Superintendent Q&A: Dr. Betsy Webb

How one superintendent is transforming teachers into leaders

By Melissa Hite Last Updated: May 07, 2019

From the outside looking in, it seems like Dr. Betsy Webb, superintendent of Maine’s Bangor School Department, is doing the impossible. Even with a
comparatively low per-pupil cost and more than half the student body qualifying for free or reduced lunch, the district is thriving. This year, one of Bangor’s 11 schools was nominated to become a National Blue Ribbon School of Excellence. It would be the district’s fourth.

“Five years ago, that school was scoring just above state average,” Webb tells SchoolCEO, beaming. “They are now the top-performing school in the entire state for mathematics.”

Webb’s 18 years of accomplishments as a superintendent speak for themselves—from establishing six high school academies to being named Maine’s 2013 Superintendent of the Year. We spoke to her about her experiences in the role, the changes she’s made in Bangor, and the ways she affords opportunities to her district’s aspiring leaders—both staff and students.

Can you tell us about your path to the superintendency?

I come from a long line of educators. I started as a teacher and then was encouraged by my principal and superintendent to think about leadership roles. I then
became a director of technology in a K-12 school system, then moved into a principalship. After five years as a principal, I was encouraged again by community
members to really look at the superintendency role.

I have been in central office administration for 18 years now, and I enjoy it immensely. I thoroughly enjoyed being in the classroom, but as you go into leadership roles, you have a greater impact. At times, I certainly miss the day-to-day relationships with students, but I really work hard to find ways to stay connected to them out in the schools.

How would you compare the principalship to the superintendency?

I believe that great educators have a skill set that will fulfill each role, but the biggest difference is that you have to multitask. You have to think about systems that work for the whole district. When you’re in a school, you’re very focused on that population, but now, for example, I’m thinking about how to move 11 different schools in the direction we want to go. I have to work with the principals, leaders, and teachers in all of those schools.

Sometimes when mentoring other superintendents that are new to the career, I find that they want to get down to the building-level details. You can do some of that, but just as working with students, you’re really trying to make sure your principals are learning how to be independent in their work. You’re trying to be that mentor that helps them think of different perspectives, helps them problem-solve, rather than just giving them an answer.

School leadership is overwhelmingly male, even though teachers are primarily female. Why do you think that is?

I was on a committee helping a doctoral student with her research, and she looked at this exact issue: why were females not going into the superintendency? One of the things that she shared is that when females look at job descriptions, they will not apply unless they have every single one of the qualifications advertised—while males, if they have at least 50% of the characteristics, feel that they are qualified. I know for myself, I’ve always made sure I had every single characteristic when applying for a job. She also found that males often seek out leadership roles without anyone telling them they’d be good in that role, but females that have sought out leadership responsibilities in education almost always point to a mentor who encouraged them. That was certainly the situation for me.

What are you doing to change this in Bangor?

I’m quite proud of the work that we’ve done in the greater Bangor region to start up leadership academies in partnership with the local university. We’ve really modeled this almost after a teaching hospital. Cohorts of teachers are learning the theory about leadership from university members, but then practicing what they’re learning in the Bangor School Department.

It’s really allowing them to try on leadership. If you look at the reasons that people don’t go into the superintendency, it’s usually fears about the time commitment, the political aspect of the job, the loneliness of the position. When teachers see that there are other parts of the job that are quite satisfying, I think it might encourage them to take that next step.

What do you do as a superintendent to find and develop leaders?

In this cohort model, I’ve tried to encourage teachers to ask themselves: Is there something in the district we should think about differently? We’re encouraging them to do research and put together a proposal of how they—and the whole district—could study that factor more deeply.

For example, two of our teachers were concerned about “summer slide.” At-risk students weren’t reading when they were on summer break and were losing the gains that we made over the academic year. So these teachers did a pilot study. They were able to get enough books donated that every student in the school went home with 10 different books for the summer. They trained parents to engage with students about their reading. These teachers even walked through the neighborhoods with wagons full of books so students could come and exchange theirs.

When they made their proposal, I talked with them about the research aspects. How are you going to make sure that you include a cohort analysis? How are you going to have a pre- and post-analysis to measure that you’ve made a difference? They not only did grade-to-grade comparisons, but cohort comparisons. Now, they’ve found that through that pilot, they have absolutely closed the summer gap.

The whole experience just expanded their ideas. They’re already working to get donations  for next year. That’s just one simple example of how you help someone grow their leadership—how you help them not only try to solve a problem, but also use research and measurement to prove that their solution works.

What qualities do you look for when choosing people for leadership positions?

You need so many characteristics, but number one, for me, is a passion about inspiring students to learn at the highest level. I want someone who’s a deep thinker, who’s a problem solver, not somebody who just checks off the boxes. You need an effective communicator, someone who can work with their faculty and staff and inspire them.

Over the course of my career, I’ve been fortunate to have so many excellent leaders. It gave me a hunger to be better and to think about things differently. A good leader makes it feel safe to take risks, to not follow the rules right to the T. We can’t have rule breakers, but how do we bend without breaking? How do we look at things differently but hold onto our values?

That is so important in the day of school choice. When you see that there are charter schools and private schools providing innovative ways to educate, I believe we can do it even better. So how do we be a school system of choice? It has to be that you have dedicated people in all positions, but if I don’t hear that passion in a leader, if they’re not someone who believes they can truly make a difference, we’re not even going to be able to get out of the gate. I’m looking for someone who is committed. I can help them with school law, I can help them with budgeting, but I can’t help someone who doesn’t have that passion.

