🐶The Underdog Story


No #139 | August 4, 2024

by Matthew Boyd

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

This is how I feel this weekend:

Enjoy the last few weeks of summer everyone🌞. Pumpkin spiced everything is just around the corner...

In this week's Lead It Cool newsletter:

  • 🐶The Underdog Story
  • 🤝Never Split the Difference
  • 🏊Safety First
  • 😂Time Machine
  • 😎Cool Links

🐶The Underdog Story

Humans love underdog stories.

We’re hardwired to instinctually root for the weaker team. From David and Goliath to the Miracle on Ice, our hearts always go out to the little guy.

Why do we root for the underdog?

Psychologists suggest that it's partly because of empathy: we see ourselves in their struggle and want to witness their triumph over adversity.

It’s also a rebellion against the status quo, a desire to see fairness and justice prevail when the odds are stacked against someone.

This is probably why many Canadians fell in love with the women’s national Olympic soccer team. They weren't the underdog because of skill, they became the underdog because of circumstance. At the beginning of the Olympics, their coaches were caught using a drone to spy on the New Zealand practice. The fallout was the suspension of coaches and a six-point group play penalty.

Anyone who is familiar with soccer knows that a six-point penalty is akin to a death sentence. This means that they had to win all three group stage matches (without their coach and amid massive scrutiny) to survive.

So what did they do?

They won all three group stage matches to proceed to the knockout stage. When their backs were against the wall the players rose to the occasion. Unfortunately they lost in a shootout to the Germans on Saturday, but the adversity they overcame in the group stage is still inspiring.

In Bill Walsh’s biography The Score Takes Care of Itself, he deeply understood the power of the underdog mentality.

Even when his 49ers were the top team in the league, he used to rile up his players by telling them that their weaker opponents were due for a win and to watch out. He made sure that his team always felt like underdogs because he understood the power of that mindset.

So if you’re ever feeling the pressure, create an underdog narrative.

Embrace the struggle, rally your team, and remind everyone that adversity is just an opportunity in disguise.


🤝Never Split the Difference

I've always been fascinated by the art of negotiation and how some people seem naturally adept at it. A few years ago, I read Never Split the Difference by Chris Voss and Tahl Raz, and it contains some absolute gems of advice.

I highly recommend this book to anyone interested in improving their negotiation skills or just trying to get a room upgrade at the hotel when they check in.

Here are some of my favorite quotes:

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.


🏊Safety First

Hey... safety first! (source)


😂Time Machine

My family just finished watching the Back to the Future series and this comic perfectly sums up my time travel goals. (by Brendan Loper).


😎Cool Links

🦉Why "Wisdom Work" is the New "Knowledge Work". As part of our routine employee-satisfaction surveys, we tested a new question: “Beyond your boss, who in the organization offers you helpful advice or wisdom?” This information allowed us to create what we called a Wisdom Heat Map, which focused on where wisdom was stored in the organization. This, in turn, allowed us to ask some of the people identified as wise, who were often older but not in leadership positions, if they’d like to be trained as internal coaches. It also allowed us to develop a list of the character qualities that most commonly defined our best informal mentors, among them: less ego and more collaboration skills, a knack at asking generative questions, and an ability to offer unvarnished insight that feels like a gift as opposed to judgment.

⏱️The 5-hour rule: How to turn a wasted day into a successful one. The fact is that we all have the same number of hours in the day, and it’s up to us to decide how we spend them. Some people will most certainly have more “free hours” than others, but for most of us, we have at least a few hours to spend as we want. And according to “the 5-hour rule,” how we choose to spend those hours might mean the difference between success and mediocrity.

How a changing Starbucks hopes to retain customers. Starbucks even has new, faster blenders. Everything is about shaving off seconds, often in ways simpler than you’d think in a world increasingly powered by algorithms and burger-flipping robots.

📖The Rise of Microlearning: Exploring Employee Potential with Bite-Sized Education. Microlearning is an innovative learning strategy that focuses on delivering short, focused bursts of information to learners. These bite-sized modules are designed to cater to a single learning objective, making the content easily digestible and highly engaging. Rather than overwhelming employees with lengthy courses, microlearning breaks down complex concepts into smaller, manageable pieces, allowing learners to absorb information quickly and effectively.

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Lead It Cool - by Matthew Boyd

🌟by Matthew Boyd | mid-career MBA survivor, strategist, pragmatic leader 📚✍️ 🔥 Passionate about storytelling through the lens of popular culture and humor 📨 Creator of the 'Lead It Cool' newsletter - your weekly leadership / pop culture digest 🎬🎧

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