08/10/2025
Some Conversations Are Harder than Others: How to Talk to People You Disagree With -
From Simplify Magazine & Celeste Headlee
I’ve been told many times in recent years that there are some people “you just can’t talk to.” One person told me she can’t speak to anyone who won’t acknowledge the existence of institutional racism. Another said that if someone he knew supported a particular presidential candidate, then “we have nothing in common and nothing to say to each other.” These days, it seems that there are more and more deal breakers than ever when it comes to who we’re willing to talk to. And yet the need to have difficult conversations has never been greater.
A good conversation is not necessarily an easy one. There are subjects so sensitive and topics so emotionally charged that discussions about them can be tricky and even dangerous. But there is not a human being on this planet with whom you have “nothing in common.” And there is no topic so volatile that it can’t be spoken of.
The Civil Rights Advocate and the Ku Klux Klan Leader
Let me tell you the story of an African American woman, named Xernona (pronounced “zer-NO-nuh”) Clayton. In the 1960s she worked for the Southern Christian Leadership Conference, or SCLC, the civil rights group whose first president was Dr. Martin Luther King Jr.
Xernona worked hard to desegregate Atlanta’s hospitals so that patients wouldn’t have to be transported miles away to an institution that catered to their race. Her work was noticed by the mayor of the city, Ivan Allen Jr. He appointed her to lead Model Cities, a program designed to improve poor neighborhoods and foster a new generation of black civic leaders.
As head of Model Cities in Atlanta, Xernona oversaw five communities. Each had a chairperson. Mayor Allen warned her about one of those chairs, Calvin Craig. Craig, at that time, was a grand dragon in the Georgia Realm of the United Klans of America, Knights of the Ku Klux Klan.
Over the course of the next year or so, Xernona and Calvin ended up talking almost every day, not just about race but about all kinds of things. For some reason, Calvin Craig kept returning to her downtown Atlanta office.
And so they would sit and chat, always friendly and always respectful. She says he never called her by her first name. “I mean, he acted so gentlemanly, and we would have such laughter,” Xernona says. “And I asked, ‘Why do you keep coming here? You and I don’t agree on anything.’ He said, ‘Ha, ha. Oh, Mrs. Clayton, you’re fun to talk to.’”
If you were unaware that Clayton and Craig were talking so often, it must have been a stunning development when Calvin Craig held a press conference in April 1968 to announce that he was leaving the K*K. He said he would henceforth dedicate his life to building a nation in which “black men and white men can stand shoulder to shoulder in a united America.”
Like most stories, this one is more complicated than it appears on the surface. Craig would eventually rejoin the K*K, only to quit again years later. But it is not an exaggeration to say that Xernona talked him out of his racism. Craig himself credited her with his conversion. Xernona has explained that she didn’t set out to change Craig’s mind. Dr. King had told her, “You’ve got to change a man’s heart before you can change his behavior.”[1]
I love this story because it exemplifies the power of conversation between two people who are willing to listen to and learn from each other. It shows us how transformative conversation can be. It’s also a response to all of the people who claim they “just can’t” talk to someone else because their opinions are too offensive.
If an African American woman can talk respectfully and openly with a grand dragon in the K*K, I find it hard to believe that you can’t talk to the guy in the coffee shop who’s wearing an offensive T-shirt or the woman in your office who can’t stop talking about her vegan diet.
At the same time, it’s obviously true that some conversations are harder than others. Some topics are riskier and carry a higher danger of offending someone or hurting their feelings. So let me offer some tried-and-true methods for having a difficult exchange without getting into an argument.
How to Talk When the Talking’s Not Easy
Through my experience and research, I’ve identified five key strategies that help facilitate a productive dialogue. They are: be curious, check your bias, show respect, stay the course, and end well.
The first component, being curious, speaks to a genuine willingness to learn something from someone else.
In 2016, former Central Intelligence Agency clandestine service officer Amaryllis Fox gave a somewhat controversial interview to Al Jazeera. Some took issue with her characterization of the war on terror, but I think her remarks are valuable for the student of conversation.
Fox explained how she was able to talk with terrorists and extremists in her work. “Everybody believes they are the good guy,” she said. “The only real way to disarm your enemy is to listen to them. If you hear them out, if you’re brave enough to really listen to their story, you can see that more often than not, you might have made some of the same choices if you’d lived their life instead of yours.”[2]
Fox wasn’t suggesting that you have to believe the person you disagree with is a “good guy.” She was offering that it’s helpful to understand how that person views himself or herself. She was talking about being interested in the culture and events and relationships that have formed that person’s opinions and considering how your thinking might be impacted if you’d been exposed to the same mixture of experiences.
She was also talking about checking your bias. Putting yourself in someone else’s shoes is one way to do that. Another is to resist the impulse—and it is a strong one—to constantly decide whether you agree with everything someone says. Listening to someone doesn’t mean agreeing with them. The purpose of listening is to understand, not to endorse.
Often we decide quickly whether or not we will agree with someone. We listen for certain words that might be clues to their politics or faith and we use them to categorize people into groups. Into one group we gather all of the people who think like we do, and into the other go all of those who think differently. The problem is, these kinds of groupings are not very accurate.
Research suggests that while most of us acknowledge that bias exists, we don’t think we are influenced by bias all that often. We accept the existence and pervasiveness of unconscious bias but aren’t conscious of our own.
Here’s the bald truth: we are all biased. Every human being is affected by unconscious biases that lead us to make incorrect assumptions about other people. Everyone.
