Author Celeste Headlee explains 'Why Everybody Needs to Talk About Racism' in new book

As a self-described “light-skinned Black Jew,” journalist and author Celeste Headlee often hears things people wouldn’t otherwise say.

In one instance, a neighbor asked her to pick up his mail so that “those people” — he said nodding toward a Black neighborhood — wouldn't know he was away. She agreed, but also said she’s one of those people. She breaks down how to have such conversations in her new book "Speaking of Race: Why Everybody Needs to Talk About Racism — and How to Do It."

Headlee spoke to scientists and researchers who all say the only way to have engaging conversations about race — especially with a racist — is to listen and ask good questions. Even former Neo-Nazi Derek Black, the godson of former KKK leader David Duke, says a couple of caring young people with good questions at college changed his mind.

Headlee says she defines racist as “someone who makes assumptions about somebody else, either positive or negative based on their perceived race.” That definition includes everyone, she says, because scientific and observational studies show all people make assumptions about one another.

“It means that when you enter this conversation, you're not coming from a place above ready to tell somebody else how wrong they are,” she says. “You're coming from a place of, you know, we're human and we have a tendency to make these assumptions about other people. And it's wrong. And here's why.”

It’s not the job of Black people to talk to white people about race, Headlee says, though she encourages Black folks who feel they have the capacity to do so. But white liberals do need to talk to family and friends about race, she says.

“What we're seeing a lot of is people avoiding their family members who are racist or say inappropriate things,” she says. “But you know what? Scientifically speaking, the most persuasive person is somebody that they care about and who looks like them, who resembles them. And that's you.”

Science suggests Americans aren’t as polarized as we think: Decades of surveys show people agree on basic issues like that Black Americans have a harder time than white Americans, Headlee says.

Asking if someone agrees with that statement is a good place to start a conversation about race. Many people will agree, she says, but some may want to argue. If that’s the case, Headlee recommends walking away.

“It's not worth your time,” she says. “This is going to be a tough conversation, and therefore you want to invest your energy and your focus on someone who's actually willing to talk.”

One tip Headlee recommends in the book is if you believe Black Americans deserve reparations, for example, write down your most persuasive arguments in support and against to put yourself in the other person’s shoes.

Studies show that getting someone to think about their ideal self and higher values opens them to criticism and realizing that they’re wrong, Headlee says.

“You don't have to hide it at all,” she says. “You can say this is the trick because knowing the trick doesn't make the magic not work.”

Headlee writes that people can find common ground in three questions or less. In one recent conversation, she agreed with another person that they both think dogs are better than people.

Something as simple as one’s favorite season of the year or a love of tacos can establish a powerful connection that moves the conversation forward, she says.

“The important thing to remember is that establishing an empathic bond is what changes people's minds,” she says. “All of your statistics, all of your facts that you have saved up, there's really no evidence that drowning someone in statistics actually changed their perspective at all.”

Practice by asking complete strangers questions about themselves, she writes in the book.

In one conversation with someone who didn’t know Headlee’s racial background, a woman started complaining about how “people of color always want to make everything about race,” she says. Headlee asked to explain why race comes up so often, but the woman declined to hear her out.

The woman was getting angry, so Headlee said this was not her intention and switched the conversation to asking about a tattoo on the woman’s forearm.

“Lo and behold, about 10 minutes later, we came back around to the conversation,” Headlee says. “And she was then more open to it and she said, ‘You know what? I'm sorry, I get defensive because it seems to me like I've been targeted and victimized before, but thank you for being patient with me.’ ”

But it doesn’t always go quite so well. When Headlee is talking to someone who keeps getting angry, she accepts they won’t agree and walks away.

There’s one key question to ask if an argument breaks out: Can you help me understand that? People respond when asked for help, Headlee says.

“You're inviting them to tell you about themselves,” she says. “And [it’s] also inherently pleasurable for a human being to talk about themselves, their beliefs, what they think.”

The book includes an example of NPR’s Don Gonyea allowing a 68-year-old white man from the Midwest to express his thoughts in 2017. The man expressed that he believes the government helps Black people in need but not white people.

“The wrong approach would be to say, you're wrong,” Headlee says. “The better thing for him to have done is talk about his own personal experience.”

If Headlee were in Gonyea’s shoes, she would have asked why he thinks this and if something happened to him like losing a job recently. People’s racist stereotypes are often “built on air,” she says, so you can lead someone to a realization by asking them to articulate their story.

Self-persuasion is so much more powerful and effective than persuasion from an exterior source. So essentially, you're inviting them by telling their story to persuade themself,” she says. “And it works.”

Join Celeste Headlee and Robin Young on Nov. 3 at 7 p.m. ET for their free virtual event presented by Porter Square Books. 

By Celeste Headlee

Chapter 4: When It Has Worked

Have you ever experienced an epiphany? The word, Greek in origin, is used in the Christian faith to describe the manifestation of the baby Jesus to the Magi; the Feast of the Epiphany is celebrated annually on January 6. The word in general use has come to mean a sudden understanding or enlightenment, a flash of insight.

