An interview with Eden Gold
We deserve grace too. No one is a perfect educator.
Teaching won’t always be easy, but it will always be worth it.
You will learn as much from your students as they learn from you.
Don’t compare yourself to others. Do what feels right for you.
Although you may feel like you don’t always have the time, find that time to develop relationships. It is for me one of the most important elements of becoming an effective educator.
The landscape of education is undergoing a profound transformation, propelled by technological advancements, pedagogical innovations, and a deepened understanding of learning diversities. Traditional classrooms are evolving, and new modes of teaching and learning are emerging to better prepare students for the complexities of the modern world. This series will take a look at the groundbreaking work being done across the globe to redefine education. As a part of this interview series, we had the pleasure to interview George Aiello, Cheshire Academy.
George Aiello is the academic technology coordinator and librarian at Cheshire Academy, the oldest boarding school in Connecticut. He holds an MBA from FAU, an MLIS from VSU and is currently working towards his doctorate in Educational Leadership. He’s at the forefront of integrating emerging technologies into education, specializing in guiding faculty and students through the ethical and effective use of artificial intelligence, blending innovation with information literacy. George leads initiatives that personalize learning, enhance research skills, and foster digital literacy, with a focus on transparency, bias awareness, and human-centered practices. He has seen firsthand how independent schools can adopt innovations more quickly than larger systems, making them ideal testing grounds for responsible AI integration.
Thank you so much for doing this with us! Our readers would love to “get to know you” a bit better. Can you share the “backstory” behind what brought you to this particular career path?
My interest and educational background in academic technologies began during my high school years. In 10th grade, I chose to transfer from my public high school to a vocational high school and major in Computer Information Systems. That, along with going to a tech-based university, formed the foundation of where I am now. I started out in an HR department focused on training employees on the use of different technologies but then my career path veered before returning to education 12 years later. I became a librarian in part because I could see how a technology background would complement and inform my practice.
Can you share the most interesting story that happened to you since you started your career? Can you tell us what lesson you learned from that?
I worked abroad for much of my time in education — first in Singapore, then in Paraguay and last in Hong Kong — before returning to the United States. In that sense, I have a lot of interesting stories from those times. I think the most interesting times might have been during COVID. Being in Hong Kong and having to figure out, really before anyone else in the world, how to transition from an in-person school to online learning was very interesting and of course challenging. I learned a lot from that experience on the importance of flexibility in the teaching and learning process and how important it is to take opportunities to both upskill ourselves and maybe even more importantly, the educators we support.
Can you briefly share with our readers why you are an authority in the education field?
I would humbly begin by saying what I always say when it comes to technology and apply it to education. Our time as experts in technology and especially in fast-moving technologies like AI is fleeting. As fast as we become an authority, we become a learner again. For me, this is the same in terms of modern pedagogy. In that sense, I have never stopped being a student. I have an MBA and an MLIS and I am currently working through my doctorate in Educational Leadership. When it comes to my job now, I work hard to stay on top of emerging technologies and library pedagogy and constantly reevaluate how they present in the classroom.
Can you identify some areas of the US education system that are going really great?
One big area I would identify as trending positivity in the US education system is the increase in STEM based education. School districts across the country have recognized the need for greater focus on STEM-based curriculum along with a gender gap for interest in STEM coursework. While much work remains to be done to match the increase in need for STEM professionals, I believe the response in K-12 has been very positive. In fact, our school has significantly enhanced our curriculum with the addition of many new STEM-based course options that will help to better prepare our students for STEM college programs and careers. This curriculum update includes new classes such as STEM & Research Methodology, Ecology, Modeling, and Green Chemistry, among many others.
Can you identify the key areas of the US education system that should be prioritized for improvement? Can you explain why those are so critical?
Equity in access to quality education is what I am leaning towards as my dissertation topic. The structure of the current US system for funding of K-12 education is not ideal leading to high variations in terms of access to resources including technology, academic support and in the quality of curriculum and instruction. For the US to continue as a global leader in innovation across industries, we need to find ways to better prepare a robust workforce. This is crucial and it begins by providing a stronger foundation for more students, actually all students. The only way we remain competitive is to prioritize equity in our education system. I work in an independent, private school that recognizes this and devotes themselves to enrolling a student body that is diverse in many ways to include socio-economically.
Please tell us all about the innovative educational approaches that you are using. What is the specific problem that you aim to solve, and how have you addressed it?
