The Striking Similarities between Teachers and Start-up CEOs (Aaron Schildkrout)

Aaron Schildkrout is a former Codman Academy charter school teacher in Boston and technology entrepreneur in creating a dating website, HowAboutMe. He is currently Entrepreneur in Residence at RRE Ventures in New York City. This post appeared February 9, 2015.

In this post he compares being a teacher to being the CEO of a start-up company, two positions that he has held. Explicitly, Schildkrout says that both roles, one public and the other private, are “strikingly” similar. Implicitly, however, in bridging both the private and the public sectors, he asks readers to take away a deeper lesson.  The dissimilar purposes of running a for-profit business and the purposes of teaching youth in a tax-supported public school are, he says, of little consequence. What really matters, according to him, is not toward what ends but how the job gets done.

When, six years ago, I made the switch from high school teacher to start-up founder I thought I was in for a rather dramatic change.

On the surface, the two vocations could not be more divergent: non-profit v. for-profit; public institution v. free market; chalkboard & textbook v. google analytics & expansion playbook; curriculum building v. consumer product design; and so on.

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

Here are some of the striking similarities between running a classroom and running an early stage company…

 Create an Unforgettable Experience

Guide them 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; focus on the essential thing. Make the process itself delightful. Engage curiosity. 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 self-sufficient 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 and express gratitude for their participation. 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 start-up CEO.

These are also instructions in curriculum design—the essential skill of the modern teacher.

 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 amidst 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, key to both is getting 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 their group on about ten individual metrics (e.g. using examples in discussion, reading for details, etc.). They had engaged in a thematic, in-depth dialogue of a difficult novel. They had practiced specific skills (e.g. noticing metaphors) They had 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.

It’s no different as a start-up 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 a culture of intense productivity and efficiency. If you achieve these four things, you will have nothing to do. (Obviously this isn’t true, but you get the idea…) Hire amazing human beings, give them the resources they need, make the goal clear and 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.

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 start-up founder. By my last year of teaching, I was often giving students dozens of quantitative grades during every class. I would put a spreadsheet transparency on an overhead (yes, back then) and would add micro-grades to it throughout the class. I would then add the grades to our school’s online grading system; 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 might have gone a bit overboard.)

It’s the same for the CEO. You want every person in your company to qualitatively understand their goals and their progress towards 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%, 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.

 Cherish Innovation (and Failure)

The teacher and start-up CEO are each solely responsible for the success of the processes they are overseeing. This means that failure holds a special place in both of their hearts — its dark side and its importance.

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 very long year. As a CEO, a mistake means company hell — also to be aggressively avoided. Both the teacher and the CEO understand well the adage: never f&#$ the same thing up twice.

The other side of this dangerous coin is that failure is the necessary fuel of success. This is particularly true for teaching and early stage company-building because in both settings it’s so unclear what’s going to work. You have to fail in order to get anywhere. Failure is the bedrock of learning.

This is obvious for the start-up CEO. A huge percentage of new companies fail; that is, you must risk failure in order to succeed. Indeed, a striking number of successful companies 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 in order to make something truly new.

This is less obvious for teaching, which people think of as a by-the-book vocation—as though a single winning curricular formulation might solve the multitude of micro challenges that pave the path to substantive learning in each unique child. Consider this: how many really good teachers did you have in the first 18 years of your life? Certainly fewer than five. Maybe just one. Maybe zero. Sounds a good bit like the ratio of successful companies to failed ones. The book on great teaching is not written. State standards are, at best, a series of guiding cairns. As a teacher, you are inventing it as you go. A hundred times a week. And so, like an inventor, you learn via failure.

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

 Start Inside

Finally, both the CEO and teacher create value by helping people understand and realize their unique potential. That is, the process of value creation starts inside.

As a teacher, over time I came to see that my fundamental task wasn’t to teach American History— but to teach young people about who they were, how their minds worked, how they could realize and unlock their huge potential. American History was the excuse, the context — and it was critical; without a rigorous learning experience, 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; the teacher will become, more and more, the teacher of the child as human rather than as repository of information and skills.

