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ITP - 145: Tech My School, TechPlan Genie, and Life After International Teaching

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In this episode, Greg talks with Robby Cobbs and Kyle Sumrow about the strange, useful, and occasionally Costco-driven paths that international teachers take after leaving the circuit. Robby and Kyle trace their journeys through Kazakhstan, Saudi Arabia, Cameroon, Switzerland, Vietnam, Puerto Rico, and the United States, explaining how classroom teaching led them into educational technology, tech leadership, nonprofit work, and school strategic planning. The conversation explores Tech My School, TechPlan Genie, Puerto Rico’s education challenges, edtech audits, leadership after international teaching, and why technology planning should always start with teaching and learning instead of shiny tools.

Guest:
Robby Cobbs, Kyle Sumrow
Host/s
Greg
Topics:
international teaching, life after international teaching, educational technology, Tech My School, TechPlan Genie, technology planning, school leadership, Puerto Rico education, edtech strategy, teacher career transitions
Countries Discussed
international teaching, life after international teaching, educational technology, Tech My School, TechPlan Genie, technology planning, school leadership, Puerto Rico education, edtech strategy, teacher career transitions

Season:

6

Episode:

145

Full Transcript

ITP - 145: Tech My School, TechPlan Genie, and Life After International Teaching
Greg:
Everybody, this is Greg from the International Teacher Podcast. Greg the single guy here. I don’t have JP, I don’t have Darian, and I’m all alone on this one. Kent is somewhere in Seattle too, right?
Anyway, I have two guests on. I’ve just briefly met them. This is Kyle and Robbie, and they’re coming at us from the States and Puerto Rico. Robbie, I think you’re in Puerto Rico right now. Welcome to the show first of all, and give us a little idea of how you fit into the international scene.
Robby:
Yeah. My name is Robbie. I’ve been an international educator since 2008. I got my start in Kazakhstan with QSI, then went through the Search Associates fairs and got different jobs in the Middle East, Africa, Asia, and places like that.
Long story short, I went from teacher to tech integrator to tech director. As a tech director, I was kind of in charge of COVID, distance learning, and those kinds of things at the height of it.
Right as COVID was ending, my contract was ending, and my wife said, “Hey, we’ve been at this for a long time. Let’s take a sabbatical year and move to an island. A beautiful island.”
So we were debating between Zanzibar, Thailand, Koh Samui, and Puerto Rico. We ended up choosing Puerto Rico because of the weather, the beach, and everything, but also because of Costco.
As an international teacher, you know how it is to be away from comfort foods, snacks, and other deals. So it was kind of like, where can we go where we still have some comfort, but at the same time it feels a bit exotic? Puerto Rico just seemed to fit the bill.
Greg:
I can tell you’ve been teaching for a long time if Costco is how you decided where to go for your one-year sabbatical.
Robby:
It was just the deciding factor. We wanted to fish, we wanted the island, it had all the check marks, but we said, “You know what? Costco. We need it.”
We’d been in Africa. It’s hard to find good stuff. Let’s just go back a little bit closer to home and keep it moving.
Kyle:
I’m glad you said it. I was wondering as he was telling you his story, “We’re on the air. Is he going to say it? Is he going to tell the truth?”
My second international stop was in Saudi. We were at the American International School of Jeddah. Robbie and I overlapped for a year there. Oh, how the tides have turned, because Robbie used to work for me, and now I work for Robbie.
We’ve had a decade-long bromance going on. We’ve always stayed in touch and get together whenever we can. You have those people you meet during your career who, for whatever reason, you really click with. Robbie and I have always had that synergy.
My wife is a teacher as well. She was a music teacher and switched to counseling now. We started in Cameroon for two years. Then we were in Saudi for four. Then we went to Switzerland and were at IS Bern for two years.
We probably would have stayed there for the rest of our lives, except my master’s degree, which I had started 14 years earlier and never finished, was not a distance learning program. I had maybe two classes left and couldn’t finish them from abroad. We were having so much fun living abroad that there was no part of our story where we wanted to go back.
But the school contacted me and said, “You have to come back if you want your degree. Your credits are expiring.” I didn’t even know that was a thing.
So if you’re listening, credits do expire, apparently.
We went back to Minnesota for a year, and I finished my first master’s. Then we moved to Vietnam and were at ISHCMC in Ho Chi Minh City.
Robbie and I have a similar career arc in a way. Both of us started in the classroom and kind of got into educational technology and then tech leadership circuitously.
My bachelor’s degree is in music. My teaching license is 5–12 life science. When my wife and I decided we wanted to go overseas, we both had music degrees and knew there was no way we were both getting music teaching jobs. So I went back and got my science credentials. I love biology and really wanted to teach biology, but all I ever taught overseas was computer science, coding, filmmaking — all tech-related — because I had a technical music degree.
I was an audio engineer before I became a teacher. These random routes and things that happen in our lives are hilarious when you look back on them. How did I end up here? I wouldn’t change it for the world. I love our story and the route we took. If you had shown me a map of where my life was going when I was 20 years old, I wouldn’t have believed it.
Greg:
I still don’t believe my map either. I fit right between you two.
I did homeroom teaching. I was a fifth grade teacher in Honduras, but I was the only one who would check out the one projector from the superintendent, and we’re talking about 2001. They started using an SMS, a student management system. They started using Rediker, and I was helping the tech guy put that together.
Another teacher and I were very computer savvy compared to a lot of people. We started putting together student lists for the management system because they didn’t know how to do it. Next thing you know, we were teaching, but also in charge of tech. Then there was this elusive tech director guy who was local, and from there it just mushroomed.
