The Art of Leading Vicariously: Build Your Web of Mentors

A Web of Mentors

To achieve organizational success in the short run, delegate. To achieve organizational success over the long run, lead vicariously. Build your web of mentors. One of our strongest human desires is to live long beyond our years. We want to leave a legacy behind, an immutable imprint on the world, a lasting impact that can…

A Short Guide to Delegation

A Short Guide to Delegation

Delegation. I know. It’s difficult. Especially if you are a new leader who desperately wants to prove your worth and your abilities. You want to take on every project. You want to make sure people are taken care of over here and machines are fixed over there. Being a leader can be like playing whack-a-mole—wherever…

The Red-Button Ultimatum

red button ultimatums

Avoid pushing the red button at all costs. But if you must, realize that there is no turning back. Every leader has an entire control board of buttons at their disposal. But not all buttons are wise to push without good reason. For the President of the United States, it might be the "nuclear" button.…

What Would Socrates Do?

What Would Socrates Do?

To gain cooperation from your team, do as Socrates would do. Get them to say “yes” first. Socrates, one of history’s most persuasive thinkers, didn’t win people over to his side by telling them they were wrong. When he and his opponent disagreed, he listened and started by asking questions that would elicit a “yes”…

What You Buy with Paper Eventually Turns to Paper

Paper money

Paper will get people to work for you. Respect will get people to work with you. For centuries, money has been used as a tool to buy allegiance, adherence, and adoration. Politicians buy votes, public figures buy silence, and every boss or business owner I’ve ever known has believed they could buy respect. This approach…

Lather Before You Shave

Lather Before Your Shave

If you’re going to criticize your team, approach it how a barber would: lather before you shave. In January of 1863, during the darkest days of the American Civil War, Abraham Lincoln sat down to write a letter to one of his Union generals, Joseph Hooker. Lincoln had appointed Hooker to the post in hopes…

The Tough Love Spectrum

Tough Love Spectrum

All leaders want both love and respect. Most only get one. The best simply let both come to them. It’s life on the tough love spectrum. It’s the delicate balance between love and respect. Most leaders stand in the arena on one extreme. On one end, there are coddlers—those who go easy on their people,…

Show Your Teeth

Show Your Teeth

A leader without authority is a shark without teeth. And a shark without teeth is no leader at all. In most cases as a leader, you should never show your teeth. Almost never should you even make it a point that you even have "teeth." But you must let it be known, because when lines…

Optimize for Character

Optimize for Character

“Let your character be superior to the requirements of the job, not vice versa. No matter how great the post, you must show you are greater.” -Baltasar Gracian It was hiring day. The clock showed 8 AM, and my team of interviewers braced for a long slog of a day. We had 500 eager job…

Of Pizza and Character

The Best Pizza or the Best Character?

“Talent will get you to the top, but it takes character to keep you there.” -John Wooden The problem with most leaders is that they always look for those who can get them to the top without ever thinking about who can keep them at the top. At the restaurant I ran, I had a…

The Yes-Man Dilemma

Yes-Man Dilemma

Being a yes-man equals safety for anyone playing status games. If safety and cheap approval are your top priorities, be a yes-man. If being idolized is your top priority, surround yourself with yes-men. But if truth and excellence are your top priorities, then you must develop an allergy to the very idea of a yes-man.…

Under the Sword of Damocles

Under the Sword of Damocles

There’s a mythical tale told by the ancient Roman orator, Cicero, about a man named Damocles. Damocles, a courtier, is in awe of the power of his king, Dionysius. He marvels at the luxury and the glory of the king’s lofty position. The king offers to switch places with Damocles so he can experience the…

How to Solve the Principal-Agent Problem

Principal-Agent Problem: Yin Yang

The Principal-Agent Problem can make or break an organization. As the leader, you must understand the roles and expectations of both the principal and the agent, and provide the thread that ties them together. To Reach the Pinnacle of Success... “I need you all to understand, business this summer is going to shrink drastically. You…

The Terrace Strategy

Terrace Strategy

How do you build your team into a well-oiled machine? Use the Terrace Strategy. From the sub-tropical hills of Vietnam to the steep mountainsides of the Andes, from the breezy Canary Islands to the vineyards of rural Italy, you’ll find beautiful, picturesque, step-like fields called terraces. Typically used to grow rice, wheat, barley, and many…

