Breaking through the Barriers: Techniques for Facilitating Difficult Conversations

Breaking through the Barriers: Techniques for Facilitating Difficult Conversations

I do not need to tell you that conversations can be difficult. You’ve experienced it. And yet, you have also had conversations that have shifted your worldview or expanded your connection to another person, community, or culture. Those beautiful outcomes arise from working through a dialogue to discover something new. Those moments motivate us.

Despite this potential, our culture continues to polarize; there are less difficult conversations and the political consequences have unfolded in front of us. We avoid dialogue, fight, “unfriend,” or pretend to agree. None of these are real conversations, but they occur every day because of communication barriers. These barriers are walls that come between us, when we have divergent viewpoints, that prevent us from gaining understanding. I want to help us move past these barriers, but first ask yourself this: 

What barriers do we experience that prevent us from having difficult conversations?

(Please, take a minute and reflect.)

You probably came up with A LOT because these barriers are so normalized in our culture. Here are four techniques used in small-group facilitation that will help you break through these barriers.

Steer Into the Conflict

This is the shortest tip, yet it’s the most powerful. It’s the choice that you can make as a leader to steer directly into a conflict existing within your community. This may feel like the last thing you want to do in a heated room. However, avoiding the conflict means succumbing to barriers, like fear or discomfort, and allowing misunderstandings and apathy to intensify. Once you’ve made this meaningful choice, you can use the next few skills to support you.

Transform Your Questions

When we enter difficult conversations, we tend to have scripts that we fall back on. These are lines (sometimes verbatim) we say over and over again to defend our opinions and prove our “side.” To bypass this barrier and create authentic responses, we ask Open-Ended Questions. Open-Ended Questions cannot be answered with a short yes/no. They require greater depth and complexity.

For example, rather than asking, “Remi, do you agree with Darren?” (he could simply answer “yes”) you might say, “Remi, what is your response to what Darren said about __________?” or “How are you reacting to what Darren just said?” Notice that these questions use What or How, not Why. “Why” is a wonderful tool for curiosity, but it often generates justifications that put the conversation into defense-mode, therefore we avoid it.

Expand Your Listening

Effective listening is an experience of full-body engagement that takes practice. Particularly in difficult conversations, we can only listen by being fully present. We also show we are listening with Reflective Listening. This tool reassures others that they are being heard and that divergent perspectives are welcome. It shows that you are truly trying to understand and reminds the group to also express empathy this way. It is valuable in clarifying ideas and themes, and it keeps everyone on the same page. For example, “Remi, it sounds like the story that Darren shared made you angry. Guess what, this statement may be wrong! However, you are helping them process what they just said, and you are telling them that they are worth being understood.

You can start a reflection with a phrase like:

  • I’m hearing you say…
  • I’m noticing that…
  • I sense that…

Then, add your mirror statement. You can reflect feelings, like the example, exact words, themes, or ideas that you are hearing “beneath” their words.

Build Meaningful Connections

This skill is essentially anything that you can do to connect people. This often involves disrupting “normal” conversation patterns that allow people to avoid talking directly to one another. For example, if people are disagreeing or avoiding conflict say, “It seems like you are responding to what Darren said, you can say it to him. Also, use open-ended questions, “Remi, what are you disagreeing with Darren about?” or “Remi and Darren, what is it like for you two to both ____(some connection)____?” Use reflective listening, “It seems like you two are actually agreeing with each other.” This is helpful when they may not realize their agreement.

I get it, this can be a social risk, but this practice will establish connections that last for the rest of the conversation and beyond.

These Techniques + Your Investment = Deeper Connections in your Community

Use these techniques to support collaboration in your communities and between communities different from your own. Beyond these skills, you will discover useful ways to surpass barriers to have more difficult, meaningful conversations. Your investment in directing people to have real dialogue will lead to deeper connections, expanded perspectives, and a stronger sense of community.


Carly Pourzand’s experience as a small group facilitator and trainer developed for over six years at World in Conversation, Center for Public Diplomacy. There, she practiced a grassroots approach to conflict resolution and facilitated cross-cultural conversations on contentious social issues. Carly continues her dialogue work as a facilitation trainer to professionals in Colombia through a community-led organization called Colombia se Escucha. She is also a full-time grad student and policy intern at Pennsylvania Immigrant and Citizenship Coalition (PICC).

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