A short book on leadership

Intentionality.

How to lead when you’re not in the room.

Roughly twenty honest pages · no doorstop


Preface

There are too many leadership books. I’ve read most of them. A lot of them are the same book in a different jacket—a tidy framework, a few logical-sounding acronyms, a promise that if you just internalize the seven habits of the five disciplines of the three pillars, your people will follow you anywhere. They make it sound like a system you install.

It isn’t. Leadership is not a framework you install. It’s a thing you do, badly at first, in front of people who can tell when you’re faking it. This book has a framework in it—you can’t write one of these without a framework, it’s practically the law—but the framework is just the skeleton. The meat is the stories, and most of the stories are about me getting it wrong before I got it right.

So before you spend your time, let me figure out whether this book is for you. I can do it with one question.

Who’s buried in Grant’s Tomb?

There are three kinds of people, and your answer tells me which one you are.

The first kind knows who’s buried in the Tomb of the Unknown Soldier. If that’s you—if you’re certain you know even the things that are, by definition, unknowable—put the book down now. You won’t get anything from it. Not because the book is empty, but because you already know everything, including the parts you’ve got wrong, and there’s no room in a full cup. I can’t help you. Nobody can. Go in peace.

The second kind doesn’t know who’s buried in Grant’s Tomb, and doesn’t much care to find out. If that’s you, this isn’t your book either. There are some long words in here, and worse, there are a lot of questions, and you’ve made it clear you’re not in the question business. No hard feelings. The remote is right there.

The third kind hears “who’s buried in Grant’s Tomb,” shrugs at the obvious answer, and asks a better question: why is Grant buried in Manhattan? If that’s you—curious, never quite full, green and growing—then I wrote this book for you, and I’m glad you’re here.

A few more things you should know.

This book is short. That’s on purpose. I had about twenty pages of things I actually believe, and I refuse to pad them into three hundred so the spine looks impressive on a shelf. If you want a doorstop, there are better doorstops. If you want the twenty pages without the filler, you’re in the right place.

This book is opinionated, and sometimes I’m wrong. I’ll tell you what I think worked and why. You’ll disagree with some of it. Good—a leader who agrees with everything they read isn’t thinking, and I’d rather you argue with me than nod along. The one thing I won’t do is pretend I have it all figured out. I don’t. Anyone who tells you otherwise is selling a seminar.

This book is for the person in the chair. The founder who can’t sleep. The CEO who can’t tell anyone how scared they are. The newly promoted manager who just figured out that managing and leading are not the same job, and that nobody handed them the second manual. If that’s you, I know exactly how alone you feel right now—I felt it for thirty years.

And this book will, at times, make jokes about serious things. That’s not me being flip. It’s how I survived a career that broke a lot of better people. If you can’t lead and laugh at the same time, the job will eat you. So we’ll laugh.

By the end, you’ll have built a single page—I call it a Leadership Canvas—that defines who you are as a leader and what your team can count on from you every day. One page. If you do the work, it’ll be the most useful page you own.

And stick around to the last page. That’s where I tell you why Grant is buried in New York City.

Let’s get into it.

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Introduction

I Was in the Hospice Business

After I sold a startup for $92 million in cash to a Fortune 500 company, I spent ten years parachuting into failing companies for private equity investors. Five of them. Without exception, every one was a failure of leadership.

“Turnaround executive” sounded glamorous to me when I took the first assignment. Then I finished my last one—shutting down a company called Intellipark—and woke up at three in the morning unable to get back to sleep. I lay there doing the math: the hundreds of people I’d laid off, the millions in assets I’d sold for parts. And I understood what I actually did for a living. I was in corporate hospice care.

Those five companies were already in a death spiral when I arrived. They weren’t going to fly. The best I could do was crash-land them softly, harvest the organs that still worked, sell them, and limit the damage. I wasn’t there to cure anyone. I was there to make the ending dignified and cheap.

I needed out of the hospice business. I wanted to reach patients before they were terminal.

So I trained as an executive coach, and since 2007 I’ve spent my days as the person CEOs can finally tell the truth to. This book is what I learned in both jobs—the autopsies and the wellness visits. By the end of it, you’ll have built a one-page document I call a “Leadership Canvas.” It defines who you are as a leader and what your team can count on. It’s the thing that lets you lead people who are a thousand miles away from you.

A warning before we start. I’ve founded companies, raised millions in venture capital, soared, failed, profited, and failed again. Those failures made me skeptical and a little mean. I don’t tolerate lying, and I tolerate even less the hope that a bad idea executed badly will somehow come out fine. For this, people once called me Mr. Cranky. I wore it like a medal. He shows up throughout this book. You’ll know him when he arrives.

Part One

WHY WE FOLLOW

Chapter 1

How I Got Here

In 2003 I walked into my second turnaround and inherited the fired CEO’s office. It was the size and quality of a Fortune 500 corner suite—except this was a failing tech startup that had never turned a profit. The walls were covered in photos of my predecessor shaking hands with celebrities, framed press clippings, awards for things that apparently didn’t include making money. The company was burning half a million dollars a month. Every two months it lit more cash on fire than it had earned in revenue across its entire five-year existence.

One weekend I brought my young son to work. He looked at the supply closet I was working out of, then down the hall at the conference room that used to be the corner office, and frowned. “Dad, if you’re the boss, why is your office the smallest one?”

“Because I had to make some of the people here go away,” I said. “And I didn’t want a big office while I did it.” He thought about that.

“So the big office is for the people who are still here.”

“Yeah. Something like that.”

How did I get there? A venture capitalist hired me. He’d backed my first turnaround, two years earlier, and apparently I’d impressed him by closing it without setting anything on fire.

That first one is the better story anyway.

When I arrived, the company had burned through $70 million in venture money and was down to its last $6 million, with two hundred employees and the very real possibility of losing its largest client. On my first day I walked into a CEO suite roughly the dimensions of a small embassy. By the end of the week it was the employee break room, and I was working out of what had been a supply closet.

On my second day, we were down to 199 employees. The masseuse had been made available to industry.

