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How Ancient Wisdom Can Transform Modern Conversations

A few years ago, a colleague of mine lost control of his temper and punched another. It was like a scene from The Office (the UK one of course).

The punch was pretty crap but the biggest damage was to relationships and trust across the team.

That thought came back to me recently while I was watching Ryan Holiday’s new masterclass on communication.

His key message? Great communication is as much about self-mastery as it is about words.

It’s about the way we approach discussions, disagreements, and the truth. Here’s what I took away and how it can help all of us communicate better.

Before we get into my 7 takeaways, here's how they started. Scribbled in my pocket notebook.

1. Understand That We All Think We’re Right

Most arguments begin with the same unspoken assumption: I’m right, and you’re wrong. If we remember this, it can help us approach others with a bit more humility. We can try and learn something from the discussion instead of just proving a point.

2. Ask Yourself These Three Questions Before You Speak

Holiday shared three questions that can transform a heated exchange into a meaningful conversation. If my colleague had these, I wonder if the punch had happened:

• When have I been wrong in the past?
• Why do I believe what I believe?
• How might someone else have come to their view?

These questions remind us that understanding should always come before judgement.

3. Show Genuine Interest in Others’ Opinions

People open up when they actually feel heard. Instead of listening just to respond, try listening to learn.

Ask thoughtful questions about someone else’s perspective. Try to create a foundation of trust and mutual respect.

4. Steelmanning: The Art of Stronger Arguments

I knew about strawmanning but I didn't know the opposite of stealmanning an argument. This is one of my favourite notes from the episode.

Before agreeing or disagreeing with the other person, try restating the strongest possible version of the other person’s argument. It shows that you’ve genuinely listened and helps clarify any misunderstandings. It can quickly defuse tension, too.

5. Manage Your Emotions, Especially Anger

Emotions can quickly spiral out of control if unchecked. The key is to pause. Take a breath before responding, especially in situations that feel personal. Oh and don't punch people. Especially at work! A tactical pause can save you from saying or doing something you’ll regret.

6. Speak the Truth, But Do It with Kindness

Telling the truth is sometimes uncomfortable, but it’s essential for trust. The key is how you deliver it.

I once turned down a role at the day job, explaining honestly that I wasn’t the right fit and framing it as a decision that benefited both me and the business. That conversation wasn’t easy, but it strengthened relationships in the long run.

7. Feedback That’s True, Good, and Honourable

Holiday’s advice on feedback resonated with me deeply.

Give feedback one piece at a time, and only when it’s constructive. Overloading someone with criticism rarely leads to growth. It'll just overwhelm the other person.

We can make feedback something that people value, not dread.

Why All This Matters

These aren’t just tips for avoiding workplace drama, they’re principles for better relationships.

Whether you’re negotiating with a client, resolving conflict with a teammate, or even managing your personal life, communication shapes how we connect with the world.

Holiday’s insights reminded me that great communication isn’t just about what we say, it’s about who we are.

I hope these takeaways inspire you to approach your conversations with more intention and care.

What’s the best communication advice you’ve ever received? I’d love to hear your thoughts.

Will

P.S.

What do you think of the new custom email layout? I finished making it in Kit yesterday.