The Custer Bias

In June of 1876, a regiment from the 7th Cavalry of the United States was in a conundrum.

Scouts had found a large encampment of Native Americans along the Little Bighorn River in the Montana Territory. This tribal encampment violated laws confining Native Americans to reservations. And the 7th Cavalry’s mission was to force them to comply.

Relations between native tribes and United States Army installments in the region were not good. Several skirmishes had broken out between the two already, and the 7th Cavalry had every reason to believe this encampment would be hostile to their demands.

And so, the regiment’s leader – Lieutenant Colonel George Custer – charted an attack. The Cavalry would be split into three brigades, encircling the encampment. The troops would trap the natives into compliance.

It was a bold strategy, but also a risky one. Custer had no idea how many warriors might be among the tribe, and how those ranks compared with his own. He also knew far less about the terrain his regiment was on than the natives.

By pressing ahead, Custer was taking a chance. And anyone who’s taken an American History class knows the rest.

The first brigade got bogged down by Lakota Sioux and Chayanne warriors just as Custer’s brigade was trying to flank the encampment. Native warriors spotted Custer’s men and attacked them with superior numbers.

The brigade had nowhere to retreat to, and not enough firepower to press on. It was systematically cut down. Every member of its five companies – including Custer – were killed.

The Battle of Little Bighorn was effectively over. But the legend of Custer’s folly was just beginning.

For generations, Americans would hear of Custer’s Last Stand. It was the ultimate cautionary tale of risk gone wrong.


Why would Lieutenant Colonel George Custer attempt such a bold maneuver? Why would he so unabashedly put the lives of his men in danger?

Military historians have been trying to answer this question for decades. For Custer wasn’t exactly a novice when he reported to the Montana Territory. He was an accomplished military leader who had led Union Army brigades in the American Civil War.

The volunteers under Custer had repelled Confederate forces at just about every turn, including the Battle of Gettysburg in July 1863. He knew what he was doing.

Or did he?

You see, at Gettysburg, Custer’s volunteers faced off with a Confederate cavalry force twice their size. Custer’s brigade was somewhat detached from the heart of the Union Army, and the Confederate cavalry caught him by surprise.

Undeterred, Custer led counterattack after counterattack with his own cavalry. The vicious fighting stalled the Confederate brigades, effectively preventing them from rendezvousing with other columns of fighters.

Once the cannon fire of the main battle could be heard in the distance, the Confederate cavalry retreated. Custer had won.

Custer had taken a massive risk exposing his cavalry so extensively. The chances of them getting overrun were as good as them prevailing.

It was effectively a coin flip. But the coin came up in Custer’s favor. The risk paid off

This certainly gave Custer confidence. Confidence to assume even more risk.

That attribute was what allowed him to rise to the rank of Lieutenant Colonel, and to get posted to the Montana Territory. And it’s likely what made his daring plan at Little Bighorn seem anything but.

Live by the sword. Die by the sword.

Call it The Custer Bias.


Lieutenant Colonel George Custer met his demise nearly 150 years ago. So, why discuss his travails in such detail.

Well, I believe they’re just as prescient in this era as any other.

We are a far different country now. A global superpower, fueled by big business.

But today’s industrial leaders are just as happy taking risks as Custer was. If not more so.

This sustained boldness perhaps most notable in big tech, where companies can shift from hypergrowth to cost cutting on a dime. But it’s also present in manufacturing, thanks to the rise of just-in-time inventory processes. It’s present in retail, where large brands venture into new product lines or sales channels time and again. And it’s present in dozens of other industries.

There are many reasons why this behavior is so present among corporate leadership. Many have pointed out that investors don’t stand still. And neither do competitors.

That’s all accurate. But the biggest reason leaders lean into risk-taking? It’s The Custer Bias.

Think about it. Just about any corporate leader has already taken a risk to get where they’re at. Maybe they were an entrepreneur, who defied the odds to found the business they now helm. Or perhaps they rose through the corporate ranks, trying something bold to fuel their breakthrough.

