On Leading With Greatness
On Leading With Greatness
Want to Lead Better? Behave Like an Iconoclast.
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Want to Lead Better? Behave Like an Iconoclast.

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The eyes of the idol with the iron head are glowing

Bob Dylan

A stained glass window depicting a woman with a crooked stick holding aloft a sort of icon

What is an iconoclast, and why should you behave like one?

Most people have little memory of their graduation ceremonies, who spoke, what they said. Do you remember your graduation speaker? Do you remember the speech? Decades after my college graduation, I still have a strong memory of our keynote speaker, the evolutionary biologist, Stephen Jay Gould. Over my many years in higher education I have heard a lot of graduation addresses, and Gould’s was one of the best because he did what all the best ones do.

There are three main categories of graduation speeches. Some speakers primarily give advice based on their experience, which is well intentioned but, like perspiration, evaporates as soon as the nylon graduation gowns come off. Others focus on their personal saga of persisting through struggle and woe. Everyone applauds fervently, many cry, most feel uplifted and inspired for a few hours before the memory fades into the background. These overcoming-adversity speeches are everyone’s favorite, but they are the mental equivalent of cotton candy: colorful, intriguing, pleasing, insubstantial, and easily dissolved. Beware cavities.

Gould, though, was the third and best type of speaker, the one who knows their audience well and throws down a serious challenge to the graduates. My college has long been known for its unconventional students, and he leaned into that reputation before giving us a charge to live the promise of our unorthodox ideals. He pointedly used a particular word to describe us, the same word several previous speakers that day had used: “iconoclasts.”

So, What Is an Iconoclast?

If you look up the word “iconoclasm” you might see something about people smashing religious icons, but that is a bit obscure and hopelessly literal. Merriam-Webster describes an iconoclast as “a person who attacks settled beliefs or institutions,” which is true, but the word “attacks” is a bit over the top and very limiting.

Really, an iconoclast, as we use the term today, is someone who is not beholden to conventions and who questions cultural assumptions. Sometimes the term is conflated with “skeptic,” but a skeptic is more a thinker while an iconoclast is more a doer.

Great artists tend to be iconoclasts. For instance, you may be surprised to learn that I am a huge Bob Dylan fan. One of the things that attracts me to him is his artistic iconoclasm. He breaks the rules so successfully that his innovations often become the new rule, which he then breaks. Nothing is sacred.

Iconoclasm in Practice

Sitting not far from me during that graduation ceremony was my good friend G. We have stayed tight since college and even pursued similar careers teaching English. A few years back, I had the privilege of spending a day in his classroom at his public high school in Philadelphia.

One of the things about teaching high school is that there is much more rigidity than in teaching college — what with standardized tests, standardized curricula, and standardized periods that terminate with a standardized buzzer. As in all hidebound bureaucratic situations, many of those standardized measures compete with the stated educational goals of the district. This situation is an example of Goodhart’s Law — “When a measure becomes a target, it ceases to be a good measure” — which describes the shortcomings of American education at every level.

Despite the obvious inadequacies, some teachers will follow the rules as closely as possible. If they are told to teach certain books, they will teach those books and only those books. Such a conformist is often rewarded for sticking to the script even when the results are mediocre.

Join the Movement!

Others will spurn the rules by doing virtually the opposite. They will teach as few of the prescribed books as they can get away with while trumpeting their contrarian ways. They pretend to be independent but are really just reacting to the same stimuli as their archenemy, the conformists. The difference between them is that the conformist thoughtlessly complies with convention while the contrarian, knee-jerk rejects it.

A third type, the individualist, will just light out on their own and do what suits them best. For instance, an individualist English teacher might teach the books they want off the assigned list but will also teach whatever else appeals to them.

With each of these types — the conformist, the contrarian, and the individualist — notice that the principle driver of what they teach and even how they teach is not what is necessarily best for the students but what is most comfortable for the teacher.

My friend G., in contrast, decides what to teach and how he teaches based on his assessment of his student’s needs. He reviews the school district’s curricular requirements, taking what he knows will work and ignoring the rest while adding what he decides — in his professional opinion — will maximize his students’ learning.

It’s risky, frankly, even with his tenure and union protections, but — in the spirit of Gould’s graduation charge to our class — G. cannot stand to do anything less than right by his classes. No surprise, but he is successful too. The day I spent watching him teach, I could not resist stopping one of his 11th-grade classes as they were filing out at the end of the period. I told them that they were reading and responding to literature at a level I would expect from college sophomores. They, of course, were unimpressed by this old man’s ranting, being all of sixteen.

G., as a professional educator, thinks and behaves like an iconoclast. He is not mindlessly devoted to what he is told to do. He does not mindlessly reject it either. Nor does he heedlessly inject his own wants and needs into his pedagogy. No, he starts with the student and ends with the student and what unfolds in between is all about the student. Oh, and by the way, his students have a stupendous track record on standardized tests even though he breaks every district rule that gets in the way of actual student learning.

What This All Has to Do with Leadership

What does all this have to do with leadership? Well, everything.

As I have asserted many times before, every leadership problem is a teaching problem. Also great teachers are great leaders and vice-versa. Therefore the connection between quality teaching and quality learning is inextricable.

Some have said that managers do things right while leaders do the right thing. In other words, bosses who follow the rules to the exclusion of all else, like teachers who strictly adhere to the assigned curriculum, are conformists. It is impossible to blindly conform and be a leader.

Same thing for contrarian bosses for the same reason. Conformists and contrarians are just two sides of the same coin, reacting to the same inputs albeit in opposite ways. Neither knows how to serve as a leader.

Individualists may show some leadership potential, but it is forever stunted by their self-serving tendencies. The arbitrary self-indulgence of the individualist is ultimately damaging. True leaders look to and serve their people first in order to achieve real and lasting success just as G. looks to his students.

Great leaders will follow the rules if the rules are sound and advantageous. Great leaders, though, also readily bend the rules to benefit the greater good. Great leaders even intrepidly break the rules when they run counter to what is right. This was Gould’s charge to my graduating class.

None of this is arbitrary since the actions of a great leader are always in service to set values, the mission, and the success of all. Every great leader thinks and behaves like an iconoclast.


Would you be best described as a conformist, a contrarian, an individualist, or an iconoclast? How can you behave more like an iconoclast?

Learning to behave like an iconoclast will bring you the most success as a leader, and I can help. Click below for your free consultation and gift.

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If you want to learn more about how to become a great leader in this world of bad bosses, visit GuidanceForGreatness.com.

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On Leading With Greatness
On Leading With Greatness
Each Thursday I share new ideas for leaders and aspiring leaders on mission clarity, self-awareness, and human skills — a slightly irreverent kit of Tools+Paradigms for leaders and aspiring leaders like you. Visit GuidanceForGreatness.com