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Thank you to the 1,400 leaders who’ve generously done the 7 questions!
I hope reading

7 Questions with Alex Zequeira

helps you in your leadership.



Jonno White

7 Questions with Alex Zequeira

Name: Alex Zequeira

Current title: Headmaster

Current organisation: Saint John's High School

Alex Zequeira was appointed the 18th Headmaster at Saint John's High School in Shrewsbury, Massachusetts in July of 2016. After graduating from the College of the Holy Cross in 1994 with a BA in history, Alex began his teaching career at Kingswood-Oxford School in West Hartford, CT where he served as teacher, coach, and advisor as we as the Assistant Director of Admissions, the 8th-grade class dean. In 2003, he was called to serve as the founding principal of the Nativity School of Worcester, MA. In 2004, he returned to his native Miami to his alma mater Belen Jesuit Preparatory School, where he served as a teacher and coach, and the Executive Director of the school's Alumni Association from 2005 to 2008. In 2008, Alex joined the Wooster School community in Danbury, CT as the Dean of Upper School, teaching Spanish, European, and Latin American History, and coaching basketball and softball. In 2011, he rejoined the Nativity School of Worcester community as its 3rd President (Head of School). In May of 2016, Alex earned a M.Ed. in Educational Leadership from the Lynch School of Education at Boston College.
Alex recently served as the chair of the Board of Directors of the national NativityMiguel Coalition of Schools and as a Board Member for the United Way of Central Massachusetts. He currently serves on the Board of Trustees of Quinsigamond Community College, on the Board of Advisors of the Latino Education Institute at Worcester State University, the Worcester Education Collaborative, and is a Corporator for the Greater Worcester Community Foundation, where he also serves as an advisor to the Nonprofit Support Center.
Alex lives in Worcester with his wife Jessika, and their three children.

7 Questions with Alex Zequeira

Which option best describes the religious affiliation of the organisation you currently work for or most recently worked for?

Christian religious affiliation

What type of organisation do you work for or support?

School (5-17 y/os)

1. What have you found most challenging as a leader in the education sector?

I believe the key factor that is most challenging and takes up a good deal of my time as headmaster at Saint John's High School is how our institution can remain relevant. The work we have been doing for 123 years, as an all-boys Catholic school, I believe, is more important today than ever before. Launching our young men into a world where they will be successful in college and, more importantly, be prepared to live lives of meaning and purpose is a growing challenge. How do we reach, teach, and inspire our young men every day in a society where they are hearing and seeing very different messages about who they are as men is a great challenge.

2. How do you structure your work days from waking up to going to sleep?

I believe in routine. I love it and thrive in it. I believe it is one of the reasons why I went into education. I like schedules. My workday starts at 5:15 am when I wake up. I hop on my Peloton bike 6-7x a week, help wake up the kids, and off to school. The actual workday varies a great deal, but I make it a point to get out of my office and check-in with students and my teaching colleagues. I joke that I "wander" a great deal when I am on campus. Additionally, I spend a good part of my day connecting with donors or individuals in the community. After a few afternoon meetings, I head home and have dinner with my family and try to enjoy time with them.

3. What's the most recent significant leadership lesson you've learned?

The most recent is tough to answer. I would frame it as what leadership lesson has been reinforced over the last 10 months in the midst of this global pandemic. I have always lived by the mantra "honor the relationship before the task." It served me well as a classroom teacher and a coach and, I believe, served me well in school leadership. The relationships I have built with my colleagues over the last five years had aided me in this very difficult time as a school. Relationships matter and it is important to invest time and energy building and cultivating them.

4. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

I very much enjoyed the book "Give and Take" by Adam Grant. The idea that by assisting others in developing as people and as employees can drive our own success speaks to my belief in the importance of relationships.

5. How do you find and keep great leaders in the education sector?

I believe the work of a head of school has changed significantly in my 27 years in education. We are asked to be a lot and every year it seems that we are asked to do more. However, I have been blessed to work with amazing Boards of Trustees in the two schools where I have served as a head. Supporting the whole leader and recognizing that we have many dimensions to our lives will keep leaders in the education sector and in your school.

6. What's most important as a leader in the education sector for developing a culture of wellbeing in your staff and students?

It is important to recognize that what we do as a school will have a profound impact on the life of everyone connected to the institution. Believing in word and deed that the whole person - mind, body, and soul - needs to be tended to in our schools will promote a culture of wellbeing.

7. What is one meaningful story that comes to mind from your time as a leader in the education sector so far?

Serving as the founding principal of Nativity School of Worcester was an amazing opportunity cut short by the unexpected and sudden death of my father. I was humbled when asked to serve as a commencement speaker for the school's first graduation and to be in a position to watch those students graduate from college in 2014. All of those young men were first-generation college students. It was at that moment when I could see and feel the transformative power of education. I continue to be inspired by that opportunity and blessing.

We're looking at doing a limited, online 30 minute leadership masterclass in the next couple of months. What topic/s would you find most valuable from a leadership masterclass?

How are you fostering authentic and healthy relationships with your leadership team and in your institution?

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