How To Have Challenging Conversations Online

In my last article, I wrote about how challenging it is to talk about charged issues like the Israel-Hamas war online. I spoke of the need to accept the brutal facts of our current reality -- not to agree with them, but to accept them. I spoke of the need to deal with the world as it is.

“Dealing with the brutal facts of our current reality means understanding what conditions need to be in place to achieve peace, which means understanding where people are coming from, even people with whom you fundamentally disagree.

If we who are sitting in safety cannot listen to each other, how can we possibly hope for leaders in the thick of things to shift their own perspectives?

If we want justice, if we want peace, if we want to change the world, we must become skilled at the art of listening to understand.”



Unfortunately, sites like X incentivize the exact opposite behavior. We get rewarded for in-jokes, for mic-drops, for joining forces with others to laugh at today’s One Main Character.

How can we hope to make progress when all incentives are aligned against us?

A more important question: Do we even want to make progress?

Because the number one requirement for us to have challenging conversations online is to take those conversations seriously.

And taking those conversations seriously means:

  • Losing out on the smug satisfaction when someone claps back SO HARD
  • Losing out on indulging our snark
  • Losing out on gleeful mockery of racism, sexism, wokeism, conservatism, or other online crimes

There is a reason our discourse has fallen so low. It’s because these things -- smugness, snark, mockery -- feel good.

It’s hard to give them up.

But if you’re ready to take those conversations seriously, here are the three commitments we need to make:

1. A commitment to avoid sarcasm. Sarcasm is simultaneously one of the most tempting and one of the most unhelpful forms of communication on the Internet. We read the tweet -- we think of the witty answer -- we imagine how all the people who already agree with us are going to laugh -- we type and hit send.

And all the people who already agree with us laugh, and the person we mocked sees us as an ever greater enemy.

Sarcasm is the enemy of open conversation.

2. A commitment not to take your prior knowledge or opinions for granted. One of the things that drives online animosity is the assumption that others know what we know -- they just don’t care.

So instead of communicating to help others see where we’re coming from, we communicate our anger that they don’t yet agree with us.

We also often assume that if someone believes A, they must also believe B -- and then we act on that assumption as if it’s fact, attacking them for their supposed belief in B.

And yet, we know that when people do this to us, our response is, “You don’t know me!”

Making assumptions about people is a recipe for mistrust.

3. A commitment to generosity. What do I mean by generosity? I’m talking about generosity in terms of the assumptions we make about other people’s intentions, motivations and actions.

When we interpret someone’s tweet in the worst possible light, when we assume bad intentions, when we demonize people who believe differently than we do as evil and uncaring… We are lacking generosity.

But, again, we know that when someone is ungenerous with us, we feel wronged, hurt, misjudged. Why would the people we are ungenerous with feel any differently?

Take conversations seriously. Avoid sarcasm. Don’t take prior knowledge for granted. Be generous in our assumptions about other people’s intentions.

Can you imagine what the Internet would look like if we all followed those commitments?

Next story loading loading..