As a single teacher, I found that as a tech person, I had more on my resume than as a teacher. Who’s going to hire a single elementary teacher? I couldn’t go to a job fair and get anything. But I did sell myself more as the tech-savvy guy who did all this other stuff.
I didn’t have a degree in computer science. I was just very good at educational technology.
Kyle:
I think curiosity is the secret sauce, Greg. It sounds like you have that gene too.
For me, I always had my fingers in different pies and I get bored easily. I do love being a classroom teacher, and I actually miss it because I’ve been a tech director for the last seven years and haven’t been in the classroom. I’m in the classroom with teachers, but I don’t have my own classroom.
I miss that connection with kids. It has been really important for me to make sure I have ways to stay connected with kids. That’s what we are as schools. We are there to serve kids. When you lose connection with kids in leadership, I think that’s dangerous. That’s a hard place to be.
Greg:
How about you, Robbie? You’re doing director of tech, right? Do you miss the classroom?
Robby:
Yeah. For me, I fell in love with tech because of my core values. I love learning and I love helping people. There are a lot of professions I could have fallen into, but I knew my freshman year of college that I wanted education.
I got an elementary education degree and started teaching elementary school. I actually started in kindergarten. But what I learned pretty quickly was that in education, technology and ed tech were always moving, changing, and evolving. I was naturally drawn to that.
As I learned new ed tech ideas or tools, I was always helping people with them, whether it was my team or the division. I knew that was my niche. I got a master’s in ed tech and knew this was my career path. I really wanted to be the tech guy.
I love technology because with it, you get to be kind of the rah-rah guy. I wasn’t big on being the combatant disciplinarian or the power-hungry guy. I wanted to go in there, jazz staff up, show them something cool, and have everyone say, “Wow, that’s amazing.” I wanted people to leave on a high note.
When they think of me, it’s always a positive, fun, interesting learning moment instead of an ego thing. Technology was just a perfect fit.
However, there is a dark side to tech. Once you get into leadership with technology, there’s a totem pole, but there’s also a totem pole within senior leadership. Technology directors often have great ideas, teaching modalities, tools, and all these different things they want to implement and showcase to teachers. They want to leave their mark and impact schools.
But we often get brushed aside. That’s the complaint among tech directors internally. We aren’t being respected, we aren’t being listened to, and we’re pushed aside. We’re there when the internet goes out, and when everything’s working, they say, “Okay, go back in your cave.”
That’s the bad side of being in tech, and that kind of led into the work I do now.
Greg:
I have a thousand questions, but that’s a great segue. I could chime in and say I tried being a tech director for four years, but I went back into the classroom.
So where did you go from there? You and Kyle are both doing things together.
Robby:
Kyle and I were buddy tech directors. When you’re a tech director, you’re kind of on an island. There aren’t other tech directors on campus you can talk to, so you need to keep a strong network of other tech directors in other schools to see what’s going on and balance that with tech bromances.
Greg:
Bromances. Yeah, tech bromances.
Kyle:
That’s right.
Greg:
He said it, not me.
Robby:
For me, COVID was heavy on everybody. Being a remote learning specialist in Africa and all those kinds of things, that was what I was brought in to do. We did the job. As soon as COVID hit, we were up and running. We were training before COVID happened. We were doing remote learning practice days because, coming from Saudi Arabia and being part of the NESA virtual learning school group, that was kind of our niche.
My wife was burned out. She said, “I’ve been teaching in 18 time zones for two years straight. I need a break. Let’s chill out.”
So we chose Puerto Rico. I had worked in inner-city schools in San Diego and Hawaii before going international, so I figured I would be fishing, relaxing, and chilling out for a year. Then I’d jump back into international teaching and continue on my path.
However, I was thrown a life curveball when my kids went into the local schools.
At first, we were looking at the schools and I thought, “Wow, these schools look very similar to Africa.” For those who don’t know, Puerto Rico is part of America. Everyone here is an American citizen. There’s Costco, USPS, National Park Service. Anyone living here can live in another state like Arizona or New York, fly there tomorrow, and get a job, and vice versa. Same passport, same everything, minus the fact that you can’t vote for president here, which might be a good thing.
I expected it to be an American education. Maybe not as good as the mainland, but still comparable. Spoiler alert: it’s not. It’s woefully not where it is in the States.
When you look at PISA scores and the data, you find that Puerto Rico scores about four to five grade levels below the lowest states on the mainland. Internationally, Puerto Ricans score worse than Mexico, worse than Chile, worse than every European country, everyone in the West. It’s the worst of the worst.
Being a global citizen, a parent here in Puerto Rico, and an American, I thought, “I’ve been telling kids for 20 years to be risk-takers, go out there, and make change in the world.” Now I’m looking at these schools with very little to no tech. There aren’t even public libraries here. Schools don’t have libraries. There are no public libraries. Very few have computers.
I thought, “These guys could use some help.”
So I went to my kid’s school and said, “Hey, school started two days ago. I know parents are wild, crazy people, and I’m a parent now, but I noticed you don’t have a library. Can we talk about that? Would you be interested in getting a library? I can possibly procure some computers for your teachers and classrooms. There’s also this thing called Epic with 40,000 or 50,000 books. We can start introducing books to your school.”
The director was new, and she said, “Yeah, go ahead.”
I said, “Great, what’s your email?” And they said, “Catlady69 at Gmail,” or something like that.
I said, “No, not your personal email. What’s your school email?”
They said, “We don’t have that either.”
As a tech director, you just start going through the checklist of what they have and don’t have. They didn’t have an LMS, an SIS, school email, any of it.
Greg:
Were you doing this in dad mode? Like, “I’m coming in, what can I help with? What do we have, what don’t we have?”
