Bridging the Unbridgeable
Standing in line at Baskin-Robbins as a young boy was overwhelming. Thirty-one flavors staring back, and you can only pick one scoop. Reading How to Have Impossible Conversations[1] by Peter Boghossian and James Lindsay feels the same way. The book lays out 36 practical techniques for navigating what they call “impossible conversations”—those exchanges that feel futile because of the unbridgeable gulfs in belief, morality, or worldview.[2] With so much on the menu, choosing where to focus is no small task. What struck me, though, was the humility of the authors. They don’t just teach from a distance; they admit the ways they’ve gotten it wrong. That posture of humility resonates with me as a pastor, husband, father, and leader. For this article, I’ll focus on three beginner-level insights: Modeling, Words, and Asking Questions.
Modeling
The first principle may be the simplest, but it’s also the most difficult: if you want your conversation partner to behave in a certain way, you must model that behavior yourself. Boghossian and Lindsay emphasize that we can’t expect others to be calm, thoughtful, or open if we ourselves are defensive, impatient, or dismissive. In one of their stories, they asked Muslim leaders a direct question about whether stoning for adultery should be carried out. While the question itself was sensitive, they modeled the very thing they hoped to receive—clarity. By showing honesty and restraint in the way they asked, they created space for a thoughtful response.
This connects to what the authors call the “Unread Library Effect.”[3] Most of us assume we know more than we actually do. When we’re willing to admit ignorance or uncertainty, we model intellectual humility. That small act gives our conversation partner permission to be honest about their own limits.
Leadership thinkers like Andy Crouch and Simon Walker deepen this insight. In Strong and Weak, Crouch argues that flourishing requires both authority and vulnerability.[4] Real leaders don’t avoid risk; they step into it for the sake of others. Similarly, Walker’s vision of “the undefended leader”[5] calls us to drop the armor of control, image-management, and self-protection. Taken together, they show that modeling in conversation isn’t just about technique — it’s about posture. By risking openness, by admitting what we don’t know, and by refusing to hide behind certainty or power, we create the conditions where others feel safe to do the same.
In pastoral work, I’ve seen this dynamic countless times. People often assume they “know” the Bible, but when pressed to explain, they realize their understanding is partial. My willingness to say, “I don’t know, but let’s explore together,” models both humility and risk-taking. It’s a small act of being undefended, and it makes room for others to admit their own limitations.
At home, this principle is just as powerful. As a father, if I want my children to listen well and admit mistakes, I have to demonstrate those same qualities. When I lose patience, the quickest way to restore trust is to confess it openly. Modeling, then, is not just a conversational strategy — it is a way of leading with integrity, courage, and vulnerability in every sphere of life.
Words
Even when we model humility and openness, conversations can falter if we aren’t speaking the same language. Boghossian and Lindsay emphasize that many arguments aren’t truly about substance—they’re about the meanings of words. The Google memo controversy illustrates this vividly: a clash erupted not over facts but over what “diversity and inclusion” meant. Without clarifying definitions, both sides assumed they were arguing about reality, when they were actually talking past each other.[6]
In pastoral and leadership contexts, this is a familiar challenge. Words like “gospel,” “Christian,” or “church” carry different meanings for different people. Clarifying those meanings before entering a discussion prevents unnecessary conflict and opens space for understanding.[7] Misunderstandings of moral language can escalate disagreements because people often tie their beliefs to their sense of moral identity. By defining terms and agreeing on their meanings, we create a shared foundation for dialogue.
At home, the same principle applies. As a father, I can prevent many conflicts with my children simply by asking, “What do you mean by that?” or clarifying expectations in ways they can understand. In ministry, careful stewardship of words creates space for authentic dialogue rather than defensive posturing. When leaders pay attention to the words they use and ensure mutual understanding, they model clarity and respect, making conversations productive rather than confrontational. Words, when handled well, become bridges instead of barriers.
