Rebel Leadership: How to Thrive in Uncertain Times

By Larry Robertson

There’s a growing pattern of not just individual leaders, but entire cultures rebelling against old and ineffectual ways that have long defined what it means to lead. At the heart of rebel leadership is the emergence of five patterns seen in leading organizations across sectors. Together, these patterns outline a framework for how to successfully meet this turbulent new century and thrive. Rebel Leadership will not only reveal these patterns, but will teach the reader how to tap into the power of this framework and make it their own.

More precisely, Rebel Leadership will teach readers:
• What lies at the heart of success, no matter how much the environmental conditions might change
• How leadership is counterintuitively at its most powerful when it moves across individuals and cultures
• That, inevitably, there is only one truly sustainable competitive advantage in uncertain times
• Where leaders can find the best source for lowering risk in a changing world
• Why a long-term view has less to do with the long-term and far more to do with this moment than you’d ever imagine

“There are few skills as important as leadership—a skill we must constantly relearn, every one of us, now more than ever. This book is your guide and compass.”
Kevin Guskiewicz, Chancellor, University of North Carolina at Chapel Hill

“There is no more timely or more important book for those who lead in these uncertain times. Uncertainty is our new normal, or as Robertson writes, our new abnormal—leaders either accept it or they perish. This brilliant, forward-thinking book, its vivid examples, and deep insights, will help you to not only survive uncertainty, but to thrive in it.”
Tom Koulopoulos, author, Revealing the Invisible and The Gen Z Effect

“We live in times of change and rapid adjustment. Many aspects of how we do things will require sensible and well-thought-through revisions. Our approach to leadership must change as well. The question is how. Larry Robertson’s newest book gives that question the needed time and attention it deserves. The result is at once insightful, revealing, and instructive. The lessons are relatable and powerful. The stories make you feel a part of them. And when you finish, you don’t just feel prepared to lead in a new way, you realize he’s already launched you on your journey. Read this book.”
Milena Z. Fisher, Ph.D., President, Co-Founder, The Creativity Post

“Bob Marley was a Soul Rebel. Ruth Ginsburg was a Gender Rebel. In his new, must-read, book, Larry Robertson challenges us all to embrace ‘Rebel Leadership.’ In the post-Covid era, we’ll need to run toward new ideas about how to create lasting change, and as usual, Larry charts a course we can follow with daring and audacity.”
Robert Egger, Founding Board Member, World Central Kitchen

“Rebel Leadership offers a refreshing approach to leading in an environment where we can no longer wait to ride out the waves of uncertainty. With a blend of surprising insights, actionable ideas, and vivid storytelling, it’s a must-read for leaders looking for new ways to navigate an ever-changing business landscape.”
Teri Evans, former Columnist Desk Editor, Inc. Magazine

“Whatever role you fill, whatever game you play, to be at your best, you’ve got to take a bigger view. Seeing beyond your own position, but also beyond the game itself, is so important—never more so than today. When that’s your habit, you see more options, make better decisions, and set yourself up to lead with excellence—no matter what role you play. In Rebel Leadership, Larry Robertson takes the meaning of all this to a whole new level. You’ll come away inspired and wiser for the read. It’s a book worthy of your time and attention, no matter what game you play.”
Terry Malone, Football Coach, New Orleans Saints, Michigan Wolverines, Bowling Green Falcons

• Language: English
• Publisher: Post Hill Press
• Release date: Jun 1, 2021
• ISBN: 9781642936902

Book preview

A POST HILL PRESS BOOK

ISBN: 978-1-64293-689-6

ISBN (eBook): 978-1-64293-690-2

Rebel Leadership:

How to Thrive in Uncertain Times

© 2021 by Lawrence V. Robertson, III

All Rights Reserved

Although every effort has been made to ensure that the personal and professional advice present within this book is useful and appropriate, the author and publisher do not assume and hereby disclaim any liability to any person, business, or organization choosing to employ the guidance offered in this book.

No part of this book may be reproduced, stored in a retrieval system, or transmitted by any means without the written permission of the author and publisher.

Post Hill Press

New York • Nashville

posthillpress.com

Published in the United States of America

This book is dedicated to those who will make the future.

It is your invitation to become one of them.

