Onboarding the Loyal Skeptic(s) on My Board

Pia Infante, Co-Executive Director, The Whitman Institute

Before becoming Co-Executive Director at The Whitman Institute (TWI) in 2014, I had been a teacher, coach, trainer, consultant, and advocate. The funder role was brand new to me. Thankfully, my previous experiences translated to the welcome challenges of co-leadership, stewarding a spendout, grantmaking, and collaborating deeply with our grantee partners.

As a newbie grantmaker, I hit a lot of speed bumps. The first couple of grant recommendations I made were marked with a hastiness and anxiety that I now think of as “sweaty handshake” grants.  In other moments, I was either too slow or too brusque in communicating the delicate news of “no.” Basically, I had no chill. I’ve gotten better over time, I think!  I’ve made amends or attempted repair when I fired off an insensitive email or wasn’t transparent enough. I’ve developed pacing that is more intuitive and relational in my grantmaking. I’ve learned that there is no such thing as over-sharing when it comes to decisions that impact people’s livelihoods, critical work, and communities.

I think the area where I will perhaps perennially have no chill is board engagement. When I was hired, the board consisted of my Co-Executive Director John Esterle’s close peers and advisors, many of whom had worked with him for years. Like many foundation boards, it was an almost entirely white, boomer-age group. (I have mad love for them all, incidentally.) It was very clear to me — and John — that if we wanted to fully embody our values of equity, then we would need to evolve the composition of our board. The process of shifting toward our multi-racial, multi-sector board took about two years.  It was both intentional and organic. Intentional in that TWI sought to center racial equity values into our programs, strategy, and organizational culture.  Organic in that the previous board members were pulled in other directions by retirement, family, work. 

So, a couple years after my hire, we had an almost 100% turnover of the board, and for the first time TWI’s board was majority people of color under 50. At the same time this new board was taking shape, John and I were getting some traction in our efforts to frame and advocate for something we were starting to call trust-based philanthropy. As we became more public about our vision, our board began to raise critical questions that made me wonder if they weren’t fully bought into what we were advocating for.

The feeling that I may not have my board’s full support was exasperating. I see now, though, that their questions were rooted in values for social change and effectiveness, and that I was avoiding conflict by not naming how I felt. I was raised in an immigrant family that skirted conflict of any kind, and I think for too long I’ve sought approval more often than I’d like to admit. Having a board meant having not one, but six authority figures who I did not want to displease. This is not me at my best as a facilitative leader, but it’s important to be transparent that even the institution that is credited with trust-based philanthropy framing (based on input from our partners) is not some kind of perfect place that has it all figured out. All of us are constantly battling deeply ingrained power structures and perceptions that exist within our consciousness and in our sector.

Eventually, I learned to address my board members' questions with curiosity rather than fear. I made efforts to listen more deeply and from a place of humility. I realized one perspective was that trust-based philanthropy could be used to propagate inequity by not taking a strong enough stand against anti-blackness and white nationalism. Another take was that we might be simplifying and overgeneralizing what equitable grantmaking looks like. Another perspective was that TWI’s distinct point of view of integrating the arts, critical thinking, listening, and principled relationship was getting lost in our focus on trust. These perspectives were important for me to absorb, and ultimately helped bring greater clarity of purpose behind trust-based philanthropy.

I share all this because it remains a powerful lesson for me. I have slowly come to embrace (not always without bracing) the concept of the loyal skeptic, the member of the board who offers insightful and incisive questions arising from a deep sense of commitment to a larger vision for social transformation. I am working on not taking it personally, and breathing when such questions arrive. Skeptics and critical questioners don’t necessarily have to take down the ship or its sweaty-palmed Co-Executive Director. If their thoughts and questions are acknowledged and integrated, if we are willing to stay in right relationship with them and most importantly if they are willing to offer critique with commitment and curiosity, there might be some space to build more collective buy in not just for trust-based philanthropy but for ways to continue to move towards a more just, equitable, and democratic expression of philanthropy.