Robby:
I was a parent. But as an educator, I was seeing through the matrix. The campus looked bad, but maybe the teaching was good. Then I went in and saw the teaching wasn’t good either. The systems weren’t in place.
I said, “Hey, I know parents can be insane sometimes, but can I help you guys?”
She was cool. I came at her very modestly. My kids were at that school. I went from new parent to training all staff in the first month, if you can imagine that.
Very quickly, I went from training to setting up systems, getting them Google for Education, getting them Epic, and getting computers for all the teachers.
I had saved a little cache of money for a boat because I really wanted to fish. This was my sabbatical year after 15 years of teaching: fish and write a book. Instead, I ended up using all the boat money to buy software systems and computers.
Greg:
Really?
Robby:
In inner-city schools, kids often come from complex backgrounds where it’s tough to overcome your living situation. But the schools are in place. They have the building, the tech, and teachers getting paid real salaries with 401Ks. I was that poor kid. School was my sanctuary, and that’s why I knew I wanted to give back.
In Puerto Rico, it’s the opposite. You have great kids and great families, but the system they’re getting is broken. You have 17-year-old kids reading at a fourth grade level, great families, great kids, but they’ve never touched a computer before and barely speak English.
How are they going to compare to their contemporaries in Florida, Arizona, or New York? These kids are getting a raw deal.
America has this equalizer called public education. In the West, education is a rope that helps you pull yourself out, whether your parents were wealthy or poor or anything in between. Everyone gets at least this baseline education.
After traveling to all these countries, we know there are many places where it doesn’t matter how hard you work or how smart you are. If you’re not the right gender, religion, tribe, or background, your life is pretty much set unless you’re part of the elite percentage.
So I thought, “How can I enjoy myself fishing while knowing all these kids are not getting what they need?” I started helping one school, essentially becoming the tech director of that school, not resting.
Then teachers started talking to each other in their local churches. “Hey, there are these gringos giving us computers and doing all this stuff for us. You should reach out to them and see if they’ll help you.”
Very quickly, I went from one school to two schools to four schools. By the end of 12 months, I thought, “We’ve got to get back to international teaching. My money is exhausted. My book is finished. I can’t afford to just keep doing this.”
Greg:
Right. You need something to give. You’ve run dry. No boat.
Robby:
Correct. I formed the nonprofit. It’s called Tech My School. You can look us up on Instagram and our website. I had raised about $3,000, and it all came from one volunteer, a really sweet lady. She was also an international teacher. She had taught in Egypt and loved our mission. She would go with us to schools and help us.
We didn’t want to take the money. She said, “Please, just buy yourself groceries.”
Then my wife and I were walking on the beach in Puerto Rico and ran into some other expats. We introduced ourselves, and they asked, “Are you here for Act 60?”
We said, “No. What is Act 60?”
They said, “Act 60 is America’s best tax haven. If you’re an American who lived on the mainland and moved to Puerto Rico, you don’t pay taxes on fixed income. You don’t pay taxes on trading stocks. If you have a business, your business pays about 4% tax instead of around 40%. You just have to start a little company here and export your services.”
I thought, “Wow, that’s amazing. No, we’re not here for that.”
They said, “Yeah, because they donate to nonprofits.”
I said, “I have a nonprofit. Where are the donations for me?”
They said, “They have to donate $10,000 a year to these nonprofits.”
I started networking for about a month and a half trying to get donations. At the end of the year, we raised $273,000 from these Act 60 donors. It’s their way of paying taxes. Local people often don’t care that much where they donate; they’re busy running companies. They’re wealthy people and don’t always have time to research every nonprofit deeply. They meet you, like your story, and say, “Here’s the money.”
So we raised $270,000 and thought, “All right, let’s stay another year and see what happens.”
We went from four schools to 14 schools, the program grew, and we raised more money. We raised a million.
Around that time, I said to Kyle, “Hey, this whole thing is happening.” Kyle was watching from afar. I said, “Let’s start bringing international teaching things to these schools, like Week Without Walls. Let’s bring Week Without Walls, where students from wealthier schools in the States can see the disparity between where they are and what’s going on in Puerto Rico.”
At that time, Kyle had just finished his tenure after COVID in Vietnam and took a director job in Houston at Episcopal High School. I’ll pass it on to Kyle because I don’t want to monopolize the conversation.
Greg:
I was thinking Kyle was one of those guys walking on the beach saying, “Hey, are you here for Act 60?” But you know him from international schools. Go ahead, Kyle.
Kyle:
I had a great job at a great school. I loved it. We had a great team. It was not so different from an international school in its makeup. We had a similar clientele: people who were wealthier and could afford a great private school education for their kids.
My experience there was quite good, but it was fun tracking with Robbie too. I’m an entrepreneur and I’ve had a few companies, so when you’re an entrepreneur it’s hard not to watch what other people are doing. Robbie and I also had that personal connection. We would talk every few months. He’d tell me what he was doing, and we’d bounce ideas off each other for our businesses.
Early on, when Robbie first started this, he said one of the things he was struggling with was finding computers to donate so he didn’t have to spend all the donation money on hardware. Hardware is expensive.
I said, “During COVID, at Episcopal, we tried so hard to give our old computers away locally.” I called e-recyclers and so many companies, and they wouldn’t take them. So I said, “Robbie, we’ve got these computers. Why don’t you take them?”
He said, “Great, let’s do it.”
We boxed everything up, put it on a pallet, and Robbie had a connection with somebody who gets great deals on shipping. It’s not international shipping, so it’s less expensive than if it were going to the British Virgin Islands or somewhere close by but not the United States. There are no import fees or tariffs.