Table of Contents

An Opening

Chapter One      The Changing Landscape of Leadership—Our New Abnormal

Chapter Two      Let Them Laugh, Soul Matters Most

Chapter Three   Leadership Moves

Chapter Four     It’s the Culture, Stupid

Chapter Five      Your Power Source is Your Superpower

Chapter Six        The Long View Matters—Right Now

Endnotes

Acknowledgments

About the Author

An Opening

Opening Up to a New View of Leadership

A certain world may be what we want and what we wish for, but it is not what we need, and it is not what we have.¹ That’s how futurist Tom Koulopoulos summed up the times we live in. He wasn’t referring to a single moment or event. He was describing this uncertain century in total, from its wobbly first twenty years, to as far forward as a futurist can see. This is our new truth: we live in a world more uncertain than certain, a fact most of us have yet to fully embrace. It’s not as though we are unaware of or ignore the uncertainty around us so much as it is that we treat it like we have always treated uncertainty—as temporary, limited, and something from which we can shake ourselves free. But the world has changed, and we must change to reflect it. As some of the wisest minds and today’s most impactful leaders will tell you, to do otherwise is a dangerous strategy and perhaps the greatest threat to people and organizations today.

Koulopoulos is one of those wise minds. Having spent the past thirty years providing thought leadership and guidance to some of the world’s leading organizations, his views are extremely well-informed. More than just an advisor of best practices, he’s a behaviorist. He doesn’t just theorize about business or technology trends; he looks at what people actually do. His insights derive from direct experience, but also from good lineage, including the likes of Peter Drucker.

A management consultant, educator, and author, Drucker was highly regarded for his oracle-like sense of things. He had an uncanny way of sifting through the obvious to see what most people missed and then, repeatedly across his career, accurately predicting the major developments to come. When I spoke to Koulopoulos in 2020, he told me a story about sitting down for lunch with Drucker in early 2000, right at the turn of the last century into this new one.² Koulopoulos wanted to know what one of the greatest minds of the last century thought about the century that was just unfolding. He said when he asked, Drucker didn’t hesitate. His thoughts about the new century had been gelling for a long time. While Drucker had much to say, Koulopoulos said one thing stood out above all the other observations Drucker made. He told Koulopoulos that he firmly believed we were entering a prolonged period of uncertainty—not simply in business or in the U. S., but as humanity and in the world at large. This, Drucker said, would reshape everything.

Why did Drucker feel this so strongly, I asked? Koulopoulos said that when he asked the same question, what followed was nothing short of a history lesson. Drucker was never one to lightly theorize. He built his views on fact, and the fact was, Drucker said, most of us were missing the elephant in the room. He believed that much of what had come to define the latter half of the twentieth century was temporary, even though to most it felt permanent. The distinction mattered enormously, Drucker told Koulopoulos. This ambiguity masquerading as certainty had had broad, sometimes imperceptible impact—including its influence on our mindsets about the future and leadership and our readiness to meet the challenges yet to come.

Drucker pointed out, for example, that for more than four decades the world viewed itself in the long shadow of two world superpowers. While today it might seem like a lesser historical fact, in reality it shaped countless aspects of our lives. Consciously or not, organizational structures and styles of leadership weighed anchor in this narrative—one of ‘us versus them,’ of supreme power concentrated at the top, and of winner take all, to name but a few storyline elements. In addition, the work environments for the overwhelming majority of sectors assumed a kind of steady state mentality and gradually, even if unintentionally, forged a strong belief that things would stay the same. Though by 2000, the facts underpinning this storyline were largely gone, Drucker believed its lingering effects were not. He also noted that while these things had been taking place, the actual landscape had continued to move. Drucker believed that movement was about to speed up. One clear indicator, he said, was the growing democratization of and access to technology and education. The more people had access to both, the faster the false scaffolding around our institutions, markets, and governments would be revealed. All of this and more, Drucker said, not only meant the unavoidable shedding away of a false sense of stability, but the emergence of a novel form of uncertainty to a populace that wasn’t practiced in dealing with it.

It’s worth noting that Koulopoulos made a point of telling me that Drucker didn’t see any of this change as inherently bad. In fact, he said, he believed that the kind of upside transformations only talked about in the past now had a high likelihood of not only becoming real but having impact far beyond what had previously been imagined. He believed those advancements would come quickly and be built upon—at least by those tuned into these shifts and willing to change with them.

Since that fateful lunch twenty years ago, a new kind of leadership has been steadily emerging—a wave of those seeing leadership through a wholly different lens, a groundswell not simply of individuals, but entire organizational cultures—cultures of rebel leadership. This book is about exploring that movement. Before we do, we need a clear sense of what we’re talking about and what we’re looking for when we say words like rebel and leadership, or culture and movement.

The Change Happening Right Before Our Eyes

The hardest thing of all, is to see what is really there, author J.A. Baker wrote.³ The same could be said about an in-depth interview with Walmart CEO Doug McMillon that appeared in Harvard Business Review in March of 2017. Just a short three years before, McMillon had taken the lead at the retail giant. It was a tumultuous time for the company. Growth was slowing. Competition was on the rise. And Walmart was still very much an organization in transition. After more than fifty years serving customers from physical stores, for instance, it was still navigating the implications of serving customers through both digital and in-person formats. All while that customer base was shifting and becoming increasingly complex.

