Chapter 96: Dave the CEO on stratospheric strategizing and subtle secrets of success

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David Cheesewright is the former CEO of Walmart International.

In that role he led over one million people, across more than 50 different businesses, and over 30 countries.

A behemoth! Both the job and the company. How much of a behemoth? Well, Walmart is literally #1 overall on the Fortune 500 which means no company in the entire world made more money than they did.

How did a small town store from Bentonville, Arkansas rise to be the largest company in the world? Well, one big way they did it is through leadership. For over 20 years, one of the seniormost leaders at Walmart was Dave Cheesewright. Humble, down to earth, soft spoken, and lightning quick, Dave epitomized Level 5 Leadership, to borrow a phrase from Jim Collins. I was lucky to have a development role working for Dave when he was President and CEO of Walmart Canada. It was the most formative role of my career and I trace many stories and models in my books directly back to conversations and lessons I learned from Dave.

There was always something magical about Dave.

He was a former gym teacher who owned only one slightly crumpled suit and drove a beat-up van to work when he wasn’t showing up sweaty in the hallways after riding his bike. He had no fancy business degrees and was a true family man who was always home for dinner with his wife Clare and their three kids. He had a smaller office than his direct reports and ate two-dollar egg salad sandwiches at lunch amongst all the employees in the Home Office cafeteria. He would sometimes mention in the morning that he knocked on a Walmart in the middle of the night so he could help stock shelves on the overnight shift. He never used email, cancelled every meeting he could, personally phoned associates across the country to say thank you, and insisted every one-pager presented to him pass “The Grandma Test” (“Would my grandma who knows nothing about this business understand it?”).

Dave was promoted from CEO of Walmart Canada to CEO of Walmart EMEA (Europe, Middle East, and Africa) and later promoted again to CEO of Walmart International. What does a CEO overseeing over a million people actually … do? Well, that’s just one thing we’re going to talk about.

If you are a fan of the strategic thinking big time CEOs offer you’re going to love this conversation with a guy who thinks 500,000-feet above sea level.

What does a CEO do? What does a board of directors do? How do you make business simpler? What is the paradox of choice? How do we take an even more global view of things? How might we think about AI? What are the basic tenets of retail? Why shouldn’t you answer emails? How do you become a better delegator? What is the S-Curve in business? And much, much, much more…

I was thrilled to sit down with David Cheesewright, former CEO of Walmart International, in his living room to talk about his 3 most formative books.

I hope you love this conversation as much as I did.

Let’s flip the page into Chapter 96 now…

What You'll Learn:

  • What is the value of taking handwritten notes?

  • How should one manage the initial stages of retirement?

  • What is the value exchange?

  • What is the job of a Fortune 500 Company CEO?

  • What is the key to cultivating talent?

  • What is the S-Curve in business?

  • How does the CEO of a major company deal with imposter syndrome?

  • What does a Board of Directors for a public company actually do?

  • What is the moral obligation of a Board of Directors?

  • How can a company truly live by its values?

  • Why is what matters most invisible?

  • How can businesses become simpler?

  • What is the paradox of choice?

  • What are some of the greatest challenges the workforce faces?

  • Is outsourcing manufacturing to China a force for good in the world?

  • What are the limitations of governance in a globalized world?

  • How does AI stack up?

  • What book will help you flirt?

  • How can good habits serve us at different stages of life?

  • Why should you not answer emails?

  • Why should we delegate more?

  • What is the importance of perspective?

  • What does achieving a balance over life mean?

Notable quotes from dave cheesewright

“What’s really important in jobs where you are not there full time is what you might call the value exchange. Do you feel valued in the experience and the knowledge and advice that you can give and does the company feel like you are valuable.” Dave Cheesewright #3bookspodcast

“It’s not about the strategy; it’s about the people.” Dave Cheesewright #3bookspodcast

“It’s about finding great people and then putting them in the right jobs at the right time.” Dave Cheesewright #3bookspodcast

“All the right leaders are authentic so you want to find roles that play to their strengths.” Dave Cheesewright #3bookspodcast

“The job of a leader is to create an environment where people excel.” Dave Cheesewright #3bookspodcast

“There is no one best line-up” Dave Cheesewright #3bookspodcast

“Success is judged in many ways.” Dave Cheesewright #3bookspodcast

“You need to be content that you are somewhere where you can be yourself, you're giving it the best shot you can and you're happy with your own contribution.” Dave Cheesewright #3bookspodcast

“Judgements are in the eye of the beholder but the only beholder that matters is me, my family and my close friends” Dave Cheesewright #3bookspodcast

“It’s very hard to know what goes on simply by listening to someone speak.” Dave Cheesewright #3bookspodcast

“The best board members are the ones who understand that getting into the business and finding those less formal conversations with leaders is the way to know what’s going on.” Dave Cheesewright #3bookspodcast

“In a formal environment there will always be an element of game playing that is going on but I find informal environments dispense with a lot of that.” Dave Cheesewright #3bookspodcast

“The challenge with big business is the bigger you are, the more misperceptions will exist irrespective of what your behaviour is.” Dave Cheesewright #3bookspodcast

“When you get big it is really hard to make sure everything is correct all the time. You will often get dealt with by your exceptions. There is no process in the world that can counter that but culture can counter that.” Dave Cheesewright #3bookspodcast

“If there is a set of values for a business they need to be more than a set of words on a wall. And to do that a leader has to be a student of them and a teacher of them.” Dave Cheesewright #3bookspodcast

“You don’t solve broad issues by policy. You change them by behaviour and values.” Dave Cheesewright #3bookspodcast

“Simplicity is about providing people with a route map.” Dave Cheesewright #3bookspodcast

“Strategy is about simplifying things for people. It’s about finding frameworks that are narrow enough that they mean people are running in roughly the right direction but broad enough that they’ll stand the test of time.” Dave Cheesewright #3bookspodcast

“Simplicity is about finding frameworks that allow people to see the wood from the trees.” Dave Cheesewright #3bookspodcast

“The simplest way to drive up your perception of choice is to take product out because the more product you take out, the easier it is to find what you really want and therefore you feel like your choice has gone up.” Dave Cheesewright #3bookspodcast

“The profound issues that face the world require very long term thinking.” Dave Cheesewright #3bookspodcast

“The theory of unintended consequence means that in almost every aspect of life, what made you great is usually your biggest downfall.” Dave Cheesewright #3bookspodcast

“What AI misses is humanity.” Dave Cheesewright #3bookspodcast

“There aren’t many things that machines can do better than humans.” Dave Cheesewright #3bookspodcast

“There is something unique about the way humans will think that machines won’t replicate.” Dave Cheesewright #3bookspodcast

“The more you read the more you see similar concepts emerging.” Dave Cheesewright #3bookspodcast

“It’s very hard for the brain to inquire once it has become judgemental” Dave Cheesewright #3bookspodcast

“There is no book out there where you won’t learn something. There is no experience out there where you won’t learn something.” Dave Cheesewright #3bookspodcast

“When you don’t answer emails, more often than not what people will do is take it as implicit permission to go and solve it themselves.” Dave Cheesewright #3bookspodcast

“With delegation risk is way lower than you think. And the reason it's low is because most things are not earth shattering, whether someone gets it right and wrong and even when they get it wrong, it's a phenomenal learning exercise for them.” Dave Cheesewright #3bookspodcast

“Different phases allow you to redress balances” Dave Cheesewright #3bookspodcast

“I think the ability not to look back and wish you were doing something that is no longer there is really important. Just look forward to the things you can do.” Dave Cheesewright #3bookspodcast

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