Epiphanies are rare. Most of us gain new understanding and insight regularly—that’s part of learning—but to qualify as an epiphany, the new idea must shift the philosophical ground on which your life or work is founded. The insight should be life-changing, like the enlightenment of the Buddha under the Bodhi tree or the conversion of Paul on the road to Damascus.

As infrequent as these moments are, it is yet more uncommon for them to happen over the course of a single conversation. We sometimes experience small epiphanies while listening to lectures or watching documentaries, possibly because we approach those events prepared to learn, so we really focus on what someone else is saying.

When it comes to the act of merely talking with another person, however, we seem to find it difficult to open ourselves to new information or absorb that information with the kind of intensity needed to significantly shift our understanding. Perhaps the fear of having to represent and defend our own views overwhelms our capacity to fully take in someone else’s.

And yet meaningful conversations have sparked epiphanies before, and will again.

The question is, How do we have these kinds of conversations? As you prepare to confront your racist family member or steel your- self to speak with a co-worker who belongs to an opposing political party, it may help to know about a few examples of conversations between real, deeply divided people that did change hearts and minds for the better. I want to share three case studies of conversations that resulted in epiphanies. After all, a great conversation is not a magic trick. We sometimes believe soul-stirring interactions just “happen,” or we wrongly assume that some people are gifted with persuasive abilities and the rest of us don’t have a prayer of doing what they do. The truth is, productive disagreement is the result not of talent, but of skill and patience. Skills can be learned and practiced and improved; patience can be strengthened. We can learn from what has worked in the past and create a set of principles that might increase our future chances for success.

To illustrate these transformative experiences, I’ve selected stories that involve extremists. Before we dig in, though, there is one big, glaring caveat to having conversations with actual, avowed white supremacists: don’t try this at home. Far-right extremists, including neo-Nazis and skinheads, were involved in 33 murders in the United States between 1991 and 2011, and the Department of Homeland Security said in 2020 that violent extremists are the “most persistent and lethal threat” in the nation.1

There are organizations, like Life After Hate and the Free Radicals Project, that help members of hate groups safely leave that world behind, but dealing with radicalized people is dangerous and requires specialized training. If you meet someone who is sporting swastika tattoos or a T-shirt with Pepe the Frog (originally an in- nocent cartoon character that was co-opted by white nationalists), I strongly suggest you avoid that person. Perhaps not all white supremacists are dangerous, but many of them are and it’s not worth risking your safety to find out which type you’re facing.

The purpose of revisiting instances in which ordinary people successfully convinced white supremacists to renounce their ideology is not to encourage you to replicate what they did, but to help you learn. I don’t expect you to have a conversation with a member of a hate group, not least because that would violate the most basic requirement for good conversation: mutual respect. If you are ever in a situation in which you feel unsafe or threatened, I hope you will get away as quickly as possible.

However, there are several cases in which people have not only sought out conversations with extremists but also continued meeting with them. In some rare instances, those conversations ultimately led to conversion, to a denouncement of hate and a turn toward love and acceptance.

First is the story of Derek Black, godson of David Duke (former grand wizard of the KKK) and son of Don Black, who founded the neo-Nazi online forum Stormfront in 1996. Derek was raised in a tradition of hate and became a true believer in the white nationalist cause. Then he went to college and two things happened: he met a girl who refused to give up on him, and a Jewish student began inviting him to eat Shabbat dinner with his friends every Friday.

In my conversation with him, Derek told me that the other students who attended these dinners were members of racial and religious groups that Derek had railed against in his writings and on the radio: Muslims, Jews, Blacks. Yet he originally didn’t see a discrepancy between what he said about all Blacks and his relationship with any particular Black person. “My idea was that individual people could be one thing,” he told me, “but my ideas about race would be true in the aggregate.”

BLACK: I did not show up at the college looking to have my mind changed. Actually, it was the opposite. I was extremely confident. I guess if there was anything I expected, it might have been that I’d be able to improve my own arguments by encountering people who genuinely believed that I was wrong. In retrospect, it was surprising, really surprising, to feel like there were legitimate grievances, that maybe there were factual problems.

HEADLEE: When you went to the first Shabbat dinner, it sounds like your friend decided—and tried to make everyone else adhere to this idea—that they weren’t going to bring up issues of race or anti-Semitism.

BLACK: He was very explicit that he didn’t want people to bring it up because he thought that would cause a confrontation and that a confrontation would maybe be a one-time thing and I wouldn’t come back because it would be incredibly tense. So he thought that by having himself and people at the dinner who were directly impacted by white nationalism, that itself would be a challenge. That [I would be] internally confronted on some level.

From the book SPEAKING OF RACE by Celeste Headlee. Copyright © 2021 by Celeste Headlee. Published by Harper Wave, an imprint of HarperCollins Publishers. Reprinted by permission.