How Schools, Teachers, and Administrators Can Learn to Think Like a Startup

Before I launched my EdTech Startup last summer, I was a teacher and a school technology director. I helped teachers use technology in the classroom. I led some major tech changes at my school. Two that I’m particularly proud of are one-to-one programs: a laptop program in middle and high school and an iPad program in K-5.

In my time in schools, I learned about change, and about educational technology. Like all teachers, I am a life-long learner. This year, I’ve been learning about startups. And not just the boring stuff about taxes, earnings, and venture capital — I’ve been interested in the attitudes and personality traits that make startup co-founders successful.

What I’ve learned is that the traits you see in successful startups are the same ones that you find in schools with excellent technology-based learning programs. If you want your school to be more like Uber and less like General Motors, here are 12 lessons from startups to keep in mind.

Startups are curious.

Josh Linker says that people at startups are “inherently curious.” We know that our best students are the curious ones. The best teachers are also curious. When the first iPad came out in 2010, the teachers at my school immediately wanted to know how they could use it in education. We experimented, tested, piloted, and tried to learn more about it. If we hadn’t been curious at that point, we might not have pushed forward and created a 1:1 program.

Startups focus on what could be, not what is.

Forbes says good entrepreneurs “let their mind’s eye travel to a future state and explore fresh possibilities rather than. . . protecting the past.” We don’t always need to throw the past away — we can learn from it, and some of the traditions we have are still good and valid. But we should always be open to new possibilities and ideas, especially when it comes to using technology in the classroom.

Startups are disruptive by nature.

Change is disruptive. Disruption is risky. Change is risky.

Emily Heyward at Fast company says that startups “value disruption.” She would “love to see ‘risk’ make an appearance right between those old standbys of ‘honesty’ and ‘respect.’” Forbes says that entrepreneurs “Conquer fear, forge ahead in face of fear.”

Many schools are affiliated with the International Baccalaureate. At IB schools, we embrace risk-taking. The IB says that learners “approach uncertainty with forethought and determination; we work independently and cooperatively to explore new ideas and innovative strategies. We are resourceful and resilient in the face of challenges and change.”

But if you are asking a school to take too many risks, and they don’t always work out, you’re not going to be in charge for long. So although it’s great to take risks and be disruptive now and then, you can’t disrupt education every day. At a school, part of the trick of being a good technology leader is picking your battles and deciding when to forge ahead in face of risk.

Learn from failure.

You’ll eventually fail. And you can learn from failure. A few years ago, it seemed trendy to embrace failure. You’d read blog posts with titles like “Fail Fast and Fail Hard” which almost glorified the awesomeness of epic failure. I think that attitude has changed in the past couple of years. Sure, learn from your failure. Recognize that not everything will work. But I like to think of failure as a step on the process of iterative improvements. Change is an improvement cycle. We can prototype, test, learn, improve, and iterate without necessarily failing.

Move with speed.

Speed is one of the biggest differences between small, nimble startups and big, old-fashioned companies. And schools are notoriously slow to embrace change. How can we help schools move faster? At most schools, it’s not a blanket resistance to all change. It’s an opposition to two things. Schools resist it when multiple things change at once, and they oppose change that doesn’t make sense.

To make your school change effectively, plan your changes for synergy. You might have three or four projects in place at once, as long as only one really affects teachers on a day-to-day basis. And make sure to plan your changes in the right order. A network improvement that makes iPads work better on the WiFi has to happen before you expand the number of iPads in the classroom. It might be important to change the hardware and the report card system, and the attendance system, and the way that teachers print. But pace those out, do the most important ones first, and try not to hit teachers with too much change all at once.

I like this analogy for change, and it’s one that anyone who has taken high school math or physics will understand — it’s a vector addition problem. If you are moving forward slowly, while the rest of the world is moving forward quickly, in essence, you’re moving backwards.

When we rolled out our iPad program, we had tested it, the community had buy-in, and the stakeholders were all on board. The last piece was to decide how fast to move. At first we thought about using the old late-90’s laptop rollout model. We could have given out iPads to each child in Kindergarten, then moved them up over the summer to grade 1. By taking it a year at a time, we could have slowed down the process to take five or six years, during which the teachers would be in radically different classrooms. Professional development would have been awkward — supporting grades with and without iPads. The teachers and parents understood that in this case, we needed to move fast to get a tablet in the hands of every child in the school.

Embrace a playful attitude.

