By: Norman Sandridge

From the book jacket: “Leadership is hard. Convincing others–and often yourself–that you possess answers and are capable of world-affecting change requires confidence, insight, and sheer bravado.”

ἐκαλινδεῖτο ἐν τῷ πειρᾶσθαι αὖθις βέλτιον ποιεῖν

(ekalindeito en tōi peirasthai authis beltion poiein)

He was consumed with trying to do better the next time.

Xenophon the Athenian on the young king Cyrus II (c. 365 BCE)

In this week’s Art of Leadership podcast Susannah Wellford, founder and president of Running Start, tells the story of how in tenth grade she transferred to a new high school and immediately decided to run for class president. It was a daring move by a younger self that surprises Susannah even today. She lost the election, but her story invites us to reflect on how being an outsider in a new environment can enable us to audition, as it were, for new leadership roles. This might be akin to how the uncertainty of a new romantic relationship creates an opportunity for us to explore and experiment with–or even invent–new aspects of ourselves, if only we have the courage to take the chance.

Stacey Abrams Shares an Anecdote about the Benefits of Being an Outsider

In her recent memoir and guide to becoming a “minority leader” Stacey Abrams, candidate for governor of the state of Georgia, shares her own story of how in high school she won a spot at the prestigious Telluride Association Summer Program in Ithaca, NY. Abrams was raised in Gulfport, MS, so this was destined to be a “stranger in a strange land” kind of story. Initially, the program was daunting both socially and intellectually:

To a person, I could not compete. I wrote poetry for our high school journal. A girl there had published a collection. One was a concert-level violinist, and the others sounded like college professors. In our classroom sessions, I was called upon to answer questions, and I got more answers wrong than I ever had at Avondale High School. The other students referenced books I’d never read and scholars I hadn’t heard of. Even casual conversations left me adrift, floundering to understand cultural references far beyond me. When I dared to introduce television into the mix, you’d have thought I cussed.

Stacey Abrams. 2018: 8. Minority Leader: How to Lead from the Outside and Make Real Change.

Abrams says that she begged her parents to rescue her from Ithaca after the first week, but they refused. Instead, her father told her that she needed to become comfortable with not being the smartest person in the room, that she must stick it out and then decide later whether it mattered to her that there were people who had had access to a better education than she. Abrams eventually embraced her father’s advice and translated this intimidating and potentially humiliating situation into an opportunity to grow:

I had always been smart, but I needed to test myself against those who were smarter, more talented, and more accomplished. My ability to dream meant hearing about, and entering, worlds far different from my own. Athletes are encouraged to test themselves against better players. Proverbs tells us that iron sharpens iron. So too does ambition sharpen ambition. Dreams hone other dreams.

Stacey Abrams. 2018: 8. Minority Leader: How to Lead from the Outside and Make Real Change.

Abrams explains that in time she came to emulate the behavior of those she deemed more educated and thus developed more poise and confidence. Ithaca, it seems, gave her (see what I’m about to do?) an Odyssean versatility. This experience led Abrams to stretch herself and explore her potential at Spelman College and then Yale Law School. Abrams does not put it this way, but we might wonder if experiences like this develop a leader’s versatility in identifiable personality types, or perhaps sub-personality types. Unlike her peers at Telluride, Abrams now had both her “prior self,” with all the wisdom and behaviors that entailed, coupled with this “new self” that was infused with the cultural backgrounds and dispositions of her fellow students. By overcoming the fear of being an outsider she became able to play multiple “roles” in multiple “theaters”, a kind of psychological bilingualism.

Trying Out Multiple Roles Using Technology

Side note: One may wonder how many “roles” and “theaters” a leader could ultimately “perform in.” This question is explored in depth in the wonderful Joss Whedon television series, Dollhouse (2009), starring Eliza Dushku as “Echo,” a human being who is under contract to a tech company that implants her with different identities and different skillsets, from the wife of a grieving widower to a hostage negotiator. These identities are supposed to be erased after each job, but Echo retains a portion of them, which ultimately gives her a tortuous but also superhuman versatility–as well as the keys to her liberation.

“I’m all of them, but none of them is me.”