For most of its history, Walmart knew their customer as the actual person who walked in the door. They knew what they did when they were in the store, what they took home with them, and often knew the person themselves, who was more likely to be a neighbor than a stranger. Now that customer was increasingly showing up as a hard-to-track blend of digital and physical. They could be a commenter on social media one day and an actual shopper the next. And they could come to Walmart from anywhere on the planet, not just from down the block. There are so many points of unknown, and therefore of potential disruption, Russell Shaffer, Senior Director of Global Culture, Diversity & Inclusion at Walmart, shared with me in an August 2020 interview.⁴ Referring to those ever more complex customers, he said, "Even if they physically walk into the store, if for any reason they don’t like the experience they’re having, they can pull out their device and shop with someone else, one of your competitors, from the comfort of your store. Or they can voice their displeasure, taking a photo or posting online, and have it immediately radiate to dozens, hundreds, or millions." It’s fair to say that when Sam Walton founded Walmart in 1962, he could hardly have imagined a customer who could shape shift from real to virtual, lover to hater, and from your customer to your competition’s in a single click.

It wasn’t just slow growth and a complex customer base challenging McMillon. The entire retail landscape was changing, fast and forever. So dramatic was the change that it was becoming hard for Walmart to confidently identify who its competition actually was or to figure out how to best them. The choice McMillon faced was how to lead in such uncertainty, or as the HBR piece put it bluntly, how to bring Walmart into the future, without blowing the franchise.⁵ In such conditions, what should a leader do?

A Whiff of Rebellion, Cloaking a Tsunami of Change

To say that Doug McMillon’s early moves at Walmart were unconventional would be an understatement. Right from the start, McMillon seemed to flaunt accepted leadership standards—not in a troublemaking or contrarian-for-the-sake-of-being-contrarian way, but in a wise, considered, and confident style. Still, his unexpected actions left many perplexed. A pointed example: where most leaders would be expected to curb expenses in tight, uncertain times, McMillon did the opposite. He boosted wages for hourly workers. This in turn increased expenses—not to mention morale, commitment, and loyalty. There were those who raised an eyebrow at McMillon’s actions, especially other leaders. Increasing wages at the bottom of the organization decidedly leaned toward the needs of labor, when tough times had long offered arguable cover to do the reverse. Why would McMillon do what he did? Because he knew leadership was no longer something he could define or pursue alone. He needed those hourly earners in a whole new way—not just as doers, but as leaders themselves.

If it had been a single move, perhaps no one would have really noticed. But as those early months and years of McMillon’s tenure unfolded, it began to feel as though nothing was off-limits to reconsider. As a further example, prevailing leadership logic would have suggested that, especially in turbulent times, he should stick with the proven—things like firming up the company’s commitment to the physical store model or leaving leadership exclusively in the hands of those who’d brought Walmart to its market leading position. McMillon did neither. First, he increased the company’s commitment to online sales. Next, he revamped the executive team. And then he told Walmart’s 2.3 million employees that his goal was "to leverage the collective perspective, wisdom, and experience of everyone."⁶ Short of that, he said, Walmart would have a tough time sustaining its leadership position deep into the new century. You, every single one of you, McMillon was saying, must lead.

It wasn’t just his actions that smacked of leadership rebellion. His language diverged from the familiar script as well. At shareholders’ meetings, in documents and memos, in interviews—pretty much every time he communicated with anyone—McMillon talked less about his role as a leader and more about the leadership necessary, not just to carry Walmart into the future, but to shape that future. I’m not doing this alone,⁷ he repeatedly said. These weren’t statements of abdication of responsibility as CEO. They were signals of how his view of leadership was something quite apart from the belief that other leaders, the marketplace, in truth, most of us default to: that the individual leader equals leadership. If I were married to the things we’ve always done, McMillon said, not only about the way Walmart had operated for decades before him, but about the role of the leader, I’d be holding the company back. It’s the kind of goodwill window-dressing statement that in the past a leader might make at a shareholders’ meeting, before returning to the top down, well-worn approach everyone expects. The difference was McMillon meant it.

These counterintuitive and bold moves were far from isolated and hardly anecdotal. They reflected a focus and a vision of leadership that began to sound like a mantra. And to the thoughtful observer, that’s precisely what it was—not his mantra as the CEO, but Walmart’s, a powerful organization whose only way to maintain that power, McMillon was signaling, was to pursue a culture of leadership. To him, it was about Walmart leaning into the future by leading in an entirely new way. And that’s exactly what he was trying to make clear to readers in his conversation with HBR.