The element of playfulness is ubiquitous in Silicon Valley, from foosball and ping-pong tables to video games — startup founders have a love of play. Playing with a new idea allows you to explore it with curiosity and creativity, but mostly with a low fear of risk. We wanted teachers to explore new apps without fear, so we created what we called “sandbox accounts.” They were Apple IDs, pre-loaded with some gift cards, that teachers could use to try out new apps before using them with students. Teachers didn’t necessarily want their playful explorations cluttering up their personal iPads, their own App store accounts, or their student’s iPads. But when you are about to have the kids explore Tangrams, you want to make sure they’re using the most appropriate Tangram app for their age level. There are so many on the App store to choose from, and the reviews don’t always help a teacher decide if it will work with their students. Loading a sandbox account with a small amount of virtual petty cash allowed teachers to be playful and explore.

Get the team right.

Teachers don’t work in isolation. Hiring decisions are critical, and so is working together as a team. Anna Counselman learned this while working at Google, before launching her own startup. She interviewed 100 engineers before she made her hiring decision. If you are in charge of hiring teachers or tech staffers at your school, you need to spend the time to make the very best hire you can. Here’s a trick. When you are attending an educator’s conference, and you see a teacher give a great presentation, go up to them afterwards and tell them you want them to apply at your school when there’s an opening. It might be a few years before it works out, but in the meantime, that teacher knows that you care about hiring. And they will tell their friends that you have good hiring practices. It’s a great way to increase your school’s reputation and also get better teachers eventually — even if it’s years down the road.

Of course, you’re not always in charge of the hiring. And unlike a startup, a school can’t always just fire people who don’t work out. At a startup, you sometimes have to fire your best friend who started the company with you. That’s hard. But still, you have to get the team right. And part of that is upskilling your team, whether it’s the tech support staff or the grade level team. If you can’t create the best team, make your existing team the best it can be.

Communication is key.

At a startup, you get financed by a small group of venture capitalists who believe in your mission. They loan you their money and want to know what you’ve done with it. Outside of dry annual reports, big publicly-traded corporations tend not to share information with their shareholders. Startups have to communicate with their stakeholders. So do schools.

At a school, your stakeholders are parents, students, teachers, and possibly a governing board — communication is no less important here. Cindy Chin Smith works at Upstart — she’s also an ex-Googler at a new company.

Keep customers informed of changes. All the stakeholders need to know what’s going on, especially when you’re planning major change. Engage in frequent parent communication, through newsletters, social media, and especially face to face meetings. Anticipate the kinds of questions they’ll have, and get the answers ready. Teachers are much more open to change when they understand the purpose and are looped in on the communication. Parents may not always understand or agree with what’s going on. But you have to keep the lines of communication open — things get even uglier if you keep secrets.

Be transparent.

When Anna Counselman founded Upstart she says “there were no secret meetings in back rooms.” As you plan your technology projects at your school, try sharing all the meeting minutes on a Google doc that all teachers can read. Do frequent surveys asking for input and guidance from stakeholders. Being open and honest about your progress will pay off. Even if you aren’t trying to hide something, if teachers think you are having secret meetings, they’ll instinctively oppose your ideas. They’ll appreciate your honesty and openness, even if they never have time to read the public minutes.

Learn together with the customers.

Startups get frequent customer feedback early in the development of their products.

Information changes so fast that the teacher can no longer be the sole source of knowledge in the classroom. At a modern school, teachers learn together with their students. The IB says that at schools “teachers and students are collaborators in the learning process.” I’ve never seen this to be so true as it was in our early years using iPads with students. Back when I used to teache technology skill courses, I was the expert who showed students how to use the various buttons on complicated interfaces. Now the students are much more able to generalize about the function of different buttons on their own. They learn the similarities — the way that the share or crop buttons in different apps have similar appearance and similar functions. They play and test and learn by doing. When a new update results in a different interface, they play and explore and share what they find with their classmates. The best teachers act as guides who learn alongside the students.

Think 10x. Dream big. Go for your moonshot.

When we first started our laptop program with upper school students, the administration was very supportive of the project. They knew it would need extra professional development. As the Director of Educational Technology, they gave me the first part of the very first faculty meeting of the year. It was a critical moment to launch a project we had been working towards for years. I started the meeting by playing Google’s inspirational Moonshot Thinking video.

Moonshot Thinking. Dream big, think 10x, and go for your own personal moonshot.

There’s a quote from John F Kennedy in there about the moon landing.

“We choose a moonshot not because it is easy, but because it is hard.” To me, that’s inspiring. We know there are going to be challenges, but we accept those challenges. And why do we do it? Well, if you’re going to ask teachers to accept a difficult challenge, you can’t just say “because it’s hard.” You had better be able to tell them why.

Startup founders “start with why.”

Why are we using iPads in the classroom? Why do we think technology is important for our students’ future? Why is one-to-one better than a shared set of devices? Start your projects with “why” and the “how” will be a lot easier.

That’s my list of twelve. What did I miss? Does this resonate with what you’re doing at your school? Let me know in the comments.