Hope is Not a Strategy

A Proper Place for Hope

“Hope is not a strategy. Luck is not a factor. Fear is not an option.” -James Cameron I love this quote. It’s saved in my phone, on my computer, and in the back of my mind. I’ve even considered buying a t-shirt of it. But it doesn’t tell the whole story. I’ve already written about…

Seeing Through Groupthink

Seeing Through Groupthink

Groupthink is the enemy of greatness. It’s the enemy of imagination, and a friend of stagnation. It’s the enemy of logic and reason, and a friend of irrationality. Leadership naturally gravitates towards it. But only the leader has the power to see through it and break it. Polaroid was one of the most revolutionary companies…

The Peacock Effect

Peacock Effect

The collective ego is like a set of peacock feathers. When you speak to one “eye,” you speak to them all. When we think of the concept of ego, we usually think of the individual. By now, we know the importance of managing individual egos and giving them a soft landing. Individual egos can be…

The Delicate Truth Principle

Delicate Truth

Any good leader can deliver the truth. But only the great leader knows how to deliver the delicate truth. Feedback is the lifeblood of your team’s progress. Whether positive or negative, feedback must always be steeped in the truth. In leadership, truth must be your north star. Without truth, there is no trust. And without…

Territorial Leadership

Territorial Leadership

Good leadership structures are hierarchical. But good leadership is not. It's territorial. The author Robert McKee says a “hack” is someone who doesn’t work from the heart, but instead, according to what the market is looking for. He’s referring to opportunistic writers who pander to their audience, thereby removing the very soul from their work…

Brick by Brick

Brick by Brick

As a leader, your job is to show your team they are building more than just a brick wall. There’s a famous tale of a traveler who came across three men working on the side of the road. The traveler asked the three, “what are you doing?” The first man, crouched low to the ground…

Win and Help Win

Win and Help Win

I no longer subscribe to the idea of “live and let live.”  Instead, there’s a more evolved version that will take me further, you further, and the world further: “win and help win.” If you’ve ever been on an airplane (and actually listened to the pre-flight safety instructions), you know that your first priority in…

Plants, Not Commodities

Plants, Not Commodities

Plants—like the flowers your dad plants in his back yard, like the cacti you see on your road trip to the Southwest U.S., or the trees that line your street—all require water, good soil, and sunlight to grow. Commodities—like the gold necklace around your neck, like the coffee beans you roast every morning, or the…

Why Pep Wins

Why Pep Wins

“We don't rise to the level of our expectations; we fall to the level of our training." -Archilochus If greatness in leadership is what you seek, let this quote sink in. Success is 80% training and 20% luck. And even then, the 20% is shaped by the 80%. Training is comprised of planning, preparation, and…

It’s Not Personal

It's Not Personal

It’s not personal. When someone blames you, When someone turns on you, When someone criticizes you, When someone outshines you, When someone speaks over you, When someone dislikes your idea, When someone ignores your idea, When someone doesn’t listen to you, When someone doesn’t follow your plan, When someone doesn’t like the decision you made,…

The Leverage of Language

As a leader, your language is the ultimate form of leverage. It costs you relatively nothing to produce words—they’re seemingly insignificant investments. But the flavor of the words that come out of your mouth can have an immeasurable impact on you and those you lead. Assuming you’ve done the hard work to build relationships, tame…

Still the Pendulum

Still the Pendulum

If there’s one useful leadership idea to be learned from the state of media today, it’s the power of a pendulum's swing. Social media and news organizations feed on the widening oscillations of the societal pendulum. One side thinks they are right, and the other is evil. One side thinks they are smart and the…

Give Ego a Soft Landing

Give Ego a Soft Landing

The ego is nothing more than a fragile vase that, if large enough, will fall to the ground and shatter. The moment you’ve collected your fragments and repaired your vase, life will smack it out of your hands and force you to pick up the pieces, yet again. It may not happen tomorrow. It may…

Do the Dirty Dishes

Do the Dirty Dishes

As a leader, you don’t deserve to be followed, listened to, trusted, or respected. You must earn it. And the best way to earn it is to get your hands dirty. Do the dirty dishes. It’s why we so often see business leaders and politicians on television, in the news, or on their website with…

Sell the Shovels

Sell the Shovels

Instead of seeking the gold and glory for yourself, sell “shovels” to your team so they can strike gold, better their lives, and achieve the team’s mission together. Depending on where you’re from, you may not have heard of Samuel Brannan. Known as the first millionaire during the California Gold Rush of the mid-19th Century,…