With those bold moves in their rearview, these corporate leaders are keen on rolling the dice once more. For all the market forces out there – consumers, competitors, investors – are yearning for them to push the envelope.

Of course, it could all go sour. And if it does, they could lose everything they’ve attained.

Such an outcome would sting. But not as much as the status quo does for others.


It’s easy to idolize the maverick leaders. To deify a Steve Jobs or a Howard Shultz or a Reed Hastings.

But for each one of them, there’s someone who failed at their mission. Someone who took a risk to create a tech company, or revitalize a small coffee shop, or disrupt the entertainment industry. And someone whose risk didn’t pay off.

These failures lurk in the shadows. You can’t prove a negative, and we have little patience for tales of what could have been.

And so, we comb through the success stories. We search for patterns and commonalities – all while forgetting about the inherent randomness.

Yes, success can seem inevitable if you weed out the duds. And that delusion can make risk-seeking appear less dangerous. Safe, even.

This is undoubtedly a tragedy. Not perhaps not in the way you might think.

Those burned by a risk gone bad will surely suffer – regardless of whether it’s the first or fifteenth risk they’ve taken. But those who avoid risk will suffer even more.

For there is no safe passage for the risk averse these days. Those who play it safe will still find themselves under the direction of renegades.

They’ll find themselves reporting to dice rollers infested with The Custer Bias. In this modern era, how could they not?

Yes, it is all too possible to stay away from the fire and still get burned. But what if that such a fate wasn’t so inevitable?

It’s time to turn the tables on The Custer Bias. To be less cavalier with the risks we take. To pay more credence to the odds of chance. And to avert our eyes from the shine of favorable outcomes.

Such actions run counter to our nature. But they’re essential to our survival.

So, let’s stop following the path of Lieutenant Colonel George Custer. Our story deserves a better ending.

Leading From Behind

On a cold day in November 1928, the Notre Dame Fighting Irish football team huddled in a locker room at Yankee Stadium.

The Irish were in the midst of a lackluster season, and the first half of this contest against the undefeated Army Cadets was going no better. Both teams had battled to a 0-0 tie, and morale on the Notre Dame sideline seemed low.

In the silence of the locker room, coach Knute Rockne spoke up. Instead of discussing strategy or tactics, Rockne evoked the memory of a former player — the All-American George Gipp. Gipp had died eight years earlier, and Rockne recalled Gipp’s final words to him:

Sometimes, when the team is up against it – and the breaks are beating the boys – tell them to go out there with all they’ve got and win just one for the Gipper.

The players responded to Rockne’s call with vigor, roaring back to beat Army. Notre Dame would go on to win national titles in the two subsequent years.

Rockne was already a legend before he urged his team to Win one for the Gipper. He had won 85 football games at Notre Dame to that point and helped popularize the forward pass.

But the halftime speech took his legend to new heights. It showed that coaches could do more than plot out X’s and O’s on a blackboard. They could lead from the front.

They could inspire with their words, command with their charisma, and blaze a trail through the boldness of their conviction.

Leading from the front was not a new concept when Rockne evoked it. It had long existed in politics, with its premium on oration and debate. But it was relatively nascent elsewhere.

Now, it no longer is.

Indeed, in the near century since Rockne’s speech, leading from the front has become the norm — in sports, in business, and in life.

Coaches are expected to say the right words to their teams at the right times. Bold keynote presentations are now expected of CEOs. And charisma is demanded of the rest of us.

The implication is clear. By taking charge and demonstrating a plan for success, leaders can inspire others to action. They can spark a movement and leave their mark on the world.

This approach has paid dividends, on and off the field. But it’s not the only way forward.


I grew up with sports.

Watching them. Playing them. And appreciating all the lessons they brought.

Throughout all that time as an aspiring youth athlete, I only remember one speech that made a difference to me. It came from my middle school baseball coach during a practice. And while it impacted my life, it didn’t raise my team’s performance on the field.

No, I didn’t rely on my baseball coaches for inspiration. My motivation came from watching pro baseball players. Not the flashy, hard-nosed ones. The quiet and consistent types.

