Bob Henderson, Board Chair

Meet Bob Henderson

It wasn’t too long after Robert P. “Bob” Henderson, Jr. became head of Noble and Greenough School in 2000 that he noticed a couple of students who really stood out. Those young people were Steppingstone Scholars — “smart, capable, confident, prepared, engaging, and eager” — and they were Bob’s first introduction to the nonprofit that he now leads as chair of the Board of Directors. 

A Commitment to Service 

When then Board Chair Brian Conway approached Bob with an invitation to join the Steppingstone board after he retired from Nobles in 2017, he gladly accepted.

Education and service are core values for Bob, his wife, Ross, and their three grown sons. During his time at Nobles, Bob embraced the school’s mission of inspiring leadership for the public good and building within students an intention to give back to their communities throughout their lives. 

A former history teacher who began his career in California and Hawaii, Bob has served on the boards of independent schools and educational foundations and has been actively involved in several regional and national independent school associations over the years. 

He is now a consultant with Resource Group 175, which partners with independent and international schools to identify, foster, and support exceptional leaders.

Preparing Leaders

Starting his term on the Steppingstone Board of Directors in 2018, Bob quickly became involved with efforts to refine the organization’s mission statement and position it for a successful and impactful future. He stepped into the role of chair in July 2021. 

“It is remarkable the number of people Steppingstone touches, and its success rate is pretty astonishing,” he said. “My vision… is that Steppingstone should be a launching pad for future leaders of the city of Boston.”

He cited one such leader: Steppingstone Alumna and board member, Dr. Mariel Novas ’00, who holds a Ph.D. from the Harvard Graduate School of Education and has been a senior advisor to Boston Mayor Michelle Wu. Equally impressive, he stressed, are the many other Alumni who are “leading their neighborhoods, raising their families, and making a difference for the people around them.”

Supporting Students of Promise

The majority of Steppingstone Scholars are Black and Latinx students from low- and moderate-income neighborhoods. “A lot of these kids face exceptional odds against them, a lot of them are first-generation college bound, and they enter environments that are well-intentioned but not always the most supportive and positive places for them,” Bob said. At a systemic level, Steppingstone’s National Partnership for Educational Access (NPEA) works with schools and other institutions to strengthen equity and belonging—connecting people, practices, and innovations essential for eliminating barriers to college and career success.

Locally, Bob notes the value in Steppingstone’s direct support for students. Advisors work closely with Scholars, offering resources and strategies for navigating challenges throughout their journey. Scholars also find support within a cohort of peers. They first meet as middle schoolers at Steppingstone’s summer program at Milton Academy, where “they feel total ownership of the space. That takes down psychological barriers at an early age that can be really potent,” Bob observed. “Scholars have said it was incredibly important to find themselves in the company of like-minded kids — overwhelmingly kids of color who are facing the same kinds of challenges — who care about learning and achieving. And model for each other and help each other through those challenges and how to stay on track.”

During his tenure as head of school at Nobles, Bob had the opportunity to connect with many Steppingstone Scholars and have some “really frank conversations” about their experience at the school. The feedback the Scholars gave to him and other school leaders sparked many changes to make the school more welcoming and inclusive, including making technology more equitably available, improving counseling and support resources, and scheduling school events so working parents could attend. “The focus and commitment to that work has only increased since my retirement,” Bob noted.

A Foundation for the Future 

With an extensive background in strategic planning and as a veteran of two capital campaigns at Nobles that raised $230 million, Bob is well-equipped to steer the organization through its next chapter. His focus, he said, will be on “ensuring funding and making this an ongoing enterprise in perpetuity.” 

“This cause is particularly compelling because the work Steppingstone does is so extraordinary,” he noted. “This is a moment for the organization. There’s a possibility here to make a profound and permanent difference.”