An Ancient Story

Leadership stories like Abrams’ are in some form or other at least twenty-five centuries old. In c.365 BCE the Athenian author Xenophon wrote a quasi-biographical account of Cyrus II (“the Great”), the first king of the Persian Empire, called the Kuroupaideia or the Education of Cyrus. The work encompasses all of Cyrus’ formal education in his home country of Persia (his father was king there), including training in justice through trials and in self-restraint and endurance through long hunting expeditions. When he is around twelve years old, Xenophon says that Cyrus went to live in Media with his grandfather Astyages, also a king. Contrary to his modest life in Persia, Cyrus is surrounded by lavish banquets, fancy clothes, heavy wine consumption (which Cyrus does not partake of), and courtly politics. It is here that he gets the chance to ride horses. He was, like Stacey Abrams, an outsider with an opportunity to grow. As Xenophon explains, Cyrus not only improved in horsemanship, and all its related martial skills, but he was able to charm his Median agemates:

“The boys liked him, too; for in all the contests in which those of the same age are wont often to engage with one another he did not challenge his mates to those in which he knew he was superior, but he proposed precisely those exercises in which he knew he was not their equal, saying that he would do better than they; and he would at once take the lead, jumping up upon the horses to contend on horseback either in archery or in throwing the spear, although he was not yet a good rider, and when he was beaten he laughed at himself most heartily. And as he did not shirk being beaten and take refuge in refusing to do that in which he was beaten, but persevered in attempting to do better next time, he speedily became the equal of his fellows in horsemanship and soon on account of his love for the sport he surpassed them” 

Xenophon Kuroupaideia 1.4.4-5, translation by Walter Miller.

Cyrus reaps a double leadership benefit for overcoming the fear of failure: (1) he learns faster because he’s created an environment where it’s o.k. to experiment and make mistakes without arousing envy or censure and (2) he is now even more agreeable to his friends, some of whom will later follow him on military campaign (Cyrus will eventually become king of the Medes on his way to establishing a vast multinational empire). Xenophon later tells a contrasting story of the king of the Assyrians who is envious of any of his subjects who are superior to him (Xenophon Kuroupaideia 4.6.4).

From the Study of Stories to the Practice of Leadership

No one becomes a better leader by treating a simple story simply. Being able to overcome one’s fears and grow as an outsider is easier said than done, and it is helpful to reflect more carefully on the stories we have just encountered. Part of what explains Cyrus’ success is that he has the trait of what in ancient Greek is called philomatheia; literally Cyrus is a friend (philos) to learning (matheia, whence the English word mathematics). What this means specifically is that Cyrus is highly observant and inquisitive, i.e., full of questions and not afraid to ask them, and he is able to grasp the lessons of any experience in an uncommonly rapid way. You don’t have to tell him twice. Cyrus also comes from a very supportive social environment. He is in constant dialogue with his father Cambyses, and his mother Mandane comes across as concerned and attentive. Cyrus is also educated in a community that prizes competition and the self-knowledge that can come from competition. We see similar hints of nurturing parents and a valuing of self-knowledge in Stacey Abrams’ Telluride anecdote. Susannah Wellford, too, speculates that it may have been friend who first put the idea in her head to run for office at her new high school.

All to say, this process of growth that a “leader from the outside” can undergo seems to have many pieces: supportive friends and family, an appreciation of competition, a craving for self-knowledge, a desire to actually be good at solving problems rather than merely appearing to be good at it, an active fantasy life (being full of dreams), high ambition, a quick intelligence, and exposure to a community of even more talented peers. It is this final piece that may give us some answer to the great question about leadership that Susannah poses at the end of the podcast, namely, how does a leader know if she is up to the task? how does she know if she is doing her best? Perhaps it is simple as asking, “is she surrounding herself with the best people?” Yes, those last two words are a reference to US President Donald Trump. For this story we’ve been telling to work in practice, the leader must have the capacity to tackle the abiding and challenging moral question of what it means to be “the best” person (in ancient Greek, kallistos).

Do you know of stories of a leader who comes from the outside or of a person who has developed a better leadership self by coming from the outside? Do you have personal experience with such leadership? We would love to hear from you. Please follow Kallion on Facebook and share your story on this post! #outsiderleaders

Norman Sandridge is an associate professor of Classics at Howard University and a fellow at the Center for Hellenic Studies in Washington, D.C.


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