I called the executive team together and told them the truth: not everyone in this room will be here in ninety days. We had two jobs. Keep the biggest client. Get from two hundred people to seventy. More innocent people were about to become casualties of someone else’s vanity, and there was nothing kind I could do about it except be honest and be fast.

Now maybe you understand the cranky. I’ve watched strong personalities in weak leadership clothing destroy things that real people depended on. I’ve cleaned up after them. I know the difference between a person who looks the part and a person who is the part. And since I joined my first startup in 1978, here’s what’s made me craziest: I keep watching the same failures repeat. And then get celebrated.

Chapter 2

Management Is for Toddlers

Is there a difference between management and leadership?

Put it this way. Is there a difference between Martin Luther King Jr. and Michael Scott—the Steve Carell character who ran a paper company on The Office into one cringe at a time? They could both hold a room. Only one of them could lead it. One you’d follow because he signs your checks. The other you’d follow into a fire—and he knew it, and that’s the whole book in one sentence.

Management is what you do with a two-year-old. You put up gates so they don’t fall down the stairs. You stick them in a pack-and-play so you can cook dinner without one of them scaling the bookcase. You take them to closely supervised playgroups where another adult is always within lunging distance. That is management, and for a two-year-old it is exactly correct.

Management fails the day your kid turns seventeen and has car keys.

There are no gates now. There is no supervision. There is a teenager, a Honda, and a Friday night. And when that kid thinks my parents would be ashamed if I drove drunk, or I told them I’d be home by midnight, and then doesn’t drink and gets home by midnight—that’s not management. You weren’t in the car. That’s leadership. Your kid did the right thing because of who you’d been for seventeen years, not because of a gate.

Management is rules, manuals, and process. Leadership is vision and direction, and then getting out of the way. Management corrects and scolds. Leadership coaches and cares. Management is the carrot and the stick. Leadership is the reason people don’t need either one.

Management fails the moment it meets a situation that isn’t in the manual. Leadership is what gives a team the judgment to handle the situation that was never in the manual. It scales where management flails. Leadership is what happens when your team does the right thing and you are a thousand miles away.

Except that leadership without discipline—random, unplanned, I’ll just be inspirational today and see what happens—is its own kind of disaster. Unintentional leadership is just management with the gates taken down and nothing put in their place. The real divide in this book isn’t management versus leadership. It’s intentional versus unintentional. Intentional leadership wins. Unintentional leadership fails, usually slowly, usually while everyone tells the leader how inspiring they are.

To understand why, you have to understand the embarrassing way human beings actually pick who to follow.

Chapter 3

We Don’t Choose Leaders With Our Heads

We like to believe we’re rational. We make pro-and-con lists. We weigh the evidence. We are thoughtful, deliberate creatures who decide things with the good part of our brains.

We are creatures of reason who reason our way to unreasonable things.

I’m going to use a piece of pop psychology here called the reptilian brain—the ancient, wordless, risk-averse part of us that’s only interested in one question: is this going to kill me? A neuroscientist will tell you the actual wiring is far messier than one lizard-brain throwing a switch, and the neuroscientist is right. So take it as a metaphor, not an MRI. But as a model for how people size up a leader in the first four seconds, before a single fact has been exchanged, it’s the best one I’ve got. So we’ll run with the lizard.

Here’s the lizard at work. You’re stuck in traffic, barely moving. Before I learned how stupid it was to get angry about traffic—which, in my adopted hometown of Washington, D.C., is roughly the same as learning not to get angry about gravity—I would sweat. Lean on the horn. Bang the dashboard. Snap at everyone in the car. Full fight-or-flight, the exact chemical state of an animal that is about to be eaten.

Why? You’re sitting in a padded chair surrounded by airbags going five miles an hour. You’re statistically safer than you are at seventy. So what’s the body responding to? This:

I’m going to be late.

My boss will be furious.

I’m going to get fired.

I’ll never get hired again.

I’ll run out of money.

I can’t afford food.

I’m going to starve to death.

Each step is reasonable. The staircase is insane. And I’m willing to bet that despite reaching I’m going to die, you have, in fact, survived every traffic jam of your life.

That’s the lizard. It can’t do math, but it gets a vote, and its vote usually wins.

Let me prove the lizard is running the show. Four quick questions.

One. I offer you five dollars and ask for one dollar back. Deal? Of course. You just made four dollars. Everyone takes this deal, every time. (Don’t ask why I stopped offering it.)

Two. A runaway trolley is barreling toward five people tied to the tracks. You’re standing at a switch. Flip it and the trolley diverts to a side track—where one person is tied down. You don’t know any of them. Five live, one dies. Do you flip it? When I ask a room this, two-thirds to three-quarters say yes.

Three. Same trolley, same five people. This time you’re on a footbridge over the track, standing next to a very large stranger. If you push him off, his body stops the trolley. He dies, the five live. Same math—lose one, save five. Do you push him? Now maybe a quarter of the room says yes.

Four. Five patients in a hospital will die without transplants—two need lungs, then a liver, a kidney, a heart. A perfectly healthy stranger walks into the waiting room with all the right parts. Do you strap him down so the surgeons can save five lives? Same math again.

In twenty years of asking, exactly one person ever said yes to number four.

Think about what that means. The math is identical to the five-dollar question—lose one, save five—and your thinking brain knows it. But you couldn’t do it. Something older than your logic reached in and voted no, and it outvoted you.

That something isn’t looking out for you. You were never in danger in that waiting room. It’s looking out for the species. A slow-breeding animal that will butcher its own kind whenever the arithmetic checks out doesn’t last—it does the math its way into extinction. So we’re built with a brake the math can’t reach. You felt it engage. Even alligators don’t eat their own.

You are not as rational as you think. None of us are. And this matters enormously, because the same lizard that won’t let you push the stranger is the lizard your team uses to decide whether to follow you.

It is constantly asking, underneath the meeting agenda and the quarterly numbers:

Is it safe here?

Does this person have my back?

Are they taking me somewhere I want to go?

Is this a good time to go to the bathroom?