We had a pretty good system going. At the end of the year, we would take used machines and send them over. Then we’d get these amazing videos back: “Here are a bunch of kids where we built a computer lab.” These kids had literally never had a computer in their school. Their faces just lit up.
I thought, “Okay, this is good work. This tugs on the heartstrings in all the right ways.”
We kept donating computers. As I talked to Robbie, he was describing this assessment process he goes through with schools in Puerto Rico. I was intrigued because it sounded like all the best practices from all the things we had learned in high-performing schools, packaged into something he could take into a school.
He said, “Listen, I’ve not run this at a really high-achieving school yet. Let’s do it at your school. I’ll do it for free because you’ve given us so many computers.”
In my ego, I thought, “This is cute. He has this thing he does for underprivileged schools in Puerto Rico. What could he possibly do for a high-achieving school, a top few school in Texas? What could we learn from him?”
So he came in, we got our team together, and he ran us through the process. It had a familiar ring to it because a lot was based on the ISTE scope and sequences we were developing when we worked together, but he had increased it tenfold.
After going through it, we learned so much about ourselves. We had solved a lot of important problems because we were well resourced, but there were other things that had nothing to do with resources. They were mindset issues or things we had never thought about before.
I thought, “This is powerful.” He could come into a school like this, where we have the best people, best programs, amazing students, and amazing resources, and we still learned a ton about who we were and what our vision was. It helped clarify our vision for tech.
I’m a veteran ed tech practitioner. I’ve been a tech director, tech integrator, tech coach. I’ve done all these things, and I was still massively impressed and moved by what we learned about ourselves.
When we got done, I told Robbie, “I’ll quit tomorrow. What do you need from me? Let’s go change the world.”
It took probably another year for me to get on full time, but I had been volunteering and doing stuff with Tech My School for a long period of time. There was a natural transition. I definitely took a step back in salary to do it, but other things lined up in our lives. My wife finished grad school and we had a second salary. My kids were graduating and moving out of the house. Lifestyle things lined up.
Greg:
Quick question. You mentioned your wife finally got her degree. Was she on the 14-year plan like you too? I’m sorry, she’s not in the room, is she? I’m digging in on you, that’s all.
Kyle:
She’s going to listen to this, so I have to be careful about how I frame this.
No, she wasn’t. She’s amazing. She is an incredible musician, an amazing songwriter, and a really warm person. She was a very successful music teacher, choir teacher, choir director, and program leader. She had accolades.
She’s the one of the two of us who has students reaching out saying, “Hey, Miss Sumrow, remember me? You changed my life.” Those emails every teacher wants? I think I’ve gotten two of them. She’s gotten a hundred.
She was an amazing teacher, but she never felt at home because she wasn’t trained to be a music educator. She had some imposter syndrome. Now she has her MSW, a master’s in social work. She’s a hospital social work counselor and is eminently qualified and very good at what she’s doing. It has been really fun to see her doing something that is right up her alley and fulfilling for her.
Greg:
This fits really well because a lot of international teachers are talking about what comes after international teaching. It seems like you guys have both stepped out of that. I’m in an international school, I’ve seen four or five different countries, and I’ve led a number of years doing it. But this is exciting for people who are thinking, “What’s next? What’s my next move after international?”
Kyle:
You make a great point. My unsolicited advice to people listening and thinking “What’s next?” is that everybody has a story to tell.
As you develop the things you’re passionate about, figure out the aspects or components of your job and life that you love and the parts you don’t love. There are hard things about being overseas. Make a list of the pros and cons, then take the things you love and build a story of yourself and what you want.
In curriculum, we talk about backwards design: start with the end goal in mind. Think five or ten years into the future and ask, “If I could be doing anything, what would it be?”
A lot of people have that thought and stop there. “I can’t do it. It wouldn’t work. It’s too aspirational.”
The question I would ask is: why not? Why not, and why not you?
That’s exactly what Robbie did. He said, “Here are all the things I loved about my job. How can I make a career out of that?”
Robby:
At lunchtime in my office as a tech director in Jeddah, one of my fellow buddy teachers, Smitty, would come eat lunch with me. He was an English and photography teacher. We’d joke around and watch dumb videos just to laugh during the day, but sometimes we’d go deeper.
We talked about what your perfect day looks like. If money is not an issue and you can do anything you want in the world, what would your day look like? Not just climbing Mount Everest or something wild, but a normal day. What does your Monday through Friday look like? What does your Wednesday look like?
We were thoughtful and intentional about that perfect day. Through that process, we asked, “Where are you living?” It doesn’t have to be a city. It could be a temperature or climate. That drove me toward Puerto Rico. I love the beach, islands, and the tropical thing, but I like it being exotic.
Then we talked about what you would do during that day. My goal was to live my perfect day for a year. I saved up and wanted to do that. Then this project came to me during that time.
For anyone thinking about what’s next, follow your gut and instincts. Write out your perfect day and go from there. Or write out your perfect job. What are the things about your job you like? What are the things you don’t like? How do you push yourself toward the things you like and away from the things you don’t?
With Tech My School and the work we do, there are different elements I picked up as I moved from teacher to coach to administrator.
As a teacher, I loved working with kids when they were passionate about what we were doing, when it was hands-on, fun, and they wanted to be there. Every teacher loves that. The worst parts were dealing with difficult parents, bureaucracy, gossip, homework, and the monotony of doing the same thing.
As a coach, I loved working with teachers. I loved going into classrooms, seeing what was happening, making connections, transferring my knowledge, seeing aha moments, and watching teachers use little strategies I had acquired through reading and practice. But I didn’t like the lull between things. As an instructional coach, you might have an appointment with a teacher, then have a gap for a couple of days where you feel unused.
