No #168 | May 11, 2025

by Matthew Boyd

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

Shout out to all the Moms out there today❤️.

Life doesn't come with a manual. It comes with a mother.

In this week's Lead It Cool newsletter:

• 👟Big Shoes to Fill
• ✈The Rehearsal
• 😆Body Breakdown
• 😎Cool Links

👟Big Shoes to Fill

Law #41 of Robert Greene's The 48 Laws of Power is very self explanatory: Avoid stepping into a great person's shoes.

In other words, if you take a role that is following a legendary figure, you must achieve twice as much to outshine them — otherwise, you'll be lost in their shadow, stuck in a past that wasn’t your making.

The sports world is full of cautionary tales about this.

When Phil Jackson left the Chicago Bulls, Tim Floyd took over and struggled to find success, recording a dismal 49-190 record over four seasons. After Bill Belichick's departure from the New England Patriots, the franchise has yet to recapture its former dominance. And when Sir Alex Ferguson retired from Manchester United in 2013 after a historic run, the club cycled through five different managers in the following decade, with only the occasional success.

So when Liverpool coaching legend Jürgen Klopp retired last year, fans braced themselves for the worst.

After all, who could possibly follow one of the most successful and beloved managers in club history?

Well... the successor Arne Slot did just that — and knocked it out of the park.

Under Slot’s leadership, Liverpool won their 20th Premier League title this year.

So, how did he succeed following a coaching legend where so many have failed?

The answer most likely lies in Klopp’s philosophy, which always put the team before himself. Unlike many iconic coaches whose egos eventually eclipse the team, Klopp remained rooted in a team-first mentality.

​One story captures this perfectly: Early in his tenure, Klopp gathered the players in the media room while the support staff (gardeners, cooks, fitness coaches) walked through one by one. Klopp asked the players, “Do you know these people? Do you know their names?” The players, caught off guard, realized they often didn’t. Klopp reminded them, “They are here to help you perform at 100 percent. They are part of the team.”

This humility and commitment to collective success set the foundation for Liverpool’s continued achievements, even after Klopp’s departure. He didn’t just build a winning team, he built a resilient culture that transcended his presence.

The lesson? Great leaders don’t make themselves irreplaceable; they make the team resilient enough to thrive without them.

Klopp understood that true legacy isn’t about being indispensable — it’s about building something that lasts. #YNWA

✈The Rehearsal

There's a famous saying that luck is what happens when opportunity meets preparation.

​UVIC alumni ​Nathan Fielder is testing this theory in his new HBO show called "The Rehearsal".

The show is a social experiment/therapy innovation where 'Nathan locates people who need to have difficult conversations or otherwise fraught scenarios. Then he meticulously recreates the conditions under which they will have this interaction, hires actors to play other people in the "scene" and rigorously rehearses the encounter, trying to anticipate all possible outcomes and prepare the "real" person for the conversation.'

For the second season, Fielder is focusing on the cause of airplane crashes and how the power dynamic in the relationship between between the captain and co-pilot may be contributing to these events.

The level of detail used to create the simulation is... well, incredible and there are certain parts you have to see to believe. Below is a photo of a Fielder trying to simulate someone else's childhood experience (Nathan is the one sitting on the bed).

​The show is a strong reminder of two things: the first is that human beings are incredibly complicated emotional creatures; and the second is that practice really does make (almost) perfect.

When we practice or rehearse simulations to prepare for the actual encounter, the probability of us achieving the outcome we desire increases.

We're often told to "fake it till we make it", but Nathan's show is challenging this framework. If you know the situations or conversations that you'll be involved with, then a more apt approach might be to "rehearse till you make it."

😂Body Breakdown

This graph always cracks me up.😆

😎Cool Links

🤔Where is your N + 1? If three people are coming over for dinner, does that stress you out? What if it’s 17? If you’re giving a talk explaining your strategy to four people, does it feel like a high-risk event? What if it’s 54?

✍️Journaling Is a Core Practice for Leadership Development. Journaling allows you to observe and analyze your thinking in a way that no other feedback tool can match. By putting your thoughts on paper, you can see how you approach a situation, frame the context, process the information, and make decisions. This perspective provides us insights and allows us to make connections that are often elusive when thoughts remain in our heads. Furthermore, journaling is something anyone can do with the simplest of tools, which means it's cheap, accessible, and easy to start.

😜The Millennial Canon Bracket. For anyone who classifies themselves as a millennial, this article will be highly enjoyable for you.

👓Auto-focusing eyeglasses? Take my money.

😂I Played 'The Boys are Back in Town' on a Bar Jukebox Until I Got Kicked Out. This will be the dumbest/most amazing thing you'll read this week, I guarantee it.

📰Fun idea: Create a hyperlocal magazine for your neighbourhood.

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