This is a really good time to talk about the innovative approach we are taking with artificial intelligence at our school. Like everyone else, we started our journey really trying to understand its implications, impacts and opportunities. We addressed it almost immediately with faculty as a way to ease concerns. We formed a strategic team to help us inform policy. Our traffic light policy allows faculty to code assignments as red light (no AI), yellow light (only use AI as indicated) or green light (use it openly). Further research and continued development in AI led us to believe we needed to shift our approach on AI to one that better embraced the reality for our students in college and beyond. As a result, Cheshire Academy is partnering with CONSYLIUM, an AI-in-education consulting group. They will be working with our school to help develop more impactful AI strategies and provide further professional development in AI for our faculty. We believe this is a unique opportunity for the school to move into a leadership space for artificial intelligence in education.
In what ways do you think your approach might shape the future of education? What evidence supports this?
AI is not a fad that will fade over time. In fact, this couldn’t be further from the truth. Students need to understand how to use AI effectively and ethically as it is quickly transforming workplaces, learning environments at all levels, and even society as a whole. Our better trained teachers can help students to understand how AI works and its best applications, but also highlight its potential for bias or error. Through this process, students can actually become better critical thinkers, problem solvers, develop better information literacy skills and become more responsible users of technology. All of these, foundations for almost any future career.
How do you measure the impact of your innovative educational practices on students’ learning and well-being?
In my specific role, this impact on students is generally measured informally through both follow-up and reflection. In developing our innovative approach to AI, we will certainly set some goals and parameters that best measure student outcomes. We will need to capture both quantitative and qualitative data that measures the effect of our new policies and strategies on teaching and learning. This data will be crucial to refining our plan and strengthening its impact.
What challenges have you faced in implementing your educational innovations, and how have you overcome them?
Teacher practice at all schools includes some balance of more traditional approaches alongside the more modern pedagogical approaches. Over my time working to integrate technology into school classrooms, I have seen plenty of the more traditional teachers learn to integrate technology into their lessons effectively and purposefully. I have also observed some of the most technology-savvy educators integrate technology with no real regard for purpose.The point is that maybe the biggest challenge is in the skillful evaluation of purpose and this is the same with how we need to use AI. As we continue our AI journey and look at forming and implementing impactful best practices for teachers and students, there also will be challenges that range from willful refusal and moderate resistance to extreme overreliance. We will need to bring everyone together to move forward.
Keeping in mind the “Law of Unintended Consequences” can you see any potential drawbacks of this innovation that people should think more deeply about?
There are some strong arguments being made about reducing our use of AI given its environmental and financial impacts. There are probably hundreds of potential unintended consequences that have already materialized to an extent, ranging from minor to quite serious. I decided this was a good question to see what an actual AI’s take was on the possible consequences of embracing…itself. Perplexity lists in no particular order of likelihood that possible risks include increased bias, reduced human interaction, threats to student privacy, and deepening educational inequities. That seems pretty honest of them. There are plenty of pending lawsuits currently out there on a variety of liability issues. I don’t see any out of the ordinary potential drawbacks on how we will work with teachers and students to understand and utilize AI based on best practices. I do believe the consequences or drawbacks of not doing so seem much greater. I also believe that we absolutely need to think deeply about potential drawbacks, be transparent about them and include ways to counteract them as much as possible in our innovation plans.

What are your “5 Things I Wish I Knew When I First Started”?
- We deserve grace too. No one is a perfect educator.
- Teaching won’t always be easy, but it will always be worth it.
- You will learn as much from your students as they learn from you.
- Don’t compare yourself to others. Do what feels right for you.
- Although you may feel like you don’t always have the time, find that time to develop relationships. It is for me one of the most important elements of becoming an effective educator.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“Anyone who has never made a mistake has never tried anything new” by Albert Einstein has always resonated with me. I have always believed in the importance of a growth mindset. In practice, I end all professional development sessions I conduct by telling educators to be brave in the classroom, to not be afraid to try something new and to be vulnerable in front of students in doing so. Students notice that and when they see you struggle a little without being afraid to make a mistake, it is a strong model for them and it resonates. I always try to follow my own advice regardless of how uncomfortable it might be.
Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them 🙂
That’s a difficult question. There are a lot of inspiring leaders in the world, a lot of authors I love to read, and a lot of musicians I love to listen to. If I have to pick one person though, it would be Malala Yousafzai. I can’t think of a braver person so passionate about education and willing to stand up for others. I would love to hear her story first hand. She has inspired so many!
How can our readers further follow your work online?
LinkedIn: https://www.linkedin.com/in/georgejaiello/
Website: Cheshireacademy.org
Thank you so much for these insights! This was so inspiring!
George Aiello Of Cheshire Academy On Innovative Approaches That Are Transforming Education was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.

