How To Have Hard Conversations (and Maybe Save the World)

Here it goes again.

You’re at home, or work, or out with friends.

And then someone,
a family member,
an acquaintance,
makes a comment about a current event or a particular social issue.

Maybe it’s intolerant, ill-informed, hopelessly biased, or downright degrading,
but nonetheless, you can’t let it go. So, you open your mouth and fire back.

Before you know it, you’re engaged in a frustrating battle of wills.
The conversation ends with both of you flustered, angry, and nowhere near close to reconciling the matter at hand.

This has happened to me too many times for me to count.

As someone who regularly speaks his mind and writes about controversial issues, I knew I had to find a way to have better conversations with people whom I disagree. Therefore, I’ve developed ten principles that have helped me navigate thorny conversations and even changed some people’s minds on difficult issues.

I hope you find them helpful and encouraging.

The Psychology of Right and Wrong


In her 2011 TED Talk, Kathryn Schulz asks her audience a very interesting question:

How does it feel to be wrong?

In the darkened auditorium, a few brave souls answer her question aloud:
“Thumbs down.”

I think a lot of us would probably answer the same way. The words “shamed,” “annoyed,” and “discouraged” come to my mind.

However, Schulz quickly delivers a devastating and insightful twist.

The words the audience members used to describe how it feels to be wrong are actually words used to describe the feeling of realizing you are wrong.

And that’s because being wrong feels just like being right until you discover otherwise.

The first couple of principles focus on what you can do before a hard conversation in order to acknowledge your own weaknesses and blind spots.

Principle #1: You are not an expert on anything (and if you are, you’re probably not arguing about it).

There is a good reason you don’t see experts in a particular field of study duking it out on online message boards and internet forums: An honest pursuit of knowledge results in humility, not self-righteousness indignation. 

And this is because the more you learn about a topic, the more you understand how much more there is to know about a topic.

Let me pull this band-aid off real quick: Simply by being human, you are far less knowledgable, rationale, competent, and objective than your ego wants you to believe.

However, our Ego Protection Drive would like us to believe the exact opposite.

The “Ego Protection Drive” is our brain’s attempt to rescue us from feeling embarrassed or looking stupid. It will go out of its way to focus on information that confirms your beliefs while ignoring information that challenges them.

No one is unbiased. There is not a single belief in your heart or idea in your head that has not been dramatically influenced by your upbringing, environment, and community.

And that’s okay.

Acknowledging your personal biases and limitations is the first step toward a constructive dialogue.

Principle #2: Set realistic expectations.

It is notoriously difficult to change someone’s mind.

Therefore, if you’re going into a hard conversation with the expectation that you’re about to rock somebody’s world, show them the folly of their ways, and win another convert to your side then you’re setting the stage for an unproductive and potentially harmful interaction.

I try to approach every interaction – whether online or in person – with the goal of changing someone’s mind by at least 10%. That doesn’t sound like much, but it primes me for a less hostile and lower stake conversation.

Additionally, anytime I write something that I suspect will be controversial or paradigm-shifting for my readers, I try to read it from the perspective of someone who I know disagrees with me.

Do my words sound overtly antagonistic? Does it have the potential to be demeaning or hurtful to other people? Am I demonizing those who think differently than me? Do I leave the door open for more conservation or am I assuming the final word?

It’s also important to evaluate your personal motivation for speaking out about a topic. From personal experience, I can tell you it’s probably more selfish than you realize.

From value signaling (I’m a good person because I believe [X]), identity formation (I’m the type of person who believes [X]) and tribal alignment (I’m part of a group who believes [X]), your rationale for holding and voicing certain beliefs may have more to do with your ego and sense of belonging than it does with any values that actually influence your behavior.

It’s vital that you’re able to tell the difference.

The Rumble Room


After you’ve acknowledged your biases, discerned your personal motivations, and set realistic expectations, it’s time to step into the ring. These next principles concern face-to-face interactions with people with whom you disagree.

Principle #3: Practice and deploy Strategic Listening.

During the initial stages of the conversation, you should be doing more listening than talking. In some cases, this is going to be extremely painful. But it’s necessary if you want to make any sort of progress.

In his book Talking Across the Divide, Justin Lee writes,

“When you begin the conversation by listening instead of talking, you accomplish more than just gathering information. Right from the start, you’re setting a tone of cooperation rather than antagonism. You’re sending a message to the other person that they aren’t going to have to fight you in order to be heard by you.”

The purpose of strategic listening is to root out the motivation for a particular belief. Some examples of motivation include fear, religious devotion, preservation of the status quo, traumatic personal experience, nostalgia, social pressure, and a desire for change.