The Inevitability of Success

Inevitability of Success

Success is a function of time. When you treat it as such, success becomes not a matter of “if,” but a matter of “when.” From day one, everyone you lead must know that success is not optional. It is inevitable. Billionaire investor Chris Sacca says the primary characteristic he tries to sense when he meets…

Empowerment All the Way Down

One of the most powerful ideas I ever learned from one of my restaurant mentors was that empowerment is like a waterfall. There are different levels of responsibility in any organization, but the waterfall doesn’t differentiate. The waterfall covers every level—no matter how high up or how far down. Every member of the team is…

The Oil & Water Strategy

Oil and Water

Every team has overperformers and underperformers. Let your people spend long enough in either camp, and complacency is sure to set in. Factions form. Physical, emotional, and ideological divides turn from hairline fractures into insurmountable valleys. The sense of team dissolves. The oil and the water settle. And it’s precisely in these moments when you…

The Architect and the Archaeologist

Architect or Archaeologist

There are two types of leaders: architects and archaeologists. Only one can see the future. Architect-leaders can be identified by their level of confidence in their own abilities. They lay out their blueprint, map out their course, plan every edge and curve, draw thrice, measure twice, cut once. Everything is in front of them, waiting…

The Power of Detachment

Detachment

One thing you learn immediately in leadership is that in the heat of the moment, it’s hard to lead from within the fishbowl. It’s hard to see what’s ahead if you’re stuck in the weeds. It’s hard to see over the trees if you’re lost in the forest. To gain a grasp of a difficult…

The Salt Shaker Theory

The Salt Shaker Theory

Always move the salt shaker back to the center of the table. That is the essence of leadership. When you’re reading dozens of books, talking with dozens of people, watching dozens of videos, or reading 100 essays on the subject of leadership, it’s easy to get lost in such a dense forest of information and…

The Deep Roots of Leadership

The Roots of Leadership

Like the roots of a tree, the roots of principled leadership dig deep beneath the soil, in all directions, and with a range far wider than what can be seen above ground. Like a tree, your leadership will encounter many storms, strong winds, droughts, and the occasional lightning strike. The more roots you have, the…

What I Learned from a Four Star General

What I Learned from a Four-Star General

I had the distinct pleasure of meeting Four Star General Michael Hayden, a former director of the NSA and CIA, on multiple occasions during my time in college. In each opportunity I took to listen to the general, I was forced into the difficult yet necessary reconciliation between my understanding of leadership in a global…

Flaunt Your Heroes

Flaunt Your Heroes

On your rise to the top, your heroes will serve as more than just inspiration—they will actively help get you there. Show them off, and they will soon precede you, stand in for you, and represent you in your follower's minds. Heroes are not just what they seem. They are all around us, in books,…

Balancing Life’s Checkbook

Balancing Life's Checkbook

There is an unusual, yet really powerful heuristic for leadership that I’ve subconsciously used throughout my life, and it’s what I now call “balancing life’s checkbook.” Today, some people still use checkbooks, but there are now far more who have never used one. So, if you’re in the latter group, here’s an example so you…

The Isolated Leader

The Isolated Leader

In leadership, isolation is an ever-present double-edged sword. There are merits to being isolated leader at times. But most often, the isolated leader will become terribly ineffective. On one hand, as a leader, you must be comfortable with being alone. In order to maintain an effective influence over your subordinates, you simply cannot become “one…

The Chosen Leader

The Chosen Leader

Take a look at all of the greatest leaders in history. Martin Luther King. George Washington. Dwight D. Eisenhower. What do they have in common? They didn't strive to be a leader for the sake of being a leader. They were chosen, for no other reason than the fact that they embodied the cause they…

The Dichotomy of Detail

Dichotomy of Detail

The dichotomy of detail: meticulousness can be your best friend, or it can be your worst enemy. On one side of the dichotomy, we have John Wooden, universally known as the all-time greatest head coach in college basketball history. With his UCLA Bruins, he won 80% of the games he coached, including 10 National Championships…

Leather-Mindedness

Leather-mindedness

I just sat in a writing group with a bunch of outstanding writers from around the world, and there was one question that fired me up more than any other that I had to jump in and answer: “How do you get to the point of not caring about what people think of your writing?”…

The Art of Leading Laterally

Leading Laterally

Leading laterally is a remarkably difficult, yet necessary form of leadership. Before you can ever be recognized as a leader, you must first master the art of leading your peers. As a leader of subordinates, you have your name on the wall, you have skin in the game, you are fully accountable, and everything begins…

