Lynette Guastaferro Of Teaching Matters: How AI Is Disrupting Our Industry, and What We Can Do About It

An Interview With Cynthia Corsetti

We want to do a lot of quick trial and error. We are going to have a lot of bad ideas. But let’s learn quickly, let’s try and fail fast. Small organizations often think they can’t participate in testing AI, but I don’t think that’s true. If we create safe workspaces where our teams can experiment then we are going to make a lot of progress a lot faster.

Artificial Intelligence is no longer the future; it is the present. It’s reshaping landscapes, altering industries, and transforming the way we live and work. With its rapid advancement, AI is causing disruption — for better or worse — in every field imaginable. While it promises efficiency and growth, it also brings challenges and uncertainties that professionals and businesses must navigate. What can one do to pivot if AI is disrupting their industry? As part of this series, we had the pleasure of interviewing Lynette Guastaferro, CEO of Teaching Matters.

Lynette Guastaferro is a seasoned education leader with a distinguished track record spanning over 30 years. As the Chief Executive Officer of Teaching Matters, she brings a wealth of strategic and leadership experience working in education as part of a complex system of service delivery. From her early days as a consultant with Price Waterhouse Coopers, where she supported city governments in developing services for homeless families, to her role as a classroom teacher in Baltimore City, and later a School Network leader overseeing 28 urban schools, Ms. Guastaferro has gained invaluable insights into how systems can either hinder or empower teachers and students, particularly in marginalized communities.

For more than two decades, Lynette’s leadership has transformed Teaching Matters into an institution committed to dismantling unequal access to effective teaching. Guided by both research and practical insights from classrooms, Teaching Matters develops, tests, and scales teacher development models in urban schools that are tailored to the specific needs of educators and designed to have a measurable impact on students. During her tenure, Teaching Matters has grown exponentially, expanding to over 1,000 schools across four states, reaching tens of thousands of teachers and hundreds of thousands of students.

Lynette holds an M.B.A. from Columbia University and a B.A. from Williams College. Her leadership in education strategy continues to shape Teaching Matters’ mission, fostering an environment of collaboration, innovation, and educational advancement. This mission is firmly rooted in her profound belief that equity and access to excellent teaching are fundamental rights for every student.

Thank you so much for joining us in this interview series. Before we dive into our discussion our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

I always credit my father for the reason that I got into education. He was an immigrant to the United States and as a young child, I sat next to him as he got his GED and worked his way into becoming a part of American society. So from a very young age, I learned that education was the path to being a part of America. For me, education is about opportunity for everybody

Out of college, I began working at PriceWaterhouseCoopers as a management consultant supporting public sector organizations, including schools. When I’d meet with teachers, I realized they had a much clearer idea of the internal challenges happening at the schools that the consultants just couldn’t understand — but they were rarely involved in coming up with solutions. With a desire to understand the system from the inside, I became a teacher. I began teaching second graders in Baltimore City and experienced the gaps in the system — the lack of data and collaboration, the absence of mentoring, the feelings of isolation, the broken copy machines and the constant barriers to getting the job done.

That’s how I ended up at Teaching Matters, a national professional learning organization that is dedicated to increasing teacher effectiveness. I was a School Network leader overseeing 28 urban schools, which only made the problems more apparent to me. So I made it my mission to give every child an excellent education, regardless of their zip code.

What do you think makes your company stand out? Can you share a story?

What makes Teaching Matters stand out are its people and their commitment to mission and purpose. Every person at Teaching Matters is committed to ensuring that every kid gets equal access to education. And they’re committed to that because of their personal experiences, or because they were a teacher in a school.

Another thing about Teaching Matters that is unique is are ability to test innovations in education which can be resistant to this. We build trust with educators and that is how we can really test and try out what is effective with teachers voices along the way. For example, we were able to test out AI for teacher feedback by partnering with an AI education company and learn how AI can super change coaching. We learned what works and what doesn’t and what teachers value about AI at this stage.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

One is just perseverance. You can call it stubbornness but I am someone who will not take a no, especially when it’s about making a difference for kids and to just keep trying till you get it right.

Another important thing is being open and listening to your critics. I believe in hearing the disruptor in an organization. I think so often what’s important in education is the ability to hear what you as the leader, the organization, and the team still need to learn. I’ve always appreciated the disruptors in an organization as they might be pointing in the direction you need to move next.

And the third is, honestly, learning. I rarely meet someone I can’t learn something from. It makes all the difference when you find people interesting and are open to others. It creates new opportunities and new ideas and makes people feel genuinely heard.

Let’s now move to the main point of our discussion about AI. Can you explain how AI is disrupting your industry? Is this disruption hurting or helping your bottom line?

I wouldn’t say that AI has yet disrupted the education industry. Education is a very human-centered field. The concerns about AI are about how it will change the future of work for the students we have right now. This is the thought that we may not be preparing our students for the skills they need for the future. This has caused a lot of thinking about what we need to do differently.

We know education is historically under-resourced. Frankly, it’s not enough to have one teacher for every thirty students. Every teacher could benefit from having an individual tutor or mentor. AI can’t do that yet, but it can already listen to teachers and provide data on how often they do certain things that matter — like ask an open-ended question, or provide wait time so kids can think before responding. It can help coaches, teachers and leaders examine by providing a new sort of mirror they can use to examine themselves and improve.