Seeking out the motivation of their stance will always result in a more constructive dialogue. It will force you to ask more personalized questions that will expand the scope of the conversation beyond combative talking points.

Here are a few questions that can help you root out someone’s motivation:

  • Can you tell me more about [X]?
  • What personal experiences led you to that conclusion? Have you had any personal experiences that have challenged that assumption?
  • When did you start thinking or feeling [X]?
  • What do you think it would take to change your mind about [X]?

(It is not uncommon for people to have the same motivation and reach different conclusions. Oftentimes, this scenario results in the best conversations).

In The Righteous Mind, social psychologist Jonathan Haidt writes,

“If you really want to change someone’s mind on a moral or political matter, you’ll need to see things from that person’s angle as well as your own. And if you do truly see it the other person’s way—deeply and intuitively—you might even find your own mind opening in response.”

Treat the first part of the conversation like a research project. Your initial aim in the conversation is to reach a point where you can confidently say, “While I don’t agree with your stance, I understand how you reached that conclusion.”

Principle #4: People are more than the issues they believe.

The world would be so much easier if everyone with whom I disagreed was a terrible person. But that’s not the case.

When we encounter someone who has a different viewpoint on an issue that’s important to us, we often cast them in the role of a villain or a dunce. We feel disgust or pity for their progressive/regressive views.

With that danger in mind, I try to exercise The Principle of Charity.

According to the Principle of Charity, you should assume the best motivations behind someone’s actions and beliefs before you assume the worst.

In some cases, this might be extremely difficult. But keep in mind, in today’s political climate, applying the Principle of Charity is one of the most counter-cultural steps you can take to ensure a more diplomatic transfer of ideas.

Principle #5: Be a good conversation partner…

In arguments, there are winners and losers. In conversations, there are participants.

Just as you’re learning from your opponent, position yourself (and the conversation) as a learning opportunity for them as well.

It would not be unorthodox to say something like, “We know we both disagree on this issue, but I want us to walk away from this conservation better informed. What do you specifically want to know about my position or people who hold my beliefs?

In other words, offer yourself as a resource rather than a sparring partner.

Additionally, strive to be a genuinely polite person. Don’t insult or interrupt the other person. If they make a good point, acknowledge it. Literally say, “That’s a good point. I haven’t considered that before.

And when you’re explaining your point of view, make sure the other person is following along. A good conversation should bust stereotypes on both sides of the issue. Say things like, “I’m not asking you to agree with me. But can you understand how I reached that conclusion?” And if they reply, “No,” ask them, “Okay, how can I clarify my position?

Try to avoid lecturing or steamrolling. Don’t talk for longer than two minutes without inviting them back into the conservation. You want them to talk more than you.

But, if the other person is beginning to preach or lecture you, establish the ground rules. Say, “I want to continue this conversation, but I feel as if you’re not listening to me or allowing me a chance to speak. How do you think we can make this a more even exchange of ideas?

Principle #6: …but respectfully call out bullshit.

However, I’m not telling you to be a passive participant.

Telling someone they are wrong is not the same as telling someone they are stupid. Unfortunately, we live in a culture where to openly disagree with someone is often considered disrespectful.

That is nonsense.

You may find yourself in a conversation in which the other person is flat-out wrong or using completely fabricated information. In an era of Fake News and rampant conspiracy theorizing, the spread of bullshit has never been harder to stop.

However, it is important to remain civil if you want anything productive to come from the conversation.

In Braving the Wilderness, Brene Brown writes,

“Generosity, empathy, and curiosity (e.g. Where did you read this or hear this?) can go a long way in our efforts to question what we’re hearing and introduce fact.”

In other words, you shouldn’t give bullshit a free pass but do so in a way that establishes and maintains a standard of truth and respect for the content and tone of the conversation.

Also, learning where someone gets their information can go a long way in understanding how someone constructs their worldview. If someone says something dubious, ask pertinent questions like:

  • Where did you get that information?
  • Can you show me where you got that information? (Use smartphone).
  • Does this article/webpage link to the original reports/study/sources?
  •  Do you know if this source has ever posted inaccurate information, and (if yes) have they ever issued a correction? (News organization that self-correct their own reporting are more trustworthy than those that do not).

Principle #7: Beware the Danger Zone

If, at any point during the conversation, you become upset and your heart rate increases and vision narrows, be forewarned: You’ve entered the Danger Zone.

In the Danger Zone, nuance evaporates and black-and-white thinking regains control. In this state, you’re more likely to resort to pithy judgments and cheap insults. It’s very rare that anything productive occurs when one of the conversationalists is in the Danger Zone.

