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Ashland - Local Town Pages

Family Legacy of Service, Desire to Meet Needs of All Students Motivates Ashland’s Assistant Superintendent

Jan 29, 2021 09:24AM ● By Cynthia Whitty

Assistant Superintendent Michael Caira with his wife Kristen and daughters +Anna, a third grader at Ashland’s Mindess School, and Caroline, a sixth grader at Ashland Middle School. (Photo/supplied)

In the midst of the Coronavirus, on July 1, 2020, Michael Caira took on his new role as Ashland’s Assistant Superintendent of Curriculum, Instruction, and Assessment. Caira has worked in Ashland as a principal for the Warren and Mindess schools for the past nine years, and before that, as a teacher, dean of students and special education coordinator, and assistant principal at public schools in other Mass. towns and in Conn. Ashland Local Town Pages asked Caira what prepared him for his current role, especially at this challenging time, and what motivates him and keeps him up at night.

Whitty: Why did you choose your career path in education?

I come from a family of educators and public servants. My father, Michael, was a long-time Town Manager in Wilmington, Mass., where I grew up. My mother was an educational assistant. I have two sisters and a brother. My sister Jennifer is a former elementary school teacher, my sister Angela is a high school counselor, and my brother Brian is an assistant principal at a middle school. My wife is also an educator, who works as a school counselor for Westborough High School.

When I was a high school student exploring future careeroptions that included detective, college football coach, and Disney animator, my father shared the following quote, “No man is so tall, as when he stoops to help a child.” The quote resonated with me, as a young man and has become a major part of my educational philosophy. I come from a family of public servants and educators. It is a privilege to serve as an educator, knowing that each day we have the opportunity to make a difference in the life of a child.


Whitty: What prepared you for your current job?

Throughout my career, I served in a variety of different capacities. Each position has played a part in preparing me for my current role. Certainly, my time as a teacher allowed me to familiarize myself with curriculum and curriculum development, as well as understanding pedagogy. In my time as a building administrator I was able to learn about the importance of communication and building based management. Working as a special education coordinator afforded me the opportunity to understand the intricacies of the special education process. 

My doctoral work at Boston College also played a large role in preparing me for this position. During my time at BC, I collaborated with educators from across New England and had the good fortune of learning from experts in the field of education. 

Most significantly, I have learned from my colleagues and the individuals who I have worked alongside over the course of my career. I consider myself very fortunate to work with the administrative team in Ashland, and I have learned a great deal from each member of the team.


Whitty: What motivates you in your job?

In my opinion, there is no greater responsibility than educating young people and keeping them safe while doing so. Knowing that our future is dependent upon the manner in which we educate our children motivates me each day. As a resident of Ashland, I am even more motivated, as I know that the decisions we make as administrators have a profound impact on our community as a whole. Having served as a principal for students who are currently in grades 3-10 also motivates me, as I have had the wonderful opportunity to watch these young men and women grow from a young age. I am motivated to always do what is in their best interest. 


Whitty: What keeps you up at night?

Staff and student safety keeps me up at night. As a teacher, I lost sleep thinking about keeping the students in our class safe. As a principal, I lost sleep thinking about keeping the students and staff in our school safe. Now, as assistant superintendent, I lose sleep thinking about keeping the students and staff in our entire district safe. Parents entrust their children to educators every day and it is our responsibility to educate them, but also to ensure they feel safe, physically, and social-emotionally. The safety of our students and staff is paramount and I think about it constantly.


Whitty: What gives you the greatest satisfaction and the greatest challenges?

It is satisfying to hear teachers and students talk about their enjoyment of the process of teaching and learning. When I walk into a classroom and feel the energy of a lesson and see and hear teacher/student discourse taking place, it is incredibly satisfying. I also always enjoy when a former student or parent provides me with a positive update regarding their own success or the success of their child. I would imagine my greatest challenge is similar to most educators. It is frustrating and disheartening when you cannot find a way to meet the needs of each child in your classroom or your school. Our goal is to ensure every child’s needs are met, and there is no greater challenge than providing exactly what everyone needs all the time.

Whitty: How are you handling the situation with Covid, personally and professionally?

When I played football in college, my coach always told us to not let the highs get too high and not let the lows get too low. I have tried to take that approach both professionally and personally during the past nine-plus months. Certainly, Covid has presented us with tremendous challenges as educators, but I am continually impressed by the resiliency of our teaching staff, our students, and our families. I am in awe of what our nurses and principals are doing on a daily basis, and I have been so very fortunate to learn from Mr. Adams during this unprecedented time. Personally, I have enjoyed the extra time with my wife and daughters, and while I have certainly missed my friends, we have created very special memories and experiences that would have never happened if our normal lives didn’t come to a screeching halt in March.

Whitty: Is there anything else you would like readers to know?

I consider myself very lucky to have found a home both professionally and personally in the community of Ashland. Nine years ago, when I was hired, I immediately fell in love with this community and I hope to work here, serving the students, staff, and families of Ashland for the entirety of my career. 

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