The Striking Similarities Between Teachers & Startup CEOs

Six years ago, when I made the switch from high school teacher to startup founder/CEO, I thought I was in for a rather dramatic change.

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

And yet, I’ve come to see that teaching is a lot more like being a startup 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

Both the CEO and the teacher are responsible for curating a memorable experience, either for employees or students. 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 content. 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 startup 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 a 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 getting out of the way.

I once mentored a talented 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 class, each student had been assessed by their group on several 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 startup CEO. They say the three jobs of the CEO are to define the vision, hire great people, and make sure there is cash in the bank. I’d add that CEOs should 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 startup 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 (remember those?) 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. (To be honest, 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 generally 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 startup 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 until 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&#$ up the same thing 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 startup CEO. A significant 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 some 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 coincidence that Jack Ma, the CEO of Alibaba — 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 theyneed 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 startup and entrepreneur-obsessed culture, we’re coming to recognize CEOs as conductors 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 startup CEO — is profoundly fulfilling independent of compensation and status. Luckily so, because the job can be 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.