It picks up danger before the thinking brain can explain it. You catch motion in your peripheral vision and you’re hyper-alert before you know why. You see a coiled black shape in the grass and you’ve already jumped before your smart brain says relax, it’s a garden hose. The whole job of an intentional leader is to make sure your team’s lizard sees a garden hose and not a snake.

Do you know what you’d call a species that stops to think about whether the coiled shape is a snake? Ancestor.

Which brings me to my suit.

I am not a prototypical leader. I’m not tall. I’m not chiseled. Left to my own devices I’m a jeans guy. But on the day I run a workshop, I wear a suit, because I know that a roomful of strangers’ lizards will make a snap judgment about me in four seconds and I would like a vote in it. As I start, I take the jacket off—we’re getting to work. Then I roll up my sleeves—we’re getting to the hard part. Rolling up the sleeves reveals an expensive watch I own for exactly one purpose: to signal that I’m successful and therefore worth listening to.

I don’t know how to read it. It’s a very expensive watch and I cannot tell you what time it is.

Every one of those moves is theater aimed at the lizard, and I’m telling you it’s theater because the fact that I’m willing to tell you is the only honest thing in the performance. We follow the people who look like they’ll keep us alive. It’s not logical. Consider that of all the American presidents we’ve elected, only a handful have been shorter than average. Are tall people simply better leaders? Or are a few hundred million lizard brains voting for the one who looks like he can win the fight?

It’s not logical. It’s just true. And once you accept that people decide with their gut and explain with their head, you stop trying to win the head and start being intentional about what you feed the gut.

Part Two

BUILDING YOUR CANVAS

Jon Stewart has a bit about preparation. He says he watches a lot of astronaut movies—mostly Star Wars—and even Han and Chewie use a checklist.

Here is the entire framework of this book, stated once, plainly, so you can draw it on a napkin.

The goal is trust. People follow leaders they trust. Trust rests on exactly three things:

  • Competence — can you actually do this? (your head and your experience)
  • Character — are you honest, consistent, the same person when no one’s watching? (your heart)
  • Intention — is where you’re taking us where I want to go? (your aim)

You need all three. A brilliant, honest leader who’s secretly steering the company off a cliff is more dangerous than a mediocre one. A trustworthy incompetent gets everyone killed politely. Trust needs the full trio.

The rest of this section is the toolkit for building all three on purpose: the traits you lead with, the Why that gives you intention, the core values that define your tribe’s character, the value discipline that lets your team make decisions without you, and the end game that points everyone in one direction. At the end you’ll put it on your bathroom mirror.

That’s it. That’s the whole canvas. Now let’s fill it in.

Chapter 4

Trust

“In God We Trust.” It’s printed on the money. And I still hold every bill up to the light. Slogans don’t build trust.

Trust is built on competence, character, and intention—and the mix you need changes with the job.

Would you board a plane if the pilot announced, “I’ve never flown one of these, but let’s see what this button does”? Of course not—you’re grabbing a parachute. But here’s the thing: you don’t actually care whether that pilot is a decent person. You don’t care if he cheats on his taxes or kicks his dog. (Okay, I care—I love dogs.) It’s still not on the list when you’re deciding whether to board. You want him extraordinarily good at flying the plane, and you’ll overlook everything else without a second thought. For a pilot, competence carries the load.

Now imagine you’re hiring someone to housesit for a week. They’ll have a key to your home, your stuff, your dog. Suddenly the PhD doesn’t matter. You want someone honest, someone who loves the dog, someone who won’t go through your drawers. Character carries the load, because character matters most when someone is inside your defenses with the door locked behind them. And you don’t care at all whether they can fly a plane.

Same two ingredients, opposite weighting, set entirely by the situation. A good leader knows which one the moment calls for.

And then there’s intention, which is the one people forget, and it’s the one that matters most over time. Two pilots. Pilot A is the best in the world, flawless, the top of the competence scale—and he intends to fly the plane into a mountain. Pilot B has a year of experience, sits just above average, and intends to land safely, go home, and have dinner with his kids. Which one do you want flying you?

You want B, and it isn’t close, and that should unsettle you, because we spend almost all our hiring energy measuring competence and almost none measuring whether someone’s aim is pointed the same direction as ours. A highly competent leader whose intentions are at odds with the team’s is more dangerous than a weak one. When your skilled, polished boss quietly subverts something you care about, the lizard doesn’t whisper. It screams.

I once worked for a man who, in public, was warm and respectful to the entire team. Behind closed doors, he fed me doubts and innuendo about my colleagues. He never corrected the behavior in them that he complained to me about. He never gave me criticism to my face, constructive or otherwise—and I was certain, with total confidence, that he was describing me to my peers exactly the way he described them to me.

Did I trust him? Did I think he held me accountable? Did I believe he had the spine to say a hard thing to my face? Did he earn my loyalty? Did I stay long?

No. No. No. No. And no.

He wasn’t a villain. He wasn’t cunningly undermining himself. He was just a weak, unintentional manager wearing a leader’s title, and his character cost him a team. That’s how trust dies—not in a dramatic betrayal, but in a hundred small signals that say this person’s aim is themselves.

Chapter 5

Your Crayon Box

Back when Clint Eastwood and Burt Reynolds were nobodies—and for you youngens, just trust me, these two were enormous movie stars once—they were sitting in a casting office, waiting to hear about a part. The casting director came out and delivered the news. To Reynolds: “You didn’t get it. You can’t act.” To Eastwood: “You didn’t get it either. Your Adam’s apple is too big.”

The director left. Reynolds started laughing. Eastwood asked what was so funny.

Reynolds said: “I can learn to act.”

Acting is a skill. An Adam’s apple is a trait. You can learn a skill. You cannot learn—or unlearn—a trait. You can teach someone to sink a free throw. You cannot teach a five-foot-one player to dunk like he’s six-foot-seven. Physical traits are obvious and mostly fixed. Personality traits are less obvious and almost as fixed. The person who gets their energy from a quiet room is not going to learn to be recharged by eight hours of angry customers, no matter how many seminars you send them to.

