Having Difficult Conversations

Authored & Created by SJE & DU DialogUes

Community + Values believes that our work as a community is best carried through deep and authentic partnerships with people and organizations across campus. One of these phenomenal partners is SJE & DU DialogUes. Through their efforts, this page presents how to share, create, and connect with others for difficult conversations.


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An introduction to difficult conversations

What a task it is to provide resources on having difficult conversations. We talk to people all the time, but do we actually have conversations?

We wanted to establish a theme that touched on the story of dialogue - whether the conversation is easy, casual, or challenging. We boiled it down to: share, create, and connect

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    Sharing thoughts, opinions, beliefs, fears, or optimistic views helps.... 

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    Create new perspectives and ideas, and ideally, more understanding.

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    This, in turn, sets the stage for deeper levels of connection and growth for individuals and groups alike.

All of the content, chosen visuals, and questions below were intentionally chosen and carefully crafted by Social Justice Education (SJE) in Student Affairs & Inclusive Excellence. As you read them, we hope they can inspire new ways of sharing, creating, and connecting in the conversations that you hold. Have questions about the content? Contact Neda Kikhia at igr@du.edu


Let's dig into how we can have difficult conversations

In this insightful talk, Celeste Headlee, a radio host for decades, shares 10 useful rules for having better conversations.

Interested in the ingredients of a great conversation? Check out this video then consider the questions below. 

    Celeste Headlee | 10 ways to have a better conversation 



    • “A conversation requires a balance between talking and listening."  Reflect on the conversations you were a part of throughout today: do you feel the balance between talking and listening was met? If not, what are some ways you or others can get closer to achieving that balance in future conversations?
    • Which of the ways that Celeste mentioned are you most likely to implement in your own life, and why?



    Edutopia: Showing Up for Conversations About Social Justice

    This video is a conversation between students and their teacher discussing the important tenets of social justice. They dive into understanding their privilege, minoritized identities, and their roles in creating change for their community. Students were able to reflect on how they can incorporate the conversations into their daily lives. 


    • Why is important to create space for conversations with young people?  
    • How can a conversation like this build community and trust? 
    • Why should conversations about social justice be and include individuals with privilege?


    Brené Brown on Empathy

    Acclaimed researcher and author Brene Brown concisely and warmly distinguishes between empathy and sympathy and describes how to respond with genuineness in the face of stressful conversations.


    • What are the dangers of "silver lining” hardships that others share with us in conversation?
    • Which quality of empathy do you believe is most important to utilize when navigating difficult discussions?


    The Danger of a Single Story | Chimamanda Ngozi Adichie

    Acclaimed Nigerian author and speaker Chimamanda Ngozi Adichie speaks in her 2009 Ted Talk about the negative impacts of stereotyping, discrimination, and what she calls the “single story”. In this talk, Adichie speaks to her own experience migrating to the United States for college and connects to her experiences living in Nigeria.


    • What does Adichie mean when she talks about the single story?
    • How can we build awareness around our implicit biases that lead to single stories?
    • How do media and other sources of information play a role in depicting a single story?



    Taking the Stress out of Stressful Conversations

    Holly Weeks, HBR

    Stressful conversations are never easy, but we can all fare better if we prepare for them by developing greater awareness of our vulnerabilities and better techniques for handling ourselves. The advice and tools described in this article can be helpful in unilaterally reducing the strain in stressful conversations.


    • Reflect on a time when you experienced an emotional or physical response while participating in a stressful conversation. How did you react when those feelings emerged? 
    • Think of a stressful conversation you may be avoiding in your life right now – which approaches would you consider using after reading this article?
    • Think back on a time when a friend, family member, colleague, or stranger responded to a stressful conversation constructively. What was their approach and why did you appreciate it?



    How to Have Difficult Conversations

    Dan Mager, MSW, Psychology Today

    Every element of a difficult conversation has the potential to give us anxiety: contemplating the conversation before it even arrives, the conversation itself, and the consequences following the conversation are all anxiety producing scenarios. However, learning how to prepare for such conversations can decrease our anxiety and increase the likelihood of the conversation going productively.


    • Which preparation skill do you feel already confident in? Which skill would you like to work on? 
    • Are some conversations inherently harder to prepare for than others, or does it depend? Why?



    From Safe Spaces to Brave Spaces

    Brian Arao & Kristi Clemens, The Art of Effective Facilitation

    This book chapter, taken from The Art of Effective Facilitation, challenges the notion of creating “safe spaces” for social justice education, and encourages facilitators and educators to strive toward creating “brave spaces.” The catalyst for this transition was the disconnect that students and participants felt between what they believed to be “safe” and how social justice conversations actually occurred. Alternatively, the term “brave” touches on the challenges and risk that is inherently built into conversations about race, identity, power and/or privilege. The authors provide a case study to exemplify their argument and propose suggestions for reframing these conversations to be more productive and promote greater authenticity among participants.


    • This article encourages facilitators and participants to “challenge by choice.” That is, individuals can choose to what extent they participate in the conversation. With this in mind, consider the following question: what may be limiting you from challenging yourself to share, explore, or understand while discussing with others? 
    • How does your response to the previous question help you conceptualize the term “brave?"

    * Image Sourced from InfoQ

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    Additional Resources

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      Greater Good Science Center: Bridging Differences Playbook 

      Designed by the Greater Good Science Center, the Bridging Differences Playbook serves as a useful resource to help people engage in healthy conversation. By outlining a series of skills and strategies at the intrapersonal, interpersonal, and group levels, think of this playbook as a companion guide for fostering greater dialogues, relationships, and understanding with whom we interact. 


      • One of the requirements for bridging differences is showing modesty and humility. That is, “accepting that you don’t have all the answers or a monopoly on the truth.” With this statement in mind, what are some personal biases, perceptions, or opinions that might be limiting your capacity to bridge differences? 
      • The playbook also notes that “bridging involves inner work, not just action.” Much of the work that is needed to bridge must be done on our own, and subsequently contributes to the conversations, gestures and relationships we have – or hope to have – with others. What inner work are you doing in an effort to bridge differences? What inner work would you like to be doing?
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      Brené Brown: Unlocking Us

      Brené shares her thoughts about why accountability is a prerequisite for change, and why we need to get our heads and hearts around the difference between being held accountable for racism and feeling shame and being shamed. She shares her personal stories of being held accountable and holding herself accountable, as well as strategies for pulling her “thinking brain” back online when experiencing the flight and fight energy fueled by shame. 


      • Reflect on an experience you had with shame – what were your physical, emotional reactions?
      • In your everyday life, how can you utilize Brown’s “transform and roll out” approach when experiencing moments of shame? 
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