Transcendental Innovation

Transcendental Innovation

The word “transcendental” in the dictionary offers definitions in three subjects: spirituality, philosophy, and mathematics. Sit with that for a moment, and you’ll notice there aren’t many words in human language that have the flexibility to play in such distinct spaces. Yet, “transcendental” manages to pull it off seamlessly—it’s a powerful word. You might have…

The Iteration Game

The Iteration Game

Playing the iteration game makes you fearless and egoless—the pinnacle of leadership. My friend Robbie Crabtree is an attorney who has worked over 100 jury trials in law career. Over the past decade, he’s honed his speaking and persuasion skills, and now runs a wildly successful and transformative online course called Performative Speaking. Back when…

Great Leaders Imitate

Great Leaders Imitate

All great leaders imitate their heroes. They realize that in order to achieve greatness, pure talent or brute force can only take them so far. To be great, they must stand on the shoulders of giants. Nobody is born a leader. We don’t come out of the womb knowing who we are or what we…

Mettle Moments

Mettle Moments

They’re the moments when you’ve reached your breaking point. They’re the moments when you want to quit, but you simply can’t. They’re the moments when you have no other exit strategy but to push forward. These are the moments that test everything inside of you with a potent dose of adversity that you never thought…

If You’re Not the Captain, Be the Lighthouse

Be the Lighthouse

If you’re not the captain of the ship, be the lighthouse that guides it. Lighthouses serve to keep the ship safe. They are grounded and reliable. Their guiding light cuts through the darkness and mist with the deliberateness of a sharp knife. They don’t tell the ship captain what he wants to hear. They tell…

Third-Order Thinking: How Great Leaders See Around Corners

Third-Order Thinking

Third-order thinking is the Mount Everest of cognitive performance. It’s a climb few people ever attempt, and even fewer ever reach the summit. It’s the kind of thinking that burns calories, takes effort, and requires a lot of brain power. But when you reach the top, you’ll see the world from a perspective that no…

Hone Your Strategic Mind

Hone Your Strategic Mind

“Strategy without tactics is the slowest route to victory, tactics without strategy is the noise before defeat.” Sun Tzu Don't be a Spartan. Hone your strategic mind. In Herodotus’ Histories, you’ll find a story about the Spartans at the height of their influence. Then known as Lacedaemonians, they sent soldiers to a town called Tegea…

Accountability is Currency

Accountability is Currency

Leadership can be bought. And the only currency accepted is accountability. Everywhere you go, everything you do, every breath you take, you are exchanging currency for a perceived benefit. When you go to work, you are spending your time. When you go on vacation, you are spending your dollars. When you run a marathon, you…

The Fine Line Between the Leader and the Manipulator

The Fine Line Between Leadership and Manipulation

When you boil it down, the leader and the manipulator are identical twins. They both cultivate relationships with people. They both wield influence over people. They both home-in on the strengths and weaknesses of people. They both aim to get other people to do what you want them to do. And the highest form of…

The Crossover to Insecurity

The Crossover to Insecurity

Insecurity is just the seed of imposter syndrome, planted. Most people confuse the two because there are such subtle differences between them. But in the same way that money doesn’t change you, it just magnifies who you really are, the same goes for power. The higher you are in the chain of command, the more…

Failure is a Force of Nature

Failure is a Force of Nature

I have a confession to make. I’ve never told anyone because it sounds utterly crazy, but in any team, organization, or business I lead, my first priority is to cultivate a culture of failure. Yes, failure. Failure is the key that unlocks hidden potential we didn’t even know we had. Failure is the conduit through…

Idolization is Impotence

Idolization is Impotence

In their song “Cult of Personality,” the band Living Colour described the idolization of a leader best: “Neon lights, a Nobel Prize, when a mirror speaks, the reflection lies, …I sell the things you need to be, I'm the smiling face on your T.V., I'm the cult of personality, I exploit you, still you love…

Tunnel Vision is for Trains

Tunnel Vision is for Trains

“A compass will point you true north from where you're standing, but it's got no advice about the swamps and deserts and chasms that you'll encounter along the way.” -Abraham Lincoln in Lincoln (2012) Over the years I’ve seen many leaders, including myself, fall victim to the consequences of tunnel vision—being so focused on getting…

The Price of Indecision

The Price of Indecision

Indecision is almost always worse than making a bad decision. On the first day of summer in 1941, Joseph Stalin stood resolutely at the head of the table in defiance of his generals. With numerous legitimate reports of almost four million Axis troops, led by Adolf Hitler, marching into western Russia, the Soviet dictator had…

The Cure for Imposter Syndrome

The Cure for Imposter Syndrome

For the cure for imposter syndrome, look no further than the blue Eurybia butterfly. You just received the promotion you’ve been working towards. Or you’ve just started a company and hired your first set of employees. Or you’re writing online on a topic you know well but aren’t recognized for. With any of these scenarios…

Don’t See Luck. Seed Luck.

