The Year of Talking Dangerously: How To Have Difficult Conversations

Graddha
6 min readDec 21, 2020

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By Marlis Jansen with Lily Boyar

With the holidays approaching, I (Marlis) was eager to find a safe way to celebrate the season. I desperately wanted to maintain some sense of normalcy and enjoy an occasion with our “covid pod.” I sat down with my family to discuss hosting a small and festive gathering, fully expecting to be met with excitement. However, it became clear that we each had a different definition of who was part of our covid pod. We couldn’t seem to agree on anything and the conversation quickly devolved into hurt feelings.

I walked away wondering where we went wrong. How did it go sideways? I took a walk on the beach and reached out to a few friends. A number of them recognized the phenomenon I was describing. The ideas in this post are the product of a few good conversations with my colleague Lily Boyar. We both realized that there is an art to navigating difficult conversations and we all can benefit from practice.

The World is Divided and it Needs our Help

This year has tested us. We’ve dealt with the presence of COVID-19 and threats to our health, community, and freedom. We’ve grieved the death of George Floyd (and too many others) amplifying a racial equity movement and inspiring many to acknowledge their privilege and take action against systemic racism. We’ve made it through a divisive election season, and still our country is more politically polarized than it’s ever been. 2020 hasn’t been easy.

As we’re all trying to make sense of our world, we are challenged to broach subjects that touch on our most deeply held convictions, values, and attitudes. Whether the conversation is about politics, race, money, or who is going to do the dishes, we are being called to, step in, speak up, and act. We are all being called, more than ever, to engage in difficult conversations.

Difficult Conversations May Feel Like the Obstacle, But in Fact, They’re Our Path Forward

Difficult conversations become high stakes when they threaten human dignity. Whether it’s about money, sex or planning for death, it can feel dangerous, messy, awkward, and uncomfortable when we’ve determined there are real consequences involved. We might disagree, offend someone, make a mistake, or worst of all, fracture a cherished relationship. So, why have them at all?

Challenging conversations have the power to shift potential energy into kinetic energy. By discussing complex or controversial topics, we put our values and ideas into motion and create a pathway for change. When conducted with empathy and mutual respect, they can deepen our relationships and make us feel more connected to our community.

It often feels easier to avoid sticky topics. But by committing to having difficult conversations you’re in part making the decision to contribute to a better future, and opening up the possibility to create deeper, more connected relationships.

Practice, Practice, Practice

After having a challenging discussion with my family about our holiday plans, I began reflecting on what makes a difficult conversation “successful.” Surely, there are times when you will fundamentally disagree with someone. There will be mistakes and missteps. But maybe these aren’t the right heuristics for evaluating whether a tough conversation was constructive. Perhaps successful dialogue is more about the process than the outcome itself.

It may never feel “easy” to discuss topics that feel controversial or dangerous, but with practice, it does become less threatening. Here are a few suggestions of ways to approach your next difficult conversation.

Start by Calling Out Your Intentions. We rarely take the time to explicitly communicate our intentions before diving headfirst into what feels like a dangerous conversation. Often, we are not even clear for ourselves what we are hoping to achieve. Do we want to change someone’s mind? Just be heard? It’s no wonder we find ourselves in murky waters. It can be helpful to stop and ask yourself, why is it important to have this conversation? What do I want? This will help you identify your intentions and shared goals for the discussion. When discussing the holidays with my family, it might have been helpful if I had vulnerably shared why it was so important to me to find a safe way to gather with loved ones. This wouldn’t guarantee that my idea would be accepted, but by verbalizing my sensitivities upfront, they might have had more empathy and understanding. This would have set the tone for navigating the conversation respectfully and generating creative solutions.

Find Common Ground. What can we both agree on? This is a helpful question to ask at the beginning of a potentially controversial conversation. If we can identify where we align (no matter how narrow it may be) we remind each other of the fundamental ideas that we share, making it easier to have a productive and respectful discussion. Take politics for example. Democrats and Republicans may align on the importance of protecting our environment, however, both parties have different reasoning, solutions, or beliefs for arriving at that conclusion. If we are able to name our commonalities upfront (in this case that both sides see an impending threat to our environment) we have a shared idea to anchor on as we explore our different points of view. By identifying where you align on a controversial issue, you are reminding each other of the fundamental ideas that you share, making it easier to find mutual solutions.

When You Have an Agenda, Name It! We’ve all been in a situation where we rehearse a difficult conversation with someone in our head before it even happens. By the time we actually hold the conversation, we already have a clear expectation of how it will go. This eagerness to be “right” or “solve” a problem too quickly can keep us from engaging in a thoughtful, exploratory discussion. Sometimes a difficult conversation requires that we let our ego take a backseat. Instead of evaluating the success of a conversation by whether we’ve agreed on a solution, we can practice simply inviting the other person to hang in there with us and explore an issue with curiosity and openness. Sometimes a tough conversation requires that we let go of our prescribed agenda. This takes practice!

Set Boundaries for the Conversation, While Maintaining Warmth. Difficult conversations require us to create a level of safety so we can speak freely and make mistakes. However, this doesn’t mean we have to overlook our boundaries. In fact, we must stay true to our values and speak up in the moment if something is said that feels harmful or hurtful. Though challenging, it is possible to maintain warmth and goodwill, while still being direct and addressing discomfort in the moment.

Be a Good Listener. Arielle Nobile is an award-winning documentary filmmaker and founder of the Belonging in the USA docu-series and Legacy Connections Films. Nobile is masterful at interviewing people and telling their meaningful stories about multigenerational legacies through film. On the topic of difficult conversations, Nobile reminds us to be aware of when we’re truly listening to someone, rather than listening for something that will validate our own point of view or assumption about the other person. Nobile acknowledges that it can be challenging to listen without expectation, however, she believes in most cases, we just want to feel heard. Nobile says we can practice active listening by referring back to the other person and summarizing what we’veve learned. Consider asking clarifying questions first, before jumping straight into your rebuttal.

Access Your Empathy. We can actually practice the exercise of adopting the other person’s stance in a difficult conversation. What does it feel like to try on their point of view? What do they see that I don’t? By approaching someone with empathy, we are able to slow down, connect with compassion, and understand them more deeply. This is essential for having a thoughtful, respectful dialogue.

Check-in With the Other Person. After the conversation, discuss how it went. How do you both feel? Whether you agree or disagree is less important than what you mean to each other. If at the end of a difficult conversation, you can reaffirm the strength of your relationship, it will make it easier to be authentic when talking about the hard stuff.

It’s Time to Start Talking

It is important that we practice having difficult conversations if we want to create a kind, sustainable and just world. The stakes are too high to be restricted by our own discomfort. It takes courage and vulnerability to fully embrace this. What I’ve learned this year is that there are real risks to not talking.

Difficult conversations invite us to connect with our purpose and humanity. Each time we have a spirited discussion, no matter how successful we may feel it was in retrospect, we are practicing valuable communication that is critical to each and every one of our futures.

Tell us about a difficult conversation you’ve had recently in the comments section below. What made it successful? What could have made it better?

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Graddha
Graddha

Written by Graddha

Wealth Dynamics Guides. Promoting human connection, empowerment and creativity by understanding wealth in all its forms.

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