As a tech director, I loved the planning, training, strategizing, getting in front of people, and making an impact. I hated sitting in the office being told, “No, not today,” or, “Not this month,” or, “The internet’s fine.”
With Tech My School, this job takes the best components of all those things.
We go into a school and do a strategic planning process. We do an audit and look at three facets of the school. First, educational systems: everything you can touch, buy, make, or create. Second, building capacity in staff: what adult learning looks like in the building. Third, student empowerment: what kids are actually doing.
Through those three lenses, we help schools create a world-class tech plan. Then we help them fulfill that tech plan through training, coaching, and conferences.
I used to think it would be great to speak at conferences, and it is great. I thought, “I should reach out to ISTE or FETC and hope they pick me so I can talk about Tech My School.” Then I thought, “Why am I doing that? I need to make my own conference.”
So we created one to give teachers in Puerto Rico a platform so they can teach, and so we can keep impacting people and get people to come to us.
When we work with kids, we do free after-school coding. Anyone in the community can come. We use different robotics programs: KaiBots, Osmo, Dash, and things like that. Everyone is excited and enthusiastic, and they’re on good behavior because it’s free. If they’re not behaving, we can ask them to leave.
So it’s super positive. We’re getting all the best parts and very little of the worst parts of education.
Greg:
I’d like to go back and give you a compliment on what I just heard. As a techie myself, I want to point out that when you talked about going into a school, you gave three points: the structure, the students, and what the staff needs. I never heard you say the word “tech.”
My compliment is that, in my personal opinion, the way I run tech in any situation — teacher, director, consultant, whatever — is that it’s not about tech. It’s about what you need to do with the tech. Tech is a tool, even when you’re talking about systems.
I appreciate that when you go into these schools, you focus first on things that are not tech. What is your system like? What are your students like? What does your staff need?
Kyle:
We’re all teachers first. We got into tech by being teachers, seeing a need, and being interested. We were not IT people shoved into a school saying, “Let’s take best practices from other industries and force them into education.”
Education operates differently. The needs are different. The users are different. Any IT person who has been in schools for a long time will tell you schools are strange. They operate differently than every other business.
That’s the piece that gives us street cred. When we go into a school and talk to academic leaders, I have a master’s in teaching. I don’t have a master’s in technology. I was a tech director and my work experience has been in technology, but I come to you as a pedagogue, someone thinking about teaching and learning. Teacher first.
Greg:
I could speak both teacher and regular person. I could speak techie, and I’ve always sold myself that way on a resume. I’m somewhere between the tech nerd who is brilliant with all the tech stuff and the teacher. But I start as a teacher.
The two of you are going into a school system and saying, “Here’s what we’ve got. Let’s look at what you have first.” You’re coming from an educator point of view. That’s so different from a technology company coming in and saying, “Here’s what we have for you.” You’re asking, “What do you need?”
Kyle:
That’s right. When we go in and run this assessment, one of the pieces is making sure all the right people are in the room. The right voices need to be at the table. We call it the tech task force. We help the school build that from their people.
We say, “These are the kinds of roles we’re looking for to make this ideal.” They put the team together, and then we run a session where they do a self-study. We are facilitators. We do not come in and tell them what they should or shouldn’t be doing, because then that would be our tech plan.
What we’re trying to do is strategic planning that aligns with their vision and what they want. We ask hard questions. Sometimes they ask for our opinion if they are at a standstill or have varied opinions, but by and large, we are data collectors. We ask a juicy question and let them wrestle with it.
Then they self-assess. We have a framework, and they assess where they are. We don’t say, “You’re a four out of five.” They tell us.
Some schools will say, “No, we’re good. We’re a five out of five.” We say, “Tell me about this part. What evidence are you seeing that you’re leading in the field?” They work through it. We don’t tell them they’re not there. We help them explain why they are. And then sometimes they say, “Maybe we’re a three.”
Those conversations are the money of the whole thing.
Once we get done with that part — 90 minutes, maybe two hours max — it can be a game changer for an organization in terms of how they’re thinking.
Then we spend time with the IT person. We have an inventory for the nerds. We need to know what the system profile looks like. We need to sit with the DTL and talk about teaching and learning. We need to know what professional development looks like. In every school, it’s a different role that comes next.
Greg:
That comes after you’ve had the deeper conversation. We need the nerdy stuff too. We have to surround ourselves with the nerds. It’s part of the team and part of the process to know the exact systems. Not just, “Yeah, we use some student system,” or, “We use some email that our tech guy built because we don’t trust Google.”
There are definite things you have to ask, and you make a laundry list.
Kyle:
For sure. What that list does is help people see what they don’t know. It’s not always negligence; often it’s ignorance. People just don’t know what they don’t know.
That was my school. There were so many things we simply hadn’t thought of. It wasn’t that we didn’t have the capacity to complete the action items. We didn’t know what they were until somebody helped us see them.
Greg:
Have you both run into that part where the school just does something because it’s legacy? They’ve always done it that way, so they keep doing it that way. You step back and ask why, and they say, “Because that’s the way we do it.”
Kyle:
Breaking status quo is hard. That whole process we just described — what we do with schools when we help them go through it — Robbie should tell you about the piece of software he built that we’re using now, because this is an important piece.
Greg:
Let’s plug this real quick too. You two are both with Tech My School. That’s the nonprofit we’re talking about for listeners to reach out, investigate, and learn more after the show. That’s TechMySchool.org.
Robby:
We’re an educational nonprofit. We have the Act 60 money, but it’s finite. There are 2,000 nonprofits on the island, and it’s kind of a cash grab. Oversight is loose, so we need other income streams to keep serving these kids.