So know which one you’re dealing with in yourself. (If you’ve never taken a personality assessment, put this book down and go take one. I like the Predictive Index, but a free DISC or Myers-Briggs online will do. Come back when you know your own wiring.)

Here’s the model I use. Think of leadership traits as a giant 120-count box of Crayola crayons—every color of leadership there is. Now think of an actual leader as the little 8-pack. Nobody gets all 120. Each leader works with a handful of dominant colors, and the genius is that the handful is different for each great one.

Martin Luther King Jr.’s box: caring, visionary, charismatic, communicator, collaborative.

George Patton’s box: demanding, accountable, impatient, unconventional, feared.

King was probably plenty decisive; it wasn’t a dominant crayon. Patton may have had caring in there somewhere; you’d need a microscope. Two extraordinary leaders, almost no overlapping colors, both of whom moved history. (And yes, some people overload their box with duplicates—a giant charisma crayon, seven identical orange ones, and no room left for thoughtful or curious. You know who you are.)

There are only three crayons I’d call non-negotiable, and the research backs me up: great leaders take action, take calculated risks, and have courage. Everything else is your unique mix.

Courage especially. People confuse courage with the absence of fear—that’s not courage, that’s stupidity, and stupidity will get your people killed. Courage is doing the hard, right thing while afraid. When I stood up in front of two hundred employees at that failing company to tell them more than half of them would lose their jobs, I was terrified—not of the room, but that every good person would walk out the door that afternoon and take my one shot at saving the place with them. But I also knew that if I stood up there and promised everything was fine, no one would believe another word I said for as long as I had the job. So I told the truth, afraid. That’s the only version of courage there is.

Different teams need different crayons. This is the part people get wrong: they have one leadership style and they apply it to everyone. You wouldn’t coach a World Cup squad the way you’d coach a field of four-year-olds. And you wouldn’t coach four-year-olds whose parents dragged them there the way you’d coach four-year-olds who begged their parents to bring them. The dragged-there kids need patience and orange slices. The World Cup team needs you to get out of their way.

And the kids who begged to be there? Some of them are going to play for the World Cup someday.

I learned this coaching youth hockey for years, kids from seven to fifteen. Most seasons I ran a house league: fourteen kids, two or three real talents, the rest somewhere between “promising” and “can barely stand up.” Everybody got equal ice time regardless. Coaching that team was about teaching—getting the better kids to bring the weaker ones along. Some seasons I coached an all-star team that played travel squads. That job was the opposite: conditioning, and making sure the best players were on the ice at the right second. Same coach. Two completely different sets of crayons, because the teams were different.

Same thing in business. Walking into a demoralized turnaround, I pulled out authentic, empathetic, patient, coaching, enthusiastic. Running a high-growth company sprinting toward an IPO, I pulled out accountable, impatient, delegating, visionary, enabling. You can argue about whether I picked right. You cannot argue that I was the same leader in both rooms.

The one rule: whatever’s in your box, it has to be authentically yours. You can’t fake caring. You can’t fake urgency. Your team’s lizard catches the fake instantly. When the all-stars saw me intense and the house-league kids saw me patient, both versions were real, because both were me. Pick the true colors for the team and the moment—and then never, ever betray the color you’ve shown them. The fastest way to lose a team is to be the consistent leader they’re counting on right up until the day you’re not.

Chapter 6

Your Why

In 2006, a man named Tom Boyle was riding in the passenger seat of his pickup while his wife waited to pull out of a shopping center. A Camaro ahead of them peeled into the road, and there was a screech and a shower of sparks—the car had hit a teenager on a motorcycle, eighteen-year-old Kyle Holtrust, and was dragging him, pinned underneath.

Tom heard the kid screaming and was out of the truck before he decided to be. He got his hands under the front end of the Camaro and lifted—held more than three thousand pounds off the ground for the better part of a minute while the driver dragged Kyle clear.

Tom was a strong man. The most he’d ever deadlifted in his life was around seven hundred pounds. The world record is around a thousand. The car was three thousand.

Where does that come from? It isn’t intellect. The thinking brain has no idea how to lift a car. It came from somewhere older—fear, adrenaline, and purpose, fused into something that briefly broke the rules of what a body can do.

Now hold that picture, because it’s what I want you to understand about leadership. Managers strike a contract: a fixed amount of effort for a fixed amount of money, fair and limited. Great leaders unlock the other thing—the thing that lifts the car. And the key that unlocks it is purpose. A Why.

People don’t show up every morning fired up to make their owners rich. Nobody’s lizard runs hot over shareholder value. People give everything to a place whose purpose lines up with their own—Southwest, Apple, a Marine pulling his buddy out of fire who’ll tell you flatly, “Because he’d do the same for me.” That’s not a benefits package talking. That’s a shared Why.

Your Why isn’t a mission statement, by the way. A mission statement is the thing nobody can recite that’s laminated by the elevator. Compare these two for the same business: one company says it “strives to be the global leader in the sporting goods industry.” Nike says it exists “to bring inspiration and innovation to every athlete in the world”—and then, in a footnote, “if you have a body, you are an athlete.” One of those is a press release. The other one I can repeat to you a year from now, and it tells me exactly who Nike is and isn’t for. Your Why should repel the wrong people as confidently as it attracts the right ones.

Let me show you the Why working, and the Why missing, both from my own life.

Mid-career, I joined a company—call it TT—to turn a one-off consulting shop into a real product company. None of the founders had ever raised institutional money. I had. I took a sub-market salary and a bonus plan in exchange for 5% equity, and I went out and raised over six million dollars from three venture firms, led by a VC who’d backed two of my previous companies.

Two years in, a founder called me into his office. “Glen, we’re renegotiating your deal. We’re cutting your options in half.” He needed more equity for new hires, he said, and he wasn’t willing to take it from the founders’ pool or share the dilution himself. I had stock he wanted. I asked the obvious question—how can you do that, what about our deal?

He said: “We could fire you instead.”

