No #179 | July 27, 2025

by Matthew Boyd

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

My amazing, super, incredible mom turned 75 years young this week. Happy birthday mom! ❤️🎂

In this week's Lead It Cool newsletter:

• 🗣️Small Talk
• ⛳Happy Gilmore 2
• ✍️Write It Down
• 🤣The Day Off
• 😎Cool Links

🗣️Small Talk

Last weekend, I found myself at a backyard BBQ surrounded by people I kind of know, but don’t really know.

You know the situation: a sea of familiar faces, all bobbing around in the shallow waters of small talk. The weather gets its obligatory mention. Someone talks about gas prices.

You nod politely at least three times too many. It’s all very… polite.

But here’s what I’ve learned (oftentimes through moments of intense awkwardness): every great conversation starts with a little dance.

It’s like solving a puzzle. The first pieces never quite fit, but once you find that magic connector, the one shared interest, story, or random fact you both geek out over, the whole conversation clicks into place.

And really, the only way to find this connecting puzzle piece is to ask questions.

Now, I know what you’re thinking: Matt’s going to give me a list of “killer questions” to use, right?

Nope.

Because those canned questions, like “What’s your greatest passion?” or “What’s your dream job?”, tend to feel as natural as a job interview.

The reality is that good conversation isn’t scripted. It’s improv.

The art of the question isn’t about knowing the right question, it’s about asking the next question. The one that’s natural to the moment. The one that feels like you’re building a story instead of reading from a script.

So next time you’re at a BBQ, or a wedding, or a random Tuesday night dinner party, forget the script and just roll with it.

⛳Happy Gilmore 2

So my son and I watched it (I think my son has already watched it twice🤣).

And you know what, it kinda, sorta lived up to the expectations.

Living up to high expectation is never easy.

Below is an expectation matrix I made a while ago that helps explain the paradox of expectations (yes, I did make a matrix about expectations...)

Expectations can amplify excitement and make moments feel bigger. But they can just as easily sabotage the experience, like a trailer that promises more than the movie can deliver.

So well done Adam Sandler, you met some very high expectations🙂

✍️Write It Down

I've written about this many times before, but I'm a firm believer in taking as many notes as possible.

This cartoon by Hidde Douna is exactly the way my brain works.

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🤣The Day Off

🎯🤣

😎Cool Links

🤔A Guide to Handing Off Work Before a Vacation. Whether you’re out for an extended weekend or taking a two-week vacation, having a strong backup at work is a good idea. It ensures that your most important tasks carry on without interruption and ensures that someone is available to act on your behalf in urgent or unexpected situations.

​💡Productivity, AI and pushback. Plato was sure that the invention of handwriting would destroy memory, and I’m confident there were scribes who thought that the Gutenberg press was the end of civilization. Yet, all around us, there are writers who use spell check, guitarists who use electronic pitch tuners and photographers who use digital cameras. Productivity wins out.

🔥6 B.C. tech startups fighting wildfires with innovation. From drones and satellite imaging to real-time grid monitoring, these B.C. startups are pioneering cutting-edge tools to detect, manage and prevent wildfires across the province.

🙂The power of expectations. When we raise our expectations for a student, a friend or a co-worker, we open the door to possibility. We offer them dignity and a chance to grow. We are offering them trust.

🦸‍♀️The 25 Best Superhero Movies of All Time. IMO number 3 should be number 1.🦇

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