No #189 | October 5, 2025

by Matthew Boyd

Good morning, welcome to the weekly Lead It Cool newsletter.

So my cat does this thing where she’s very particular about which door she uses to go outside in the morning. I’ll open the front door for her, and she’ll turn around and sprint to the sliding door instead, like the world (and weather) will be different from another door😂.

But maybe she’s onto something. If the door you’re walking through doesn’t feel right, find one that does.

In this week's Lead It Cool newsletter:

• 🏆Annual Traditions
• 🤝The Godfather
• 🤔Normal/Chaos
• 🤣Do What You Love
• 😎Cool Links

🏆Annual Traditions

One thing that getting older has taught me is just how much fun, and how important, annual traditions are.

What’s an annual tradition?

It’s that one thing you do every year with your friends, your family, or even your colleagues. It doesn’t have to be elaborate. It just has to repeat.

Yesterday, my friends and I held our 23rd annual hockey pool draft.

Twenty-three years!

Same crew, same jokes, a lot more grey hair. The anticipation, the rituals, the inside jokes, they’re all part of the magic.

Annual traditions are like cultural glue.

Across human history, repeating shared rituals like harvest festivals, community feasts, or hockey pool drafts have been essential for maintaining social bonds. They strengthen trust, reinforce community, and remind us that we belong to something larger than ourselves. In modern life, where so much feels temporary and digital, these rituals ground us in something real and enduring.

So here’s to the annuals: the camping trips, the parties and the fantasy drafts.

PS, my hockey pool team looks amazing this year! 😜

🤝The Godfather

I rewatched The Godfather Part II this week, and that famous line: “I’ll make him an offer he can’t refuse”, reminded me of Chris Voss’s book Never Split the Difference, a masterclass in negotiation written by a former FBI hostage negotiator.

Now, Voss’s methods don’t involve mob tactics, but the underlying psychology is similar: understanding emotion, reading intent, and crafting offers that appeal to what people truly value. Here are a few key notes that I too from the book.

❓Ask questions that the other side can respond to but that have no fixed answers. It buys you time. It gives your counterpart the illusion of control, they are the one with the answers and power after all, and it does all that without giving them any idea of how constrained they are by it.

👂When individuals feel listened to, they tend to listen to themselves more carefully and to openly evaluate and clarify their own thoughts and feelings. And they tend to become less defensive and oppositional and more willing to listen to other points of view.

💬Repeat the last three words of what someone has just said. By repeating back what people say, you trigger this mirroring instinct and your counterpart will inevitably elaborate on what was just said and sustain the process of connecting. The intention behind most mirrors should be “Please, help me understand.” Every time you mirror someone, they will reword what they’ve said.

0️⃣Numbers that end in 0 inevitably feel like temporary placeholders, guesstimates that you can easily be negotiated off of. But anything you throw out that sounds less rounded, say, $7,269, feels like a figure that you came to as a result of thoughtful calculation.

👁️Only 7 per cent of a message is based on the words while 38 per cent comes from the tone of voice and 55 per cent from the speaker’s body language and face.

⚓Experienced negotiators often lead with a ridiculous offer, an extreme anchor. And if you’re not prepared to handle it, you’ll lose your moorings and immediately go to your maximum.

🤔Normal/Chaos

Normal is an illusion. What is normal for the spider is chaos for the fly. (source)

🤣Do What You Love

(source)

😎Cool Links

💡A Smarter Way to Disagree. Over the decades there has been a plethora of recommendations from academics and consultants on how people can disagree constructively. Some instruct people to think and feel in certain ways toward their counterparts: “Put yourself in their shoes.” “Have compassion and empathy.” “Try to understand them rather than judging them.” Others tell them what to do and say: “Ask clarifying questions.” “Make ‘I,’ not ‘you,’ statements.” “Use open body language to signal receptiveness, friendliness, and a willingness to engage.” Nevertheless, despite this wealth of advice, conflict persists.

🤖Sora 2 makes me realize the AI future is really hear. It's wonderful, and terrifying. OpenAI's new Sora 2 video app is fun. It's delightful and silly and goofy and creative. I have genuinely loved making funny videos that use images of me and my friends. But read that last sentence again. The flip side of all this wonder is also the terrifying part. This is the first time I've felt AI get close to mimicking real life. In other words, you might have a hard time telling what's real and what's fake when you watch these Sora-made videos.

🤔Reciprocity. Our biggest commitments, the things we are most dedicated to, rarely pay us back in equal measure. That might be the point.

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