Being former international teachers doesn’t go away. Even if you’re thinking about your next step, you don’t forget where you came from. Thinking about Week Without Walls, relationships like Kyle, other educators, and other schools — you don’t have to give that up.
We attended NESA conferences and had booths because we tried to offer our services to international schools. The technology plan process is called the Individual Tech Plan, or ITP, like an IEP but for a tech plan.
Through that process, we complete plans and then help schools with whatever else they need on an individual basis. But it’s a labor-intensive process. You have to be there. It requires a certain mind with certain experiences to pull it off.
We were at FETC in January about a year ago.
Greg:
What is FETC, for the listeners?
Robby:
FETC is one of the biggest ed tech conferences in the United States. There’s ISTE, FETC, TCEA in Texas, and BETT, which is the largest ed tech conference in the world and happens in London. Tech My School will actually be there.
At the conference, we were talking to people: “Random teacher, come to our conference in Puerto Rico. It’s the educator conference in the Caribbean: beautiful beaches, five-star resort, right on the water. Come with your bathing suit and learn about ed tech.”
If we ran into speakers, we’d say, “You’re an amazing speaker. Come be a speaker at our conference.” If we ran into school directors, we’d say, “Let us come and do the ITP for you.”
Another big part of our company is working with ed tech companies. We’d say, “Hey, founder, we love this application. We want to push it into schools. Partner with us and let’s get discounts for schools so they can use your product, and we can get a little off the top to help keep us going as a nonprofit.”
If anyone listening wants cheaper software for their school, reach out to us first. We’ll fight for you and get you a lower price. That’s part of being a nonprofit.
Anyway, we were talking to a guy whose badge was flipped over, so we couldn’t see his name. We were explaining who we are and what we do. He said, “I really love your product. I really love your process. We need that for our schools.”
I said, “Sounds great. We’d love to do it.”
He said, “I run about a thousand schools in southern Florida. I’m with Google. Can you do it for a thousand schools this spring?”
I said, “No,” because our team was about five people. We can’t do a thousand schools tomorrow.
We had known we wanted to put the process into software, but it needed the brain component. The year before, I had ideated the process and tried to put it into software, but the development price was too high and the AI wasn’t good enough. It was producing too much junk. It just wasn’t ready.
This year, we went through the process again, got a more favorable development price, and AI had come a long way. Now we have a product called TechPlan Genie. It takes our process and puts it into software with teams.
You don’t necessarily need us. A school can run through the modules. It aggregates the data. The most powerful part isn’t the AI. The most powerful part is the process, the conversations, and the artifacts.
As you report the data, eventually you get to the end of the modules, click “generate tech report,” and it creates a beautiful editable PDF. It has all the metrics, your scope and sequence, your professional development schedule, and all these different pieces.
The AI is probably going to get 90 to 95% correct. It has data from surveys and stakeholders, DTL, finance, and other people. It gives you a comprehensive, legitimate tech plan that is probably better than most tech plans on the market because we looked at every tech plan we could find and took the best pieces.
Once the tech plan is there, that’s just the start. One of the things about strategic planning is the process of building it is great, but once it’s built, it often sits in a drive somewhere. A year later, someone says, “Yeah, we were supposed to do that.”
With TechPlan Genie, there’s a module where every month you record the things you’re doing for the tech plan. As the months go by, you get great data. At the end of the year, you click “generate end-of-year report,” and it gives you a beautiful editable PDF with all the things you did that year.
You have a wonderful artifact to share with board members. If you’re doing accreditation, it’s phenomenal for both the plan and the follow-through. If any tech director feels underappreciated or undervalued, and people ask, “What do you even do back there in that office?” — boom. You have a great document, an artifact, a yearbook of everything you’ve done.
There’s nothing else like it on the market. It’s a one-of-one product, and we’re really excited about it. We released it about a month ago.
Greg:
Good timing for the podcast. We can tell people about this.
Kyle:
If you have any tech directors listening, one of the things that happens to us is your boss hits you up in May, when you’re already super busy winding down for the year, and says, “What did you do this year? Give me a report.”
Then you’re scouring emails, your calendar, notes, and talking to people. This gives you a way to click “generate report” and in two minutes get a polished report that celebrates your wins for the year. You don’t have to remember every little thing you did because you’ve been putting them in all year. It’s process change.
Robby:
International schools have a lot of different profiles. For high-performing tier one schools, people might look at this and say, “We’re already great. We have all these awesome things.” But as a tech director, it’s still nice to have because it streamlines things. You’ll see things in there where maybe you already know 90%, but that 10% you didn’t know is something you can implement. It’s another tool in the toolbox.
Then there are other schools where you’re a principal or head of school and you don’t have a tech director. Maybe you have an IT guy who keeps the internet on, but that’s it. Meanwhile, you’re tasked with grappling with AI policy and thousands of applications being built every day. Teachers are asking, “Can we do this? Can we buy this?” You have a finite budget and you’re wondering what to buy.
You see what other schools are doing or what someone presented at a conference and think, “I guess we’ll buy that.”
TechPlan Genie gives you a vision based on your data, your mission, and what you’re doing in your school. It gives you confidence that you’re buying the right things, training the right way, and following a roadmap. There’s also a roadmap module. You can see that you’re hitting metrics and moving in the right direction.
If you’re a principal or head of school tasked with technology, you don’t feel overwhelmed or lost. There’s also a bot inside a walled garden. You can ask questions like, “You said in October we should do this training. I have this third grade teacher who needs something for science. What do I do?”
Based on your data and plan, it will tell you how to support that teacher at a granular level. Normally, you’d need to ask a tech director or tech coach, and they can be expensive or may not even be knowledgeable enough to make that recommendation.