And I expect that same passion of myself. If I don’t, then the whole organization is in trouble. But I’m somebody who enjoys the challenge of problem-solving. I’m most energized when we are creating new opportunities for students.

Speaking of opportunities, can you tell us about the different high school academies you’ve created?

In the last decade, I’ve developed this sense of urgency. How can we make sure that all students have opportunities to go to the highest level possible while they’re with us, so that we improve the number of college graduates? We’re partnering with universities and community colleges, as well as businesses, to gain the support we need to provide those opportunities.

Take our STEM Academy, for example. A few students were doing scientific research that was gaining them a little attention, so I went to my faculty in the science department and I challenged them. How do we do this for all students, not just the few that are super driven?

So now, through our partnership with the university, students in our STEM Academy are getting dual credit. If they graduate with a STEM Academy endorsement, they can enter the honors program in the College of Engineering or the College of Natural Sciences as sophomores. It’s not just a few students anymore—right now, we have more than 40 students taking the highest level of mathematics that the university offers, while they’re still seniors in high school. Isn’t that amazing?

Other STEM careers don’t need an engineering degree, so we also created an academy that allows students to earn an associate’s degree from our local community college one year after they graduate high school. Then they can to go out into the workforce in a STEM-related industry, or they can apply their degree to a bachelor’s and go on to the university level.

image: futuristic school

What has the STEM Academy taught you about implementing new programs?

For me, it’s thinking about how to create pathways. Working with young people, they often will say to me, “I don’t know what I want to do.” We have to do a better job of giving them options. With No Child Left Behind and some of the federal and state mandates, there were fewer and fewer electives that we could offer to students. But young people want choices. There’s tons of research on this.

So we tried to look at things like U.S. History. It’s a mandated course, but how could we give options for that? Now at Bangor, if you want to study U.S. History through theatre and art, you can. You can study the Industrial Revolution and the rise of business. You can study pop culture. Students flock to those different courses. We’re trying to find those pathways that inspire, engage, and motivate students to work at the highest level possible.

How do you change perceptions of what’s possible in a public school system?

We really have to be student-focused, with everybody believing that high expectations make a difference. Then we need the students themselves to be hardworking. In our student code of conduct, one of the characteristics we look for is ambition. Sometimes students are afraid to take risks, but I think when you’re learning, you have to take risks. Just like a scientist, you fail more often than you succeed, but usually, you learn more when you fail.

We do a lot of acceleration. We don’t want students sitting in classes feeling bored. I remember when I first started as a superintendent, and teachers would say to me, “I have a student reading at three grade levels higher—what do I do?” I said, “Well, get books from three grade levels higher!”

I think about all that we’ve learned with brain research. We used to believe that there was this proximal zone of development: that if the work was too hard, students would shut down, or if it was too easy, they would be bored. With brain research, what we’re finding is that the sweet spot is actually just above that proximal zone. Think of things that you’ve learned on your own. The ones that you’ve worked the hardest for are the ones that you’re most proud of.

So how do you inspire all students to take on these challenges and stay engaged?

If you take the STEM Academy, we have them working on problems like the lack of clean water across the nation. They are coming up with amazing solutions. They’re not going to remember Question 15 at the end of Chapter 10, but they’ll remember that forever.

I want students to be hungry to learn, to try to solve a problem, to experiment, and I think the more we can think that way, the higher engagement we’ll have. That’s how you sell the benefits of public education.

In bringing about all these changes to the district, what have you learned about how to get buy-in from the community?

It’s really important that you involve all stakeholders; that you repeatedly communicate how you make decisions; that you really think about the core experience for all students, no matter what.

One thing I’ve found is that it can’t be one mode of communication. I mean, I desperately wish I could have conversations with everybody face-to-face, but that’s
not always the way. I don’t always love conversations over Twitter, but I have to realize that’s the way some of my parents communicate. They expect communication to come to them. They don’t always want to make an appointment with me.

Although at times it pushes me out of my comfort zone, it keeps me energized. It keeps me learning. Really, I think it has taught me that there isn’t one form of communication that is successful. You have to remember that you have a variety of people.

If you’re keeping yourself on the edge, staying a little uncomfortable all the time, how do you prevent burnout as a superintendent?

I wouldn’t be able to say I’m a perfect role model or anything. I have a hard time shutting it off, and I really feel like being a superintendent is part of me each and every day. But I certainly do a great job talking to my administrators and teachers about taking care of themselves.

It’s important to make sure you are learning, because there isn’t an educator out there that didn’t go into this field without loving to learn. So make sure that’s part of your routine.

Make sure that you have a safe network of people that you can brainstorm with. I think when I first started, I didn’t realize that. I made the mistake of sometimes being very isolated. I didn’t realize that until I was talking to some of my friends
who were lawyers or doctors, and they said, “Are you networking with people to problem-solve?”

Having that network has made it so much healthier for me—understanding that we all go through challenges, but I have people out there to support me.

If you were going to teach a lesson to every superintendent in the country, what would you teach?

Don’t let the negative aspects of the job pull you down. When I was ten years old, I desperately wanted a unicycle for my birthday. I have no idea why—I didn’t have any friends who had a unicycle—but I just wanted to figure it out.

So when I finally got one, I tried, I fell down, I skinned my knees, I scratched my hands, I scratched my new unicycle. I finally got so angry that I looked to where I wanted to go—and in doing that, I figured it out. I had been spending all my time looking down, trying to avoid getting hurt, but when I focused on where I wanted to go, I found my balance.

I think of that all the time, even on those toughest days. What’s my focus? Where are we going? Where do we need to go?

You can follow Dr. Webb on Twitter at @BetsyMWebb.

Image: A unicycle


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