Through much of the interview, they covered the typical questions leaders are asked—about competition, dealing with labor, and whether or not Walmart was serious about bold future-looking initiatives like energy conservation and sustainability. Though the queries were familiar, within each answer, McMillon seemed to be saying something more, something different, subtle at first, but consistent and growing. And then he was asked a question out of step with the rest: Do you ever feel that the pace of change is out of control?⁸ It was a question refreshingly freed from the expectations of what any of us, good leaders included, should think or do in such times or with such disquieting feelings. It was also precisely the question that increasingly each of us wants to ask. McMillon was not only ready to answer it; he’d already been living it.

As if taking the conversation to that next level he’d been aiming at all along, he answered this way. Once upon a time, he began, as if giving a nod to an old story before telling a new one, a company like ours might have made big strategic choices on an annual or quarterly basis. Today, McMillon said, (they’re) daily. He said he even joked with other leaders that in truth such dilemmas are now hourly. Such a challenge stretches beyond the scope of any one leader, as McMillon had made clear throughout the interview. It requires not a mythological superhero, but a whole new mindset around what it means to lead. His blunt admission was a moment of authentic candor, a brief window through which to glimpse what the most impactful leaders are thinking about now. It was a chance to hear a leader like Doug McMillon talk about the most vital elements of successful leadership in this new century—of leadership being shared and moving, of innovation permeating the entire organization, and of things that sound so simplistic, like purpose, yet hold the key to success. It was nothing short of a gift. Yet seen through an old lens, it was easy to miss.

Doug McMillon is a leader in touch with the very world Peter Drucker said would come and indeed has come. In response to that changed world, McMillon is creating a culture of leaders, 2.3 million globally to be exact, who sense and embrace the same uncertainty and know it is their collective job to meet it successfully. Russell Shaffer made that clear with this simple, poignant anecdote. One of the things Doug says all the time, Shaffer told me, is that at Walmart, the only constant is change. It’s something every one of us knows it’s our job to lean into, including Doug. He actually carries a list of retailers around with him, a top ten in each of the decades going back to the beginning of Walmart’s history. What’s most telling is how many of those organizations no longer exist, Shaffer said.⁹ We don’t plan to be one of those. We is what makes it an odds-on bet that they won’t be.

The New Abnormal

McMillon’s response to HBR was first and foremost a bold admission. No one knows for sure what will happen in a world where big strategic choices occur hourly—not even one of the most informed and influential leaders on the planet. If you’re skeptical of the relevance or ramifications, or if perhaps you’ve already concluded that McMillon and Walmart are outliers, consider this as well. In a 2017 PricewaterhouseCoopers (PwC) survey of 1,749 CEOs spanning dozens of sectors and countries, a stunning 82 percent of leaders said that the economic future of their organizations was, to put it bluntly, unpredictable.¹⁰ 82 percent. Then take note of this: It’s the very same answer a majority of leaders have given every single year for more than a decade in similar surveys. If that doesn’t give you pause, check your pulse.

That’s the view from current leaders, but the impact of this changing landscape extends further, to include future leaders. Not long before she came to Airbnb as Global Head of Diversity and Belonging, Melissa Thomas-Hunt was a member of the leadership team at the University of Virginia’s Darden School of Business. Darden is a proving ground for future leaders, and known to be a tough one. I asked Thomas-Hunt what she’d observed not only in the range of leadership roles she herself has filled over the past twenty years, but also among those in training to become leaders. Even the way she began her answer spoke volumes.

I don’t talk about this often, Thomas-Hunt told me, but the thing that has been most profound is seeing the steep rise in the stressors people feel, she said, referring specifically to the up-and-coming leaders admitted to Darden.¹¹ They’d be tested in any event (in the program), challenged just to get a handle on what it means to lead in the world and to succeed. But the assumption is built in that they’d have time to learn and adjust to it all. And then they quickly realize that’s now gone. There’s no cushion, no time to learn or absorb as there once was. The impact is huge, including the impact on the psyche. Our students weren’t just aware of the challenges, mental and otherwise, the new demands were so great and insidious they began to openly articulate them, and to concede a greater demand on leadership than they’d ever anticipated.

Tom Koulopoulos calls it the ‘uncertainty principle,’ the idea that as uncertainty increases, the time to react decreases.¹² When that happens, Koulopoulos says, People don’t want to speed up to keep pace with the change. They want to slow down. They want to take more time to consider their options. Trouble is, as Thomas-Hunt makes clear, that added time no longer exists, even, it turns out, in a simulated environment.

The world has changed. When it comes to meeting that change, the old ways aren’t working. And yet by and large we, our leaders included, are not changing with the times. This is the new reality Doug McMillon and others you’ll hear from in this book are trying