Invest in People: This lasts long after grant funding has gone away. Our school-based expansion grants rarely go to brick and mortar. We provide coaching for principals, professional development for teachers starting new grades, or extended summer or vacation sessions for incoming students.

As a part of this series, I had the pleasure of interviewing Will Austin.

Will Austin is the Founder and Chief Executive Officer of Boston Schools Fund, a nonprofit aimed at advancing educational equity. Will served as a math teacher at Roxbury Preparatory Charter School and was nominated for Massachusetts Teacher of the Year. He subsequently served as Co-Director for Roxbury Prep, and then as Chief Operating Officer for Roxbury Prep for Uncommon Schools, overseeing the school’s expansion from one to four campuses. A lifetime resident of Boston and a graduate of Boston Public Schools, Will holds an A.B. in Government from Harvard College and a master’s degree in Education from Tufts University.

Thank you for making time to visit with us about a ‘top of mind’ topic. Our readers would like to get to know you a bit better. Can you please tell us about one or two life experiences that most shaped who you are today?

One of my most formative experiences that set me on the path I am today happened when I was just 11 years old: taking the test for one of Boston’s three exam schools on a Saturday morning in November 1989. Like magnet schools in other cities, these public schools have great resources and the college placement track records to match, with life-changing opportunities that hinge on the successful completion of this test for admission.

I passed, attending Boston Latin School. My sister and I became the first in our family to graduate college, our academic and professional paths made possible from our time at BLS.

It wasn’t until years later — when I was a tutor for Boston middle school students while I was a student at Harvard University — that I asked myself some difficult questions. Surrounded by students of color, as I was in elementary school, I thought back to that exam school test morning in 1989, when I got into the backseat of our family’s gray Dodge station wagon: Why weren’t there more kids from my school in that car? At the test? Why weren’t my friends — many of whom had less social capital and a different skin color from me — there, too?

There could have been seats for four other boys on my street in Dorchester: John, Mike, Matt, and Joel. We were the same age. We walked to school together. In the summer, we played baseball or basketball all day and stayed out at night playing hide-and-go-seek. At the time, I was so nervous about the test it never occurred to me to ask why they weren’t coming.

Matt was the only one of the four other boys to graduate high school. John and Mike were both incarcerated by the age of 20 for drug- and weapons-related offenses. Joel was murdered in 2001.

What separated me from them was a seat at an exam school, which was no accident or good fortune. It was the consequence of a system and culture that provides opportunity and access for some and deprives it from others. The stubborn strictures of racism and classism led me to teach.

You are a successful leader. Which three-character traits do you think were most instrumental to your success? We would love to hear a few stories or examples.

As an educator at heart, I believe most things can be learned. That includes leadership. I think most honest and self-aware leaders can point to specific people and experiences that they learned from or can emulate.

Preparation: At the aptly named Roxbury Prep, I learned the value of preparation. The school’s founders, John King and Evan Rudall, and the following leaders — Josh Phillips and Dana Lehman, were so effective because they were always ready. There was no winging it at school — there was always work that had to be done ahead of time: orientations, staff meetings, lesson plans, and curriculum documents were created with enormous care and precision, setting everyone up for success from the start. Preparation resulted in better plans, improved execution, and the capacity to improvise and reflect. The details matter.

Empathy: In my experience now of working alongside over 40 principals, I deeply respect the ability of leaders who are attuned to and observant of the human needs of an organization. Truly good leaders can block out the day-to-day noise and tasks and focus on the needs and interests of the person right in front of them. This emotional availability fosters a culture of trust and communication that drives effectiveness and innovation.

Communication: All great leaders — from an elementary school teacher to the President of the United States — share a common trait: the ability to convey complex ideas simply, and ideally have people remember them. Concision takes real effort, and at times some risk taking. But it falls on leaders to set a course, and if a group wants to go somewhere, it must be clear.

What’s the most interesting discovery you’ve made since you started leading your organization?

I have been surprised to gain the insight that high-quality schools are essentially similar, despite differences in programmatic models. Our 38 partner schools are diverse in all ways: governance model, grade span, geography, pedagogical approach, and more. But below that surface, you always find the same things: a strong, consistent culture, outstanding principals, effective teachers, and student and family engagement and buy-in.

Can you please tell our readers more about how you or your organization intends to make a significant social impact?

A child’s access to an excellent education and the potential for a bright and productive future should not be determined by that child’s street address, background, the livelihoods of their parents or guardians, or the luck of the draw. That access is truly a right, and it is the obligation of schools to secure that right on behalf of the children and families they serve.

Boston is home to some of the finest educational institutions in the country and resourced with significant public and private funding, yet the majority of our children — particularly Black, Latino, English Learners, and students with special needs — are not enrolled in a school that will prepare them for success in college and careers. For decades, the state of educational opportunity in Boston already demanded significant change; COVID-19 has only brought these disparities into greater focus, as Boston communities are inequitably impacted by the virus and as families have differential resources to support students amid schooling.