If you’re approaching the Danger Zone, say, “This topic is very personal to me and I don’t want to jeopardize our relationship by becoming upset. Is it okay if we talk about something else?”

If you sense the other person is approaching the Danger Zone, say, “I can tell we’re both emotionally invested and passionate about this topic. I think we should table this discussion for now before we say something hurtful.”

Principle #8: A good story is better than a good statistic.

Facts and figures only go so far. Statistics may change minds, but they don’t transform hearts. A person will probably forget a number, but they won’t soon forget a story that left a mark on their soul.

In Christ Plays in Ten Thousand Places, theologian Eugene Peterson writes,

Stories open doors to areas or aspects of life that we didn’t know were there, or had quit noticing out of over-familiarity, or supposed were out-of-bounds for us. Stories are verbal acts of hospitality.”

A few years ago, a couple of co-workers were making fun of #MeToo Movement during an off-site lunch. Before speaking up, I made a point to take several deep breaths to stall my approach into the Danger Zone.

I shared with them my experiences working as a hotline operator for the local Sexual Assault Resource Center (SARC), a nonprofit advocacy group that provides free counseling and legal services to survivors of sexual assault.

Was it an awkward moment? Yes. But it was also an opportunity to personalized and localized a hot-button issue that they didn’t fully understand.

If you don’t have any stories, then you probably need to get some. If you’re truly passionate about an issue, you should be looking for opportunities for hands-on experience.

The End Game


At some point, the conservation will reach a natural conclusion. The final two principles concern how to handle two very different outcomes.

Principle #9: A healthy conversation is a first step, not the end of the journey.

If the conversation is winding down and you think it’s gone well, it’s time to take the issue outside of the bounds of the dialogue. I call this “the follow-up.”

The follow-up can be as simple as scheduling another time to talk after you’ve both had an opportunity to process the conversation. Or you can commit to reading a book or watching a documentary about the topic together.

And if you have a personal stake in the issue, invite them into that space with you. Bring them to your church small group, or the gun range, or a support group for trans people. Disturb their echo chamber, but be open to the same being done for you.

Remember, the goal was never to win – it’s to push each other to a place of mutual respect and understanding. But, if you can ascertain that you’ve changed their mind by at least 10%, then I would consider that a victory worth celebrating.

Principle #10: Know when to fold.

It may sound trite, but the only person you can control is yourself. You don’t get to choose how someone responds to your story or facts or worldview. The conversation may not end the way you want it to end.

You may have stepped into the conservation and quickly realized you were in way over your head. The other person was simply better prepared and more informed than you.

Or (and this is entirely possible), you may be wrong.

If you find yourself outmatched, then take the opportunity to learn from the other person. Ask questions to help fill in your personal blindspots. Instead of withdrawing, lean into the conversation – especially if you find some of your preconceived notions about the world being challenged.

On the other hand, if the other person is simply being an asshole it’s probably wiser to shut the conversation down. Some people may claim they want to dialogue, but what they really desire is to lecture you on all the ways they’re right and you’re wrong.

If this begins to happen, I recommend clearly laying out your expectations for the conversation (as detailed above). If they continue to violate the dialogue’s integrity, it’s okay to back out.

Say, “I really wanted to discuss [X], but I don’t feel as if you’re interested in listening or respecting my side of the story. Until you’re willing to show me that you’re willing to do that, I don’t think we should have this conversation.

Addendum: But What About Evil?


Okay, you might be thinking, this is great and all, but what about true evil?

I totally empathize with the concern. Recent events have made it very apparent that gross and intolerant views and attitudes are very much still prevalent in American society.

Do we extend the Principle of Charity to Neo-Nazis, KKK members, and people who wave homophobic protest signs? How do we interact with people whose views are actually harmful and dehumanizing to other people groups?

I think everyone has a line. For a lot of people, interacting and conversing with legitimate hate groups would be physically and emotionally unhealthy.


I believe some people may be uniquely equipped – either through personal experience or a natural diplomatic skillset – to bridge the gap.

The Internet is filled with inspiring stories of hate-filled individuals repenting of their old ways and embracing newfound respect of all life – but usually only after someone else has taken the time to form a meaningful relationship with them.

I know this is a tricky and nuanced topic, fraught with power dynamics and oppression narratives that need to be legitimately addressed in the light of history and modern society – which is why I can’t make a sweeping recommendation in fear of overgeneralizing very sensitive issues.

I can only hope that all people have the capacity to change for the better, just like they can change for the worst. And that, I believe, is how we can save the world.




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