Teaching Profession Opinion

How Teachers and CEOs Are Alike

By Aaron Schildkrout — March 13, 2015 7 min read
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When, six years ago, I made the switch from high school teacher to startup CEO, I thought I was in for a rather dramatic change.

On the surface, the two vocations could not be more divergent: nonprofit vs. for-profit; public institution vs. free market; chalkboard and textbook vs. Google Analytics and business-expansion playbook; curriculum-building vs. consumer-product design.

And yet, I’ve come to see that teaching is a lot more like being a CEO than our teacher-degrading, CEO-fetishizing society wishes to know.

Here are some of the striking similarities between how good teachers run their classrooms and good CEOs run their companies:

They create an unforgettable experience. Guide your students (or your consumers) into the experience. Clarify their purpose. Hint at the great value that lies ahead if they stick with the process. Assure them that they have everything they need to succeed. Don’t clog the experience with superfluities and distractions. Build them up through small victories and motivate them through moments of profound, perceived value. Release them from any scaffolding you’ve constructed so they experience their own competency. Understand and evaluate their success in order to further refine the experience. Individualize things. Promote collaboration. Reward them for contributing value to the ecosystem. Inspire them to share unabashedly with anyone who will listen. Find the very best among them and let them go wild. Make it real. Make it matter.

These are instructions in product design — a core competency of the modern CEO. These are also instructions in curriculum design—the essential skill of the modern teacher.

At root, both the CEO and the teacher have a unique, inspired vision that they need to share—be it with children or consumers.”

They get out of the way. Getting a group of tremendously smart, motivated, skillful, sleep-deprived adults to rapidly deploy, iterate on, and market multiple product lines amid fierce competition and an unpredictable and fickle market is approximately as hard as getting a group of disgruntled, previously poorly educated, sleep-deprived, profoundly curious young people with hearts of gold to learn something of genuine import.

Surprisingly, the key to both is to get out of the way.

I once mentored a gifted student-teacher who decided to apply for a full-time teaching role at our school. As part of her interview, she taught a “sample class” in a structure called literature circles, in which students talk in small groups about a book they’re reading. The kids came in. She said, “OK, literature circles, get to it.” And for the next hour she walked around the classroom with a clipboard, silently watching the students as they talked about Native Son. She was essentially unnoticeable.

What was noticeable was the students. By the end of the class, each student had been assessed by his or her group on maybe six individual metrics. They had engaged in a thematic, in-depth dialogue of a difficult novel. They had practiced specific skills. They’d collaborated in teams. And there was palpable excitement about the protagonist Bigger and his disturbed journey. It was a killer class, so to speak.

To the untrained eye, the teacher did almost nothing. But every teacher knows that behind each minute of classroom fluidity lies hundreds of hours of preparation: building processes, setting expectations, clarifying vision, and much more.

It’s no different as a CEO. They say the three jobs of the CEO are to make sure there is cash in the bank, to hire great people, and to define the vision. I’d add to that: to build highly effective processes. (I’ve written more about that here.) If you achieve these four things, you will have “nothing to do.” Hire amazing human beings, give them the resources they need to be amazing, make the goal super-clear and profoundly inspiring, get everyone on the same page about how all the parts work together to ensure maximum productivity—and then get out of the way.

They measure it, or it won’t happen. Data-driven companies are all the rage. Precisely the same principles apply to the classroom.

I became a data-driven teacher long before I was a data-driven CEO. By my last year of teaching, I was often giving students 10 or more quantitative grades during every class. I would put a spreadsheet transparency on an overhead and would add micro-grades to it throughout the class. I would then add the grades to our school’s online grading system. Consequently, the students got addicted to checking — and improving — their grades. I had essentially created a transparent, real-time metrics dashboard for my students — and for me. (Honestly, I probably went a bit overboard.)

It’s the same for the CEO. The goal is for every single person in the company to qualitatively understand their goals and their progress toward these goals. When you measure things and make the goals quantitatively clear and attainable, people rally around them and make things happen. When you don’t, everything floats in a dangerous land of vagueness. If the goal is to improve conversion rates, they will stay flat. If the goal is to move conversion rates to 15.4 percent, they will get there.

The teacher and the CEO both need to set clear, smart goals and ensure that data is transparently and accurately available about the degree to which these goals are being realized. Then magic happens — and everyone knows damn well it isn’t magic.

They win by Failing. Failure holds a special place in the hearts of both the teacher and the CEO— its dark side and its importance.

The book on great teaching is not written. You are inventing it as you go. And so, like an inventor, you learn through failure.”

As a teacher, a mistake means classroom hell. And classroom hell is a special kind of hell that you want to avoid at all costs. There’s a reason they say you should never smile till Christmas— and it isn’t because you’re holding out for presents. If you err in October, you’re going to have a very long year. As a CEO, a mistake means company hell — also to be aggressively avoided.

And yet, failure is also the necessary fuel of success. This is particularly true for teaching and company-building, because in both settings it’s so unclear what’s going to work. Failure is the bedrock of learning.

This is obvious for the CEO. A huge percentage of new companies fail, and a striking number of companies only find success after various earlier struggles. Innovation, by its very nature, is a flirtation with failure. You have to break the rules of prior success to make something truly new.

This is less obvious for teaching, which people think of as a rote, by-the-book vocation. But consider this: How many really good teachers did you have in the first 18 years of your life? Certainly fewer than five. Sounds a good bit like the ratio of successful companies to failed ones. The book on great teaching is not written. You are inventing it as you go. And so, like an inventor, you learn through failure.

For the CEO and the teacher, every failure is both wrenching and precious.

They start inside. Finally, both the CEO and the teacher create value by helping people know themselves and become their very best. That is, the process of value creation starts inside.

When I was a teacher, I came to see that my real task wasn’t actually to teach American history or Native Son ,  but to teach kids about who they were, how their minds worked, how they could realize and unlock their unique potential. American history was the excuse, the context — and it was critical. Without a rigorous learning process, the deeper learning would end up groundless. But without the deeper learning, the American-history learning would be superficial and ultimately deadening.

This will become increasingly the case as curriculum design becomes commoditized by the Internet. More and more, the teacher will become the teacher of the child as human, rather than as repository of information and skills.

Related to this is the awareness that part of your job as CEO— an important part — is to build a culture at your company that inspires the people working there to be great. Obvious, right? Your team is spending a majority of this part of their lives working in your company, and we only have so long on this planet. So, everyone’s experience of work  should be more than just productive. It should be personally transformational. Said otherwise, as a CEO your company culture should be as magical and value-creating as the products you make for consumers.

The striking similarities are really not so surprising. It’s no mistake that the CEO of the company with the most successful initial public offering (IPO) in all of history, Jack Ma of Alibaba Group, was first a teacher. At root, both the CEO and the teacher have a unique, inspired vision that they need to share—be it with children or consumers.

And yet while we are collectively coming to see CEOs as conductors of the culture’s creative progress, we have a disturbingly long way to go before our teachers feel that society is rooting for them. While we pay lip service to the importance of education and the nobility of teaching, we don’t come close to offering teachers the concrete manifestations of honor that we afford CEOs.

Luckily, being a teacher — like being a CEO—is profoundly fulfilling, independent of compensation and status. You know how much what you are doing matters, but stamina is hard-wrought. So, it’s a good thing that the task itself is so fundamentally rewarding.

Even so, every bit of support from the outside helps. Every cheer matters. Every dollar, the most concrete manifestation of our collective respect, makes it more likely that great teachers stay teachers, that great students become great teachers, and that all of our teachers become better and better.


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