Strategies for Navigating Challenging Conversations

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Bob: Hi, and thanks for listening to the Practicing Connection Podcast. I’m Bob. My co-host Jessica is here as well. Today we’ll be talking about having challenging conversations and Jessica will be sharing a practice with us. I’m looking forward to that. Hey, Jessica. How are you?

Jessica: I am great. I’ve actually been binging a show, a very old show called Deadwood. I think it’s 20 years old at this point. Never seen it before. Had never heard of it. I’ve just been obsessed with it lately. I am by no means a history buff, and I’m not sure I should be admitting that anywhere, but honestly, every single character I’ve been looking up. Is this a real person? Then if it is a real person, I end up going down this rabbit hole, learning all about them.

This is both a testament to the quality of the show, but that’s not really what has gotten my curiosity piqued. It’s really, once I find out it’s a real person, I’m like, “Did they really do this thing? How long did they live? Did they live through Deadwood?” Because that is a pretty rough place. I’ve just been really excited to learn about a piece of our nation’s history. Again, never heard of it. This snuck up on me. I’m absolutely hooked and fascinated.

Bob: That’s awesome. First of all, I’ve not watched Deadwood, but I have been to Deadwood, South Dakota. That’s something. I get what you’re saying. I had the same experience with a show called The Great, which is much more fictionalized, it sounds like, than what you’re talking about, but deals with Catherine the Great and real characters. I was busy. I spent more time on Wikipedia trying to see what was actual and what was not accurate as I did watching the show. It was a fun two screen experience.

Jessica: Was the acting also incredible? That’s one thing I’ll say in Deadwood, the acting is incredible.

Bob: I think so. I think it’s a crazy show. Don’t turn it on and say, “Why did Bob recommend this show?” I’m not recommending it. I’m just saying I had this experience. Lately, I’ve been watching the Olympics as we’re recording this in early August 2024. It’s Olympics time in Paris. It’s been a beautiful Olympics just in terms of the camera shots and scenery, by the way, in the city of Paris, which has been really awesome. I’ve really been inspired by the stories that have highlighted community support and self-care.

We are in the US, as most of our listeners know so most of the stories that I hear are about American athletes. I wish that the coverage had more stories about athletes from around the world. Just admitting that my biased lens that I have to look through this, it’s been really inspiring to see how the athletes in gymnastics have supported each other, both in the men’s and the women’s competitions. I was watching some of the individual apparatus competitions and competitors really seem genuinely happy for each other’s success.

Again, we’re watching on TV, so everything is just seeming, but it seemed like they were just as interested in each athlete achieving the best that they are capable of as they were in terms of winning or losing. I saw a feature about American swimmer Caleb Dressel’s struggles with panic attacks and depression and how therapy and family support has helped him really change his self-talk and become better balanced. I think it just speaks to how much more we are talking about mental health and self-care that even in this ultimate competition, the best of the best, the Olympics, that we are talking to each other about how to become better balanced and more healthy.

Jessica: Wow, I love that perspective. It’s almost like the Olympics is both the original and the healthiest reality TV that we have available to us. That and The Great British Baking Show, because they also support each other.

Bob: They really do. I do love that about The Great British Baking Show. We’d love to hear what’s inspiring you. Please share what’s inspiring you by clicking the send us a text message link at the top of the description of this episode. When you click the link, your text messaging app will open. You’ll see a seven digit number and the words do not remove. Type your message after that and click send. Don’t remove the number or we won’t receive your message.

To protect your privacy, we won’t see your phone number and we can’t text you back, but we will share your feedback on a future episode. If you’re listening on a computer, you can email us with what inspires you at [email protected]. Let us know what’s inspiring you right now. We’d love to hear from you.

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Let’s learn more about having challenging conversations. Jessica, this is something as we’ve been talking about financial well-being over the last couple of weeks now. That is really important. Those are one of the most challenging conversations you can have, I think, are conversations about finances and money. Can you tell us a little bit more about the practice that you’ll be sharing today and why you chose it?

Jessica: There’s a lot of emotions that can come up around money. A lot of things can come up and there’s a lot of practices out there for starting conversations that can be uncomfortable, like conversations about money. Things like our past experiences and our upbringing and our emotions around those experiences can really cause us to go into immediate fight, flight, freeze modes, and then it just ends up being unproductive. A lot of my background is in civic engagement, and I really thought there’s some healthy practices within the civil dialogue area.

Because of my experiences with seeing them work, and because I think they provide a great foundation for talking about any challenging topic where we might find ourselves dealing with heightened emotions, I just thought it would be a really interesting place to start. This particular activity that I chose for today, it’s called Hopes and Concerns. I find it to be a really effective way to discuss our own discomfort with the act of talking about challenging topics.

Really, essentially, it’s a disarming way to begin. Collectively, either you and another person or you and the group that you’re talking with will end up with strategies for how you’re going to handle or support each other when the conversation turns challenging. The practice focuses on the conversation. It focuses on the mechanics of that conversation, not on the challenging topic itself. It also does not focus on the challenging dynamics that come up.

I got this from the Constructive Dialogue Institute, where they say that this activity can help lower tension and anxiety before it ever starts to creep up. By focusing on the mechanics of the conversation, so the things that you hope you’ll get out of the conversation and the things that you might find challenging about having a conversation, that’s what I’m talking about when I say it focuses on the mechanics of the conversation rather than digging right into the hard topics.

