Corrected: A previous version of this article misstated the university from where Scott Tombleson received his master’s degree. His degree is from Boston College.
Scott Tombleson had been a band director, a software professional, and a technology teacher in an international school in Egypt. But he’d never thought of becoming a principal of a public school in the United States.
“I used to think it’s the most underappreciated job in the world,” Tombleson said in a phone interview. But fueled by a conversation with a mentor in Egypt, and his experience of introducing a whole new Chromebook-based tech curriculum in his school, Tombleson felt up to the challenge.
So, in July 2022 when he walked into South Portland Public High School in Cumberland County, Maine, armed with a master’s degree from Boston College, Tombleson thought he was ready to be a principal. But nothing could have prepared him for how complicated and tough the principal gig had become post-pandemic. Academic decline. Student absenteeism. Mental health challenges. And the report of a student who was threatening to attack the school.
Plus, there had been lots of turnover in the district’s leadership.
“We’d just had a new principal before Scott. We were in the process of rebuilding after the pandemic. We wanted a principal who would listen to existing leaders within the school and understand the dynamic needs of our student community. We have a lot of new students from other countries and a lot of new teachers,” said Tania Ferrante, head of the English Department at the school. “He joined [as principal] at a challenging time.”
Tombleson intended, right off the bat, to build a coherent school culture and a sense of community with teachers and students. But in his excitement to shake things up, Tombleson said he missed a few steps, and moved further away from his goal of assimilating in the school’s culture. “When you come in and change things quickly, what you’re telling [the school] is that everything you did up to this point is rubbish. That leads to conflict,” he said.
Over the last year, Tombleson has tinkered with several large and small changes as a principal. Some, like instituting a digital hall pass system, have worked. Others, like adding intervention blocks to help students catch up academically, are still being debated by the faculty.
The most significant change, said Tombleson, was his own attitude shift: “To give everyone a larger voice, I realized I can’t ignore conflict.”
Efficiency or representation?
Tombleson spent 15 years as a software professional before he returned to education. “In the business world, if something isn’t working, you have the pressure to change it because you must deliver a product. In American schools, there are constraints,” he said.
Despite the challenges, Tombleson’s first agenda item was to change the way decisions were being made in the school. The previous administration had thought convening one large body of teachers, all holed up in one room, would make better decisions. But it clearly wasn’t working.
“The meeting had become a venue for some groups of people to lob complaints at the administration. This type of meeting didn’t play to anyone’s strengths. It wasn’t moving the school forward,” he said.
He decided to whittle down, re-brand, and re-focus this leadership team. Pared down to just department heads, this became a venue for instructional leaders to decide on things like curriculum and grading practices.
“We’ve tripled the time we used to spend on improving instruction,” Tombleson said.
The pared-down version of the big, raucous group may have suited the new principal and some of his colleagues. But Tombleson soon realized that actual operational challenges his staff brought up had nowhere to go now—and bubbled up in a different venue, like the staff room.
“The easiest way to make a teacher angry is to change their schedule without proper communication. This happened a lot because no one was thinking through the operational challenges behind introducing a new change. This caused conflicts,” he said.
Tombleson added two more teams to his restructure: an operations team and a vision team, both comprised of school staff members. The latter is responsible for setting long-term goals for the school. The operations team meets once a week for 30 minutes and works through how to implement operational changes in the school. He’s particularly proud of how this team decided to implement the digital hall pass system. Digital passes would replace the older system of teachers handing students a paper pass if they wanted to go to the bathroom, for instance.
“We wanted to collect data to recognize patterns in student behavior. Teachers would have resisted this since it’s one more thing for them to do. The operations team made this transition smoother. They decided they would communicate the shift to their colleagues, instead of leaving it up to the administration,” Tombleson said.
The easiest way to make a teacher angry is to change their schedule without proper communication. This happened a lot because no one was thinking through the operational challenges.
Digital hall passes are a win for the operations team, said Ferrante, the English department head. It’s also helped involve newer teachers in decision making.
While Ferrante is supportive of the three teams approach, she’s still unclear if the instructional leadership team—which she sits on—includes all the voices it needs to have. “There’s a lot of strong leadership in our school. So that team would benefit from more voices,” she said.
Learning the art of difficult conversation
Tombleson spent his first year trying to rope in different factions of teachers, and smooth out conflicts with those who felt left out. At a personal level, he was struggling to connect with one teacher in particular.
“We just couldn’t get on the same page, no matter how hard we tried. Everything I’d say to her wasn’t being received well,” he said.
As he walked by the teacher’s classroom one day, for example, he noticed she was doing a science experiment that involved fire. “When she asked for feedback, I threw my hands up in admiration and said, ‘you have a fire going!’ She thought I was blaming her for not keeping the kids safe,” Tombleson said.
This encounter was a tipping point. The teacher initiated a conversation with Tombleson, which was facilitated by a neutral colleague whom both parties trusted. Initially, Tombleson was hesitant. “I thought this conversation would lead to more conflict. But I had to go back to my core belief: everyone wants to do good.”
The mediation helped, and Tombleson said the two were able to work through their differences. “Beneath all the mistrust, we respected each other,” he added.
At difficult junctures in his time as a principal, Tombleson has sought advice from mentors and executive coaches. He reached out to a former principal, Shayne Evans, who coached him through conflicts that came up in the first year.
“First time principals have to win over everyone,” Evans said. “The teachers, the students, their parents. If there are 700 people in your school community, you’re building 700 unique relationships.”
Evans helped Tombleson get comfortable with talking through conflicts, and listening to staff members’ perspectives, even when they completely disagreed with him.
“When Scott had these conversations, I think he realized it wasn’t as bad as he’d thought it would be,” Evans said. “These are hard conversations to have. People are going to disagree. But as the year went on, I noticed that Scott was willing to have more difficult conversations.”
More conversation, more conflict
Tombleson is candid that he’s still trying to become more comfortable with conflict.
“It’s still aspirational that I can have that open conversation with everyone who disagrees with me,” he said.
Still, his first year as principal allowed him a chance to start building that comfort.
Last year, the instructional leadership team had its first “planning summit” to decide on academic reforms to implement. Tombleson found substitutes for the teachers on the leadership team, ordered lunch, and spent a day trying to decide on the changes to pursue.
The group identified two: an intervention block and re-purposing study hall.
As the team started preparing for these changes, Tombleson felt pushback against the intervention block.
Even though the team has temporarily abandoned the idea, Tombleson said he’s happy that the leadership team built the muscle of gathering in a room, debating, and developing an implementation plan.
Tombleson said he’s not ready to give up on either the intervention block or study hall. And he may have allies ready to try again.
“When the team dropped the idea of the block, Scott might have assumed people weren’t open to it. But he was only hearing from the louder dissenting voices. We might bring it up in the leadership team again,” said Ferrante.
Principals are in an impossible situation: They’re expected to lead, but also make room for every voice.
As Tombleson continues in his second year, he has more fundamental changes in mind at South Portland High School. And becoming more comfortable with conflict has better equipped him to pursue them, he said.
“There’s always going to be tension between teachers and management,” Tombleson said. “But once you empower the second line to make decisions, that’s when things significantly and pretty quickly shift into a realm of positivity.”