It’s not a one-size-fits-all perfect tool, but there’s nothing else like it, and it’s really solid.
Kyle:
It’s a thought partner.
Greg:
Let’s hit that while the iron is hot. People listening will see it in the show notes, but how do they get in touch with you? Is it on your website? Another medium? How do they get a hold of this product and learn more about your organization?
Robby:
Tech My School is the nonprofit. We do lots of things: the conference, Week Without Walls in Puerto Rico, and all those kinds of things. You can email info@techmyschool.org or go to TechMySchool.org. You can also see us on Instagram.
For the software, TechPlan Genie, go to TechPlanGenie.com.
One of the pricing strategies we use is different from most companies. Most companies say, “Contact us if you’re interested,” then they look at your school profile and give you a price based on tuition and other factors, trying to squeeze as much money as possible.
For us, we have a fixed price: $1,000 per year for the software. We feel any school internationally or locally can afford $1,000 for software that walks them through this.
However, if you want us to be part of the process, hold your hand, act as a thought partner, or white glove it by coming to your school and running the whole thing, then contact us and we can do pricing based on region, tuition, and those kinds of things in the classic way.
But if you just want to try the software, there’s a seven-day free trial. You put in your credit card, but it doesn’t charge you. You get it for a week. You can play around with it, put in phantom data just to get to the end and see what it looks like. If you want it, meet with your team and go forward. If not, cancel, and it doesn’t charge you anything.
So there are two ways: TechMySchool.org for the nonprofit and TechPlanGenie.com for the software.
Greg:
I like that. I have to say it again. TechPlan Genie and Tech My School start with teaching. It grows from your history as tech directors at international schools across the world and your team’s experience. Then it’s tech.
I always tell people it has to start with education, then tech gets added on. Tech fine-tunes it.
Kyle looks like he has something to say.
Kyle:
There’s also a leadership piece here. We were talking about what happens after international teaching and what else you do with your career. You should be thinking about the things you want to put on your resume too.
Leadership is huge, and this is a really good way to show leadership. You don’t have to be a tech director to do this. It could be a teacher, someone in teaching and learning, someone tech-adjacent, an integrator, or whoever.
If you bring in a process like this, the software allows you to be a leader. You lead a group of people through a self-study.
The most valuable pieces of my resume are the things I’ve led. If you’re a tech director or someone with time-bound opportunities during the year, but also lulls where you’re doing less, leverage those lulls. Use that couple of weeks in the middle of the semester. Hit us up. Let us talk you through it.
We can help set you up for success as a leader. The people around you will say, “Wow, this person is a go-getter. They brought us this amazing process, and we learned so much about ourselves.”
They’re not thinking about Tech My School. They’re thinking about you and your leadership. That’s part of what we want to do: help build leaders and give them a voice in the process.
We’ve done this literally a hundred times in schools. We don’t need accolades for the process, but you might need a win. This process can give you that.
It’s also a gift that keeps on giving. Once your data is in the system, you have a living strategic plan. It’s not collecting dust on a shelf. It is process-based and regenerative. You can go back and regenerate your plan any time. It takes into consideration the things you’ve already completed because you’re telling it what you’ve done.
If something was on the original plan and you’ve completed it, it won’t show up again. It will put something else aspirational in your plan.
Robby:
You can also be a great leader at a great school, but one of the issues with great schools is that when you have talented people with drive, everyone wants to make their impact. Sometimes that creates internal competition and silos.
The DTL is doing their thing. The high school principal is doing their thing. The tech person is doing their thing. People are operating productively, but maybe not together. There can be resentment or negative dynamics.
This process gets everyone in the room and breaks down those silos. It allows people to talk about what they’re doing in their section or school.
We ask the DTL: “What’s important to you this year? What are your goals? What do you want to accomplish, and how can we support you through technology?”
Rather than saying, “You need to do my thing because it’s important to me,” you’re saying, “Let me learn what you’re doing and see how we can blend that into our tech plan so we can support you.”
The same goes for divisional heads and finance. What are the goals? What’s going on with finance? How can we help support those goals?
You get people in the room and allow them to take their hats off, working in the spirit of what’s best for the school. It creates a safe space, almost like a counseling session: “Let’s take a step back and talk about what’s going right and what’s going wrong. What does everyone care about, and how can we incorporate that?”
Because tech is so ubiquitous in schools — security, academics, behavior, transportation, lunch — it taps into everything. You want to make sure everyone is rowing the boat in the same direction. This software and process help with that.
Greg:
I’m going to have to stop us here. I could talk for another hour, but I need to respect your time and keep this within an hour.
I can’t wait for people to visit your website and see what’s out there. Even if they don’t have experience in tech, if they’re a leader, they could look into the TechPlan Genie tool. It just came out, but all of this is backed by experience and proof in the pudding from the Houston school Kyle was at. It transformed that school even though it was already a well-run, successful school.
Let me change the tone just a little bit for the ITP, the International Teacher Podcast. Not the ITP for technology. I have one question, and I’ll keep it to one question, not two.
Since you’re both super experienced overseas teachers, I’d like to know three things you normally take with you when you go to a new country. They can’t have a heartbeat. You can’t say your wife, your kids, or your dog. We’ve had a lot of those answers. Think about three things that make you feel at home when you move to a new country.
Robby:
For me, I always bring my Vitamix because I’m a big smoothie guy.
I also used to bring my football jersey from my local team. I’m from San Diego, so that would be the Chargers. They left, so I got rid of all of them. All I have left is my Ryan Leaf jersey as a testament to that organization.
