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

鈥淚 knew if I could find a way to get him to embrace technology, I would have success within the whole department,鈥� she says. 鈥淚t 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.鈥�

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 鈥渂ottom-up, top-down, bottom-up.鈥� That means, first, consult teachers and other staffers on their needs and ideas, then adopt a plan and ensure it鈥檚 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 , it鈥檚 all about listening closely to the people in the trenches.

Kathy Harris-Smedberg, Bangor鈥檚 assistant superintendent, says Webb has a gift for encouraging people to reach their potential: 鈥淪he has a genuine belief that everyone has something to contribute, and she tries to pull that out and make them shine.鈥� 

Adds school board member Warren Caruso: 鈥淢ost of the time when she鈥檚 doing it you don鈥檛 know she鈥檚 doing it, and I think that鈥檚 one of the reasons she鈥檚 so effective.鈥�

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鈥檚 work, she saw the impact of sports play on students and now includes extracurricular or co-curricular activities in each student鈥檚 learning plan. With 95 percent of Bangor鈥檚 students participating in clubs or sports, she is convinced the engagement increases attendance and achievement. It鈥檚 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鈥檚 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 鈥� this one to address a shortage of students pursuing math and science degrees 鈥� the district and university created a STEM program at the high school that enables students to earn as many as 36 college credits. 

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