In 2008, I joined the board of Alternatives in Action, an organization founded by students to create their own high school. As I became more involved, I sketched an idea for a lesson planning tool to help teachers collaborate. Projects and opportunities kept me from being able to dedicate any real time. Last year I shut down one of my three ventures, stopped taking contract work and focused on the idea.

I met with the co-principals of the school with a proposal and they agreed to the project. I was paired with the 10th grade humanities teacher. For the spring semester, I would sit in the classroom at least once a week, observe her teaching, and meet with students for feedback. The experience would have its successes, missteps and frustrations and was more personally rewarding than I ever expected.

The tool would include curriculum management and assessment features. Students would view resources, read materials and answer questions during class. After discussing options between Chromebooks and Android tablets, we decided on Nexus 7s. I was able to purchase the devices with contributions from two generous supporters of the organization.

The tablets were delivered the morning of January 16. An hour later I was in the classroom for an introduction and training. Two students were online before I finished my presentation and volunteered to go around the room to help others. They would become active participants throughout the semester and are still providing feedback and guidance today.

The support and enthusiasm from our teacher was critical. She spent much of her limited free time transferring content. Her current methods had been successful over the years and she had no reason to change. This project was a risk for her, and more importantly, her students. In addition to teaching high school, she was finishing her PHd, teaching university classes in the evening and was mom to a two year old. She kept me humble.

In the second week, she unexpectedly had to leave for a funeral on the east coast. She created assignments on Seed Lesson for the students to complete. She asked if I would attend the class to provide the assigned substitute teacher with support. Although she had prepared a full schedule, she gave me the option to create my own lesson. I have never taught a classroom, but it would be an opportunity to immerse myself and better understand what it’s like to be a teacher.

To prepare, I asked the advice of my friend and neighbor Julia, a 30 year high school educator. She suggested I change the pace of the classroom in 10-15 minute intervals. It would keep the students off balance and always reacting. Most importantly she added, let them see how much you care.

I decided to create a class on entrepreneurship, beginning with a reading assignment about an African American business woman, Madam C.J. Walker. After reading the articles, and sharing my own experiences, I prompted the students to complete an online assessment. They answered questions about what motivated Madam Walker to start a hair care line in the early 1900s. I reviewed and discussed their answers as they submitted them on Seed Lesson. I then divided them into groups and had them talk about their own business ideas.

The students responded with beauty salons, piercing parlors, and record companies. One group had an idea for a network of recording studios. Together, we outlined a program for donating free time to youth. Student artists would sign up to a notification list. If a studio had any last minute unsold studio time they would notify the members. I then created teams and had the students choose between marketing, talent, operations and business development.

I had a brief insight into how challenging it is to teach. When the hour was over I was exhausted but felt I had been a productive substitute. Viewing every student response was incredibly helpful and guided the class. This wouldn’t have been possible without technology, but it was secondary to the experience.

In the weeks to come I would connect with students, find my co-founder, deal with the frustrations of beta software, see the problems of standardized testing, and better understand the limits and potential of technology.

What would I have done differently?

I was too optimistic about students being able to focus and not browse other sites. Also, if a student was done with their work, why not go to Facebook? However, when academic technology critics need to lock their wi-fi routers in a time locked safe, this was naive.

Tablets are great for portability, but not writing assignments. We improved this somewhat by providing $20 bluetooth keyboards. We also brought in a Chromebook for students to review. They overwhelmingly preferred the tablets.

The tablets would prove to be more of a maintenance burden than expected. 20% completely failed, one was lost, five were broken. A separate support plan was critical. I would have tried a variety of devices, probably from Samsung and HP which felt more solid.

A few weeks into the semester I recruited students to provide tech support. For next semester we’ll create a program at the very beginning to handle hardware and peer support and teach them additional skills.

What would I not change?

Seeing students as peers, sharing my own story, and embracing theirs.