Asking Questions
The third beginner-level insight is deceptively powerful: ask questions, and ask them well. Boghossian and Lindsay highlight the Socratic approach, which relies less on argumentation and more on targeted, thoughtful questioning.[8] Good questions aren’t closed yes-or-no prompts; they are open-ended, inviting your conversation partner to explain their reasoning and thinking. “How” and “what” questions, in particular, allow dialogue to unfold naturally, creating space for reflection and exploration.
In ministry and leadership, this skill is invaluable. Asking calibrated questions such as, “What do you mean by that belief?” or “How did you arrive at that conclusion?” allows people to articulate their thinking without feeling attacked. It also surfaces assumptions or gaps in understanding—what the authors call the “Unread Library Effect”—without the discomfort of direct confrontation.
At home, the difference is even more apparent. I’ve noticed it countless times with my own children: the moment I launch into a monologue, their eyes glaze over. I may be explaining profound spiritual truths or trying to convey a timeless life-changing insight, but my lecture often shuts them down. The breakthrough comes when I pause and ask, “What do you think about this?” or “How would you handle that?” Suddenly, the conversation becomes two-way, and they engage instead of retreat.
The key, Boghossian and Lindsay note, is authenticity.[9] Questions should reflect genuine curiosity, not a hidden agenda or attempt to “win” the conversation. In practice, this means listening attentively, following up thoughtfully, and being willing to modify your own thinking based on what you learn. Asking questions, then, is not just a conversational tool—it is a posture of humility, engagement, and care. In a world of “impossible conversations,” asking the right questions may be the single most effective way to create understanding where there once was division.
Conclusion
At first glance, modeling, clarifying words, and asking questions may seem like small things. But in practice, they open space where genuine dialogue can happen. They shift the focus from winning an argument to building a relationship. That shift is what makes “impossible” conversations possible. As I reflect on this book alongside others we’ve read—Humble Leadership[10], Thinking, Fast and Slow[11], and even the biblical example of leaders who paired truth with humility—I see a common thread: flourishing conversations emerge from trust, curiosity, and patience. For pastors, parents, and leaders, the invitation is simple but challenging. We don’t need to master all 36 techniques. We can begin with practicing these three. Small as they are, they create the conditions for bridges to be built where walls once stood.
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[1] Peter Boghossian and James Lindsay, How to Have Impossible Conversations: A Very Practical Guide, (New York: Hachette Books, 2019).
[2] Boghossian and Lindsay, How to Have Impossible Conversations, 3.
[3] Boghossian and Lindsay, How to Have Impossible Conversations, 36.
[4] Andy Crouch, Strong and Weak, (Downers Grove, IL: IVP Books, 2016), 11.
[5] Simon Walker, The Undefended Leader, (Piquant Editions, 2010).
[6] Boghossian and Lindsay, How to Have Impossible Conversations, 40.
[7] Boghossian and Lindsay, How to Have Impossible Conversations, 41.
[8] Boghossian and Lindsay, How to Have Impossible Conversations, 43.
[9] Boghossian and Lindsay, How to Have Impossible Conversations, 45.
[10] Edgar H. Scheinand Peter A. Schein, Humble Leadership, Second Edition: The Power of Relationships, Openness, and Trust. (N.p.: Berrett-Koehler Publishers, 2023).
[11] Kahneman, Daniel, Thinking, Fast and Slow, (Farrar, Straus and Giroux. Kindle Edition, 2011).
About the Author
Chad Warren
A husband, father, pastor, teacher, and student seeking to help others flourish.13 responses to “Bridging the Unbridgeable”
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Chad, looking forward to seeing you in Cape Town.
In your experience as a pastor and leader, which of the three practices, modelling humility, clarifying words, and asking questions, has been the hardest to sustain consistently, and what safeguards have you found helpful in keeping it alive over the long haul?
Chad,
Like Glyn, I am looking forward to seeing you in Capetown. If you anticipate future conversations that might come up, what technique might you think would be good to employ?
Looking forward to Cape Town! That’s a helpful question. One technique I want to keep practicing is what I’d call curious framing. Instead of starting with my position, I’d begin with questions that frame the conversation around values and hopes. For example, asking, “What do you most want to safeguard in your understanding of this issue?” or “What part of this gives you hope?”