To a certain extent, bias is a necessary survival skill. If you’re an early human, perhaps Homo erectus, wandering the jungles, you may see an animal approaching. You have to make fast assumptions about whether that animal is safe or not, based solely on its appearance. The same is true of other humans. You make split-second decisions about threats in order to have plenty of time to flee, if necessary. This could be one root of our tendency to categorize and label others based on their looks and their clothes.
Decades ago, some psychologists thought prejudice was an unfortunate side effect of bad parenting. We now know that it’s based both in survival instinct and in our need to make sense of a complicated world.
It might be tempting to believe that all stereotypes are rooted in history and ignorance, but some are actually quite modern and new ones arise regularly. For example, it wasn’t all that long ago that pink was considered a masculine color. Obviously, the opposite gender stereotypes prevail today. While the color of a baby blanket may seem like a frivolous example of stereotyping, its very silliness shows us how flimsy stereotypes are.
When we enter a conversation, all of our preconceived notions—most of which have no basis in reality—will affect its outcome. No matter how right and true your opinion feels, consider that it may be a stereotype and not fact. Try to acknowledge your bias and set it aside for the duration of the conversation. Do your best to listen without judgment and to stop yourself from making minute-by-minute decisions about what you agree with.
My third suggestion is to show respect at all times. In my opinion, respect is the cornerstone of any meaningful exchange of ideas. It is more important than finding common ground. In order to show respect, you’ll have to view the other person as a human being, deserving of respect. And you’ll need to find a way to empathize with them, in spite of your disagreements.
One way to do this is to assume that everyone is trying to bring about some kind of positive result in their lives. When you encounter someone you don’t like or don’t understand, try to identify what that goal is. Focus on their positive intentions. It’s not easy, is it? But it’s essential if you want to respect that person. Perhaps they have made different decisions than you have, perhaps they’ve learned different lessons, but in their mind, they are doing their best.
I try to practice my empathy skills in the car, which, for me, is challenging. If someone cuts me off or runs a red light, my first instinct is to assume—and sometimes say aloud—terrible things about their intelligence and their upbringing. But what I’ve tried to do lately is imagine why they are in such a hurry or why they’re in such a bad mood. Instead of the expletives that I want to say, I’ll think, She’s probably had a bad day. Maybe she’s just trying to get home to see her kid. As a parent, I can empathize.
It doesn’t really matter if my imagined scenario is true or if the person is just a terrible driver, because the point of the exercise is to train my mind to see others as individuals who face daily challenges that are equal to mine. The point is to get into the habit of viewing others as fallible human beings who are just trying to make it in a difficult world. The exercise benefits me, not the other person.
It is hard to have a productive conversation with someone you don’t respect, and your opinion of them, and what they say, is not likely to be accurate.
My next piece of advice for navigating difficult conversations is to stick it out. If you’re talking to someone and a taboo topic comes up—whether it’s death, divorce, or race—don’t try to change the subject. Don’t make a joke or go off on a tangent. Conversations on tough issues are often uncomfortable, especially when you don’t know what to say. But try to avoid getting frustrated and walking away. Silence is preferable to flight.
If you truly have nothing to say, then just listen. Accept that you may not reach an agreement and that disagreement is okay. Not every conversation, or even most, will end with a hug and an epiphany. Sometimes, just learning what someone else thinks, without changing any minds, is more than enough. Take joy in the exchange, or, at the least, take satisfaction.
And my final piece of advice really applies to all conversations but is especially true of difficult ones: end well. You don’t need to have the last word. Let go of that impulse if you want to maintain friendly relations with the other person.
Also, take a moment to thank them for sharing their thoughts. It can be scary to talk about politics or religion with someone else, so express your gratitude for their time and their openness. If you end the conversation in a friendly and gracious way, you set the groundwork and the tone for future conversations.
If It Still Goes Badly…
Of course, you will not always follow these suggestions, and that’s all right. I don’t expect you to be a perfect conversationalist, as I certainly am not. I once let an argument over police shootings get out of control to the point where my spouse and I slept in different rooms for a couple of days. Remember, emotion isn’t a character flaw—we are hardwired as emotional creatures. Sometimes you’ll succumb to the drama of the moment and your best intentions will go out the window.
If that happens and you say something you shouldn’t, apologize immediately. Acknowledge that your comments were hurtful or wrong and make no excuses. Then you can put the mistake behind you and move forward.
Sometimes a tough conversation spirals out of control—intentions or words are misunderstood, people become angry, feelings get hurt. There’s only one way to move forward: someone has to say they’re sorry.
Apologizing isn’t easy. It can be painful and awkward, but that’s the point. When we apologize, the other person sees us struggling, knows we feel uncomfortable, and their compassion response kicks in. Sincere apologies are powerful agents for reconciliation. I have found that a heartfelt apology can work miracles in a conversation and I have, at times, apologized for things for which I was not responsible.
Conversations That Change the World
If we can learn to talk about the hard things, if we can find common ground and begin to discover the issues on which we can agree, it could be possible to solve some of the more intransigent problems we face. I encourage you to open your mind and your mouth and ask some new people new questions. It only takes one good conversation to change your understanding of someone else’s world, your world, and the world at large.
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Celeste Headlee is an award-winning journalist, professional speaker, and author of Do Nothing: How to Break Away from Overworking, Overdoing, and Underliving and We Need to Talk: How to Have Conversations That Matter, the book from which this article is adapted. She is a regular guest host on NPR and American Public Media and a highly sought consultant, advising companies around the world on conversations about race, diversity, and inclusion. Her TEDx Talk sharing 10 ways to have a better conversation has over 23 million total views, and she serves as an advisory board member for ProCon.org and The Listen First Project. Celeste is recipient of the 2019 Media Changemaker Award.