Which specific AI technology has had the most significant impact on your industry?

We’ve been using AI in education for grading materials and papers, but it’s been very behind the scenes. ChatGPT has woken us up to what AI can do in the world and how education can evolve given the emerging technology of AI.

Can you share a pivotal moment when you recognized the profound impact AI would have on your sector?

What is of great interest in education is AI that can hear what the teacher is doing and provide data on what’s working and what’s not working in the classroom. We’ve had a lot of data on what kids do — “Can they read this sentence? Can they solve this math problem?” — but in real-time we have not been able to capture data on whether a teacher can ask an open-ended question. This new data can focus teachers in a way that had not been possible before.

How are you preparing your workforce for the integration of AI, and what skills do you believe will be most valuable in an AI-enhanced future?

One of the things that we know is that the last vestige of AI will be human-centric skills — developing relationships and connecting with students and teachers. In terms of preparing your workforce, you have to create a low-stress, low-risk environment for people to test and experiment. At Teaching Matters, we’ve said, “If you want to write your report with AI, go ahead and try it!.” Allow your staff to feel that AI isn’t going to replace their jobs, so they feel comfortable using it in several ways and sharing what works and what doesn’t work.

What are the biggest challenges in upskilling your workforce for an AI-centric future?

Some teachers have been in this profession since the beginning of the internet, and it can be challenging to convince a great teacher that a new system can make them an even greater teacher, especially when that system takes time to learn and understand. Comprehensive and continuous teacher training programs, like the ones Teaching Matters offers, are essential to bridge this gap.

Furthermore, there are still many schools that have broken copy machines. Not all schools, especially in under-resourced communities, have access to the computers and reliable internet needed to implement AI in the education sector. Adequate funding and resources are necessary for the development of AI in the education sector.

What ethical considerations does AI introduce into your industry, and how are you tackling these concerns?

One ethical consideration that we often hear about is the diversity and inclusion of folks in how we use AI. What does it mean if we don’t have all of us involved in the design, and what are the implications of it? It’s one thing to say that, but it’s another to see it in action. I’ve been in classrooms where AI that was trained on white male voices could hear white male teachers in a different way than teachers of color. It listened to and responded to them differently and judged them as less effective at the task because it couldn’t tell who was the teacher and who was the student. Seeing that in action is really something, and it speaks to how important it is to include all voices in this technology.

What are your “Five Things You Need To Do, If AI Is Disrupting Your Industry”?

1 . Set human-centered goals

When you’re thinking about how to use AI to improve your organization’s work, start by thinking about the jobs and roles that your team has and think about the human work that is going on. Ask your team about the work they love to do, and what things they don’t like about their jobs. Begin to think not just from the perspective of increasing your bottom line, but instead about the joy and satisfaction of your team.

2 . Listen to your team

At Teaching Matters, we ask our staff what parts of their role they love the most and what parts they would like to eliminate. We use that list as a place to start, to ask the hard questions about whether AI can do any of these tasks. Because if we succeed in using AI to help our employees do the work they enjoy least, we will be working with partners, and not against our team.

3 . Research and learn from best practices.

There is so much learning to be done in the work of AI. Now is the time to be talking to others in your industry. Have those conversations, share and learn about what is working. Don’t keep things secret. It’s important to have a dialogue so we can learn from each other.

4 . Power up, don’t replace your employees

If you have someone who is riding a bike, AI can be a battery that electrifies that bike to power it up and move faster. Allow your team to focus on the things that matter to them. Teachers get into their roles to have an impact on children. I think about teachers who teach kids in special education with diverse needs — there is so much work to document and record, so how can we use AI to free up the teacher to spend more time developing that relationship with the child?

5 . Repeat!

We want to do a lot of quick trial and error. We are going to have a lot of bad ideas. But let’s learn quickly, let’s try and fail fast. Small organizations often think they can’t participate in testing AI, but I don’t think that’s true. If we create safe workspaces where our teams can experiment then we are going to make a lot of progress a lot faster.

What are the most common misconceptions about AI within your industry, and how do you address them?

That it is somehow going to replace the role of the teacher. What we know is that one of the most important parts of teaching is the interaction and the relationship between teacher, and student and that cannot be replaced by AI. So I hope that we start to see AI as a teacher’s assistant that supports a teacher in the classroom with the many many many things on a teacher’s plate that make their job incredibly difficult.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

Leaders choose lemonade. Things are hard because they are either wrong and you have to make an important change or you have a real life opportunity to learn. Obstacles are opportunities to transform in ways that will grow and evolve you and your team.

Off-topic, but I’m curious. As someone steering the ship, what thoughts or concerns often keep you awake at night? How do those thoughts influence your daily decision-making process?

One thing that worries me is the state of morale in education. We know that teachers are leaving education in droves, and that keeps me up at night and impacts my decision-making. I’m increasingly asking myself, are we making this job better and more doable? Are we bringing more joy to the work or are we piling on in a way that makes the job worse? Anyone working in education must constantly ask themselves, “Are we making this job more tenable for teachers?” Because if not, you may be contributing to the problem.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I think I’m already in the movement that matters to me. Teaching matters. And it’s a movement to say that we have to take care and support our teachers.

How can our readers further follow you online?

You can follow the work of Teaching Matters on TwitterFacebookLinkedIn and Instagram by searching for @TeachingMatters

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.