The Content of Her Character

Why Harriet Tubman was such a great leader

Feb 28, 2023

As Black History Month draws to a close today, it seems appropriate to inquire into the formation principles of one of America’s greatest leaders…as adjudged “not by the color of her skin but the content of her character,” to quote the Rev. Dr. Martin Luther King, Jr.

“Moses” at age 73 (1895), 32 years after leading a raid into the heart of The Confederacy, as daring as anything undertaken by SEAL Team 6 or the OSS.

On June 2, 1863, at about 2:30 a.m., six months after President Lincoln issued his Emancipation Proclamation, Harriet “Moses” Tubman led 150 Black soldiers inland, after her eight hand-picked male scouts had surveilled the area east of Beaufort, South Carolina, and alerted the slaves to an impending raid. Once the signal was given, everyone dashed towards the Combahee River, where row boats were waiting to transport the emancipated slaves to three Union gunboats anchored off-shore. Bedlam ensued as men, women and children bolted east into the darkness, lugging babies and bales of food, herding squawking chickens and squealing piglets. The plantation overseers and local militia shot anything that moved. One Black girl was killed but close to 800 slaves got away, then Union troops torched plantations, grain mills, warehouses, mansions, fields, and a pontoon bridge.

Tubman’s daring raid dealt a huge blow to Confederate morale—and gave a huge lift to Union morale, just a month before Gen. Robert E. Lee’s Army of Northern Virginia was defeated at Gettysburg, and mighty Vicksburg fell on the same day. Though she bore no rank, wore no uniform, and wasn’t paid a penny for her efforts, Tubman was the first woman to lead a major U.S. military operation, let alone one so resoundingly successful.

How did she pull it off? Leadership was how, powered by four principles.

Principle 1. Temper your vision with realism

Isaiah says: “Without vision, the people perish.” But reckless vision can kill, as Lot’s wife discovered on the outskirts of Gomorrah.

Born a slave in 1820, in rural Maryland, Tubman learned a lot about the harsh reality of life. On the anvil of this brutal unjustness was forged a powerful and progressive pragmatism.

When the Civil War broke out in 1861, the U.S. population of 32 million included about 4.5 million Blacks. As about 500,000 were free, four million Citizens were deprived of their basic Right—just on account of their skin color.

Yet 16 million weren’t free just on account of their gender. Tubman learned a lesson from the struggles faced decades prior by Sarah Grimké, who (against the advice of many) insisted on battling racism and sexism simultaneously. Called Moses because of her success at freeing slaves via the Underground Railroad, Tubman knew that if Slavery weren’t defeated, if any human being could be treated as chattel, no Right was safe, so she focused all of her energy and talent on helping Blacks escape the plantation pharaohs.

Every successful leader understands that perfection can be the enemy of the good. Vision boards are nifty but reality, like politics, boils down to the art of compromise. Knowing when to compromise, when not to, and why—are hallmarks of leadership.

So: next time there’s an impasse at work, during a vestry or PTA meeting, wherever, reach out, listen for some principled common ground, then temper someone else’s visionary idealism with your nuts-and-bolts pragmatism, or vice-versa.

Principle 2. Play the hand you’re dealt

Academia (where I’ve spent much of my life in one capacity or another) has played a very important role throughout history. But like all institutions it can sometimes fall prey to self-defeating credentialing criteria. Take the august Faculty Senate Tenure Committee at your typical Big University, the bureaucratic organ responsible for deciding who gets tenure, and who doesn’t. Typically, the decision equation is very simple: the value the candidate “up for tenure” contributes to the proclaimed mission of higher education essentially = the number of prestigious diplomas hanging on her wall + the number of peer-reviewed scholarly articles she’s authored (partial credit for co-authorship) in high-caliber journals or textbooks (points deducted for People) + the number of times those articles are cited by other scholars (points deducted for South Park). There’s no silo like the Ivory Tower Silo.

As for me, I’ve always felt adjunct faculty have played a huge, unheralded role. Take The New School, which has educated so many great minds, hearts, and achievers; 87% of its faculty are adjunct. Some of its best educators have always been recent immigrants, who had a 0% chance of receiving tenure at conventional universities. Many have struggled with English, yet their struggles have brought the Real World into the classroom.

Tubman never learned to read or write, yet she’s been educating people regarding the highest virtues of Real World servant-leadership for nearly 200 years. How was this illiterate house servant & field hand able to become the Underground Railroad’s #1 conductor, one of Lincoln’s top spies, and the first woman to lead a major U.S. military operation? Much had to do with her impressive oratory and memory.

Socrates never wrote a thing (at least nothing has survived); Plato listened to him, observed him, and wrote about him. Buddha and Jesus didn’t write anything, either (apart from a few scribbles in the dirt, per The Gospel according to John). Tubman also had a way with words. Once the freed slaves were aboard the row boats on the Combahee River, the rough water terrified them (many didn’t know how to swim), but Moses calmed them, as she had many a terrified Railroad passenger, by singing Go Down Moses and Bound for the Promised Land. When conducting, she’d modulate the tempo to indicate whether it was safe enough to venture out.

Her powers of recollection were prodigious. She knew what the inhabitants of a remote Scottish island still do to this day: when a visiting priest apologized for being unable to discuss Scripture because he’d forgotten his Bible, the locals said, “Why do you need to read? Can’t you just remember?” Tubman could quote whatever she’d overheard, verbatim. She could explain the topography of any terrain she’d traversed better than the best mapmakers of the day. And her memory had a very long shelf life: she grew up in Maryland’s marshy lowlands in the early 1820s; 40 years later, she put her powerful memory to use in planning and executing the raid in South Carolina’s marshy lowlands.