That was the whole man, in five words. His intention was to maximize himself at my expense, and now I knew it. I happened to have relationships with two of the board members and managed to claw back my position and most of my stock. But something was already gone. That morning he turned me from a guy who’d run through a wall for the company into a guy who’d do exactly what it took to protect himself until we hit a profitable exit. He didn’t lose an employee. He lost the lift-the-car version of me, permanently, to save a few points of equity.

Before TT, I’d taken a job at a small, well-funded startup—also a sub-market salary, also a stock plan, also a bet on the future instead of the paycheck. I started in sales, got promoted to selling manager, then to regional director. The company and I had the same intention: build value together, share it together.

Three years in, the company had grown from $2.5 million to $30 million. At the start of year three, the president came to me and offered—unprompted, outside our contract, nobody asking him to—a significant chunk of additional options for a small cut in salary. He didn’t have to do that. There was no clause requiring it. It was a signal: we see what you’re doing, we want you to stay, and when this pays off we intend to share it.

I went back to work with more loyalty and more fuel than I’d had the day before. The company went public. Everyone who built it, including this guy, got paid. Same setup as TT—sub-market salary, equity, a bet on the future. Opposite intention. Opposite result.

That’s the entire lesson. Aligned intention is the most powerful and most underpriced asset a leader has.

My own Why, since I’m asking you for yours.

I’ve watched more failure than success across my career, and every corporate failure I ever saw had the same root: a failure of leadership. And here’s what almost no one says out loud about leadership—it is lonely. In thirty-plus years surrounded by boards and executive teams and family, I have never felt more alone. I couldn’t show fear. I couldn’t show doubt. I couldn’t think out loud, because everyone in the room had an agenda that colored their advice, and any crack I showed would be priced into the next negotiation. So I modeled confidence I didn’t always feel, and I carried the real version by myself.

If you’ve been the one in the chair, you know exactly the isolation I mean. And here’s the part I’ll just say plainly instead of dressing up: that isolation is how good leaders fail. Not stupidity—the good ones aren’t stupid. Loneliness. The slow corrosion of having no one you can hand the whole truth to.

That’s my Why. I exist, professionally, to be the one person a leader can finally stop performing for. The honest broker with no agenda, who asks the question no one on your payroll will ask you, who you can tell the 3 a.m. version to. I believe in asking questions, in questioning answers, in finding the truth even when it’s expensive, and in not letting good people fail alone in a corner office. I am trying to be the cure for the loneliness at the top. That’s it. That’s the thing that gets me out of bed.

One more, because purpose has two speeds. I once coached a firm that floated along at a comfortable revenue line. The partners made a great living and put in exactly enough energy to keep the boats and the second homes. Then every eighteen months or so, one of their big contracts would come up for renewal, and three to five million dollars of pure profit was suddenly at risk—and with it, the lifestyle. And every single time, the energy in that building spiked. The partners caught fire. The urgency rolled downhill to the staff. They lifted the three-thousand-pound car, found a replacement client, saved the year. And then the partners put their feet back on the desk and went back to counting their money.

When their survival was threatened, they were leaders—purpose-driven, inspiring, unstoppable. When it wasn’t, they were managers reading the newspaper. Their company was capped at “comfortable” not because they couldn’t grow it, but because their purpose was lifestyle, and lifestyle only summons the car-lift when the lifestyle’s in danger.

Think about what they left on the table. If they’d brought the threatened-survival energy on an ordinary Tuesday, they’d have doubled the company. If they’d shared the upside with the people doing the work—real equity, not a holiday bonus—they could have built something that outlived them and made their kids wealthy. They had all of it within reach.

They preferred the newspaper.

Compare DTE Electric. In 2008, at the start of the Great Recession, this Detroit utility was watching its world collapse—factories (its biggest customers) shuttering, residential customers losing jobs and leaving town, demand falling off a cliff. The executive team did the reflexive thing and recommended layoffs. CEO Gerry Anderson—an engineer, a head-not-heart guy by his own description—had a different instinct. He told his people the truth about the danger, and then he made a deal: the last lever we will ever pull is layoffs, and we will do everything in our power to avoid them—but in return, I need you to fight for this company with an intensity you have never brought before.

They did. One example: a $30 million renovation already past the point of no return. The team squeezed vendors and got it to $27 million—fine, normal cost-cutting. Then somebody asked the purpose question: what are we actually renovating here? The answer was that they were replacing entire systems when really only the logic boards inside them were obsolete. So they went back to the vendors and asked them to just swap the boards. Final cost: three million dollars. One-tenth of the original estimate, because a team with a survival purpose asked a question a comfortable team never would.

DTE survived. And then Anderson did the thing that separates good from great: he noticed that “survive” had stopped being motivating once they’d survived, and he changed the Why. From preservation to aspiration—not “let’s not die,” but “let’s be the force that helps Detroit come back.” He pointed ten thousand employees’ energy outward at a wounded city. Between then and 2017, shareholder return ran roughly 275% against a peer average around 83%.

Survival can summon the car-lift. But you can’t threaten people’s survival forever, and you shouldn’t want to. The leaders who build something lasting trade fear for aspiration before the fear wears off.

Chapter 7

The Ghost Orchid

“Culture eats strategy for breakfast.” —attributed to Peter Drucker (who, for the record, almost certainly never said it—which is its own small lesson about taking famous quotes on faith)

In 1987, NFL players went on strike, and for three weeks the teams fielded replacements—guys off the street, no-names, the football equivalent of understudies. On one Monday night, the replacement Washington Redskins faced a Dallas Cowboys squad stuffed with veterans who’d crossed the picket line: real pros, Hall of Famers, household names.

Nobody gave the replacements a prayer. They won, 13–7, in one of the great upsets in league history.

Why? The replacements were playing for the love of getting to play at all. The veterans were playing for the next paycheck. Culture just ate talent for breakfast.

Here’s what culture actually is, and why most leaders never get one worth having. The ghost orchid is one of the rarest flowers on earth—since it was first found in 1954, it’s been spotted in the wild only a couple dozen times. In a greenhouse, though, with the right conditions, you can grow it by the thousand.

