What Winning Online Arguments Looks Like

An exploration of techniques for productive online arguments, highlighting the importance of understanding over winning.

Sat Apr 13 2024

a greek statue arguing online

Ever ripped into someone online?

Have you ever proven someone wrong in the comments section? It feels good to win the exchange and come out on top. You may have won the argument in your opinion, but did you change the other person’s mind?

Part 1: No one really wins

No one changes their mind at the end of an argument.

The sides become more dug in. You may have made some good points but most of the time you are giving the other side motivation to go prove you wrong. If you embarrassed the other side, you now have an enemy. They now look at you and people who hold your views as the mean, heartless and smug.

When people feel attacked, they respond with flight or fight or freeze. The more you try to “win” the more likely you are creating an enemy.

Part 2: Redefining Winning as Learning

The true winning in argument is when both sides learn something.

Adopting a mindset geared towards understanding is hard to do when you want to win and be right. This approach involves “steel manning” the other side. Steel manning an argument is when you represent the other side’s argument in its strongest form. This is in contrast with “straw manning.” Straw manning an argument is when you make the opposing view seem weak and dump. Straw manning commonly done by mainstream media misrepresents a viewpoint by explaining it in a inadequate way where the viewpoint can be easily attacked and dismissed.

To steel man an argument is harder to do. But in doing so, you demonstrate both a genuine understanding and respect for the opposing views and lay the ground work for meaningful dialogue.

Part 3: How To Argue Online When You Want Actual Progress

First of all, you probably won’t be able to have the conversation you want online. But if you have to, here is what you should do. The key to a productive argument is trying to understand before you try to be understood. And most of the productive work is done before the argument starts (you need the right framing).

Here are 4 steps to having productive arguments online:

  • Step 1: Change Your Mindset From Combative to Seeking to Learn

You are not here to preach, you’re here to learn.

Before you respond, take a moment to truly absorb what the other person is saying, considering their perspective as valid and informed. Reflect on how their experiences and knowledge might lead them to their conclusions, fostering empathy rather than opposition. This shift from a combative stance to one of learning allows for more open and effective communication, where both parties can grow.

Once you have thoughtfully considered their point of view, you are ready to start typing.

  • Step 2: Find Common Ground By Narrowing the Point of Contention

Start with what you agree on. Find the common ground. It’s easier to build a conversation when you’re not coming from opposing corners. You should be upfront and clear that you disagree about something; however, you should take the time to narrow the disagreement.

Voice or type out what you likely agree on before arguing.

  • Step 3: Be Vulnerable To Unlock Deep Levels of Understanding

Admit that you don’t have all the answers. If you are emotionally involved in your argument, express your feelings. This helps you connect human to human, making you relatable rather than just another shouting head on the internet.

Once you have displayed the courage to be vulnerable, you give the other side permission to be vulnerable as well. This sets the stage for a productive conversation.

  • Step 4: Set a Learning Goal and Open With A Thoughtful Question

After doing the above, your opening statement should lead to a specific question. Most people lead with an accusation, and the conversation is doomed from then on. Crafting an open-ended, specific, and good question is a skill, and it is one that is worth trying to get good at. It starts with being genuinely curious about why people think the way they do.

Bonus Step: Ask the Other Side to Correct Your Understanding

This is how you speed-run an argument towards progress. Once you open yourself to correction, the walls come down. This displays not only humility but also shows the other side that you have thought deeply about their viewpoint. Plus, it forces you to do the work of trying to understand the other side.

If the other side takes the time to try to understand your views, you are not having an argument anymore.


I hope these tips help you experience what winning feels like.


We are making something 👷🔨 join the waitlist

Find out the similarities and differences
between you and anyone