The Virtue of Fallibility for Leaders

Mark Frein
7 min readMay 21, 2019
By Alvaro Marques Hijazo, https://commons.wikimedia.org/w/index.php?curid=75835795

The notion of ennobling character traits or virtues has a long history. Greek philosopher Aristotle described a system of ethics based on virtues of character. Chinese philosophers including Confucius articulated similar ways of understanding “doing right” as “being good” — i.e., being an upstanding person by habit and self-discipline.

Prominent virtues include honesty, courage, charity, prudence, and love. At InVision, the company where I work, we hold humility in high esteem given it not only informs our behaviors with each other but is critical for the empathy needed to listen deeply to customers. We place our customers’ voices first and listen deeply not only to understand problems but to resonate with the person articulating the problems.

Properly, “fallibility” is a word meaning the “capability of being wrong” and is a bit of a stretch as a virtue without further explanation. Given that we humans are imperfect, we are all fallible. I mean here something more pointed, however. I sometimes ask executives, “How is your practice of being fallible?” It is a question similar to asking someone how their yoga practice is, or about someone’s chops on a musical instrument, or the battle against oneself in improving one’s putting game in golf. My intent in asking it this way is to suggest that something like fallibility is a core component of the overall art of being a leader (as putting is to the overall golf game).

It is different than being humble but related. If humility, in a way, is ensuring that you do not overreach your sense of your impact on the world, fallibility is ensuring you do not overreach your confidence of your beliefs and judgements about the world.

Shakespeare’s King Lear is one of the ultimate demonstrations of the lack of fallibility. Lear awards his kingdom to two of his three daughters after they have professed false and exaggerated love to him. To the daughter that actually does love him (Cordelia), but will not embellish her declaration, he gives nothing.

No attribution, Creative Commons

Lear is many things — proud, vain, blind. He is also clearly narcissistic, a character trait I believe is the most direct opposite of having a good practice of fallibility. Lear says, after he has descended into madness from his mistakes, “They told me I was everything, ‘tis a lie, I am no ague-proof.”

Power can corrupt in an insidious way. Sometimes it is not the risk of overt abuse of power gained, but rather the risk of ego inflation so great the leader sees himself or herself as superhuman — incapable of error. Making this problem worse are the echo chambers that can surround senior leaders. Many subordinates do not feel comfortable challenging their senior leaders and leaders can unconsciously or consciously surround themselves with the proverbial “yes” individuals.

After all, it is very satisfying and emotionally boosting to be right. I believe all leaders struggle with the demon of narcissism. As an executive myself, I will cast stones only after recognizing my own journey to fight this demon. Over a 20 year leadership career, I have had feedback I’m stubborn, arrogant, don’t listen, make assumptions, create spin, etcetera. All the things and all of them no-fun to receive as feedback. I consider myself fortunate that very early in that leadership journey there were people around me that had the courage to call me on my BS. Many years ago, a person in the office I managed simply gave me a little red ball to put on my desk — a subtle reminder to ask a question before giving an answer.

At its most basic, fallibility in the way I’m using it here is the readiness to admit you are wrong. More importantly, it is not simply the readiness to admit one is wrong in the face of overwhelming opposition or when doing so is tactically to your benefit. Nor is it the readiness to begrudgingly admit one is wrong after making everyone else feel belittled.

It is a demeanor, a high standard, and an approach to life, hence a virtue even in the classical sense. It is consistently showing up as a person who is capable and willing to be wrong when engaged in rational inquiry. It is showing up — behaving in such a way — that others know you are open to new ideas, challenges, and to revising your viewpoints on a wide array of things. It is being transparent about what beliefs you hold that are and are not revisable, and always seeking to inform yourself about those.

It is showing others you are capable of self-doubt.

Some leaders assume that admitting mistakes is equivalent to admitting weakness which in turn makes one weaker as a leader. It seems to be true, at least in part, that some followers want a leader that continuously asserts with some degree of bravado in their perpetual “rightness”. Indeed, when we look around at the world leaders of today, it is rare to find anything other than this posture.

I can’t claim that leading from perpetual “rightness” is ineffective just given what is obviously true of whom has risen to the top in a wide variety of corporations and governments. It has worked for leaders in a wide variety of contexts, at least to gain them power.