A great culture is exactly the same. It is almost never found in the wild. The leader who gathers a group of decent people and hopes a high-performing culture will bloom on its own is wandering the woods waiting to trip over a ghost orchid. It doesn’t work that way. You build the greenhouse. You plant deliberately, you control the light and the water, and the rare thing grows on purpose because you made the conditions for it. Culture doesn’t happen. Culture is farmed.

Let me tell you how I learned this, in my own legs.

According to my 23andMe report, I am not built to be a sprinter. The genetics say so right there in the printout—not a power athlete, sorry. Lucky for me, I didn’t have the report in 1974, when I ran the mile relay for J.P. Stevens High in Edison, New Jersey, and we placed third in the state, 3:23.20, a hair behind Montclair and Tenafly.

Here’s the strange part. In individual events, I ran exactly like my DNA predicted—mediocre, forgettable, a guy who finishes in the middle. But on that relay team? In three years of varsity I can count on one hand the number of times anyone passed me. Twenty-one races over two years, twenty-one medals. Same legs, same lungs, same allegedly non-sprinter genetics. So what was different?

The team was different.

We were Flick, Flea, Wally, and me—Hellboy. (Walter went by Wally because Walter wasn’t, creatively, a guy who needed a nickname.) We hung out at each other’s houses after school. We ate dinner together. We went to prom together—not as each other’s dates, thank you, we each had our own, settle down. We designed our own warm-up shirts with our nicknames on the back, and we wore knee-high white socks so we’d stand out in the blocks. Other teams laughed at the socks. We laughed back when we collected the medals.

We’ve never stopped being a team. Flea, Flick, and I all went to the University of Maryland and won the intramural track title. Decades later we still get together. In 2013 we took our old coach to dinner in New York. In 2016 we took him to lunch in New Brunswick. If I called any of those men tonight and needed something, they’d be in the car before I finished the sentence.

So: why did I run faster for them than I ever ran for myself?

The 440 is a race against pain. It’s a long, brutal sprint, and raw speed only gets you so far—at some point it comes down to whether you’re willing to drive yourself through agony to the line. And here’s the truth I didn’t understand until years later: I was not willing to suffer like that for me. I genuinely did not care enough about my own individual result to pay that price. But I would not let Flick down. I would not let Flea and Wally cross the line knowing I’d held something back. I didn’t mind letting myself down. I could not stomach letting my team down.

That’s culture. That’s the whole thing. A real culture—built on a shared purpose, shared goals, and trust—pulls performance out of people that they are unable or unwilling to summon for themselves. It made a non-sprinter fast for two years, and then released him back to mediocre the moment he ran alone.

And it didn’t appear by magic. Our coach built the greenhouse. He set clear rules and clear goals. He was a relentless reader, always chasing the latest training research. He was demanding to the point of cruelty—he made us sprinters run cross-country, made us show up ninety minutes before school for morning workouts because, he insisted, we lost conditioning in our sleep. The morning runs were just the warm-up. The real torture came after school, in the sessions he cheerfully called “workouts.” He’d blow the whistle while we were already gasping and make us go again, laughing while we cursed him under our breath, calling us names that would not survive a modern HR department.

We hated him at 6:45 a.m. We loved him by graduation. We love him still. Because under all the torture, he was fair, he obviously knew his craft, and we never once doubted he had our backs. He gave us a common purpose—do your best, win medals, don’t let each other down—and he forged four ordinary kids into something that ran above its own ability for two undefeated seasons.

Culture doesn’t just happen. It takes a leader, a clear purpose, and trust. A high-performing team is a ghost orchid. You don’t find it. You grow it.

Culture evolves. You don’t farm them once and walk away. I sat on the board of a D.C. startup called Social Tables, run by a sharp young CEO named Dan Berger. Early on, with an average employee age of twenty-two, nobody married, nobody with kids, the culture was “ship all day, party all night,” and one of its core values was the best one I’ve ever heard: Yes, If.

The company culture didn’t accept “no, because.” It was always “yes, if you give me the resources,” and “yes, if you give me the time.” I watched that value hold up in a blizzard.

One January I traveled through a foot of snow for a board meeting—Dan and I were the only board members who made it. The storm was bad enough that even Metro shut down, though to be fair, Metro shuts down on days ending in y. What stopped me cold was the office itself: most of the team had trudged in through the same snow. Why? Because Social Tables’ customers around the world had shown up to work that morning, and someone had to be there for them. Culture just ate snow for lunch.

Years later, when the company was older and the staff had spouses and children, that culture had matured into “it takes a village” and “hospitality matters.” Cvent bought them for a hundred million. The culture that won wasn’t the one they started with. It was the one they kept intentionally re-growing as they changed.

Chapter 8

Pick a Lane

Imagine building a football team by just grabbing the best available athletes, one after another, with no plan. You’d end up with ten quarterbacks, a single running back, and zero receivers. Congratulations: you have assembled a very expensive disaster and not a football team.

Real teams start with a focus and then draft to it. No elite pocket passers available, but a deep pool of mobile quarterbacks and bruising backs? Fine—you’re a running team. Now you go find linemen who can road-grade for a ground game. You tell everyone, out loud: we are a ball-control team. We win on the ground, we control the clock, we grind. And once that’s drilled in, here’s the payoff—if you’re not on the sideline one Sunday, your quarterback doesn’t suddenly improvise a wide-open passing attack. He knows who you are. He runs the ball. The focus calls the play when you’re not there to.

My wife pointed out that some readers don’t give a damn about football, and asked how this works for a restaurant. Fair. Okay, honey, here’s yours.

Say we open a down-home fried chicken joint. Our focus: the best fried chicken north of the Carolinas. People line up for our rustic picnic tables. They take whole pies home. We’re known for one thing. Then I take a desperately-needed week of vacation, and while I’m gone, the staff decides the place should pivot to high-end French cuisine. I come back to an empty dining room and a closed business. And that’s my fault—not theirs. I never drilled the focus deep enough for them to protect it when I wasn’t looking. They didn’t believe in it, because I never made them.

