INTRODUCTION Kicking Leadership’s Gluteus Maximus

Good judgment is the result of experience and experience is the result of bad judgment.
—Mark Twain

At some point, every leader is confronted with the reality that his or her leadership is seriously and substantially flawed. It is at this precise moment when a leader faces a choice: learn and grow or remain blindly loyal to ignorance. All leaders worth their salt will get a psychological kick in the rear end eventually. It is a critical and inevitable part of the leadership experience. Choosing to learn from the experience requires exploring the leader you’ve become and clarifying the leader you want to be. It also involves suffering through temporary embarrassment and insecurity. As the renowned psychologist Carl Jung said, “There is no coming into consciousness without pain.”

Some leaders refuse to accept any culpability when they get kicked, choosing to double down on their conviction that their way of leading is “right,” regardless of how the people they’re leading respond to their leadership. They view the kick not as a learning experience to embrace, but as an insult to reject. While this choice skirts the psychological discomfort that growth requires, the end result is often self-righteousness, rigidity, and leadership narcissism. Ultimately, though, failing to accept and learn from a backside jolt is as futile as trying to keep a beach ball under water. No matter how often a leader rejects feedback that runs counter to his self-identity, the beach ball will keep popping back up in the form of negative consequences. The leader who gets fired from a dozen companies rather than capitulate and accept that his approach to leading needs to change will end up having a lot of empty seats at his retirement party.

How leaders deal with, or fail to deal with, butt-kick moments will make all the difference toward their future effectiveness, impact, and well-being as leaders. In fact, a good old-fashioned kick in the tail can be the turning point in one’s career—the moment at which a leader stops swimming against the tide of his limitations. After a gigantic and very public psychological ass kicking, involving getting sacked from the company he founded, Steve Jobs said, “Getting fired from Apple was the best thing that could have ever happened to me.”

Confidence, Humility, and Balance

The best leaders, those we most admire, are comfortable in their own skin and help us become more comfortable in ours. The best leaders are centered, grounded, and nontoxic. They lead not so their power can grow, but so ours can. Through giving the best of themselves, they draw out the best in us. The best leaders are confident and humble, and in balanced proportions. The goal of this book is to help you grow from whatever kicks you may endure so that you can lead from a place of confidence and humility. More than ever, the world needs more confidently humble leaders.

Much of this book centers on confidence, humility, and the balance between the two. They are like siblings, forever bonded, each existing in relation to the other. Each matters to leading, and the absence of one has a crushing impact on the other two. Too much confidence causes a leader to get too far out over his skis, leading to a wipe-out. Too much humility can lead to timidity, weakness, and leadership impotency. We want our leaders to display both confidence and humility, but not too much of either. When the two become wildly out of balance, the needs of those being led get sacrificed at the altar of leadership dysfunction.

Functional and Dysfunctional Leadership

We consider leaders functional when they carry the right blend of confidence and humility. Conversely, we view leaders who are excessively one or the other as dysfunctional. The leaders we most want to follow know who they are and what they stand for, yet are also gracious and not stuck up.

The best leaders are centered, grounded, and nontoxic. They lead not so their power can grow, but so ours can.

When confidence becomes untethered from humility, arrogance follows. Arrogant leadership is selfish leadership, and arrogant leaders fixate on getting their way. Without the moderating effect of humility, confidence slips into conceit and self-centeredness. The self-centered leader loses sight of the very purpose of leadership: to improve the conditions of those being led. Unless he gets his way, he will be irritable, combative, and controlling.

If confidence minus humility equals arrogance, then humility minus confidence equals weakness. Whereas arrogant leaders are selfish and insist on getting their way, weak leaders are ineffective, ceding the way to more dominant or persuasive people. Weak leaders lack backbone, influence, and ultimately relevance. In the worst instances, weak leaders are useless. They don’t get things done. They don’t effect change. They don’t wield influence. Few things are as pitiful as an impotent and irrelevant leader. Nobody wants to be led by a wuss.

The Rude Awakening

Eventually, arrogance and weakness lead to the same outcome: a humiliating wake-up call for the leader. Ass kicks are startling and embarrassing experiences, often brought on by the leader’s own behavior. They are the natural consequences of overly strong or anemically weak leadership. Leaders mature, progress, and evolve based on how they respond to hurtful moments. This book provides practical guidance to ensure that you benefit whenever you get your butt kicked. By exploring the concepts of confidence and humility—as well as other important leadership concepts like self-respect, selflessness, and resilience—the book aims to help you be a more functional leader. Or, at the very least, the book will help you minimize the impact of your leadership dysfunctions!

Leadership with Pimples and Warts

I need to be clear right up front that I have no intention of dressing up leadership with a rosy veneer. My work with leaders has convinced me how immensely difficult it is to get leadership right. Leading other people, for a host of reasons that we’ll explore, is really, really hard. Indeed, the sheer glut of leadership books may be the best evidence of how hard leadership truly is. If it were easy, budding leaders wouldn’t be so thirsty for leadership advice. Rather than try to glamorize the topic, I intend to strip it down, so you can have a more grounded, authentic, and reality-based view of what it takes to lead. Unlike other leadership books you may have read, A Leadership Kick in the Ass proposes that

leadership is easier to get wrong than to get right,

leaders are often their own worst enemies, and often get in their own ways,

the most enduring and transformative leadership lessons come from humiliating leadership experiences well navigated,

not everyone is cut out to lead (but everyone can grow in their leadership influence),

to be most effective, leaders need both confidence and humility; deficiencies in either cause poor or damaging leadership.