I do not, however, think it is leadership that supports and sustains open, democratic society nor open, transparent and principled private sector organizations. Fundamentally, leaders are granted power by followers. I don’t personally find “Always Right” bravado in leadership appealing and generally-speaking, no one I’ve ever worked with that was creative, adaptable, reflective or emotionally self-aware does either.

Being fallible is a cornerstone of participating in a society or organizational culture that seeks to evolve its practices openly and rationally. It creates space for dialog and creativity and is highly engaging for people that want to have full voice and contributions. It enables participatory, inclusive, and diverse human systems.

Let’s call the extremes of the two styles Open Leadership or Closed Leadership. The first is, I believe, required for successful participatory and transparent cultures and societies. The second is fundamentally autocratic. Each can “work” in so far as there are clear examples of each both historically and at present around the world in all types of communities and human systems.

However, if there is a reason to insist on Open Leadership not only in governments but in private sector organizations where we do not vote our leaders into office, it is this: Open Leadership … leadership where there is a strong practice of fallibility … encourages and builds attitudes and norms that we desperately need to preserve to sustain open, democratic institutions in general. If all of our private institutions are examples of Closed Leadership, and if all the myths and narratives of corporate success celebrate autocratic-style leaders, we may become numb to the need for Open Leadership in our governments.

I would hazard to say that may just be where we find ourselves, at least in the United States. I find myself saddened by the degree to which popular media is dominated by leaders across the political spectrum continually asserting — shouting and fist-waving — their “rightness”.

We need to ask, “How might we all be wrong here?” “How might we be wrong about always needing to be right?”

Dr. Seuss’ Bartholomew and the Oobleck has one of the greatest parables I can think of illustrating fallibility. Like Lear, it is the story of a king that loses touch with his humanity.

King Derwin wants something different to fall from the sky other than rain, fog, snow, etc. (HIS sky). The king proceeds to go to every length to obtain what he wants and disregards the advice of his young page, Bartholomew Cubbins. The king leers over Bartholomew and rages “Boy, don’t you dare tell me what I can or cannot have! Remember, Bartholomew, I am King!” He gets for his demands a disastrous green guck that glues up his entire kingdom.

When finally, almost drowning himself in the green oobleck, Bartholomew confronts the king and roundly scolds him for his pride, the king at last says simply, “You’re right! It is all my fault. And I am sorry!”

In many ways the story illustrates pride, lack of humility, and hubris. It also illustrates something about the nature of certainty. The king refused to believe his page that he couldn’t have what he wanted. Bartholomew was, for King Derwin of Didd, utterly wrong in contradicting the king’s desires. Further, it is easy to see that prior to the story, the King was unable to be wrong in general.

We live in an age in technology work where leadership “distortion fields” are celebrated. In many scenarios, they are rightly celebrated for providing the impetus and vision for people to contribute and create beyond their own self-imposed limitations. Great leadership does indeed call out of people things they did not think possible.

It is equally true that the most devious distortion field for a leader is the field that self-deceives — a leader can fall easily prey to the demon of narcissism and believe his or her own deceptions. One of the worst of these is the the irony of the self-deception that one is always right. It is a lie about truth itself that leaders can tell themselves.

The more authority and responsibility I get in my career, the more at risk I feel I am to falling prey to losing a practice of fallibility and the more I must work on it. As with all character virtues, it requires habit, diligence, and work. It is the daily “chopping of wood” in the mind’s eye of self-reflection. My mantra is “I am human, and I am wrong, about a lot of things, all the time. I look forward to finding out where I’m wrong not so I can be right, but so I can remind myself of my humanity.”

The best advice I can give leaders for their ongoing journey — their practice of fallibility — is to ensure that they have as many Bartholomew Cubbins around them as possible. People that express themselves with compassionate candor (another one of InVision’s principles) and, when necessary, as Bartholomew did for King Derwin, take leaders to task with righteous fury.

Mark Frein — A soul on the profoundly human journey of making mistakes

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Mark Frein

Failed Philosopher, Musician, HR/Startup Executive, Game Enthusiast, Imaginarian