Similarly, I like to set the tone early by getting agreement as to the purpose of the conversation.
I’m looking forward to Cape Town as well! In answer to your question, for me, the hardest practice to sustain has been asking questions instead of slipping into lecture mode. As a pastor (and a parent), I often feel the pressure to have the answers ready. It’s easy to default to explaining or teaching rather than drawing someone out.
A safeguard that I’ve learned to try and remember is a simple mental cue: pause before pronouncing. When I feel the urge to jump in with an explanation, I try to pause and instead ask, “What do you think?” or “Can you tell me more?” It’s not foolproof, but it helps when I remember to use it.
great post Chad. Thank you for sharing this. Can you describe an impossible conversation you’ve had as a pastor recently. How was that conversation different then it could have been? Where would you take the conversation differently if you could?
Yes, I actually had a recent “impossible conversation” with a congregant around the topic of eschatology. She came with a very firm perspective and asked me to explain mine, but it quickly became clear that she wasn’t open to considering another view. She wasn’t combative, but the posture was more about defending her framework than exploring together.
Looking back, I realize I defaulted into giving explanations—laying out my position and some of the biblical reasons behind it. That’s not wrong, but it didn’t make the conversation as fruitful as it could have been.
If I could take the conversation differently, I would lean into questions instead of explanations. For example, I might ask, “What’s at stake for you in holding this view?” or “How does your hope in Christ get shaped by this perspective?” That would have honored her position, helped me understand her motivations, and perhaps opened space for a richer exchange.
Hi Chad! I really enjoyed reading this. You mentioned your willingness to say, “I don’t know, but let’s explore together,” which models both humility and risk-taking. Might it also suggest you are also bringing forth vulnerability? What part do you feel vulnerability plays in these impossible conversations?
I think vulnerability is essential in “impossible conversations.” It signals that the goal isn’t control but connection. When I risk vulnerability, I’m modeling that relationships aren’t built on having airtight answers—they’re built on trust, honesty, and mutual learning. Vulnerability creates room for the other person to be honest, too, instead of posturing or pretending.
Chad, I’m sure you are a really good dad, husband, and pastor. You demonstrated that last year while we were in DC and you had an emergency at your home church that had to be handled while you were away.
I’m curious: how do you personally handle a conversation with a family member or parishioner when you’ve already modeled humility and asked clarifying questions, but the other person remains defensive and unwilling to engage?
Thank you—that’s kind of you to say. And that’s a really good, real-life question. Honestly, there are times when, even after I’ve tried to model humility, clarify words, and ask questions, the other person still stays defensive or closed off. That’s hard, because my instinct is to keep pressing until there’s some breakthrough—but that usually makes things worse.
In those moments, I’ve learned that the best move is often to release the conversation, but not the relationship. I might say something like, “I can tell this matters a lot to you, and I don’t want to push too hard. Maybe we can revisit it another time.” That acknowledges their perspective without escalating the tension.
I also try to remember that the Spirit does the deeper work of conviction and transformation—not me. My role is to be faithful in how I engage, not to force an outcome. Sometimes the most Christlike thing I can do is step back, pray, and keep showing up in a relationship so the door stays open.
Hi Chad – thanks for highlighting modeling humility, clarifying the meaning of words, and asking authentic questions. Which of these three practices do you find the most challenging for yourself and in those you lead? I’d love to hear any insight on the “why” as well!
Thanks for that question! Since I’ve alluded to asking authentic questions in some of my other responses, I’ll say here that it’s definitely the most challenging for me. As a pastor, it’s tempting to default to answers or explanations, but genuine curiosity requires both humility (admitting I don’t know everything) and vulnerability (risking what the other person might say). I see that same struggle in those I lead as well. Still, when we push past the urge to lecture and choose curiosity instead, the conversation almost always becomes more meaningful.
Thank you, Mr. Chad for the wonderful and insightful post. When you mentioned the ’36 techniques’ it makes me go back and re-read for I realize that I was too general in scheming through the text, thank you. You mentioned that flourishing is nourished by authority and vulnerability. What would authority look like when one is vulnerable? Thank you, Mr. Chad.