Don't See Luck. Seed Luck.

Luck is the tree you planted last week, last month, or last year. It is the culmination of a series of good decisions compounded over time. Nothing more, nothing less. Most see luck as happenstance—something that just happens out of nowhere. Very seldom does it work that way, however. There are four types of luck…

To Ask is Human

To Ask is Human

To ask is not weakness. To ask is human. One of my deepest flaws as a young leader was my pathological inability to ask for help. I always believed that to be a leader in anything, you had to be an expert on everything. You had to avoid asking the “stupid” questions, and you had…

No Experience? Learn the Canon

Learn the Canon

Here’s a secret everyone knows but no one does: if you have no experience in a particular field, reading and learning from the canonical—most important—books in the industry will accelerate your path to leadership. I’m often asked what I did to become a general manager of a large restaurant with no previous restaurant experience. My…

Live the Long Game

Live the Long Game

Becoming a leader is a lot like squeezing toothpaste. You can’t put it back in the tube, but you’re free to let it go down the drain. Life is a game. Some people are winning the game, and many are losing. Some people play the long game. Most people play the short game. And others…

Hungry, but Not Starving

Hungry, but not Starving

Here’s the optimal setting for you and every individual you lead: hungry, but not starving. Too much success or too much desperation are recipes for mediocrity and/or failure. The former makes it hard to maintain focus and work ethic, the latter makes it hard to prioritize anything over money. The former serves to reduce motivation,…

Not All Great Writers Lead. But All Great Leaders Write.

Writing Makes You a Better Leader

My favorite college professor once said something that has always stuck with me, “great leaders are among the greatest of writers.” I never understood or appreciated what that meant until I began writing consistently on my own. In doing so, I studied other great writers and their influences, habits, and philosophies. Eventually, I stumbled upon…

Think Like an Owner

Think Like an Owner

“If you think like the owner and you act like the owner, it’s only a matter of time until you become the owner.” -Naval Ravikant Sean McVay is one impressive leader. He’s polished. He’s confident. He’s got every tool in the belt to succeed at his job. He has the enduring respect of his superiors…

Eustressing?

Eustressing?

Hell Week is the infamous five-day period of Basic Underwater Demolition/SEAL (BUD/S) training when Navy SEAL candidates engage in physical training for at least 20 hours a day, often carrying a heavy boat over their heads on virtually no sleep, and being continuously cold and wet from Sunday evening until Friday night. In other words...stress!…

Wear the Purple Tunic

Wear the Purple Tunic

If you’re afraid to look bad, you’ll never be an effective leader. Tyrian purple was an expensive, fashionable color in Ancient Rome during the 1st century BC. It could only be produced from tens of thousands of sea snails found on the coast of Tyre (hence Tyrian) in modern-day Lebanon. For that reason, this flavor…

Permissionless Leadership

A gentle reminder: You don't need permission to lead. It’s often said that good things come to those who wait. While that may be true, there’s a fundamental problem: Everyone confuses waiting with stillness. Stillness might be good for the mind every morning, but when it comes to creating opportunities or attaining leadership positions, stillness…

Run the Extra Mile

Run the Extra Mile

Don't just go the extra mile. Run. It was 3:00 in the afternoon on a chilly February day. Tryouts for the 7th grade baseball team were just about to start and I was eager as ever to put my skills to the test for the first time. In those days (circa 2004), to try out…

Mamba Mentality: Defining (and Living by) Kobe Bryant’s 10 Rules for Greatness

Kobe Bryant 10 Rules for Greatness

"Mamba mentality" has a nice ring to it. It has a cerebral connotation--one of toughness, of grit, of greatness. Greatness is a nebulous word. Greatness is not tangible. You can’t hold it, you can’t touch it, you can’t transfer it. It’s a word you know, yet cannot neatly define. It’s only when you see someone…

Cross the Rubicon: Give Yourself Permission to Write History

There will come a time when you realize that no one is coming to save you. As depressing as this may sound, it is the most freeing belief you will ever have. It opens the door for you to do absolutely anything you put your mind to. So give yourself permission. Cross the Rubicon. Write…