Educating others should be an enabling act of love and liberation, not didacticism and indoctrination ~ Jon Sills

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JMcCT (c) 2019 all rights reserved

Jon Sills

“I’ve always believed that educating others should be an enabling act of love and liberation, not didacticism and indoctrination.”

Jon Sills, who formally departed from the Bedford Public Schools on August 30, shared that philosophy in a letter to teachers, staff members, and the School Committee. He also told them, “The relationships that you have built, and continue to build, will, for many of our students, be remembered throughout their lives.”

Sills, 69, succeeded Thomas Duggan as Bedford High School principal in 2001. He followed Dr. Maureen Lacroix as superintendent in the summer of 2012 and actually retired on June 30, continuing another two months as associate superintendent to assist in the transition with his successor, Philip Conrad. He called Conrad “an educational leader who truly cares about teachers, who listens, and who places kids at the forefront of every decision.”

Jon Sills’s pre-Bedford resume spans almost 30 years of teaching and administration, much of it at Brookline High School near his home. Indeed, he was a finalist for the position of Brookline superintendent of schools four years ago.

“When I came to Bedford, I thought I would stay for three or four years. My heart was in more urban education,” Sills reflected during a lengthy interview. “But some of the things that attracted me to the Bedford Public Schools – a unique level of diversity, given it’s a small suburban community, and the values that were embedded in the strategic planning — really made it attractive. I came to fall in love with the community.”

“Every community has its own culture,” Sills continued “I found a unique blend, including military retirees, that give [Bedford] a really interesting feel. It’s also a community of engineers, and engineers, I’ve come to find, have a can-do ethos. Basically, they say, ‘Show us the data and we will help problem-solve,’ through New England pragmatism expressed in a really wonderful process called town meeting.”

“I came to feel privileged to serve this community. I met so many wonderful people who truly were committed to education, without trying to micromanage it,” Sills commented. “There has been a certain modesty or humility that I have come to associate with the Bedford community. That has been really refreshing. The town puts a lot of trust in its educators and gives educational leadership a lot of latitude to improve education and meet the needs of all the children.”

He emphasized that “every positive step in which I have been involved was built on the foundation established by Joe (former Superintendent Joseph Buckley) and Maureen. That’s putting kids at the center of all decisions, a very professional culture that’s not easily found.”

“That has been expressed really strongly by the school committee, which is the envy of many of my colleagues,” he said. “A school committee that’s smart, hard-working, does the research, and really has strong values around kids’ equity and isn’t personal agenda-driven has a reputation beyond Bedford.”

Revisiting his accomplishments, Sills observed, “Every leader brings his or her own perspective and passion and approach to pedagogy. I am proud of the work we have done.” He noted that he uses the first-person plural because any achievements are also a credit to the leadership team, ranging from central office personnel to facilities management to building principals.

Sills cited the “tremendous emphasis on district-wide coherence, curricular and instructional, but a coherence that is animated by lots of creative expressions. I worked hard to build a leadership team that together defines direction for the district so that everybody is on the same page. Often the alternatives are either a more autocratic direction from the top down or almost complete autonomy. There is power in coherence and power in that team.”

“Also central to that is promoting teacher leadership and teacher initiative and making schools collaborative structures that you create — facilitate teachers learning from each other and from all the things they are doing in their classes.”

Sills said he always has been devoted to education’s “civic mission. I worked nonstop to help us create curriculum instruction that really centered around the development of kids as deep and complex thinkers who can define their own place in the world and have the wherewithal, the knowledge and the skills to do that.”

“That may be expressed in things like project-based or student-centered learning  – challenging intellectual work reflected in the complexity of the tasks we ask,” Sills said. “It’s a very well-rounded education with robust arts and music and health and physical education – the whole-child approach.”

Sills also reflected on his “commitment to educational equity, particularly its expression as anti-racism. This has driven my work. It is absolutely critical if we are going to educate all kids and provide them with the opportunity to thrive in a school system and society” that continue to be permeated by “insidious inequities.”

“Despite some really good work we have done in equity and diversity, the road ahead is longer than the road we traveled,” he commented. Among the needs are continued efforts toward staff diversity; recruiting visits to historically Black colleges and universities were curtailed by the pandemic last spring. Sills also has a vision of town-owned property that could be a residence for these young teachers.

JMcCT (2016) all rights reserved

Jon Sills (far right) with BHS graduates who returned to help with the 2016 Tenacity Challenge – Click to view the full-sized image

Sills crafted the Tenacity Challenge in 2011. It is an annual academic scholarship competition for teams of Latino and African-American students from urban and suburban high schools across the state. Massachusetts. Teams of up to 6 students compete in four events. The event was named in Sills’s honor earlier this year.

“One area where we haven’t put enough effort is building those bridges of understanding among our kids. That requires adults to continue learning, growing, and changing,” Sills said. “The biggest influence on kids in many ways is their peers. As long as we haven’t made sufficient progress to move desegregation to a more deliberate, active integration process, and really creating relationships, then we will not have gotten to where we need to get.”

“There’s a project I helped to launch this year with the Parents Diversity Council called the Boston Bridges Initiative, and Bedford is going to be the pilot,” Sills said. A philanthropist is underwriting “bridge-building activities among families and students across race and geography. The Diversity Council will arrange activities and events, and the schools will sponsor retreats. “The problem is Covid is going to delay some of this work.”

“Passive desegregation can reinforce stereotypes rather than overcome them. That’s why Bridges is such a critical piece.”

Sills is beginning his fifth year teaching equity and the law and labor relations at Boston University’s Graduate School of Education.  Most of the students are master’s degree candidates and also student-teachers. He also is teaching a course in equity practices in a new doctoral program directed by Dr. Robert Weintraub, the former headmaster at Brookline High School. The experience, which will be remote this semester, is “much more engaging than the typical college lecture.”
“It’s great to be teaching again,” Sills said, adding that “I’m using methods from teachers I have observed in Bedford. I’m trying to find ways to build relationships because it’s that person-to-person connection that I so enjoy and rely on.”

Sills also has what he calls a more demanding job: he was recruited to join other retired school superintendents coaching and facilitating in the induction program for 28 new superintendents, sponsored by the Massachusetts Association of School Superintendents and the state Department of Elementary and Secondary Education.

At times it feels like a Bedford program. Sills’s two predecessors in Bedford, Lacroix and Buckley, are veteran coaches. And his successor Conrad, as well as two of his former BHS assistant principals, Kristen Vogel (Lynnfield) and Brian Regan (Waltham), are participants.

“I had to say no already to four or five other things,” said Sills, who continues to serve on the Metco Board of Directors.

The teaching and coaching are much less demanding than working as superintendent of schools, Sills said, so he expects to find time for “golf and reading and just finding a new balance.” In his memo to the school community, he mentioned returning to “drawing and sculpture that once so interested me.”

“I’m not yet done trying to make a difference, but I also need to slow it down and have more free time.”

Mike Rosenberg can be reached at, or 781-983-1763
Click this link to learn more about The Bedford Citizen’s first community reporter.

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