The Art of Leadership

Introduction

This is a book full of small things. Simple, memorable leadership acts and practices that I’ve gathered and refined over the years.

Here’s my favorite: I’ve preached 1:1s, weekly recurring meetings with direct reports, for decades. I believe a 1:1 represents the simplest and most reliable way to build trust between you and your coworkers, by providing a weekly high-bandwidth conversation on current events affecting the team. 1:1s are the first meeting I schedule when I show up at a new gig and they are the last meeting I’ll reschedule or cancel during busy times. 1:1s have been my team-building go-to move for years.

Where’d this belief come from? Why do I think they’re so important? I discovered 1:1s at Netscape in the mid-1990s. A recurring weekly meeting with the boss. It was a thing that managers did, but that didn’t make them relevant. Just work that I was supposed to do, so I scheduled them.

Months and years passed, and I dutifully did my 1:1s. A habit? Perhaps a better term to describe what’s contained inside this book would be leadership habits—​small acts, repeated over time until they become second nature. There is an intersection between my list of small things and habits, but you’re not going to learn from these practices just by having them become second nature.

What I discovered after hundreds of 1:1s was that these meetings presented the highest signal of the week. Real conversations about the important topics that week. Critical bidirectional conversations revealing information that I have found no other reliable way of discovering.

My belief in 1:1s, the reason I schedule them for 30 minutes, every week, no matter what, is because I’ve now done thousands of them. I’ve learned how to always productively fill the time, I know how to get the curmudgeonly engineer to appreciate them, I know what to do when they go sideways, and I have a good idea what’s up when someone declines them without reason. They are a habit, but the habit isn’t what taught me that 1:1s are important—it was the compounding value of the experience gained performing each one.

I learned that 1:1s are the single best way to build professional trust and respect with your team—but you won’t truly believe me until you’ve done a couple hundred of them and seen the results for yourself.

Sounds like a lot of work, right? It is.

I originally pitched this book as a set of “leadership hacks.” The title fit. Sort of. I’m an engineering leader. I am surrounded by talented engineers who often pride themselves on developing hacks. I spend a lot of time writing about leadership and packaging that wisdom, and the concept of a hack feels efficient and familiar.

Problem is: you can’t hack leadership.

The term hacker originated at the Massachusetts Institute of Technology and is meant to describe someone who does interesting or creative work at a high-intensity level. This applies to anything from writing computer programs to pulling a clever prank that amuses and delights everyone on campus. An example: in 2009, a group of students put a half-scale model of the lunar lander on the Great Dome at MIT to celebrate the upcoming anniversary of humans setting foot on the moon.

Clever. Amusing. Not leadership.

Leadership, like any complex skill, can’t be hacked; it must be thoughtfully and patiently built. Leadership is built on a set of practices, but the judgment of choosing when to use or deploy a certain habit is the art of leadership. One of the primary reasons there are not noteworthy university degrees in leadership is because leadership is a set of skills you must learn from the job.

At this point in our history as a species, we are unfortunately addicted to the idea of time-saving “hacks—simple,” clever ways to quickly achieve or know a thing. This is not that book. This is a book of repeatable practices that over time will combine to form sustainable, self-improving leadership.

Pick a small thing, practice it for three months, and discover for yourself how it will make you a better leader.

Interested? Let’s begin.

How to Use This Book

There are two ways you can approach reading this book: randomly or linearly. Let’s talk random first.

Like in my previous books, many of the chapters of this book are standalone. Coming from decades of writing on my blog, I have a penchant for self-contained chapters. Each of these chapters contains at least one small thing. To help you pick a small thing to get started with, I’ve compiled a complete list of Small Things contained within the book (you’ll find it after this introduction). If you’re looking for help on a specific small thing, you can skim the list and jump to wherever inspiration strikes. Are your staff meetings feeling a little dull? Are you doing all the talking? Check out my tip for adding a recurring agenda topic to encourage gossip, as discussed in Chapter 13.

The linear path within this book provides a more narrative structure. The book is broken into three acts, with each section representing a key leadership stage in my career: manager, director, and executive. Each of these sections begins with a very brief history of the company where I truly learned about the role—Netscape, Apple, and Slack, respectively. The section openers also contain brief definitions and descriptions of the responsibilities of the leader as a manager, a director, and an executive.

For any given chapter, you might start it and think, “Good idea.” Or you might think, “Well, that’s dumb, I’d never do that.” Turns out, you have the mutant power of knowing the time without ever looking at a clock. I wish I did, but I don’t, so whenever I enter a meeting my first move is to turn a clock to face me so I can check the time without interrupting the flow of our meeting. Skip a chapter if it doesn’t speak to you. It’s fine, you won’t miss part of the narrative.

While this book contains a comprehensive list of small things compiled over three decades of leadership, I’m not actively using all of them. Many may not cleanly apply to your current situation. As each company culture is different, so is each team, and each team member. Starting meetings on time is nonnegotiable in my book, but in some company cultures every meeting starts five minutes late, no matter how many times I attempt to set the tone by showing up two minutes early.

Regarding names: there are proper names throughout this book. Just about all of them are fake, with some notable exceptions for CEOs, founders of companies, and mentors. Similarly, while I attribute these lessons to my time in these companies, the stories I tell to explain them are fake.

Finally, throughout the book you’ll notice I interchangeably refer to myself as both my last name (Lopp) and my online persona (Rands). The latter is a name I began using in the mid-1990s for my online presence and is predominantly featured on the Rands in Repose weblog. The former is, well, my name.

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Acknowledgments

My professional career would be in shambles without 1:1s—and by 1:1s I mean recurring meaningful meetings with my team. A significant number of the small things you will discover in this book were defined and refined with the talented humans I’ve worked with over the past decade.

I’d like to acknowledge and thank the following humans who unknowingly contributed to the creation of this book:

• Julia Grace. I have never met a human who has more drive and is also always prepared with incredibly thoughtful and penetrating questions.

• Marty Kaplan. My coach. Thank you for teaching me the importance of feedback by consistently and constructively giving it to me.

• Cal Henderson. You taught me the importance of listening to every single word being spoken and understanding those words—and, when understanding wasn’t obvious, the importance of stopping everything to ask clarifying questions.

• Brandon Jackson. I have never professionally argued more with anyone. These arguments built our trust and respect, and that’s when the real lessons began. Thank you, my brother.

Finally, to Rachelle, Spencer, and Claire. My family. Thank you for sitting with me at dinner and laughing. The best part of every day.