions-during-a-difficult-conversation. Accessed 7 July 2020.
  5. Mission — Listen First Project. “Listen First Project.” Listen First Project, 7 July 2020, www.listenfirstproject.org/mission. Accessed 7 July 2020.

Liesl Ulrich-Verderber

CEO of Ever Widening Circles, Founder of EWCed

Since 2015, Liesl has been a writer, editor, and is now the CEO at Ever Widening Circles. She is a life-long camera-toting traveler, a global story seeker, and an aspiring—but more often root-tripping—outdoor enthusiast. She can be found on Instagram @Liesl.UV