The third thing I like to bring is Phil’s barbecue sauce. Phil’s Barbecue is San Diego’s best barbecue. I always grab a couple bottles of Phil’s. Even now, I’ve got Phil’s in my cabinet.
Greg:
A food involved there. Some kind of sauce that makes you feel at home. Great answers.
Kyle?
Kyle:
That’s hilarious. For people listening who haven’t lived overseas, this question is so easy for international people to answer. My list is way longer than three, but I’ll pick three.
First, let me say something about Robbie’s Vitamix. If you ask my kids, who are college-aged now, what they remember about Robbie Cobbs, they’ll say his smoothies with his Vitamix. My son would show up at his house in second grade and say, “Robbie, will you make me a smoothie?”
Robbie is still Uncle Smoothie to my kids. So I’m glad you brought your Vitamix all those years.
For me, the first thing is my deodorant. I’m an Old Spice guy. I can’t deal without it. I don’t care if I can’t get the same toothpaste or shampoo, but I’ll be doggone if I’m going to use some foreign deodorant instead of my Old Spice.
Greg:
You bring a whole year’s worth with you? Or two years’ worth?
Robby:
Correct. That was the first thing I brought from Amazon: Old Spice, a year’s supply.
Kyle:
A year’s supply of Old Spice, yeah. Back to Costco, because that’s where we get the giant packs of Old Spice.
The next thing, and arguably the most important, is Cholula. I grew up in Texas and traveled to Mexico a lot as a kid. I’m a huge fan of Tex-Mex. I love Mexican culture. It’s such a part of Houston culture.
Giant bottles of Cholula. We put it on everything, and you can’t get it everywhere else. I think maybe we found it once in Switzerland, but moving to Vietnam or Saudi Arabia? Not finding Cholula.
The third thing is interesting: over-the-counter sleeping pills because of travel. I don’t take these very often, but they’re essential for the first night after a long flight. If I can get a solid 10-hour sleep, it overrides my circadian rhythm and my body’s desire to wake up.
That one is important for me. Usually by day two I’m good to go. It doesn’t matter how many time zones I changed, because I forced my sleep rhythm back into place. They say naturally it takes about a day per time zone. When I went to Vietnam, I was 12 time zones from home. That does not work for me. I’m not spending two weeks adjusting.
It makes me sound like a drug addict, but it’s over-the-counter stuff.
Greg:
I love it. It could have been something else, so over-the-counter is fine.
I do have to apologize that you’re from Minnesota. I’m sorry about that.
Piggybacking on that, have you ever heard of Borotalco?
Kyle:
No, I don’t think so.
Greg:
Borotalco is a Swiss deodorant. It’s like having baby powder in a roll-on or spray. It has very little scent. I used to have my three things I needed overseas, and still do, but after I lived in Switzerland for three years, I brought Borotalco with me to Saudi. I brought a suitcase, then went back again and bought another suitcase because I couldn’t find it anywhere.
Kyle:
Greg, you know what that sounds like to me? That sounds like you justifying having to stop over in Switzerland every time you travel anywhere near it.
We do the same thing. We were in Bern for two years, and I swear it was like living in a postcard. It was unbelievable.
Greg:
That’s part of it. You’re right. You have to have a reason to go back and see your people.
Next time, go back and get Borotalco. It’s fantastic. I don’t know if you can get it at Costco because I haven’t been to Costco in about 10 years, but it will change your idea of Old Spice. I dare both of you to try it. You might have to order it online.
Kyle:
I like to position myself as an open-minded person, Greg, but I would sooner root for the Packers than switch away from Old Spice. Old Spice is part of my identity at this point.
Greg:
That’s why the challenge is even more important.
Well, listen, you guys, I want to give each of you an opportunity to say a few last words, either about what you’re doing now or advice for listeners. Robbie, why don’t you go first?
Robby:
Everything we’re doing is in the spirit of serving children and serving schools. We serve schools throughout Puerto Rico. We have schools in the US. We’ve served international schools, including Pinewood in Kenya.
We’re looking to grow, continue our service, expand, and continue to help America’s most underserved and underprivileged schools.
You can support in a number of ways. One way is to go on Instagram and follow us. The more followers, the more impact. You can go to our website and check out our services. If your school is looking for an ITP or discounted software, we’d love for you to be part of that.
Finally, check out TechPlan Genie. We didn’t really talk about it, but Relief Roster is another one of our softwares. Check those out. It would be a huge help to us, and hopefully a huge help to your school.
Support Tech My School. Support the mission. That’s the boss. I’m not the boss. Kyle’s not the boss. The mission is the boss. The mission is serving kids. We’re global citizens, wherever those kids may be.
Greg:
Thank you, Uncle Smoothie.
Kyle, final thoughts?
Kyle:
I would say the same thing I would always say to my students: stay curious.
I think curiosity is the secret sauce in every successful educational experience. George Couros has a great quote in The Innovator’s Mindset that has always stuck with me: if kids are less curious when they leave us than when they got there, then we’ve failed them.
The way you keep kids curious is to keep yourself curious. Whatever your passions are, do them and let kids see you doing them. If you love DJing, show them. If you write music, show them. Let them see you in the creative struggles in your life. It makes you more human and makes you better at your job because it deepens connections with kids.
So I would just say: stay curious.
Greg:
I have no words after that.
This is Greg with the International Teacher Podcast. I’ve had Robbie from Puerto Rico and Kyle from Houston, Texas. It has been a joy to talk to you both. We hope to have you back on the show at some point.
Teachers need to reach out, and techies also. Thank you for being on our show. This went really fast.
I’m going to hit record now, and that was the practice.
Robby:
Thanks so much for having us. I’d love to be back.
Greg:
That’s our other joke, right?
Kyle:
You’re horrible.

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