Inside the Belly of the Philanthropic Beast

Two weeks ago I started my Education Pioneers Graduate School Fellowship at the Highland Street Foundation. A couple of basics before I get deep into this post:


  • Education Pioneers is a national nonprofit organization that “identifies, trains, connects, and inspires a new generation of leaders dedicated to transforming our educational system so that all students receive a quality education.” Fellows are placed in educational organizations for a 10-week high impact project during the summer between their graduate school years.
  • The Highland Street Foundation is a small family foundation based in Newton, MA, which is a suburb of Boston. The foundation boasts a $190 million endowment and funds education, youth, mentoring, health care, and cultural institutions in Massachusetts and California.


When I was placed with the Highland Street Foundation in May, I was slightly concerned because I didn’t know if I would be able to connect with the grant-making side of the nonprofit world. For over a decade, my worldview and context has been shaped by grant-seeking organizations. Yet here I am spending 10 weeks with the good folks at Highland Street, and thus far the experience has been eye-opening.


My project this summer is to do an evaluation of one of the foundation’s grant programs, Free Fun Fridays. The Free Fun Fridays program opens up the doors of over 20 of Massachusetts’ most famous cultural institutions for free this summer. Highland Street will underwrite all of the admissions costs of the cultural institutions. This is the third year that the foundation has implemented Free Fun Fridays, and this year they were interested to learn about the economic and social impact of the program — what is the economic impact on museums, neighboring businesses and families?


The interesting thing is that the foundation doesn’t have a history of doing evaluations or assessments of their grant programs (other than a post-grant report that grantees must submit). I’m literally starting from scratch and have called on my professors and friends who are experts in the field of program evaluation to lend me their expertise.


I’ve also noticed that being on the grant-making side of the table provides a completely different angle, and I feel a shift in the power dynamic. I accompanied my executive director on a site visit to one of our grantees. The grantees (who will not be named) included over 20 bigwigs from their organization to the meeting, and I thought they would overtake the meeting since we were significantly outnumbered. Instead, however, my ED ran the show sharply and with such certitude and ownership. He threw out questions quickly, and the grantees’ staff tried to answer as adeptly and succinctly as possible. You could feel the power hovering strongly over the Highland Street side of the room. It was an absolutely new feeling to know that you were on the side of the room that held all of the chip, while the other side of the room wanted those very chips. To their credit, they didn’t exude any overt desperation. I did, however, sense that the balance of power was definitely on the corner that held the potential to give them another $1 million grant.


Since I’ll be in the belly of the philanthropic beast this summer, I hope to learn about what truly makes philanthropy work and how to build relationships with decision-makers at foundations. So far, my assumptions have been challenged, and I’m looking forward to sharing more of what I learn as the summer progresses.


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