Profile: Betsy M. Webb

Considering All Angles Before Proceeding
BY PAUL RIEDE/School Administrator, October 2019

Betsy Webb

AS A DIRECTOR of educational technologies early in her career, Betsy Webb faced a key challenge: How could she move her school’s English department into the digital mainstream when the tech-shy department chair was reluctant to lead the way?

“I knew if I could find a way to get him to embrace technology, I would have success within the whole department,” she says. “It was a study in leadership. I knew it had to start with a relationship first and then building trust and bringing up his knowledge in a way that he always felt safe and comfortable.”

Slowly but surely, the strategy succeeded. For Webb, now superintendent of the 3,800-student Bangor School Department in central Maine, it was one leadership strategy among many that she has pocketed over the years. She describes her approach as “bottom-up, top-down, bottom-up.” That means, first, consult teachers and other staffers on their needs and ideas, then adopt a plan and ensure it’s working across the district before consulting the grassroots again and improving the plan as necessary.

For Webb, 58, who was one of three national finalists for the 2019 AASA Women’s Leadership Award, it’s all about listening closely to the people in the trenches.

Kathy Harris-Smedberg, Bangor’s assistant superintendent, says Webb has a gift for encouraging people to reach their potential: “She has a genuine belief that everyone has something to contribute, and she tries to pull that out and make them shine.” 

Adds school board member Warren Caruso: “Most of the time when she’s doing it you don’t know she’s doing it, and I think that’s one of the reasons she’s so effective.”

Webb counts several mentors who encouraged her to develop her leadership talents, but she says her best teachers were her parents. Her mother was an elementary teacher and later a principal in Bangor. Her father was a professor and multisport coach at nearby Husson University.

Through her father’s work, she saw the impact of sports play on students and now includes extracurricular or co-curricular activities in each student’s learning plan. With 95 percent of Bangor’s students participating in clubs or sports, she is convinced the engagement increases attendance and achievement. It’s one reason, she says, why a district with 54 percent of students eligible for free and reduced-price lunch boasts higher-than-expected test scores and three national blue-ribbon schools.

Webb, who has led the district since 2008 and was Maine’s 2013 Superintendent of the Year, was quick to tackle a looming shortage of educational leaders in Maine. In a collaboration with the University of Maine called the Bangor Educational Leadership Academy, district teachers who aspire to be administrators can take graduate-level courses on site. That has expanded into the Maine Educational Leadership Academy, with teachers from 22 surrounding districts eligible for classes.

In another collaboration — this one to address a shortage of students pursuing math and science degrees — the district and university created a STEM program at the high school that enables students to earn as many as 36 college credits. 

Webb’s advice to other administrators: “Don’t be pushed back and worried about this initiative and that initiative and things coming down from the state. That’s not going to define us. Be a problem-solver and look through things with different lenses, see it from every angle and look forward. … We want students to be everything and anything they possibly want to be, so be bold and be brave.”

PAUL RIEDE is a freelance education writer in Syracuse, N.Y.


CURRENTLY: superintendent, Bangor, Maine

PREVIOUSLY: assistant superintendent, Bangor

AGE: 58

GREATEST INFLUENCE ON CAREER: My parents, Bruce and Chris MacGregor, both gifted educators, taught me to follow my passion and make a difference in students’ lives daily.

BEST PROFESSIONAL DAY: Any day I celebrate the successes of students, no matter how large or small.

BOOKS AT BEDSIDE: No Place for a Woman: A Life of Senator Margaret Chase Smith by Janann Sherman; Limbo: Blue-Collar Roots, White-Collar Dreams by Alfred Lubrano; The 21st Century School Leader: Leading in Today’s World by Denver Fowler; and Today Matters by John Maxwell

BIGGEST BLOOPER: I mixed up the company name of a business donor. I’ve since learned to make sure I always know supporters’ names and companies.

WHY I'M AN AASA MEMBER: The opportunities to network with the greatest leaders and thinkers on how to best educate students has been phenomenal. With every AASA interaction and experience, I have grown as a leader and person.