This is what Michael Treacy and Fred Wiersema, in The Discipline of Market Leaders, call a value discipline—a fancy term for “the one thing you’re built to win on.” There are three:

  • Operational Excellence — fast, convenient, reliable, well-priced. Amazon. You don’t shop Amazon for the world’s most innovative product; you shop it because you can order at midnight, read the reviews, and have it tomorrow without leaving your couch.
  • Product Leadership — the innovative thing you didn’t know you needed. Apple. You’re not on the Apple Store for the lowest price or the fastest checkout. You’re there for the product nobody else makes yet.
  • Customer Intimacy — they know you, they take care of you, they make it right. Nordstrom. You could buy the same sunglasses cheaper elsewhere, but the salesperson actually knows the inventory, and when you snap the frames three years later, Nordstrom replaces them, no questions asked.

I can buy sunglasses from all three. Amazon, Walmart-style operational excellence: cheap, fast, in stock, short lines. Apple-style product leadership: the thing that just launched and everyone wants. Nordstrom-style intimacy: the knowledgeable clerk and the legendary return policy. Same product category, three completely different companies, because each one picked a lane and committed.

Here’s the rule that matters: you must be at least competent at all three, and excellent at one. You don’t get to be terrible at the other two. Walmart can’t have hostile employees and empty shelves and survive on low prices alone—do that, and they’d be Kmart, which is to say—gone. You have to clear the bar everywhere and clear the roof in exactly one place.

And the reason this is a leadership chapter, not a strategy chapter, is the same as for everything else in this book: a clearly articulated value discipline is what lets your team make decisions when you’re not in the room. When I bring my three-year-old broken sunglasses back to Nordstrom, the clerk doesn’t phone the CEO to ask whether intimacy applies today. She knows what kind of company she works for, so she knows the answer. Define the lane, drill the lane, and you’ve just replaced a thousand-page procedure manual with one shared instinct.

Chapter 9

The End Game

A real Big Hairy Audacious Goal—Jim Collins’s term, and his image is the best one: the BHAG sitting by your bed at night with glowing eyes, saying good morning, I own your life—is enormous. It’s the ten-to-thirty-year mountain. Put a man on the moon. Collins meant it big, and you should have one that big, the one your company is ultimately for.

But a mountain you can’t see the top of doesn’t create urgency on a Tuesday. So you do two things at once. You name the giant, decade-long summit so everyone knows which mountain we’re on—that’s directional guidance, the north star that keeps a company from chasing every shiny distraction like a dog who just heard the word “squirrel.” And then you break the climb into camps: one- and two-year campaigns with a clear beginning, middle, and end. You name them. You promote them. You track them. You throw a party when you summit one, and then you point at the next camp. That’s how you keep urgency alive on the long climb without burning everyone out staring at a peak that’s still years away.

Why bother breaking it up? Because a goal with a deadline feels nothing like a treadmill, and too many companies are just hamster wheels for adults—show up, spin, collect a check every other Friday, repeat until retirement.

Picture two boats. One crew takes a sailboat out for a lazy afternoon around the harbor. No goal, no urgency, everyone does what they like, the boat drifts where the wind goes. It’s pleasant. It’s also forgettable, and nobody on it is becoming anything. The other crew is in a race. Every person has a job and knows it cold. There’s one goal—finish first. There’s adrenaline, tension, exhaustion. And when it’s over, win or lose, that crew is tighter than the harbor crew will ever be, because they suffered toward the same thing at the same time. A BHAG turns the harbor cruise into the race.

Let me tell you about a camp we summited.

I was running a company whose whole future hinged on one product release—a multi-million-dollar software platform for managing telecom networks. Our customers were rolling out bundled phone, internet, and TV, and all that new equipment needed managing. If we couldn’t ship a product that handled it, we were finished. Simple as that.

We named the campaign Operation Scarecrow and split it into three phases: design it, build-and-test-and-debug it, and install it on-site for our first real customer. When install time came, we sent a team of developers and support people into the field with a promise: get this thing up and running in four weeks, on budget, and there’s a party waiting.

A few days in, after a brutal day on-site, the install team—holed up in a hotel, a little punchy—decided to shave their heads in solidarity. And their foolish leader, hearing about this, made a promise of his own: finish on time and on budget, and you can shave mine when you get home.

Two months later I rented a party boat for a dinner cruise on the Potomac. I stepped off that boat with a freshly shaved head. So did our VP of R&D. So did half the people who’d backed up the install crew.

We sold the company for $92 million in cash, and all of us went to work for a Fortune 500 buyer.

Now that’s a successful BHAG—and notice what it actually was. Not a slogan. A named, time-boxed, all-hands climb with a clear finish, a real reward, and a leader who put his own scalp on the line right next to the team’s. That’s the end game. Point at the mountain so they know where we’re going. Then run the next race so they feel why it matters this week.

Chapter 10

The Mirror

Here’s the uncomfortable truth about everything you’ve just read: knowing it changes nothing. Intention isn’t a thing you understand once. It’s a thing you do, every day, on purpose, especially on the days you don’t feel like it—because even leaders who know all of this will quietly drift back to autopilot and stop doing the things they know are right.

The danger has a name, and I want to be precise about it, because it’s counterintuitive. Picture a surgeon who’s done the same abdominal procedure a hundred times this year. She is not in danger because she’s bad at it. She’s in danger because she’s so good at it that she could do it without thinking—and the day she does it without thinking is the day she leaves a sponge inside a patient. Mastery that runs on autopilot is the trap. So her team counts the absorbent sponges going in. Then they count them coming out. And because even a checklist can fail, the sponges contain a metal filament, so an x-ray catches the one the count missed. Competent people, a checklist, and a backstop—because the better you are, the more sure you are you don’t need one.

You know this feeling from driving. A new driver is white-knuckled and hyper-alert—every oncoming car a threat, every parked car noticed, every ounce of attention engaged, because they can’t afford to coast. The veteran breezes past exits barely aware of their own hands, which is exactly when they change lanes without checking the blind spot, forget the turn signal, or commit the high crime of doing precisely the speed limit in the passing lane. The veteran isn’t worse than the rookie. The veteran is complacent, and complacent is how good people get sloppy.