I recognized from an early age that the best baseball teams had more than big sluggers or lights-out pitchers. They had glue guys — seemingly ordinary players who did all the little things right.

Oftentimes, their attention to detail would cause others to follow suit. And if those with the greatest athletic abilities were also attending to the details of the game — well, that made the team nearly unbeatable.

There’s a name for this quiet leadership. It’s called leading from behind. And I’ve been fascinated with it ever since those boyhood days on the diamond.

For leading from behind is hard. It requires us to show up each day and do our best.

There are no shortcuts to success. And no glamour to be found in the process.

When leading from behind, our best hope is for the steady drip of our actions to inspire others. Our best wish is to serve as a north star, illuminating the road ahead for our team. And our best reward is to garner the respect of those around us.

Embracing this mentality can be a tough adjustment, especially in a society that lionizes towering personalities. But the journey can prove worthwhile.

After all, those who lead from the front tend to have big egos. And egos can be mighty polarizing.

Yes, for all his glory and accolades, Michael Jordan wasn’t exactly beloved by his teammates. Despite his visionary leadership, Steve Jobs might be best remembered as a vindictive jerk. And Stanley Kubrick was as tough to work for as he was brilliant.

These character flaws might seem immaterial. But the dissent they spawned diluted the leadership abilities of these great men and tarnished their legacies.

Those leading from behind don’t face these problems. Their actions speak volumes all their own.


When I was in college, I decided I wanted to work in television news.

But my self-determined role in this industry was a strange one.

Instead of reporting from the field or sitting behind an anchor desk with the bright studio lights upon me, I wanted to produce the nightly newscasts. I yearned to compile stories, write scripts, wrangle footages, and – yes – manage the egos of news personalities. And I pined to do this behind the scenes, far from the discerning eyes of the viewing audience.

I knew that I’d get little acclaim for doing this. I wouldn’t be recognized when I walked down the street. Heck, I might not even be feted in my own newsroom.

And yet, I knew the value of the producer role. Without it, the newscast would be a rudderless ship, short on information and full of chaos.

Producing the nightly newscasts would provide me a great opportunity — the opportunity to lead from behind.

I seized that opportunity for nearly three years, making friends and garnering respect along the way. And when I left the news media, I didn’t abandon those principles.

As I’ve built a career in marketing, I’ve led from behind. I’ve put in the work, deflected credit, and sought to elevate my team at every turn.

This strategy certainly has its risks. There was always the chance that I’d be overlooked for a promotion or a similar opportunity.

But the benefits have far outweighed the risks. I’ve earned the respect of colleagues, made new friends, and helped accomplish far more than I would have if I had gone it alone.

But I’m not unique. Many others could reap these same benefits by shifting their conceptions of leadership.

We don’t need to be up front to make a difference. There’s plenty of merit in leading from behind.

It’s high time we explored it.

The Err of Bluster

The team is staring down a challenge.

Great opportunity lies ahead. But so do obstacles. Obstacles determined to keep this opportunity out of reach.

With the fog of adversity looming, a leader steps in front of the group and gives a fiery speech. The words energize the team. They overcome the odds and reach their goal.

Chances are, you’ve seen this situation unfold. Maybe you experienced it in real life. Or you saw it in a movie about sports or war.

It’s become the de facto playbook for wide scale leadership.

Bluster on. Rally the troops. Achieve victory.

It sounds good on paper. But that playbook has a fatal flaw.


Speak softly and carry a big stick.

If you weren’t nodding off in history class, you might remember that this quote comes from Teddy Roosevelt.

Roosevelt talked the talk. But he also walked the walk.

He made his name in the Spanish-American War, when he led his regiment — the Rough Riders — in a daring charge up a hill in Cuba. He often ventured out to the Dakota wilderness to hunt ferocious animals. And he treated the United States as a global power — even though it was yet to truly be one.

Roosevelt became the 26th President of the United States in 1901, when his predecessor was assassinated. And he instantly stood out. For in its 125 previous years, the U.S. had never quite seen a leader with his level of bluster.