The Boston Schools Fund team wakes up every day with one goal: increase the number of children in Boston attending a high-quality school. We provide grants and technical assistance to high-performing and high-demand schools to help them add students. We inform families and caregivers about schools and school options. We serve as a trusted source to a growing demand for data transparency that results in successful outcomes for Boston’s children, particularly those most marginalized. We believe that by providing capacity and resources for high-quality schools to expand and improve, sharing data and information, collaborating with families and partners, and influencing policy will result in the dramatic improvement of student outcomes and life opportunities for Boston’s students, particularly those historically marginalized.

What makes you feel passionate about this cause more than any other?

I know from my own experience at a Boston exam school, how much a seat in a high-quality school can change someone’s life. I am fortunate to be able to work to provide that opportunity and access for others. I am passionate about each seat, and the system. Our organization has a rare position. We have the ability to get to the classroom level, finding outstanding instruction and ensuring even just one more kid can be in that room. But we also engage in broader, systemic questions around enrollment, school funding, and strategy. Being able to do “big and small” work on the same day is very energizing.

Without naming names, could you share a story about an individual who benefitted from your initiatives?

One of Boston Schools Fund’s biggest projects has been the creation of Boston School Finder, a website where families can find information about all the city’s schools in eight different languages to make the selection process easier and more accessible. It’s the city’s only comprehensive guide to navigate school selection across sectors. One parent in South Boston was able to use the site to find the right-fit school for her rising freshman daughter who lives with ADHD and depression. She was so inspired by her experience; she became one of our Parent Ambassadors to help other families connect with the website.

We all want to help and to live a life of purpose. What are three actions anyone could take to help address the root cause of the problem you’re trying to solve?

  • Attain and Respect Lived Experience: What distinguishes most of the Boston Schools Fund team from many other education non-profits and philanthropic organizations is our deep experience in teaching, school leadership, and system leadership. The majority of Boston Schools Fund staff and Board are people of color. The majority of Boston Schools Fund staff and Board are parents of school-aged children. I am certain our expertise and diversity of our experience helps us better understand the root causes of the problem we are trying to solve, educational inequity.
  • Consume Information: Knowledge and data is widely available. Seek to deeply understand the content and context of a social problem before you seek to solve for it.
  • Commit to a Process: Addressing complex requires time and multiple rounds of inquiry. Our team uses informal and formal structures to identify issues and align work, often with significant editing along the way.

Based on your experience, what are the “5 Things You Need to Create Philanthropy That Leaves a Lasting Legacy?” Please share a story or example for each.

  1. Start Small, Pilot, and Then Scale: The first year of BSF, we had only two full-time staff members and three Board members. This allowed us to move, achieve, fail, and learn very quickly, so as we began to expand staff and our Board, we had a strong point of view developed.
  2. Identify a Discrete Problem (and Help to Solve it): We did not set out to invent Boston School Finder. We engaged in a months-long research project about how Boston families choose their schools. That research identified a need for Boston School Finder, the first and only tool for Boston families to navigate the school selection process.
  3. Set Clear, Tangible Goals: We had laser focus for our first five years: increase high-quality school enrollment by 7,000 students. That focus allowed us to ground all of our programmatic work, and gave us a clear, consistent frame for all our external communications.
  4. Invest in People: This lasts long after grant funding has gone away. Our school-based expansion grants rarely go to brick and mortar. We provide coaching for principals, professional development for teachers starting new grades, or extended summer or vacation sessions for incoming students.
  5. Engage All of Your Stakeholders: We do not have a specific bar or cut score to determine school quality. Data and outcomes are important, but our diligence process is what helps to make this determination. We engage all members of a school community — from school leaders and faculty, to families, students, and school partners — to determine whether or not a school has the consistent culture and system to sustain quality over time.

How has the pandemic changed your definition of success?

The pandemic has not changed our mission and vision but has changed some of the ways we get there. As an example, over the past 20 months, we have not added many new partner schools. Rather, we have shifted our funding and support to our current partner schools to respond to the pandemic, maintain enrollment, and plan and support recovery.

How do you get inspired after an inevitable setback?

Short of a true tragedy, almost nothing is as bad the next day after you wake up. Unless it is a true emergency, I wait to react. I process the setback emotionally, which may include some venting sessions with people I trust. With the air and my head clearer, I ask myself two questions: What did I learn from this setback? And is there anything I have to actually do? If the answer is, yes, you get back to work, and those first new steps and tasks are usually enough for me to get going again.

We are very blessed that very prominent leaders read this column. Is there a person in the world who you would like to talk to, to share the idea behind your non-profit? He, she, or they might just see this, especially if we tag them. 🙂

Barack Obama. As a matter of course, I routinely take a shot at trying to talk to or meet Barack Obama.

You’re doing important work. How can our readers follow your progress online?

You can find out all about Boston Schools Fund by visiting our website For anyone interested in education news and data, particularly in Boston, sign up at our website for our widely read weekly newsletter, FYI from BSF. You can also follow us on social media at Twitter (@BosSchoolsFund), Facebook (@bostonschoolsfund), and Instagram (@bosschoolsfund).

Thank you for a meaningful conversation. We wish you continued success with your mission.