Tubman converted her illiteracy from a disability to an asset. It was the perfect cover for a spy. Stealthily effacing, she circulated unnoticed in the North and South, amidst grand mansions and sitting parlors, cotton fields & tobacco drying sheds, overlooked by the slaveowners, bounty hunters, and Confederate partisans who felt she couldn’t possibly be a threat. She excelled at playing dumb.

While others needed to refer to a map, or find a lamp in order to read a courier’s letter at night, she could recite specifics in granular detail, instantly. And in her clandestine line of work, speed often spelled the difference between life and death.

So: play your hand. Maybe it’s to lead HR, to organize the office Holiday party, or, like entry-level George Bodenheimer, to deliver the mail, then go on to run ESPN; in part, he says, because “when you deliver the mail, you get to know everybody.”

Principle 3. Remember: Rome wasn’t built in a day

Some argue that today's conspicuous lack of principled leadership is a direct result of the socio-cultural degradation of Patience. When I was growing up in the 1960s, I was often told: “Patience is a virtue.” Then, in 1973, Domino’s Pizza began offering its famous 30-minute guarantee, and FedEx began delivering packages overnight. Come 1981, George Will said America was toast because “the linchpin of civilization…is the discipline that enables people to defer gratifications.” Today, we are instantly gratified at every turn, from on-line Everything and Instacart instant oatmeal to our skies filled with Amazon drones.

Yet in our heart of hearts most of us still appreciate the power of patience, which is why even my secular-hedonist friends say “So-and-so has the the patience of Job”—2,500 years after the fact. A thousand years earlier, OG Moses wandered the desert for 40 years, all the while badgered by his posse, who kvetched about not having much to eat, the oppressive heat, carping: “Was life in Egypt really that bad? Did you really have stick your nose in it when that satrap was beating one of us?”

Moses never did enter The Promised Land. That wasn’t in the cards.

Tubman also had legendary patience. After the Civil War, though she lamented the sputtering Emancipation and Reconstruction, she continued to play the hand dealt…passing the baton to other leaders, who followed in her footsteps.

However, purpose-guided patience shouldn’t be confused with meaning-challenged procrastination, as the insightful and hilarious Tim Urban reminds us in his hugely popular Wait but Why book, blog, and TED Talk (the first TED video to ever reach 10 million views in its first year, and still in the top ten most-watched), and reinforces in his new bestseller, What's Our Problem?: A Self-Help Book for Societies. But as an intentional tool in your leadership kit, patience is a paradoxically propulsive virtue.

So: whether you’re a high-energy entrepreneur, a stolid shop steward, or a worthy cause petition-organizer, be wise like the farmers and gardeners of millennia, who’ve always known they can no more make the sun come out than the clouds open up. Like Dostoyevsky’s general Kutuzov advised in War and Peace, today's wise leaders also avoid “useless aggressive movements…Patience and time are my warriors, my champions.”

Principle 4. Be brave, because courage is more powerful than any cannon

Courage is often the glue that binds and catalyzes every other leadership virtue. Alan Mulally demonstrated remarkable courage in declining federal assistance while leading Ford during The Great Recession, as did Frances Hesselbein in agreeing to lead the Girl Scouts—at age 61.

Reminiscent of what the Moses of Egypt fame did so long long ago, Moses Tubman also demonstrated her valor early on. When an incensed plantation overseer chased after another slave and hurled a hunk of metal, Moses stepped in between them, and was rewarded with a terrible head injury, and insomnia that plagued her for the rest of her life. Yet her reputation was cast.

While whites like Sarah Grimké and Horace Greeley could pretty much come and go as they pleased, do and say whatever they pleased, Tubman lived on a razor’s edge. Being Black and a woman, she knew that if she were caught helping slaves escape—the punishment would be unimaginably severe. Yet she never blinked. She stepped up, again and again.

Many studies have shown that courage is the most inspiring leadership trait. Tubman inspired people like few others, before or since.

So: whenever you get the chance to be brave—take it! People will notice.

The result will far more than them rubber-necking. It’ll be you ripple-making…

When leaders exhibit courage and selfless service for the Greater Good, it creates a ripple effect. People stop sitting on the sidelines, being observers.

During her days as an Underground Railroad conductor, a Union spy, and a military operative, Tubman herself freed “only” 900 or so slaves, but her bravery inspired countless others to step up and be conductors on The Railroad, spies, and soldiers. For instance, she inspired the legendary 54th Massachusetts.

Denzel Washington, Morgan Freeman and Matthew Broderick starred in Glory, about the mostly white-led but otherwise Black regiment, which also undertook a frightful raid in South Carolina. After her successful Combahee River raid, Tubman served meals to the 54th, including—remarkably—the final meal to its commanding officer, Robert Gould Shaw (played by Broderick).

Tubman witnessed the tragic battle for Fort Wagner, impregnably defended by a Confederate garrison. The rebels seemed to have won, but it was pyrrhic. Yes, the 54th suffered a horrific 40+% casualty rate, with more than 270 of the regiment’s 650 soldiers killed, wounded, captured, or missing and presumed dead. However, quoting The U.S. National Park Service, the manifest courage “inspired the nation to begin mass recruitment and mobilization of Black soldiers. The 54th paved the way for more than 180,000 Black men joining the United States forces, which ultimately helped turn the tide of the war.”

So: next time you get the chance to be brave, to storm a citadel of calcified and unjust office convention, or support a marginalized colleague with a great idea to whom no one seems to be listening—follow Moses’ lead, and part some waves!