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13 tips on how to have difficult conversations without losing your cool

On Feb. 3, Evergrey co-founder Mónica Guzmán and storytelling producer Ana Sofia Knauf led “We Disagree and That’s OK,” a panel about the art of navigating difficult discussions, for Crosscut’s local politics festival. The following tips and resources were collected with help from panelists Boting Zhang, Mozart Guerrier, and Warren Etheredge.

Tense conversations are hard, and we believe that the decision to engage in one, or stay in one, or see any value in one, is entirely personal. These tips are suggestions, and whether you choose to follow them is contingent on your feelings of safety and welcoming in a conversation. Thanks to conversation facilitators Bob Stains, Peggy Holman, Bo Zhang, and Heidi Petak for their tips.

How to engage:

1. Pay attention to the context of your conversation.
Ask: Can the participants feel “welcome and connection”? And can the participants feel safe enough to be “genuine in their speaking and generous in their listening”? (Bob Stains)

2. Clarify your intentions.
Moving from “I want them to understand me better” to “I want to understand them better” can be a productive shift, because you can only control your own actions. (
Peggy Holman)

3. Listen to understand.
Speak to be understood. Try to get to what’s at the heart of the matter in the issue, beyond reactions, emotions, assumptions, etc. (
Bob Stains)

4. Connect on human terms.
“We adults often need help removing our armoring and finding the vulnerability that connects us with others. Early in the conversation, look for ways to recall having been blank slates once upon a time. For example, ask your conversation partner about their childhood, or bring up a time when you yourself learned, grew, or changed your mind about something.” (Bo Zhang)

5. Offer your story.
“Tell the story behind how you came to your conclusion. Biomedical research shows that our bodies actually release positive neurotransmitters when we share stories. These neurotransmitters allow us to connect with each other.” (Heidi Petak)

6. Take a step back.
If the conversation feels stuck, step back and ask, what are our goals for this conversation? (Bo Zhang)

“If you want to share facts and the logical reasoning that has informed your values or beliefs, share them within the context of story. Where you first read the information or who shared the information with you, how that information affected you and what you chose to do about it afterwards.” (Heidi Petak)

7. Ask curious questions more than leading questions.
Curious questions start with “What is it about this issue that…?” or “Help me better understand…?” Loaded questions embed a statement and often start with the word “Why,” as in, “Why do you expect your party to do anything different now?” (
Heidi Petak)

How to navigate difficult moments and feelings:

1. Remember the power of fear.
“Fear drives vigilance for signs of danger, missing opportunities for affiliation.” (
Bob Stains)

2. See where you can turn trigger opportunities into learning opportunities.
When you want to say “I disagree,” say, “That’s an interesting perspective. Tell me more.” (
Peggy Holman)

3. Don’t feel like you have to jump in at the point of disagreement.
Especially if you haven’t established trust. “You could start with something totally light-hearted instead, OR start with a shared question — for instance, you might strongly disagree about policies, but maybe you’re both concerned about polarization. Start there: why are we polarized? Why do we feel so strongly in opposite directions? Then your disagreement becomes a case study. Each point of frustration and stuckness becomes a clue rather than a road block.” (Bo Zhang)

4. Watch for when you no longer feel safe enough to speak genuinely or listen generously.
You might need to press pause, revisit the context, or just walk away. (Bob Stains)

5. Do express things that hurt to hear from the other person.
Try to do it when you can identify the source of the trigger, share it, and communicate how it feels. For example: “My heart hurts when I hear something that I believe causes suffering.” (
Peggy Holman)

6. When positions feel tied to identity, connect on something more universal.
“Some beliefs can be changed in light of new information. Other beliefs are more core to our identities. In a world where belonging can sometimes feel hard to come by, our political affiliations have sometimes become core to our identities and sense of belonging. If that’s where your conversation is getting stuck, you might be able to find a larger struggle for belonging that encompasses you both. For instance, I’ve found that I can connect to just about anyone on the topic of modern loneliness and isolation.” (Bo Zhang)

Finally, here’s a list of questions to keep handy when you’re in a tough conversation and aren’t sure what to ask someone next:

  • What should we be talking about now that we’re not?
  • What would help you to hear as legitimate the fears/hopes/positions of others on this?
  • Tell me a story from your personal experience that led you to your position on this topic.
  • What single value do you think best defines what you want to see here?
  • What do you think is the single biggest threat to the greatness of this topic?
  • What would change look like for you?
  • What’s at the heart of moving forward for you?