Bob: This sounds really exciting. It makes me think of a couple of things. I’m going to use a word that is not quite I mean. The word I’m going to use is detachment. It’s like when we’re talking about holding space, we talk about how we can be there for someone without judgment. That’s what I mean by that detachment, is that sort of maybe trying to set aside some of our core beliefs and what might trigger us. This sounds like a really great way to do it. I’m wondering if you might walk us through the practice.

Jessica: It’s actually really easy. Again, it’s called the Hopes and Concerns activity from the Constructive Dialogue Institute. We’ll include a link to the activity itself in the show notes. You can do this on your own to prepare for a conversation that you believe will be challenging or you can do this with another person or with a group of people to prepare for a shared conversation about challenging topics. I’ve modified the activity slightly from the original, but you’ll get a link to the original rather than to my modification of it. It’s really slight.

I’m going to share the activity as though you were going to do this with others. Again, you can just as easily do this on your own to prepare for a challenging conversation. First, you’re going to have everyone reflect on a conversation that did not go as well as they had wanted or hoped. You could let them know that it could be a conversation from work or with a friend or with a stranger. Have them really think about what happened, how they felt about what happened, and what they could have done differently at that moment or what they wish the other person would have done differently.

The second step is to take a moment to pause to remind everyone that the goal of this activity is not to replicate what you just had them think about. The goal is to come up with a new type of conversation. This is where we start to get into identifying the hopes and concerns that they have. As you’re taking this moment to pause, give them the two questions to ponder. Ask them to contemplate their hopes. Thinking about our group or purpose when it comes to engaging in constructive dialogue about issues that are challenging to discuss, what do you most hope for?

Then the other question is what do you worry about most when you think about these types of conversations? What do you worry about engaging in a conversation like this? The third step then is sharing. We’re past the reflection stage and now we’re going to start sharing a lot more. Have everyone use note cards or sticky notes. Instruct them to write hopes at the top of one note card or sticky note and write the word concerns on another card or sticky note.

Then just have them start brainstorming as many hopes and concerns as they want. You can either instruct them to list it on the card or you can have them have a brand new one for each card. It doesn’t matter. It’s really up to you. When they’re done, you can have them fold up their cards or sticky notes and put them into a bowl where they can take turns plucking them out one by one and discussing each of them as a group or you can have them stick or tape the notes to the wall and have everyone silently walk around reading them.

Either way, make sure that you’ve got a way of sharing where things are being equitably looked at. Then number four, discuss. How can we support each other in achieving some of these hopes? How can we support each other in mitigating or avoiding some of these concerns? The answer to these questions can be used then to guide the conversation as you get into those challenging topics. I want to just repeat those last two questions. How can we support each other in achieving some of these hopes and how can we support each other in mitigating or avoiding some of these concerns? That’s really it. It’s reflection, sharing, and discussing about the challenging conversation that you will be having as a group rather than having the conversation.

Bob: Thanks for guiding us through that, Jessica. I’m wondering if we could talk a little bit about how we might use this if we aren’t in a group. If we’re doing it to prepare for a challenging conversation and it occurs to me that maybe it’s going to require some perspective taking so that we can not just focus on our hopes for a conversation.

Jessica: I would still have you go through the steps of, so reflect on a conversation that didn’t go as well as you had wanted or hoped. What happened? How did you feel? What could you have done differently or what do you wish the other person would have done differently? Then I’d still want you to write through what your hopes are and concerns are about that. Just like we would have gone through the activity with others. When it comes to this conversation that you’re preparing for, what do you hope for?

Then when it comes to this conversation, what do you worry about the most when you think about the conversation you’re going to have? I think for the sharing, I think you could formulate your response to this. When you meet with the person, when you do get to that point of meeting with a person, you can share. I really hope for this. How does that sound to you? You can check in with them. They didn’t have the benefit of going through the other parts of the activity with you. You could also choose to take them through the first two parts.

You guys, when you get to the sharing, you could share together. I think that once it gets to the sharing, that’s where it involves other people. You could choose to share when you get into the conversation and you could check in using that. Then you could ask for their hopes and their concerns. I want to be careful that you’re not crossing a line into trying to steer a conversation in a way that you only hope for it to be. I do feel like you can still have a hope for the conversation. I think a lot of people do when they go into one. I think if you’re not going to share what that hope is, then I think just be really careful that you’re not using that to steer. I do think you could have a plan for how you’re going to support yourself through some of those concerns.

Bob: You anticipated where my mind was going about if we’re only concerned with our hopes. I love the idea of actually saying, “Here are my hopes for this conversation. What are yours?” That’s really powerful.

Jessica: I really find this activity to be helpful, especially if you’re the kind of person who has a hard time with challenging conversations. If you at least know how you’re going to support yourself through some of the concerns that you have, and if you have your hope articulated to a point where you could share them with other people and it could help take some of the tension down in the room, I think that could go a long way toward actually getting to the challenging topic.

Bob: Thank you so much again for sharing that practice.

Jessica: You’re so welcome.

Bob: That’s it for this episode. Thanks for joining us. If you enjoyed this episode, click the share button in your podcast app to share it with a friend. We’ll be back next week with a practice for perspective taking. Until then, keep practicing.

Kalin Goble: The Practicing Connection Podcast is a production of OneOp and is supported by the National Institute of Food and Agriculture, US Department of Agriculture, and the Office of Military Family Readiness Policy, US Department of Defense. Under award numbers 2019-48770-30366 and 2023-48770-41333.

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