This probably isn’t the first book about leadership that you’ve picked up to read. Nor is it the first leadership book I’ve written. My hope, though, is that it will be the first leadership book that pushes you forward with a footprint on your bum. If you read this book and nothing about your leadership changes, then I haven’t done my job as an author. You won’t change if all I give you is leadership platitudes and niceties. Your brain doesn’t need any more leadership cotton candy. Rather, the book’s aim is to rattle you, provoke you, and challenge you. So along the way, and at the end of each chapter, I’ll give you a little kick so that the concepts sting enough to hold you accountable to your leadership potential. To write a book about the importance of butt kicks and then not give you any would be out of step with the book’s message, don’t you think?

A good ass kick can provoke a great comeback. Sprinkled throughout the book are stories about people who succeeded not in spite of their kicks, but because of them. These stories are under the heading “Kickass Comebacks,” and I included them to inspire great comebacks from you, too.

A Word on the Word

It took a while to settle on the title of this book. My publisher and I considered easier, softer words. In the end, though, we settled on a three-letter swear word. Why? Because of the truth of the word. Sometimes situations are just so perplexing, embarrassing, and leveling that they kick your ass. I mean, haven’t you ever heard someone describe a situation as being so upsetting that it’s “kicking my ass”? Sure you have. Maybe you’ve even said the words yourself. That said, I promise not to toss the word around like a New York City dockworker. Besides, you’re not a Mayflower pilgrim, right?

Consider, too, that the phrase has a strong positive connotation. When you talk about wanting to give someone a good kick in the fanny, it’s to inspire change, help someone perform to his or her potential, and inspire accountability. It’s a way of kick-starting positive action and forward movement.

Finally, it may help to know that my eighty-year-old mother approved of the word, saying, “Let’s be honest, Bill, ass isn’t really much of a swear word.”

Nobody wants to be led by a wuss.

This Kick’s for You

In particular, you’ll get a lot out of A Leadership Kick in the Ass if you’re still smarting from the last you had. In other words, if you’re a leader who has been humiliated by a recent hardship or failure, this book is for you. You’ll also benefit from the book if you’re

someone who is new to the leadership ranks—a rookie or a greenhorn,

an experienced leader who is moving into a new or substantially bigger role,

a participant in a leadership development program, or a leader going through a 360-degree feedback process,

a recently fired executive who is suffering from a crisis of confidence or questioning your ability to lead,

an experienced leader who has become disillusioned with how massively hard and perplexing leading others has turned out to be.

You know who else can benefit from this book? Know-it-all leaders who think they’ve got the topic all figured out, and that they have nothing left to learn about leadership. In other words, leaders whose bloated egos could use some downsizing. These folks might want to put on their Kevlar underwear!

How the Book Holds Together

Startling Change

Heavyweight boxer Mike Tyson famously once said, “Everybody has a plan until they get punched in the mouth.” By definition, a swift kick in the ass is painful. Essential as they are to the leadership maturation process, the learning starts after you pick yourself up off the mat. A leadership kick in the tuckus can be the moment where everything changes for you as a leader. These stark and startling moments can rattle your confidence to the core, often provoking serious thoughts of rejoining the nonleader ranks or quitting altogether. But these moments can also be the starting point where you assess your strengths, clarify your values, and develop an authentic and true leadership voice and style. Ass-kick moments are important because they can make you set aside a false leadership identity so that a more genuine and grounded identity can emerge. These events have the potential to inspire what I call transformative humiliation, and when that transformation happens, you’ll be more respectful of yourself and those around you. Thus, your leadership experiences preceding the kick are just a prelude to the real leadership story that begins afterward.

Above all, benefiting from A Leadership Kick in the Ass requires choosing adaptability over obstinacy. It means assuming responsibility for your own actions and the consequences they bring. It involves having the courage to soberly acknowledge the leader you are today while you diligently work to be a better leader tomorrow. It means heeding the pure voice of your conscience. It means accepting the challenge of personal change and letting go of outdated preconceptions. As Viktor Frankl once said, “When we can no longer change a situation, we are challenged to change ourselves.”

The core of this book is really about independence. Once you’ve juiced out all the lessons that your kick hits you with, you’ll be unencumbered by doubt and self-consciousness. You won’t be dependent on the validation of others to judge your worth as a leader. You’ll stop over-compensating for your weaknesses by being falsely confident and overdominant, and, instead, will gain strength in the humble recognition that leading and influencing others is a privilege to be honored and treasured. Your kick will ultimately teach you that the only way to bring out the best in those you’re leading is to lead with the best of yourself.

Gaining leadership independence hinges on understanding, anticipating, and contending with the harsh experiences that bruise your ego. That’s what this book will help you do. As you’ll come to learn, butt kicks are really gifts that can make your leadership more authentic, effective, enjoyable, and wonderfully liberated.

The only way to bring out the best in those you’re

leading is to lead with the best of yourself.