INTRODUCTION

Ancora imparo. (Yet, I am learning.)^*

—MICHELANGELO

Jennifer materialized in the doorway of my brand-new office without a sound. I nearly jumped when I looked up and saw her standing there. Her pursed lips struggled to keep her face from spilling the emotion that was clearly damned up. It wasn’t good. It was my first week as a manager—my first week having an office with walls and a door that closed, not to mention a big window and a fancy Herman Miller chair.

What did I do? Thoughts of self-doubt welled up in me. I had been promoted to lead the team that I had been a member of just days earlier. She’s probably upset they chose me, or she thinks I don’t deserve it, that I’m too young, too inexperienced. Could she be right? I’m only 27, and she started her career when I was in grade school.

“Oh! Hey, Jennifer. What’s—” I didn’t get to finish.

“Ryan, my husband cheated on me,” she said. Her voice quivered. “He wants . . . a divorce.”

What? If this moment had a soundtrack, Jennifer’s words would’ve cut the music with a giant record-scratch. Why is she telling me this? What am I supposed to do? My mind reeled. I couldn’t imagine divulging this kind of information to my boss (especially someone I only knew casually as a peer a few days ago), let alone having any clue what to do when I was the “boss” getting it dropped in my lap. I had not counted on this kind of conversation in my new leadership role. Nobody told me that a manager would have to deal with situations like this.

Welcome to management.

If you are holding this book because you’ve just been promoted and are in a new management position, congratulations. You are now the subject of the dinner table conversations of every person who reports to you. You have become the individual your employees complain about to their spouses and children. You are now responsible for the careers of those who report to you. You are now “the boss.” Did you realize what your manager did when you were an individual contributor? Did you think they had it easy?

If you’re like I was, you probably couldn’t wait to get your promotion and become the boss. Unfortunately, you don’t fully appreciate everything management entails until it’s your job to do.

With Jennifer standing there, waiting for me to respond, I quickly realized there was so much more to leading a team than I had previously thought. In that moment, it dawned on me: I wasn’t sure what a manager actually did.

THE FIRST PROMOTION

I grew up professionally in sales organizations. Telephonic sales was my first “real” job after my arena football career ended, and I was focused on figuring out how to win. For me, winning meant not just consistently hitting my sales quota, but staying at the top of the sales rep stack rankings.

After making my mark for several years, my success as an individual contributor earned me the opportunity to interview for a leadership role. With the leadership skills I developed as a Division 1 college and professional quarterback, I was certain I was ready. Then I had my conversation with Jennifer, and I realized I had to learn an entirely new way of operating if I wanted to avoid becoming the latest proof that the Peter Principle is quite real.

The Peter Principle is a concept in management developed by Laurence J. Peter, which observes that people in a hierarchy tend to rise to their “level of incompetence.”¹ Employees are promoted based on their success in previous jobs until they reach a level at which they are no longer competent, as their skills in one job do not necessarily translate to another. Though an employee may be a high performer in one area, managing others to do the job is a wholly different skill set—one dependent on the ability to lead more than on the ability to perform. In other words, the fact that you were a top performer in your previous role does not guarantee that you have the skills to become an effective manager. That said, you are more likely to be promoted into a management role because of your high performance. Kind of a Catch-22, isn’t it?

I’ve always had an interest in performance excellence and leadership. Having grown up as an athlete, I spent much of my formative years learning how to work with others in a team setting. I’ve been on winning teams and on losing teams, and both experiences taught me about the tactics and psychology it takes to sustain excellence. Despite these experiences, it was still difficult to know exactly how to put all of this into action when I became a manager for the first time.

My story is not an anomaly. Few first-time managers know what it really takes to lead, to earn the trust and respect of your team, to develop a culture that leads to high performance, or to communicate in a way that moves people.

Being promoted up the ranks is exciting, but unfortunately, the typical organization does an underwhelming job of preparing its new managers for success. There is no single handbook on how to go from being responsible for your own success to being responsible for the success of many. As a result, the first promotion you land, moving from team member to team leader, will be the toughest transition of them all. There are few directions that prepare you for the surprising roles you will play for your team. There aren’t many guides that will show you how to navigate the tricky social dynamics of being a good coach to people who previously saw you as a peer. I hope this book fills that gap.

BECOMING THE LEARNING LEADER

I believe that every person has the ability to lead. It’s just a matter of learning how.

