No #163 | April 6, 2025

by Matthew Boyd

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

The other night, my wife and I attended a parent session at our daughter's dance studio. The focus was on how we, as parents, can help our kids thrive, not just in dance, but in life.

One piece of advice really stuck with me. The instructor said we should strive to be the edge of the pool - a place our kids can always return to when they need to feel safe. A steady presence. A touchpoint. A home base.

Great advice.

In this week's Lead It Cool newsletter:

• ✈The Wingman
• 🎤American Idol
• 🤔Overwhelmed
• 🤣Flippy Guy
• 😎Cool Links

✈The Wingman

Hollywood lost a legend this week

Movie superstar Val Kilmer died after years of health struggles. It's a loss that hits deep, not just for what he gave us on screen, but for the roles he made unforgettable.

Kilmer will be remembered for many performances (The Doors, Tombstone, Heat, Batman Forever), but for many of us, he’ll always be Iceman from Top Gun.

There’s something irresistible about a good character arc, the slow burn from the antagonist to good guy.

At the start of Top Gun, he’s Maverick’s rival: aloof, competitive, cocky. The classic foil. But by the final dogfight, he’s the one who shows up when it matters most. Iceman becomes Maverick’s wingman. And in doing so, he becomes a hero.

Decades later, Kilmer returned to the role in Top Gun: Maverick, a moving appearance that served not only as a nod to their bond, but also to real-life friendship, aging, and the passage of time. In that scene, Iceman is no longer the hotshot pilot, he’s the grounded, quiet mentor. A trusted friend. A wingman in the truest sense.

And that’s the thing about wingmen: we all need them. Those people who have your back when the skies get rough. If we’re lucky, we get a few Icemans in our life, those friends who step up and show up.

This quote from David Whyte in his book Consolations beautifully captures the role of friendship in our lives:

Kilmer’s Iceman was that kind of friend: a role model for loyalty, humility, and grace.

So here’s to you Iceman, rest in peace.

🎤American Idol

My daughter and I were flipping through TV channels the other night when we stumbled onto American Idol.

Apparently, the show is in its (checks notes)... 23rd season (!). I feel old.

The episode we landed on was “Hollywood Week”. This is the stage where they whittle down the 100ish contestants who made it through the initial auditions. The format is simple but brutal: all the singers sit in an arena, and the judges call them up one by one, in random order, to sing in front of everyone else.

Some contestants absolutely rise to the moment.

Others? Well… it's hard to watch.

I’ve spent the past few years teaching a business course at UVIC, and one of the things we focus on a lot is public speaking (if you're one of my former students reading this you know what I'm talking about😜).

One thing I always remind students is that the audience is always rooting for you.

No one sits in a crowd hoping to see someone crash and burn. We’re all pulling for the speaker, the singer, the presenter to succeed. We want to feel something. We want to be impressed. We want the moment to work.

When you remember that, the fear loses some of its grip.

The lights feel a little less bright.

Your hands shake a little less.

And your voice starts to find its power.

So whether you're in a classroom, on a stage, or standing under the lights on live TV, just remember: the crowd wants you to nail it.

(But just don't forget the lyrics😜).

🤔Overwhelmed

Really love this advice from Blake Burge.

🤣Flippy Guy

I'm a big fan of flippy guy humour 🤣 (source)

😎Cool Links

🤖AI Leadership: The Hard Truth No One Wants to Admit. AI is not a magic bullet. It cannot fix fundamental business problems overnight. Instead, it amplifies what’s already working or exposes what’s broken. Yet, many leaders rush into AI adoption, underestimating the complexity of the journey. This gap between expectation and reality is what separates AI hype from true AI transformation.

🎵The Greatest Two-Hit Wonders. Two-hit artists sit in a weird space, though. Pop stars a remembered because they are very famous. One-hit wonders are remembered for the opposite. Their un-memorableness makes them great answers to bar trivia questions. Two-hit wonders are stuck in the middle. Some might be able to parlay those two hits into careers, but others are lost in a musical no man’s land, too many hits for trivia, not enough to be legends. Still, there’s got to be a greatest two-hit wonder.

💡Our Favourite Management Tips on Strategic Thinking. This is a great reference list from HBR.

🔉In a loud world, a calm voice can lead the company through unsteady times. Leading from a place of composure rather than reactivity is not only a healthier mindset, but it allows your team to focus on advancing the company’s mission rather than panicking about every passing hurdle—including your reaction to it.

🥓You can cook bacon this way? CHAOS BACON!!!

For anyone who watches White Lotus, enjoy the season finale tonight!

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