You are going to get complacent as a leader. Guaranteed. So here’s the backstop.

Take the work you’ve done in this book—who you are, your dominant traits, your Why, your team’s values, your lane, your end game—and boil you down to five leadership traits. The five your team should be able to count on every single day, no exceptions. Write them down.

Put the list on your bathroom mirror.

In the morning, while you brush your teeth, read it and ask: How do I want to show up today? How do I make these five visible before lunch? At night, brushing again, ask the harder one: What did I do today that confirmed these five—and what did I do that betrayed one of them? And if you betrayed one, what’s my plan to recover it tomorrow?

That’s the whole practice. Two minutes, twice a day, in front of a mirror, for the rest of your career. It’s not glamorous. Neither is counting sponges. That’s the point. The truly great aren’t the ones who improvise heroically without a checklist—that’s a story we tell ourselves because checklists feel beneath us. The truly great are the ones humble enough to know that competence runs on autopilot, and disciplined enough to check the mirror anyway.

Conclusion

The Canvas

You came here for a one-page document that defines you as a leader. Here it is, assembled, the way it should hang together.

The goal is trust. People follow leaders they trust, and trust stands on three legs:

  • Competence — can you do this? (your head and your experience)
  • Character — are you honest, consistent, the same in the dark as in the light? (your heart)
  • Intention — is your aim pointed where the team wants to go? (and is it, really?)

You build those three on purpose, with five tools:

  1. Your Traits — the five crayons you’ll show your team every day. Authentic ones. The ones you’ll put on the mirror.
  2. Your Why — why this team exists, what it’s for, what lifts the three-thousand-pound car. The thing that attracts the right people and repels the wrong ones.
  3. Your Core Values — the conditions of your greenhouse. What binds your tribe, what they can expect from each other, the culture you farm instead of hope for.
  4. Your Value Discipline — the one lane you win in, drilled deep enough that your team makes the right call when you’re a thousand miles away.
  5. Your End Game — the mountain you’re climbing, named, so everyone’s pointed the same direction, broken into races so the climb has urgency this week and not just this decade.

Now you’ve got the canvas. You understand what trust is made of and how to build each piece on purpose. So declare it. Write down who you are and what you stand for. And then check the mirror, morning and night, to make sure the person in it matches the document.

Do that, and one day you’ll be on a beach somewhere, or stuck in a meeting two time zones away, and your team will face a hard call you’re not there to make—and they’ll make the one you would have made. Not because there was a gate. Not because someone was supervising. Because they know exactly who you are and what you’d do, and you made sure of it on purpose.

That’s leadership. The rest is just management with a bigger office.

I gave up the bigger office years ago. Turned it into a conference room and took the closet. The team noticed. They always do.

That was the whole idea.

We are what we repeatedly do. Excellence, then, is not an act but a habit. —Will Durant, summing up Aristotle (and getting the credit Aristotle usually gets)

The End
A deal’s a deal

Why Grant Is Buried in Manhattan

I promised you this on the first page. A deal’s a deal.

Ulysses S. Grant—the general who won the Civil War, the two-term president—died in 1885, broke and dying of throat cancer, racing to finish his memoirs so his wife wouldn’t be destitute. (He made it. He finished the book days before he died, Mark Twain published it, and it sold enough to take care of Julia for the rest of her life. The man met his deadline from his deathbed. Respect.)

When he died, every city wanted him. He could have gone to Washington, to West Point, to Illinois, where he’d come up. But Grant had spent his last years in New York City, and his wife Julia wanted him close, somewhere she could eventually be buried beside him. So New York said: we’ll take him, and we’ll build him something worthy.

And here’s the part that makes it a leadership story instead of a trivia question.

New York didn’t get a government to pay for it. The city raised the money the hard way—roughly ninety thousand people chipped in, the largest public fundraising effort in America up to that point, more than six hundred thousand dollars in 1880s money. Schoolkids sent pennies. When it was finished in 1897, it was the largest mausoleum in North America, and a million people came to the dedication.

Ninety thousand people, most of whom never met him, voluntarily reached into their own pockets to honor a man who was already dead and could never thank them, never promote them, never do a single thing for them in return.

You don’t get that with management. You don’t get ninety thousand people opening their wallets for a dead man because he hit his quarterly numbers. You get it because of who he was—because for four years he carried something enormous on behalf of people he’d never meet, and they knew it, and they remembered. That’s the longest arc of leadership there is: the trust you build outlives you. People still show up for you when you’re not in the room. Even when the room is a tomb.

So. Who’s buried in Grant’s Tomb?

Grant is. That was never the interesting question.

The interesting question is why a city full of strangers loved him enough to build it. And if you’ve read this far, you already know the answer. It’s the whole book.

Colophon

About the Author

Glen Hellman has spent his career on both ends of leadership—the kind that builds things and the kind that buries them. After selling a startup for $92 million in cash, he spent a decade as a turnaround executive parachuting into failing companies for private equity investors, where he learned, five times in a row, that the cause of death is always the same: a failure of leadership.

Since 2007 he has worked the other side of that equation as an executive coach and CEO peer-group facilitator, helping leaders fix the company while it’s still breathing. He is Distinguished Faculty at the University of Maryland’s A. James Clark School of Engineering, where he coaches deep-tech researchers through the NSF I-Corps program, and he runs CxO Elevate, his executive coaching practice. Tech.co once named him the number-one angel investor in America, which he’ll mention exactly as often as you’d expect.

In a previous life he was an investigative tech blogger known as Mr. Cranky, whose work calling out fraudulent startup executives occasionally found its way into the hands of the FBI. He is also a performing songwriter and a recovering stand-up comedian, which explains a great deal about this book.

He lives in Oakton, Virginia, with his wife Nancy, who edits everything he writes, including this paragraph.

If the bathroom-mirror page is the most useful one you own—the book is the cheap part.

Buy a copy