For me, that meant pursuing my master’s degree in business in the hope that it would help me improve as a manager. While I’m glad I earned my MBA, I didn’t entirely enjoy the experience. It was too restrictive, and the classes didn’t cover topics I needed to know at a deep level. I wanted to learn directly from the people who fascinated me the most.

As fate would have it, the serendipity of a seat assignment for a flight to Lake Tahoe in 2014 set me on the unexpected path of doing just that. As I sat down and stretched my legs in my exit row seat, I found myself next to a friend of Todd Wagner. Todd Wagner founded Broadcast.com and eventually sold it to Yahoo! for billions. He did this with his partner, future investment “shark” and Dallas Mavericks owner Mark Cuban.

Over the course of this flight out west, I told my new friend about my desire to learn more and to create my own cast of teachers in the form of people who have lived lives of excellent leadership. By the time we landed, he had agreed to connect me with someone on Todd’s team. Soon after, I met Todd for dinner.

Todd arrived about an hour early at the hotel where we were going to have dinner, and I was fortunate to spend this time with the self-made billionaire at the bar.

He was as kind as he was wise. I was blown away by his intelligence and his humble nature. I peppered him with questions. I wanted to learn about the what, who, why, and how at Broadcast.com. I was eager to hear how they looked the leaders of Yahoo! in the eye and said, “Look, you’re either going to buy us or you’ll have to compete with us. You decide.” Todd and Mark concluded their meeting and walked away with $5.7 billion.

It was an incredible story, but I had one regret. I wished I had recorded the conversation. I wanted to pass along what I had learned to others. That dinner gave me a taste of what I could learn if I went directly to the source of the knowledge I so badly wanted to gain. In fact, I started thinking about how to have more conversations like that one—and how to share them with others. Through that confluence of events, I decided to create an interview-format podcast as my own virtual PhD program and call it The Learning Leader Show. By doing this, I would not only give influential leaders a reason to sit down for a conversation with me, I would also be able to share it and serve others in their leadership journey.

This is also why I’ve written this book. I understand your pain and dilemmas. I was there, too. I made countless mistakes during my years as a first-time manager, so in this book, I’ve taken everything I’ve learned from my own experience, research, and interviews with over 300 of the brightest leadership minds in the world, and I’m sharing it with you. I’ve distilled hard-won wisdom from my messy experiences and those of others I’ve learned from in order to make it easier and faster for you to become an excellent leader.

This book is for and about you. Many of you have worked for a bad boss (as have I). I care deeply about great leadership and recognize that it is exceedingly rare. The leaders in our lives have broad influence. When you earn a role as a new leader, my hope is that this book helps you use your power for good. My goal is to help accelerate your leadership education. I want you to be better able to make great decisions and to avoid some of the mistakes that I made as a first-time manager. Bad leadership is a costly epidemic. This book is part of my contribution to help eradicate that in whatever way I can. I want your contribution to the world of leadership to be a long-lasting net positive.

Here’s how I’ve structured the book:

Part I: Lead Yourself. I very much believe in the mantra “You can’t lead anyone without first leading yourself.” So before we get to how to lead others, we will start with you—how you learn, what you learn, who you learn from, and why it’s so important to continue learning throughout your life. We will explore the challenges of leading yourself both inside and out, and examine the tools and tactics for overcoming any and all obstacles.

Part II: Build Your Team. Before the roster of an effective team can be assembled, the idea of what makes for an effective team must be established. That means building a healthy team culture, and Part II will start there. With an understanding of culture in place, we will then move to the nuts and bolts of building the roster through hiring (and firing), as well as developing trust and earning respect.

Part III: Lead Your Team. Finally, we will discuss how to succeed at doing what managers actually do: setting a clear strategy and vision for your team, communicating them (and a myriad of other things) effectively, and ultimately driving the results everyone is counting on your team to deliver.

Throughout the book you will find helpful mental models, templates, key takeaways, insights, and advice from some of the most forward-thinking leaders around the world. Through case studies, research, personal stories, and the messages of the many leaders I’ve interviewed, this book will provide every new leader with the guidance needed for this important step in your career.

This is the book I wish I had when I was first promoted to a management role. I hope it will help you make the leap from individual contributor to manager with greater ease, grace, courage, and effectiveness.

^*Ancora imparo is an Italian phrase meaning “Yet, I am learning.” It is often attributed to the Renaissance genius Michelangelo, supposedly observed by him at the age of 87.