Likewise, part of your job as CEO — an important part , particularly in the early stages— is to build a work culture that inspires your team to be great. Obviously, right? Your employees are spending the majority of this part of their life working in your company, and we each only have so long on this planet. So, everyone’s experience of work — including your own! — 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.

It’s no mistake that Jack Ma, the CEO of the company with the most successful IPO ever, was first a teacher.

At root, the early-stage CEO and teacher share an unquenchable drive to create deep value for humans. They have a unique, inspired vision that they need to share—be it with children or consumers.

Collectively, we are doing a tremendous job honoring and supporting our early-stage CEOs. Indeed, as an increasingly start-up and entrepreneur-obsessed culture, we’re coming to recognize CEOs as conductor’s of our culture’s creative progress.

But we still have a disturbingly long way to go until our teachers feel that society is rooting for them. Teachers—the people who are taking care of our most important asset, the people who come to work each day with a task equal in so many ways to our CEOs—do not feel that we are behind them.

While we pay lip service to the importance of education and the nobility of teachers, we don’t come close to offering them the concrete manifestations of honor that we afford our CEOs.

Luckily, being a teacher — like being a start-up CEO—is profoundly fulfilling independent of compensation and status. Luckily, because the job is lonely and humbling. It puts a mirror in front of you that you can’t avoid. It requires that you understand your unique vision and that you fight tooth and nail to pass this vision on to the world, day in and day out.

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 each of our teachers becomes better and better, that our great teachers stay teachers, and that our great students at least consider becoming great teachers.

 

8 Comments

Filed under how teachers teach, technology use

8 responses to “The Striking Similarities between Teachers and Start-up CEOs (Aaron Schildkrout)

  1. Reblogged this on Reflections of a Second-career Math Teacher and commented:

    I could not agree more with Aaron’s comparisons of a start-up environment (whether in the role of a CEO, VP, middle management, engineer, or accountant) and that of a “new” teacher.

    My point of view parallels Aaron’s, yet is directionally opposite, much like a vector. I worked for 25+ years in high-tech, often at start-ups or start-up environments. Innovate or die was my mantra for those many years. I take the same passion to my classroom where I received a key to my classroom and a “good luck” from the administration. While I crave some outside support, mostly in terms of parental support, I know I am on an incredibly important mission that few understand, much less appreciate. To do so, one must have taught as if they were on fire, which is how I describe how one must feel if you really want to teach; otherwise, look elsewhere, as you will not survive, or our students will not receive the education they deserve.

    • larrycuban

      Thanks, Dave, for re-blogging post on similarities between teaching and CEO-ing of a start-up. Also I appreciated your comments where you agreed and disagreed with Aaron Schildkrout.

  2. Ann Staley

    This is an amazing essay: Let’s compare T & CEO! I did always feel I should have been paid more though I loved every minute in the classroom. I found that I could smile after the first set of report cards were out, and after I’d finished writing a postcard to every parent about some of what their son or daughter was doing right/excellently in my classroom. One parent phoned me and said she had NEVER in twelve years of having her son in school received “a positive report!” And I knew why. Her son was a ticking, time bomb who learned how to diagram sentences and understand Shakespeare (read, listen, watch) in my class. He received a well-deserved B all year long.

    • larrycuban

      It is curious, Ann, that Aaron Schildkrout did not mention the differential in salaries. Thanks for commenting.

  3. Another comparison I like, which I made to a frustrated first-year teacher at the end of the day today, is between teachers and professional athletes: Even when you’re on top of your game, you can be sure that failure of some kind is around the corner, and it will surely be public. (I’m thinking right now of Madison Bumgarner, who in his first spring training appearance with the Giants last week gave up 4 runs in less than 2 innings, a few months after winning the World Series with such a remarkable performance.) Teaching really is one of the hardest jobs there is.

    Thanks so much, Larry, for posting this. I also really appreciated your last piece about education and the economy. You are such a powerful voice for those of us in schools; I need to read your blog more often!!

    • larrycuban

      Nice analogy, Matt. Always good to hear from you. The work you and your colleagues do inspires many of us.

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