Indeed, the three other presidents immortalized on Mount Rushmore with Roosevelt — George Washington, Thomas Jefferson and Abraham Lincoln — conducted themselves much differently.

Washington led the fledging Revolutionary Army to victory over the British. But he didn’t achieve this feat by charging at the enemy in broad daylight. Instead, he used a series of skirmishes and retreats to lure them into a trap.

One need only look at the most famous painting of Washington to understand that he was more about guile than bile. That painting shows him and his troops crossing a frigid river for a surprise attack.

As President, Washington maintained his understated style. Despite the divisiveness all around him in the early days of the nation, he refused to resort to bravado.

The same went for Jefferson. As President, he’s perhaps most famous for purchasing land from the French. All the bluster was reserved for Vice President Aaron Burr, who got into an infamous duel with Alexander Hamilton.

And Lincoln? He led the United States through a Civil War with candor and compassion. His most famous speech — The Gettysburg Address — was more solemn than boisterous.

Yet, Roosevelt blazed a different path. And in his stead, a new form of leadership emerged.

The blustering style was in to stay.


Bluster has had a long run. Nearly 125 years in the daylight, to be precise.

But now, the sun might be setting on it.

Indeed, as a global pandemic tears its way through humanity, the virus at its center punishes defiance. And yet, many leaders have felt compelled to bluster on.

One of these blustering leaders was Boris Johnson, the Prime Minister of the United Kingdom. As the virus ravaged nearby nations — first Italy, then Spain, then France — Johnson seemed convinced that those in the British Isles had nothing to worry about.

Johnson blustered on about the strength of those across the UK. He continued to shake hands. And he resisted initial calls for a national lockdown.

This behavior all seemed reckless. But Johnson was not one to bow down to an opponent. He preferred the familiarity of a rally-the-troops style — even if it put his nation on a collision course with disaster.

Then, Johnson caught the virus.

He carried on with his duties at first, albeit remotely. But his condition worsened. Soon, he ended up in an Intensive Care ward at a London hospital, his life in the balance.

Johnson pulled through, and ultimately recovered from the virus. But he emerged from the ordeal deeply humbled. His brush with death had seemingly convinced him that the virus couldn’t be scared away with bold talk.

Johnson’s messaging has since taken a more pragmatic tone. And his voice has seemed to carry more weight.

The situation in the UK has remained dire. But the nation has avoided calamity, even as others have dealt with surging caseloads.

Perhaps this is a coincidence. But I think not.


It shouldn’t have to come to this.

Leaders shouldn’t have to risk falling in the abyss to see the light.

For the truth lies in front of us. Bluster just doesn’t work.

Sure, bluster might seem tantalizingly shiny when times are good. But when the going gets tough, all that glitter is as good as lead paint.

It’s dangerous. Even fatal.

Yes, when uncertainty takes hold, when fear and doubt infest us, we don’t look for the loudest voice in the room. We look for the steadiest hand.

We choose a Lincoln over a Roosevelt. Every time.

And yet, those in power can’t help themselves. After all those years watching war movies and all those months on the campaign trail, their egos have deluded them.

Noise becomes their most trusted tool. Their only trusted tool. And in the teeth of a crisis, they just turn up the dial.

It’s a self-fulfilling prophecy. A prophecy in the form of a doom cycle.


Crises are good for precious few things.

But a fresh start is one of them.

The global pandemic has forced us to part with life as we once knew it. It’s compelled us to sacrifice so much that we once considered essential, in the name of survival.

So, why should we cling to a warped notion of leadership? Why should we tolerate the err of bluster?

Now is the time to celebrate a new class of leader. A leader who speaks through actions, rather than a bullhorn. A leader who is more deliberate than forceful. A leader who embraces humility over hubris.

Such a leader might not bring an aura. Their story might not catch the eye of Hollywood script writers.

But they will be the one that we follow out of the darkness.

It’s on us to make sure we continue to follow them in the light as well. That we make it clear precisely what we will tolerate from our leadership — and what we won’t. That we snuff out bluster once and for all.

Our future depends on it. No more. No less.

The stakes are high. Let’s make sure we meet them.